The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors

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The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors (en)
Синтеза аминохинолина и њихових деривата као антималарика и инхибитора ботулинум неуротоксина А (sr)
Sinteza aminohinolina i njihovih derivata kao antimalarika i inhibitora botulinum neurotoksina A (sr_RS)
Authors

Publications

Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives

Novaković, Miroslav M.; Simić, Stefan; Koračak, Ljiljana; Zlatović, Mario; Ilić-Tomič, Tatjana; Asakawa, Yoshinori; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Elsevier, 2020)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomič, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3867
AB  - Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.
PB  - Elsevier
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
SP  - 104520
DO  - 10.1016/j.fitote.2020.104520
ER  - 
@article{
author = "Novaković, Miroslav M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
abstract = "Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
pages = "104520",
doi = "10.1016/j.fitote.2020.104520"
}
Novaković, M. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia
Elsevier., 142, 104520.
https://doi.org/10.1016/j.fitote.2020.104520
Novaković MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia. 2020;142:104520.
doi:10.1016/j.fitote.2020.104520 .
Novaković, Miroslav M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives" in Fitoterapia, 142 (2020):104520,
https://doi.org/10.1016/j.fitote.2020.104520 . .
1
1
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1

Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867

Novaković, Miroslav M.; Simić, Stefan; Koračak, Ljiljana; Zlatović, Mario; Ilić-Tomič, Tatjana; Asakawa, Yoshinori; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Elsevier, 2020)

TY  - DATA
AU  - Novaković, Miroslav M.
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomič, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3889
PB  - Elsevier
T2  - Fitoterapia
T1  - Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867
ER  - 
@misc{
author = "Novaković, Miroslav M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867"
}
Novaković, M. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867. in Fitoterapia
Elsevier..
Novaković MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867. in Fitoterapia. 2020;..
Novaković, Miroslav M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Supplementary data for the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520.oxic activity of ester derivatives http://cherry.chem.bg.ac.rs/handle/123456789/3867" in Fitoterapia (2020).

Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives

Novaković, Miroslav M.; Simić, Stefan; Koračak, Ljiljana; Zlatović, Mario; Ilić-Tomič, Tatjana; Asakawa, Yoshinori; Nikodinović-Runić, Jasmina; Opsenica, Igor

(Elsevier, 2020)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomič, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3890
AB  - Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.
PB  - Elsevier
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
SP  - 104520
DO  - 10.1016/j.fitote.2020.104520
ER  - 
@article{
author = "Novaković, Miroslav M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
abstract = "Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
pages = "104520",
doi = "10.1016/j.fitote.2020.104520"
}
Novaković, M. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia
Elsevier., 142, 104520.
https://doi.org/10.1016/j.fitote.2020.104520
Novaković MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia. 2020;142:104520.
doi:10.1016/j.fitote.2020.104520 .
Novaković, Miroslav M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives" in Fitoterapia, 142 (2020):104520,
https://doi.org/10.1016/j.fitote.2020.104520 . .
1
1
1
1

Development of an efficient biocatalytic system based on bacterial laccase for the oxidation of selected 1,4-dihydropyridines

Simić, Stefan; Jeremić, Sanja; Đokić, Lidija; Božić, Nataša; Vujčić, Zoran; Lončar, Nikola L.; Senthamaraikannan, Ramsankar; Babu, Ramesh P.; Opsenica, Igor; Nikodinović-Runić, Jasmina

(2020)

TY  - JOUR
AU  - Simić, Stefan
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Božić, Nataša
AU  - Vujčić, Zoran
AU  - Lončar, Nikola L.
AU  - Senthamaraikannan, Ramsankar
AU  - Babu, Ramesh P.
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3356
AB  - Biocatalytic oxidations mediated by laccases are gaining importance due to their versatility and beneficial environmental effects. In this study, the oxidation of 1,4-dihydropyridines has been performed using three different types of bacterial laccase-based catalysts: purified laccase from Bacillus licheniformis ATCC 9945a (BliLacc), Escherichia coli whole cells expressing this laccase, and bacterial nanocellulose (BNC) supported BliLacc catalysts. The catalysts based on bacterial laccase were compared to the commercially available Trametes versicolor laccase (TvLacc). The oxidation product of 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate was obtained within 7–24 h with good yields (70–99%) with all three biocatalysts. The substrate scope was examined with five additional 1,4-dihydropyridines, one of which was oxidized in high yield. Whole-cell biocatalyst was stable when stored for up to 1-month at 4 °C. In addition, evidence has been provided that multicopper oxidase CueO from the E. coli expression host contributed to the oxidation efficiency of the whole-cell biocatalyst. The immobilized whole-cell biocatalyst showed satisfactory activity and retained 37% of its original activity after three biotransformation cycles.
T2  - Enzyme and Microbial Technology
T1  - Development of an efficient biocatalytic system based on bacterial laccase for the oxidation of selected 1,4-dihydropyridines
VL  - 132
DO  - 10.1016/j.enzmictec.2019.109411
ER  - 
@article{
author = "Simić, Stefan and Jeremić, Sanja and Đokić, Lidija and Božić, Nataša and Vujčić, Zoran and Lončar, Nikola L. and Senthamaraikannan, Ramsankar and Babu, Ramesh P. and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2020",
abstract = "Biocatalytic oxidations mediated by laccases are gaining importance due to their versatility and beneficial environmental effects. In this study, the oxidation of 1,4-dihydropyridines has been performed using three different types of bacterial laccase-based catalysts: purified laccase from Bacillus licheniformis ATCC 9945a (BliLacc), Escherichia coli whole cells expressing this laccase, and bacterial nanocellulose (BNC) supported BliLacc catalysts. The catalysts based on bacterial laccase were compared to the commercially available Trametes versicolor laccase (TvLacc). The oxidation product of 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate was obtained within 7–24 h with good yields (70–99%) with all three biocatalysts. The substrate scope was examined with five additional 1,4-dihydropyridines, one of which was oxidized in high yield. Whole-cell biocatalyst was stable when stored for up to 1-month at 4 °C. In addition, evidence has been provided that multicopper oxidase CueO from the E. coli expression host contributed to the oxidation efficiency of the whole-cell biocatalyst. The immobilized whole-cell biocatalyst showed satisfactory activity and retained 37% of its original activity after three biotransformation cycles.",
journal = "Enzyme and Microbial Technology",
title = "Development of an efficient biocatalytic system based on bacterial laccase for the oxidation of selected 1,4-dihydropyridines",
volume = "132",
doi = "10.1016/j.enzmictec.2019.109411"
}
Simić, S., Jeremić, S., Đokić, L., Božić, N., Vujčić, Z., Lončar, N. L., Senthamaraikannan, R., Babu, R. P., Opsenica, I.,& Nikodinović-Runić, J.. (2020). Development of an efficient biocatalytic system based on bacterial laccase for the oxidation of selected 1,4-dihydropyridines. in Enzyme and Microbial Technology, 132.
https://doi.org/10.1016/j.enzmictec.2019.109411
Simić S, Jeremić S, Đokić L, Božić N, Vujčić Z, Lončar NL, Senthamaraikannan R, Babu RP, Opsenica I, Nikodinović-Runić J. Development of an efficient biocatalytic system based on bacterial laccase for the oxidation of selected 1,4-dihydropyridines. in Enzyme and Microbial Technology. 2020;132.
doi:10.1016/j.enzmictec.2019.109411 .
Simić, Stefan, Jeremić, Sanja, Đokić, Lidija, Božić, Nataša, Vujčić, Zoran, Lončar, Nikola L., Senthamaraikannan, Ramsankar, Babu, Ramesh P., Opsenica, Igor, Nikodinović-Runić, Jasmina, "Development of an efficient biocatalytic system based on bacterial laccase for the oxidation of selected 1,4-dihydropyridines" in Enzyme and Microbial Technology, 132 (2020),
https://doi.org/10.1016/j.enzmictec.2019.109411 . .
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Bisaurones – enzymatic production and biological evaluation

Novaković, Miroslav M.; Ilić-Tomić, Tatjana; Tešević, Vele; Simić, Katarina; Ivanović, Stefan; Simić, Stefan; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Royal Society of Chemistry, 2020)

TY  - JOUR
AU  - Novaković, Miroslav M.
AU  - Ilić-Tomić, Tatjana
AU  - Tešević, Vele
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Simić, Stefan
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4052
AB  - The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Bisaurones – enzymatic production and biological evaluation
VL  - 44
IS  - 23
SP  - 9647
EP  - 9655
DO  - 10.1039/d0nj00758g
ER  - 
@article{
author = "Novaković, Miroslav M. and Ilić-Tomić, Tatjana and Tešević, Vele and Simić, Katarina and Ivanović, Stefan and Simić, Stefan and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2020",
abstract = "The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Bisaurones – enzymatic production and biological evaluation",
volume = "44",
number = "23",
pages = "9647-9655",
doi = "10.1039/d0nj00758g"
}
Novaković, M. M., Ilić-Tomić, T., Tešević, V., Simić, K., Ivanović, S., Simić, S., Opsenica, I.,& Nikodinović-Runić, J.. (2020). Bisaurones – enzymatic production and biological evaluation. in New Journal of Chemistry
Royal Society of Chemistry., 44(23), 9647-9655.
https://doi.org/10.1039/d0nj00758g
Novaković MM, Ilić-Tomić T, Tešević V, Simić K, Ivanović S, Simić S, Opsenica I, Nikodinović-Runić J. Bisaurones – enzymatic production and biological evaluation. in New Journal of Chemistry. 2020;44(23):9647-9655.
doi:10.1039/d0nj00758g .
Novaković, Miroslav M., Ilić-Tomić, Tatjana, Tešević, Vele, Simić, Katarina, Ivanović, Stefan, Simić, Stefan, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Bisaurones – enzymatic production and biological evaluation" in New Journal of Chemistry, 44, no. 23 (2020):9647-9655,
https://doi.org/10.1039/d0nj00758g . .

Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G

Novaković, Miroslav M.; Ilić-Tomić, Tatjana; Tešević, Vele; Simić, Katarina; Ivanović, Stefan; Simić, Stefan; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Royal Society of Chemistry, 2020)

TY  - DATA
AU  - Novaković, Miroslav M.
AU  - Ilić-Tomić, Tatjana
AU  - Tešević, Vele
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Simić, Stefan
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4078
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G
ER  - 
@misc{
author = "Novaković, Miroslav M. and Ilić-Tomić, Tatjana and Tešević, Vele and Simić, Katarina and Ivanović, Stefan and Simić, Stefan and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2020",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G"
}
Novaković, M. M., Ilić-Tomić, T., Tešević, V., Simić, K., Ivanović, S., Simić, S., Opsenica, I.,& Nikodinović-Runić, J.. (2020). Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G. in New Journal of Chemistry
Royal Society of Chemistry..
Novaković MM, Ilić-Tomić T, Tešević V, Simić K, Ivanović S, Simić S, Opsenica I, Nikodinović-Runić J. Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G. in New Journal of Chemistry. 2020;..
Novaković, Miroslav M., Ilić-Tomić, Tatjana, Tešević, Vele, Simić, Katarina, Ivanović, Stefan, Simić, Stefan, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Supplementary data for the article: Novakovic, M.; Ilic-Tomic, T.; Tesevic, V.; Simic, K.; Ivanovic, S.; Simic, S.; Opsenica, I.; Nikodinovic-Runic, J. Bisaurones – Enzymatic Production and Biological Evaluation. New J. Chem. 2020, 44 (23), 9647–9655. https://doi.org/10.1039/D0NJ00758G" in New Journal of Chemistry (2020).

Supplementary data for article: Simić, S.; Jeremic, S.; Djokic, L.; Božić, N.; Vujčić, Z.; Lončar, N.; Senthamaraikannan, R.; Babu, R.; Opsenica, I. M.; Nikodinovic-Runic, J. Development of an Efficient Biocatalytic System Based on Bacterial Laccase for the Oxidation of Selected 1,4-Dihydropyridines. Enzyme and Microbial Technology 2020, 132. https://doi.org/10.1016/j.enzmictec.2019.109411

Simić, Stefan; Jeremić, Sanja; Đokić, Lidija; Božić, Nataša; Vujčić, Zoran; Lončar, Nikola L.; Senthamaraikannan, Ramsankar; Babu, Ramesh P.; Opsenica, Igor; Nikodinović-Runić, Jasmina

(2020)

TY  - DATA
AU  - Simić, Stefan
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Božić, Nataša
AU  - Vujčić, Zoran
AU  - Lončar, Nikola L.
AU  - Senthamaraikannan, Ramsankar
AU  - Babu, Ramesh P.
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3357
T2  - Enzyme and Microbial Technology
T1  - Supplementary data for article: Simić, S.; Jeremic, S.; Djokic, L.; Božić, N.; Vujčić, Z.; Lončar, N.; Senthamaraikannan, R.; Babu, R.; Opsenica, I. M.; Nikodinovic-Runic, J. Development of an Efficient Biocatalytic System Based on Bacterial Laccase for the Oxidation of Selected 1,4-Dihydropyridines. Enzyme and Microbial Technology 2020, 132. https://doi.org/10.1016/j.enzmictec.2019.109411
ER  - 
@misc{
author = "Simić, Stefan and Jeremić, Sanja and Đokić, Lidija and Božić, Nataša and Vujčić, Zoran and Lončar, Nikola L. and Senthamaraikannan, Ramsankar and Babu, Ramesh P. and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2020",
journal = "Enzyme and Microbial Technology",
title = "Supplementary data for article: Simić, S.; Jeremic, S.; Djokic, L.; Božić, N.; Vujčić, Z.; Lončar, N.; Senthamaraikannan, R.; Babu, R.; Opsenica, I. M.; Nikodinovic-Runic, J. Development of an Efficient Biocatalytic System Based on Bacterial Laccase for the Oxidation of Selected 1,4-Dihydropyridines. Enzyme and Microbial Technology 2020, 132. https://doi.org/10.1016/j.enzmictec.2019.109411"
}
Simić, S., Jeremić, S., Đokić, L., Božić, N., Vujčić, Z., Lončar, N. L., Senthamaraikannan, R., Babu, R. P., Opsenica, I.,& Nikodinović-Runić, J.. (2020). Supplementary data for article: Simić, S.; Jeremic, S.; Djokic, L.; Božić, N.; Vujčić, Z.; Lončar, N.; Senthamaraikannan, R.; Babu, R.; Opsenica, I. M.; Nikodinovic-Runic, J. Development of an Efficient Biocatalytic System Based on Bacterial Laccase for the Oxidation of Selected 1,4-Dihydropyridines. Enzyme and Microbial Technology 2020, 132. https://doi.org/10.1016/j.enzmictec.2019.109411. in Enzyme and Microbial Technology.
Simić S, Jeremić S, Đokić L, Božić N, Vujčić Z, Lončar NL, Senthamaraikannan R, Babu RP, Opsenica I, Nikodinović-Runić J. Supplementary data for article: Simić, S.; Jeremic, S.; Djokic, L.; Božić, N.; Vujčić, Z.; Lončar, N.; Senthamaraikannan, R.; Babu, R.; Opsenica, I. M.; Nikodinovic-Runic, J. Development of an Efficient Biocatalytic System Based on Bacterial Laccase for the Oxidation of Selected 1,4-Dihydropyridines. Enzyme and Microbial Technology 2020, 132. https://doi.org/10.1016/j.enzmictec.2019.109411. in Enzyme and Microbial Technology. 2020;..
Simić, Stefan, Jeremić, Sanja, Đokić, Lidija, Božić, Nataša, Vujčić, Zoran, Lončar, Nikola L., Senthamaraikannan, Ramsankar, Babu, Ramesh P., Opsenica, Igor, Nikodinović-Runić, Jasmina, "Supplementary data for article: Simić, S.; Jeremic, S.; Djokic, L.; Božić, N.; Vujčić, Z.; Lončar, N.; Senthamaraikannan, R.; Babu, R.; Opsenica, I. M.; Nikodinovic-Runic, J. Development of an Efficient Biocatalytic System Based on Bacterial Laccase for the Oxidation of Selected 1,4-Dihydropyridines. Enzyme and Microbial Technology 2020, 132. https://doi.org/10.1016/j.enzmictec.2019.109411" in Enzyme and Microbial Technology (2020).

N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa

Aleksic, Ivana; Jeremic, Jelena; Milivojević, Dušan; Ilić-Tomić, Tatjana; Šegan, Sandra B.; Zlatović, Mario; Opsenica, Dejan M.; Senerovic, Lidija

(American Chemical Society, 2019)

TY  - JOUR
AU  - Aleksic, Ivana
AU  - Jeremic, Jelena
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Opsenica, Dejan M.
AU  - Senerovic, Lidija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3771
AB  - Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.
PB  - American Chemical Society
T2  - ACS Chemical Biology
T1  - N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
DO  - 10.1021/acschembio.9b00682
ER  - 
@article{
author = "Aleksic, Ivana and Jeremic, Jelena and Milivojević, Dušan and Ilić-Tomić, Tatjana and Šegan, Sandra B. and Zlatović, Mario and Opsenica, Dejan M. and Senerovic, Lidija",
year = "2019",
abstract = "Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.",
publisher = "American Chemical Society",
journal = "ACS Chemical Biology",
title = "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa",
doi = "10.1021/acschembio.9b00682"
}
Aleksic, I., Jeremic, J., Milivojević, D., Ilić-Tomić, T., Šegan, S. B., Zlatović, M., Opsenica, D. M.,& Senerovic, L.. (2019). N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology
American Chemical Society..
https://doi.org/10.1021/acschembio.9b00682
Aleksic I, Jeremic J, Milivojević D, Ilić-Tomić T, Šegan SB, Zlatović M, Opsenica DM, Senerovic L. N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology. 2019;.
doi:10.1021/acschembio.9b00682 .
Aleksic, Ivana, Jeremic, Jelena, Milivojević, Dušan, Ilić-Tomić, Tatjana, Šegan, Sandra B., Zlatović, Mario, Opsenica, Dejan M., Senerovic, Lidija, "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" in ACS Chemical Biology (2019),
https://doi.org/10.1021/acschembio.9b00682 . .
1
6
6
6

N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa

Aleksic, Ivana; Jeremic, Jelena; Milivojević, Dušan; Ilić-Tomić, Tatjana; Šegan, Sandra B.; Zlatović, Mario; Opsenica, Dejan M.; Senerovic, Lidija

(American Chemical Society, 2019)

TY  - JOUR
AU  - Aleksic, Ivana
AU  - Jeremic, Jelena
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Opsenica, Dejan M.
AU  - Senerovic, Lidija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3772
AB  - Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.
PB  - American Chemical Society
T2  - ACS Chemical Biology
T1  - N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
DO  - 10.1021/acschembio.9b00682
ER  - 
@article{
author = "Aleksic, Ivana and Jeremic, Jelena and Milivojević, Dušan and Ilić-Tomić, Tatjana and Šegan, Sandra B. and Zlatović, Mario and Opsenica, Dejan M. and Senerovic, Lidija",
year = "2019",
abstract = "Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.",
publisher = "American Chemical Society",
journal = "ACS Chemical Biology",
title = "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa",
doi = "10.1021/acschembio.9b00682"
}
Aleksic, I., Jeremic, J., Milivojević, D., Ilić-Tomić, T., Šegan, S. B., Zlatović, M., Opsenica, D. M.,& Senerovic, L.. (2019). N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology
American Chemical Society..
https://doi.org/10.1021/acschembio.9b00682
Aleksic I, Jeremic J, Milivojević D, Ilić-Tomić T, Šegan SB, Zlatović M, Opsenica DM, Senerovic L. N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology. 2019;.
doi:10.1021/acschembio.9b00682 .
Aleksic, Ivana, Jeremic, Jelena, Milivojević, Dušan, Ilić-Tomić, Tatjana, Šegan, Sandra B., Zlatović, Mario, Opsenica, Dejan M., Senerovic, Lidija, "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" in ACS Chemical Biology (2019),
https://doi.org/10.1021/acschembio.9b00682 . .
1
6
6
6

Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa

Aleksic, Ivana; Jeremic, Jelena; Milivojević, Dušan; Ilić-Tomić, Tatjana; Šegan, Sandra B.; Zlatović, Mario; Opsenica, Dejan M.; Senerovic, Lidija

(American Chemical Society, 2019)

TY  - DATA
AU  - Aleksic, Ivana
AU  - Jeremic, Jelena
AU  - Milivojević, Dušan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Opsenica, Dejan M.
AU  - Senerovic, Lidija
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3773
PB  - American Chemical Society
T2  - ACS Chemical Biology
T1  - Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
ER  - 
@misc{
author = "Aleksic, Ivana and Jeremic, Jelena and Milivojević, Dušan and Ilić-Tomić, Tatjana and Šegan, Sandra B. and Zlatović, Mario and Opsenica, Dejan M. and Senerovic, Lidija",
year = "2019",
publisher = "American Chemical Society",
journal = "ACS Chemical Biology",
title = "Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa"
}
Aleksic, I., Jeremic, J., Milivojević, D., Ilić-Tomić, T., Šegan, S. B., Zlatović, M., Opsenica, D. M.,& Senerovic, L.. (2019). Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology
American Chemical Society..
Aleksic I, Jeremic J, Milivojević D, Ilić-Tomić T, Šegan SB, Zlatović M, Opsenica DM, Senerovic L. Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology. 2019;..
Aleksic, Ivana, Jeremic, Jelena, Milivojević, Dušan, Ilić-Tomić, Tatjana, Šegan, Sandra B., Zlatović, Mario, Opsenica, Dejan M., Senerovic, Lidija, "Supplementary data for article: N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" in ACS Chemical Biology (2019).

Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida

Ajdačić, Vladimir

(Универзитет у Београду, Хемијски факултет, 2019)

TY  - THES
AU  - Ajdačić, Vladimir
PY  - 2019
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7600
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:22540/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51816719
UR  - http://nardus.mpn.gov.rs/handle/123456789/17444
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4386
AB  - Sintetisan je i okarakterisan katalizator magnetnih osobina na bazi paladijuma (Pd/Fe2O3) kao i katalizator na bazi paladijuma gde je kao nosač upotrebljena bakterijska nanoceluloza (Pd/BNC) i ispitana je njihova primena u reakciji dekarbonilovanja aldehida. Optimizovani reakcioni uslovi primenjeni su na aromatičnim i heteroaromatičnim aldehidima i na alifatičnim aldehidima koji imaju vodonikove atome na α- i δ-ugljenikovim atomima. Istovremeno, određen je mehanizam reakcije dekarbonilovanja i ispitana je mogućnost reciklovanja katalizatora.Pored reakcije dekarbonilovanja sintetisani katalizator Pd/Fe2O3 upotrebljen je i u reakciji reduktivnog dehalogenovanja arilhalogenida.U nastavku istražena je i reakcije dekarbonilativnog bromovanja 5-ariltiofen-2-karbaldehida. Eksperimentalnim i računarskim metodama ispitan je mehanizam reakcije kao i njena primena u sintezi triarilsupstituisanih tiofena.
AB  - Palladium-based catalysts obtained by palladium immobilization on maghemite (Pd/ γ-Fe2O3) and bacterial nanocellulose (Pd/BNC) as solid supports were synthesized and characterized and their application in the decarbonylation reaction was investigated. Optimized reaction conditions were applied to a series of aromatic and heteroaromatic aldehydes as well as to several aldehydes having alpha and beta hydrogen atoms. The mechanism of the mentioned transformation as well as the possibility of catalyst recycling has also been investigated.In addition to the decarbonylation reaction, the synthesized catalyst Pd/γ-Fe2O3 was used in the reductive dehalogenation reaction of arylhalides.The decarbonylative bromination reaction of 5-arylthiophene-2-carbaldehydes was also investigated. By combining experimental and computational methods, the mechanism of this reaction was examined, as well as its application to the synthesis of triaryl-substituted thiophene derivatives.
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida
ER  - 
@phdthesis{
author = "Ajdačić, Vladimir",
year = "2019",
abstract = "Sintetisan je i okarakterisan katalizator magnetnih osobina na bazi paladijuma (Pd/Fe2O3) kao i katalizator na bazi paladijuma gde je kao nosač upotrebljena bakterijska nanoceluloza (Pd/BNC) i ispitana je njihova primena u reakciji dekarbonilovanja aldehida. Optimizovani reakcioni uslovi primenjeni su na aromatičnim i heteroaromatičnim aldehidima i na alifatičnim aldehidima koji imaju vodonikove atome na α- i δ-ugljenikovim atomima. Istovremeno, određen je mehanizam reakcije dekarbonilovanja i ispitana je mogućnost reciklovanja katalizatora.Pored reakcije dekarbonilovanja sintetisani katalizator Pd/Fe2O3 upotrebljen je i u reakciji reduktivnog dehalogenovanja arilhalogenida.U nastavku istražena je i reakcije dekarbonilativnog bromovanja 5-ariltiofen-2-karbaldehida. Eksperimentalnim i računarskim metodama ispitan je mehanizam reakcije kao i njena primena u sintezi triarilsupstituisanih tiofena., Palladium-based catalysts obtained by palladium immobilization on maghemite (Pd/ γ-Fe2O3) and bacterial nanocellulose (Pd/BNC) as solid supports were synthesized and characterized and their application in the decarbonylation reaction was investigated. Optimized reaction conditions were applied to a series of aromatic and heteroaromatic aldehydes as well as to several aldehydes having alpha and beta hydrogen atoms. The mechanism of the mentioned transformation as well as the possibility of catalyst recycling has also been investigated.In addition to the decarbonylation reaction, the synthesized catalyst Pd/γ-Fe2O3 was used in the reductive dehalogenation reaction of arylhalides.The decarbonylative bromination reaction of 5-arylthiophene-2-carbaldehydes was also investigated. By combining experimental and computational methods, the mechanism of this reaction was examined, as well as its application to the synthesis of triaryl-substituted thiophene derivatives.",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida"
}
Ajdačić, V.. (2019). Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
Ajdačić V. Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida. in Универзитет у Београду. 2019;..
Ajdačić, Vladimir, "Dekarbonilativno bromovanje i dekabronilovanje aromatičnih i heteoaromatičnih aldehida" in Универзитет у Београду (2019).

Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions

Jeremić, Sanja; Đokić, Lidija; Ajdačić, Vladimir; Božinović, Nina S.; Pavlović, Vladimir D.; Manojlović, Dragan D.; Babu, Ramesh P.; Senthamaraikannan, Ramsankar; Rojas, Orlando; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Elsevier, 2019)

TY  - JOUR
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Ajdačić, Vladimir
AU  - Božinović, Nina S.
AU  - Pavlović, Vladimir D.
AU  - Manojlović, Dragan D.
AU  - Babu, Ramesh P.
AU  - Senthamaraikannan, Ramsankar
AU  - Rojas, Orlando
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2850
AB  - Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions
VL  - 129
SP  - 351
EP  - 360
DO  - 10.1016/j.ijbiomac.2019.01.154
ER  - 
@article{
author = "Jeremić, Sanja and Đokić, Lidija and Ajdačić, Vladimir and Božinović, Nina S. and Pavlović, Vladimir D. and Manojlović, Dragan D. and Babu, Ramesh P. and Senthamaraikannan, Ramsankar and Rojas, Orlando and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2019",
abstract = "Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions",
volume = "129",
pages = "351-360",
doi = "10.1016/j.ijbiomac.2019.01.154"
}
Jeremić, S., Đokić, L., Ajdačić, V., Božinović, N. S., Pavlović, V. D., Manojlović, D. D., Babu, R. P., Senthamaraikannan, R., Rojas, O., Opsenica, I.,& Nikodinović-Runić, J.. (2019). Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. in International Journal of Biological Macromolecules
Elsevier., 129, 351-360.
https://doi.org/10.1016/j.ijbiomac.2019.01.154
Jeremić S, Đokić L, Ajdačić V, Božinović NS, Pavlović VD, Manojlović DD, Babu RP, Senthamaraikannan R, Rojas O, Opsenica I, Nikodinović-Runić J. Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. in International Journal of Biological Macromolecules. 2019;129:351-360.
doi:10.1016/j.ijbiomac.2019.01.154 .
Jeremić, Sanja, Đokić, Lidija, Ajdačić, Vladimir, Božinović, Nina S., Pavlović, Vladimir D., Manojlović, Dragan D., Babu, Ramesh P., Senthamaraikannan, Ramsankar, Rojas, Orlando, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions" in International Journal of Biological Macromolecules, 129 (2019):351-360,
https://doi.org/10.1016/j.ijbiomac.2019.01.154 . .
14
14
14

Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions

Jeremić, Sanja; Đokić, Lidija; Ajdačić, Vladimir; Božinović, Nina S.; Pavlović, Vladimir D.; Manojlović, Dragan D.; Babu, Ramesh P.; Senthamaraikannan, Ramsankar; Rojas, Orlando; Opsenica, Igor; Nikodinović-Runić, Jasmina

(Elsevier, 2019)

TY  - JOUR
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Ajdačić, Vladimir
AU  - Božinović, Nina S.
AU  - Pavlović, Vladimir D.
AU  - Manojlović, Dragan D.
AU  - Babu, Ramesh P.
AU  - Senthamaraikannan, Ramsankar
AU  - Rojas, Orlando
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2866
AB  - Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions
VL  - 129
SP  - 351
EP  - 360
DO  - 10.1016/j.ijbiomac.2019.01.154
ER  - 
@article{
author = "Jeremić, Sanja and Đokić, Lidija and Ajdačić, Vladimir and Božinović, Nina S. and Pavlović, Vladimir D. and Manojlović, Dragan D. and Babu, Ramesh P. and Senthamaraikannan, Ramsankar and Rojas, Orlando and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2019",
abstract = "Bacterial nanocellulose (BNC) emerged as an attractive advanced biomaterial that provides desirable properties such as high strength, lightweight, tailorable surface chemistry, hydrophilicity, and biodegradability. BNC was successfully obtained from a wide range of carbon sources including sugars derived from grass biomass using Komagataeibacter medellinensis ID13488 strain with yields up to 6 g L −1 in static fermentation. Produced BNC was utilized in straightforward catalyst preparation as a solid support for two different transition metals, palladium and copper with metal loading of 20 and 3 wt%, respectively. Sustainable catalysts were applied in the synthesis of valuable fine chemicals, such as biphenyl-4-amine and 4′-fluorobiphenyl-4-amine, used in drug discovery, perfumes and dye industries with excellent product yields of up to 99%. Pd/BNC catalyst was reused 4 times and applied in two consecutive reactions, Suzuki-Miyaura cross-coupling reaction followed by hydrogenation of nitro to amino group while Cu/BNC catalyst was examined in Chan-Lam coupling reaction. Overall, the environmentally benign process of obtaining nanocellulose from biomass, followed by its utilisation as a solid support in metal-catalysed reactions and its recovery has been described. These findings reveal that BNC is a good support material, and it can be used as a support for different catalytic systems.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions",
volume = "129",
pages = "351-360",
doi = "10.1016/j.ijbiomac.2019.01.154"
}
Jeremić, S., Đokić, L., Ajdačić, V., Božinović, N. S., Pavlović, V. D., Manojlović, D. D., Babu, R. P., Senthamaraikannan, R., Rojas, O., Opsenica, I.,& Nikodinović-Runić, J.. (2019). Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. in International Journal of Biological Macromolecules
Elsevier., 129, 351-360.
https://doi.org/10.1016/j.ijbiomac.2019.01.154
Jeremić S, Đokić L, Ajdačić V, Božinović NS, Pavlović VD, Manojlović DD, Babu RP, Senthamaraikannan R, Rojas O, Opsenica I, Nikodinović-Runić J. Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions. in International Journal of Biological Macromolecules. 2019;129:351-360.
doi:10.1016/j.ijbiomac.2019.01.154 .
Jeremić, Sanja, Đokić, Lidija, Ajdačić, Vladimir, Božinović, Nina S., Pavlović, Vladimir D., Manojlović, Dragan D., Babu, Ramesh P., Senthamaraikannan, Ramsankar, Rojas, Orlando, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Production of bacterial nanocellulose (BNC) and its application as a solid support in transition metal catalysed cross-coupling reactions" in International Journal of Biological Macromolecules, 129 (2019):351-360,
https://doi.org/10.1016/j.ijbiomac.2019.01.154 . .
14
14
14

Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole

Selaković, Života

(Универзитет у Београду, Хемијски факултет, 2019)

TY  - THES
AU  - Selaković, Života
PY  - 2019
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7017
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:20625/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51648783
UR  - http://nardus.mpn.gov.rs/123456789/11673
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3901
AB  - Ebolavirus je rod virusa iz familije Filoviridae, endemski prisutan u Subsaharskoj Africi. Vrste koje pripadaju ovom rodu uzročnici su smrtonosne hemoragijske groznice kod ljudi i primata, a otkrivene su, kao i njima srodni virusi marburga, u drugoj polovini 20. veka, kada su registrovani prvi slučajevi. U ovom trenutku ne postoji odobrena vakcina niti lek protiv ove opasne infekcije. Nekoliko imunoterapeutika, kao i složenih makromolekulskih formulacija, predstavlja obećavajuće kandidate za lek, a ostvaren je i napredak u istraživanjima sa malim molekulima. Oslanjajući se na ranija istraživanja u našoj istraživačkoj grupi, u okviru ove teze sintetisane su dve grupe jedinjenja za koje se pretpostavljalo da mogu imati antivirusnu aktivnost – derivati 4,10-diazahrizena i 1,5-naftiridina. Ukupno je testirano 29 jedinjenja, a po aktivnosti naročito su se istakla dva diazahrizenska derivata koji su imali veoma dobru in vitro aktivnost i štitili su 9/10, odnosno 10/10 inficiranih miševa pri dozi 10 mg/kg. Urađen je veći broj ogleda sa ciljem utvrđivanja mehanizma dejstva ova dva jedinjenja, pri čemu je otkriveno da ona inhibiraju ulazak virusa u ćeliju domaćina, na način koji se razlikuje od do sada poznatih inhibitora ulaska virusa. Dobijeni rezultati ukazuju da su molekuli razvijeni u ovoj tezi značajni i jedinstveni i da zavređuju dalja ispitivanja.
AB  - Ebolavirus is a genus of viruses from the Filoviridae family, endemic to Sub-Saharan Africa. Species from this genus cause a lethal hemorrhagic fewer in humans and non-human primates. Like the related Marburgviruses, they were discovered in the second half of the 20th century, when first cases were reported. Presently, there is no approved vaccine or other therapeutics to treat this dangerous infection. Several immunotherapeutics, as well as sophisticated macromolecular formulations, have shown promising results, and advances have also been made in small molecule research. Based on our previous results we developed two new chemotypes as possible antivirals – derivatives of 4,10-diazachrysene and 1,5-naphthyridine, respectively. A total of 29 compounds were tested, with two of them showing very good results: they had excellent in vitro activity and they protected 9/10 and 10/10 infected mice from a fatal Ebola challenge, respectively (10 mg/kg dose). A number of experiments were carried out to determine the mechanism of action of these two compounds, and it was discovered that they prevent viral entry into cells, albeit in a manner that differed from other known entry inhibitors. The results obtained in this thesis show that the developed compounds are unique and worthy of further examination
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole
ER  - 
@phdthesis{
author = "Selaković, Života",
year = "2019",
abstract = "Ebolavirus je rod virusa iz familije Filoviridae, endemski prisutan u Subsaharskoj Africi. Vrste koje pripadaju ovom rodu uzročnici su smrtonosne hemoragijske groznice kod ljudi i primata, a otkrivene su, kao i njima srodni virusi marburga, u drugoj polovini 20. veka, kada su registrovani prvi slučajevi. U ovom trenutku ne postoji odobrena vakcina niti lek protiv ove opasne infekcije. Nekoliko imunoterapeutika, kao i složenih makromolekulskih formulacija, predstavlja obećavajuće kandidate za lek, a ostvaren je i napredak u istraživanjima sa malim molekulima. Oslanjajući se na ranija istraživanja u našoj istraživačkoj grupi, u okviru ove teze sintetisane su dve grupe jedinjenja za koje se pretpostavljalo da mogu imati antivirusnu aktivnost – derivati 4,10-diazahrizena i 1,5-naftiridina. Ukupno je testirano 29 jedinjenja, a po aktivnosti naročito su se istakla dva diazahrizenska derivata koji su imali veoma dobru in vitro aktivnost i štitili su 9/10, odnosno 10/10 inficiranih miševa pri dozi 10 mg/kg. Urađen je veći broj ogleda sa ciljem utvrđivanja mehanizma dejstva ova dva jedinjenja, pri čemu je otkriveno da ona inhibiraju ulazak virusa u ćeliju domaćina, na način koji se razlikuje od do sada poznatih inhibitora ulaska virusa. Dobijeni rezultati ukazuju da su molekuli razvijeni u ovoj tezi značajni i jedinstveni i da zavređuju dalja ispitivanja., Ebolavirus is a genus of viruses from the Filoviridae family, endemic to Sub-Saharan Africa. Species from this genus cause a lethal hemorrhagic fewer in humans and non-human primates. Like the related Marburgviruses, they were discovered in the second half of the 20th century, when first cases were reported. Presently, there is no approved vaccine or other therapeutics to treat this dangerous infection. Several immunotherapeutics, as well as sophisticated macromolecular formulations, have shown promising results, and advances have also been made in small molecule research. Based on our previous results we developed two new chemotypes as possible antivirals – derivatives of 4,10-diazachrysene and 1,5-naphthyridine, respectively. A total of 29 compounds were tested, with two of them showing very good results: they had excellent in vitro activity and they protected 9/10 and 10/10 infected mice from a fatal Ebola challenge, respectively (10 mg/kg dose). A number of experiments were carried out to determine the mechanism of action of these two compounds, and it was discovered that they prevent viral entry into cells, albeit in a manner that differed from other known entry inhibitors. The results obtained in this thesis show that the developed compounds are unique and worthy of further examination",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole"
}
Selaković, Ž.. (2019). Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
Selaković Ž. Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole. in Универзитет у Београду. 2019;..
Selaković, Života, "Razvoj novih 4,10-diazahrizenskih i 1,5-naftiridinskih inhibitora virusa ebole" in Универзитет у Београду (2019).

Razvoj novih inhibitora proliferacije parazita Plasmodium falciparum i malignih ćelija

Selaković, Milica

(Универзитет у Београду, Хемијски факултет, 2019)

TY  - THES
AU  - Selaković, Milica
PY  - 2019
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7185
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:20883/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=51819791
UR  - http://nardus.mpn.gov.rs/123456789/11834
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3910
AB  - Malarija spada u najrasprostranjenije parazitske bolesti na svetu. Širenje rezistencije parazita malarije prema dostupnim antimalaricima i potreba za efikasnijim delovanjem u više faza životnog ciklusa parazita, razlozi su za intenzivno istraživanje na polju iznalaženja novih potencijalnih lekova. U ovoj disertaciji prikazana je sinteza novih jedinjenja koja sadrže poznatu 4-aminohinolinsku farmakoforu, kao i rezultati ispitivanja njihove biološke aktivnosti u različitim fazama životnog ciklusa parazita malarije. Jedinjenje 38 (MVNP001) se istaklo svojom izuzetnom aktivnošću u eritrocitnoj i sporozoitnoj fazi, a umerenom aktivnošću prema gametocitima u in vitro uslovima. Inhibitor proliferacije parazita u in vitro uslovima, nije toksičan prema zdravim miševima i embrionima zebra-ribica. U modelu eksperimentalne malarije na miševima, jedinjenje 38 (MVNP001) dva puta produžava život inficiranih jedinki u poređenju sa kontrolom. Dodatno, jedinjenje 38 (MVNP001) iskazalo je i značajnu in vitro antitumorsku aktivnost prema ćelijskim linijama karcinoma dojke MCF-7 i MDA-MB-231, kao i u ksenograft modelu tumora u embrionima zebra-ribica uz supresiju angiogeneze. Rezultati ispitivanja antimalarijske i posebno antitumorske aktivnosti derivata 38 (MVNP001) pokazane ksenograft testom, nedvosmisleno ukazuju na značaj daljeg istraživanja farmakoloških osobina ovog jedinjenja.Sintetisani su i novi derivati benzotiazola i ispitano je njihovo antiproliferativno dejstvo prema malignim ćelijama u in vitro uslovima. Pokazano je da najaktivnija jedinjenja prema MCF-7 ćelijskoj liniji karcinoma dojke dovode do apoptoze zaustavljanjem ćelijskog ciklusa u G2/M fazi. Paralelno sa indukcijom apoptoze, jedinjenja smanjuju nivo produkcije reaktivnih kiseoničnih vrsta. Karbamati benzotiazola, koji efikasno inhibiraju rast NT2/D1 ćelijske linije humanog teratokarcinoma u in vitro uslovima, remete adhezivnu sposobnost ćelija sukcesivno ih uvodeći u apoptozu. Sposobnost novih derivata da inhibiraju migraciju i invanzivnost NT2/D1 ćelija ukazuje na moguće antimetastazno dejstvo.
AB  - spread of malaria parasite resistance to currently available drugs and need for more efficient inhibitors that target multiple stages of malaria parasite growth, there is an extensive research in the field of new therapeutics development. This doctoral dissertation presents synthesis of new derivatives of the known 4-aminoquinoline pharmacophore for evaluation of their antimalarial activity at various stages of the parasite life cycle. The compound 38 (MVNP001) showed excellent activity against both erythrocytic and exoerythrocytic stages, and moderate activity against late stage gametocytes in vitro. Moreover, derivative 38 (MVNP001) proved to be non-toxic in host toxicity studies in vivo, both in mice and zebrafish. The evaluation of antimalarial activity in mice showed that compound 38 (MVNP001) prolonged survival of infected mice twice in comparison to untreated infected animals. In addition, compound 38 (MVNP001) showed significant antitumor activity against human breast cancer cell lines, MCF-7 and MDA-MB-231 in vitro, as well as in embryonic zebrafish xenograft assay of human cancer development with anti-angiogenic potential. The results obtained during investigation of antimalarial and especially antitumor activity using embryonic zebrafish xenograft assay of derivative 38 (MVNP001), clearly emphasizes the importance of further research on pharmacological properties of this drug.New benzothiazole derivatives were also synthesized and their antiproliferative activity was evaluated against malignant cells in vitro. It is shown that the most potent compounds against MCF-7 human breast cancer cell line induced apoptosis caused by cell cycle arrest in G2/M phase. Along with apoptosis induction, new benzothiazoles reduced intracellular ROS level. Benzothiazole carbamates, the most potent inhibitors of NT2/D1 human teratocarcinoma cell line growth, affected cell adhesion leading to apoptosis. Reduction in cell ability to migrate and invade, indicated possible antimetastatic potential.
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Razvoj novih inhibitora proliferacije parazita Plasmodium falciparum i malignih ćelija
ER  - 
@phdthesis{
author = "Selaković, Milica",
year = "2019",
abstract = "Malarija spada u najrasprostranjenije parazitske bolesti na svetu. Širenje rezistencije parazita malarije prema dostupnim antimalaricima i potreba za efikasnijim delovanjem u više faza životnog ciklusa parazita, razlozi su za intenzivno istraživanje na polju iznalaženja novih potencijalnih lekova. U ovoj disertaciji prikazana je sinteza novih jedinjenja koja sadrže poznatu 4-aminohinolinsku farmakoforu, kao i rezultati ispitivanja njihove biološke aktivnosti u različitim fazama životnog ciklusa parazita malarije. Jedinjenje 38 (MVNP001) se istaklo svojom izuzetnom aktivnošću u eritrocitnoj i sporozoitnoj fazi, a umerenom aktivnošću prema gametocitima u in vitro uslovima. Inhibitor proliferacije parazita u in vitro uslovima, nije toksičan prema zdravim miševima i embrionima zebra-ribica. U modelu eksperimentalne malarije na miševima, jedinjenje 38 (MVNP001) dva puta produžava život inficiranih jedinki u poređenju sa kontrolom. Dodatno, jedinjenje 38 (MVNP001) iskazalo je i značajnu in vitro antitumorsku aktivnost prema ćelijskim linijama karcinoma dojke MCF-7 i MDA-MB-231, kao i u ksenograft modelu tumora u embrionima zebra-ribica uz supresiju angiogeneze. Rezultati ispitivanja antimalarijske i posebno antitumorske aktivnosti derivata 38 (MVNP001) pokazane ksenograft testom, nedvosmisleno ukazuju na značaj daljeg istraživanja farmakoloških osobina ovog jedinjenja.Sintetisani su i novi derivati benzotiazola i ispitano je njihovo antiproliferativno dejstvo prema malignim ćelijama u in vitro uslovima. Pokazano je da najaktivnija jedinjenja prema MCF-7 ćelijskoj liniji karcinoma dojke dovode do apoptoze zaustavljanjem ćelijskog ciklusa u G2/M fazi. Paralelno sa indukcijom apoptoze, jedinjenja smanjuju nivo produkcije reaktivnih kiseoničnih vrsta. Karbamati benzotiazola, koji efikasno inhibiraju rast NT2/D1 ćelijske linije humanog teratokarcinoma u in vitro uslovima, remete adhezivnu sposobnost ćelija sukcesivno ih uvodeći u apoptozu. Sposobnost novih derivata da inhibiraju migraciju i invanzivnost NT2/D1 ćelija ukazuje na moguće antimetastazno dejstvo., spread of malaria parasite resistance to currently available drugs and need for more efficient inhibitors that target multiple stages of malaria parasite growth, there is an extensive research in the field of new therapeutics development. This doctoral dissertation presents synthesis of new derivatives of the known 4-aminoquinoline pharmacophore for evaluation of their antimalarial activity at various stages of the parasite life cycle. The compound 38 (MVNP001) showed excellent activity against both erythrocytic and exoerythrocytic stages, and moderate activity against late stage gametocytes in vitro. Moreover, derivative 38 (MVNP001) proved to be non-toxic in host toxicity studies in vivo, both in mice and zebrafish. The evaluation of antimalarial activity in mice showed that compound 38 (MVNP001) prolonged survival of infected mice twice in comparison to untreated infected animals. In addition, compound 38 (MVNP001) showed significant antitumor activity against human breast cancer cell lines, MCF-7 and MDA-MB-231 in vitro, as well as in embryonic zebrafish xenograft assay of human cancer development with anti-angiogenic potential. The results obtained during investigation of antimalarial and especially antitumor activity using embryonic zebrafish xenograft assay of derivative 38 (MVNP001), clearly emphasizes the importance of further research on pharmacological properties of this drug.New benzothiazole derivatives were also synthesized and their antiproliferative activity was evaluated against malignant cells in vitro. It is shown that the most potent compounds against MCF-7 human breast cancer cell line induced apoptosis caused by cell cycle arrest in G2/M phase. Along with apoptosis induction, new benzothiazoles reduced intracellular ROS level. Benzothiazole carbamates, the most potent inhibitors of NT2/D1 human teratocarcinoma cell line growth, affected cell adhesion leading to apoptosis. Reduction in cell ability to migrate and invade, indicated possible antimetastatic potential.",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Razvoj novih inhibitora proliferacije parazita Plasmodium falciparum i malignih ćelija"
}
Selaković, M.. (2019). Razvoj novih inhibitora proliferacije parazita Plasmodium falciparum i malignih ćelija. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
Selaković M. Razvoj novih inhibitora proliferacije parazita Plasmodium falciparum i malignih ćelija. in Универзитет у Београду. 2019;..
Selaković, Milica, "Razvoj novih inhibitora proliferacije parazita Plasmodium falciparum i malignih ćelija" in Универзитет у Београду (2019).

Thin-layer chromatography in medicinal chemistry

Šegan, Sandra B.; Opsenica, Dejan M.; Milojković-Opsenica, Dušanka

(Taylor and Francis Inc., 2019)

TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Opsenica, Dejan M.
AU  - Milojković-Opsenica, Dušanka
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3686
AB  - Among widely used chromatographic methods modern thin-layer chromatography is not only the simplest to perform but is also considered as respectable analytical method in various phases of drug discovery and development processes such as monitoring of synthesis, identification of bioactive substances from various natural sources and their isolation and purification, determination of lipophilicity and other physico-chemical parameters, quantitative structure-activity relationship studies, bioautography, as well as qualitative and quantitative analysis of drugs and their metabolites. An overview of recently published papers dealing with application of thin-layer chromatography in medicinal chemistry is presented.
PB  - Taylor and Francis Inc.
T2  - Journal of Liquid Chromatography and Related Technologies
T1  - Thin-layer chromatography in medicinal chemistry
VL  - 42
IS  - 9-10
SP  - 238
EP  - 248
DO  - 10.1080/10826076.2019.1585615
ER  - 
@article{
author = "Šegan, Sandra B. and Opsenica, Dejan M. and Milojković-Opsenica, Dušanka",
year = "2019",
abstract = "Among widely used chromatographic methods modern thin-layer chromatography is not only the simplest to perform but is also considered as respectable analytical method in various phases of drug discovery and development processes such as monitoring of synthesis, identification of bioactive substances from various natural sources and their isolation and purification, determination of lipophilicity and other physico-chemical parameters, quantitative structure-activity relationship studies, bioautography, as well as qualitative and quantitative analysis of drugs and their metabolites. An overview of recently published papers dealing with application of thin-layer chromatography in medicinal chemistry is presented.",
publisher = "Taylor and Francis Inc.",
journal = "Journal of Liquid Chromatography and Related Technologies",
title = "Thin-layer chromatography in medicinal chemistry",
volume = "42",
number = "9-10",
pages = "238-248",
doi = "10.1080/10826076.2019.1585615"
}
Šegan, S. B., Opsenica, D. M.,& Milojković-Opsenica, D.. (2019). Thin-layer chromatography in medicinal chemistry. in Journal of Liquid Chromatography and Related Technologies
Taylor and Francis Inc.., 42(9-10), 238-248.
https://doi.org/10.1080/10826076.2019.1585615
Šegan SB, Opsenica DM, Milojković-Opsenica D. Thin-layer chromatography in medicinal chemistry. in Journal of Liquid Chromatography and Related Technologies. 2019;42(9-10):238-248.
doi:10.1080/10826076.2019.1585615 .
Šegan, Sandra B., Opsenica, Dejan M., Milojković-Opsenica, Dušanka, "Thin-layer chromatography in medicinal chemistry" in Journal of Liquid Chromatography and Related Technologies, 42, no. 9-10 (2019):238-248,
https://doi.org/10.1080/10826076.2019.1585615 . .
1
6
6
6

Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands

Šegan, Sandra B.; Penjišević, Jelena; Šukalović, Vladimir; Andrić, Deana; Milojković-Opsenica, Dušanka; Kostić-Rajačić, Slađana

(Elsevier, 2019)


                                            

                                            
Šegan, S. B., Penjišević, J., Šukalović, V., Andrić, D., Milojković-Opsenica, D.,& Kostić-Rajačić, S.. (2019). Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Elsevier., 1124, 146-153.
https://doi.org/10.1016/j.jchromb.2019.06.006
Šegan SB, Penjišević J, Šukalović V, Andrić D, Milojković-Opsenica D, Kostić-Rajačić S. Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences. 2019;1124:146-153.
doi:10.1016/j.jchromb.2019.06.006 .
Šegan, Sandra B., Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Milojković-Opsenica, Dušanka, Kostić-Rajačić, Slađana, "Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands" in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 1124 (2019):146-153,
https://doi.org/10.1016/j.jchromb.2019.06.006 . .
2
3
3

Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006

Šegan, Sandra B.; Penjišević, Jelena; Šukalović, Vladimir; Andrić, Deana; Milojković-Opsenica, Dušanka; Kostić-Rajačić, Slađana

(Elsevier, 2019)


                                            

                                            
Šegan, S. B., Penjišević, J., Šukalović, V., Andrić, D., Milojković-Opsenica, D.,& Kostić-Rajačić, S.. (2019). Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Elsevier..
Šegan SB, Penjišević J, Šukalović V, Andrić D, Milojković-Opsenica D, Kostić-Rajačić S. Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences. 2019;..
Šegan, Sandra B., Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Milojković-Opsenica, Dušanka, Kostić-Rajačić, Slađana, "Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006" in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences (2019).

Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates

Marković, Olivera S.; Pešić, Miloš P.; Shah, Ankita V.; Serajuddin, Abu T.M.; Verbić, Tatjana; Avdeef, Alex

(Elsevier, 2019)

TY  - JOUR
AU  - Marković, Olivera S.
AU  - Pešić, Miloš P.
AU  - Shah, Ankita V.
AU  - Serajuddin, Abu T.M.
AU  - Verbić, Tatjana
AU  - Avdeef, Alex
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2924
AB  - Although solubility-pH data for desipramine hydrochloride (DsHCl) have been reported previously, the aim of the present study was to critically examine the aqueous solubility-pH behavior of DsHCl in buffer-free and buffered solutions, in the presence of physiologically-relevant chloride concentration, using experimental practices recommended in the recently-published “white paper” (Avdeef et al., 2016). The computer program pDISOL-X was used to design the structured experiments (pH-RSF method), to process the data, and to refine the equilibrium constants. Low-to-high and high-to-low pH assays (using HCl, H 3 PO 4 , or NaOH to adjust pH) were performed on phosphate-buffered (0.12‑0.15 M) saturated solutions of DsHCl in the pH 1.3–11.6 range. After equilibration (stirring 6 h, followed by 18 h stir-free sedimentation), filtration or centrifugation was used for phase separation. Concentration was measured using HPLC with UV/VIS detection. The 2:1 drug-phosphate solubility product (K sp 2:1 = [DsH + ] 2 [HPO 4 2− ]) was determined from data in the pH 4–9 region. The free base of desipramine was prepared and used to determine the K sp 1:1 ([DsH + ][H 2 PO 4 − ]) in chloride-free acidified suspension. In addition, phosphate-free titrations were conducted to determine the intrinsic solubility, S 0 , and the 1:1 drug-chloride solubility product, K sp DsH [rad] Cl = [DsH + ][Cl − ]. Under the assay conditions, only the phosphate-free solutions showed some supersaturation near pH max 8.0. In phosphate-containing solutions, pH max was indicated at higher pH (8.8–9.6). Oils mixed with solids were observed to form in alkaline solutions (pH > 11). Notably, soluble drug-phosphate complexes appeared to form below pH 3.9 and above pH max in saturated phosphate‑containing saline solutions. This was indicated by the systematic pH shift to higher values in the log S-pH curve in alkaline solution than expected from the Henderson-Hasselbalch equation. For pH < 3.9, saturated phosphate-containing saline solutions exhibited elevated solubility, with drug-hydrochloride as the sole precipitate. Salt solubility products, intrinsic solubility, and complexation constants, which rationalized the data, were determined. Elemental, thermogravimetric (TGA), differential scanning calorimetric (DSC), and powder X-ray diffraction (PXRD) analyses were used to characterize the precipitates isolated from suspensions at different pH.
PB  - Elsevier
T2  - European Journal of Pharmaceutical Sciences
T1  - Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates
VL  - 133
SP  - 264
EP  - 274
DO  - 10.1016/j.ejps.2019.03.014
ER  - 
@article{
author = "Marković, Olivera S. and Pešić, Miloš P. and Shah, Ankita V. and Serajuddin, Abu T.M. and Verbić, Tatjana and Avdeef, Alex",
year = "2019",
abstract = "Although solubility-pH data for desipramine hydrochloride (DsHCl) have been reported previously, the aim of the present study was to critically examine the aqueous solubility-pH behavior of DsHCl in buffer-free and buffered solutions, in the presence of physiologically-relevant chloride concentration, using experimental practices recommended in the recently-published “white paper” (Avdeef et al., 2016). The computer program pDISOL-X was used to design the structured experiments (pH-RSF method), to process the data, and to refine the equilibrium constants. Low-to-high and high-to-low pH assays (using HCl, H 3 PO 4 , or NaOH to adjust pH) were performed on phosphate-buffered (0.12‑0.15 M) saturated solutions of DsHCl in the pH 1.3–11.6 range. After equilibration (stirring 6 h, followed by 18 h stir-free sedimentation), filtration or centrifugation was used for phase separation. Concentration was measured using HPLC with UV/VIS detection. The 2:1 drug-phosphate solubility product (K sp 2:1 = [DsH + ] 2 [HPO 4 2− ]) was determined from data in the pH 4–9 region. The free base of desipramine was prepared and used to determine the K sp 1:1 ([DsH + ][H 2 PO 4 − ]) in chloride-free acidified suspension. In addition, phosphate-free titrations were conducted to determine the intrinsic solubility, S 0 , and the 1:1 drug-chloride solubility product, K sp DsH [rad] Cl = [DsH + ][Cl − ]. Under the assay conditions, only the phosphate-free solutions showed some supersaturation near pH max 8.0. In phosphate-containing solutions, pH max was indicated at higher pH (8.8–9.6). Oils mixed with solids were observed to form in alkaline solutions (pH > 11). Notably, soluble drug-phosphate complexes appeared to form below pH 3.9 and above pH max in saturated phosphate‑containing saline solutions. This was indicated by the systematic pH shift to higher values in the log S-pH curve in alkaline solution than expected from the Henderson-Hasselbalch equation. For pH < 3.9, saturated phosphate-containing saline solutions exhibited elevated solubility, with drug-hydrochloride as the sole precipitate. Salt solubility products, intrinsic solubility, and complexation constants, which rationalized the data, were determined. Elemental, thermogravimetric (TGA), differential scanning calorimetric (DSC), and powder X-ray diffraction (PXRD) analyses were used to characterize the precipitates isolated from suspensions at different pH.",
publisher = "Elsevier",
journal = "European Journal of Pharmaceutical Sciences",
title = "Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates",
volume = "133",
pages = "264-274",
doi = "10.1016/j.ejps.2019.03.014"
}
Marković, O. S., Pešić, M. P., Shah, A. V., Serajuddin, A. T.M., Verbić, T.,& Avdeef, A.. (2019). Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates. in European Journal of Pharmaceutical Sciences
Elsevier., 133, 264-274.
https://doi.org/10.1016/j.ejps.2019.03.014
Marković OS, Pešić MP, Shah AV, Serajuddin AT, Verbić T, Avdeef A. Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates. in European Journal of Pharmaceutical Sciences. 2019;133:264-274.
doi:10.1016/j.ejps.2019.03.014 .
Marković, Olivera S., Pešić, Miloš P., Shah, Ankita V., Serajuddin, Abu T.M., Verbić, Tatjana, Avdeef, Alex, "Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates" in European Journal of Pharmaceutical Sciences, 133 (2019):264-274,
https://doi.org/10.1016/j.ejps.2019.03.014 . .
7
11
12

Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates

Marković, Olivera S.; Pešić, Miloš P.; Shah, Ankita V.; Serajuddin, Abu T.M.; Verbić, Tatjana; Avdeef, Alex

(Elsevier, 2019)

TY  - JOUR
AU  - Marković, Olivera S.
AU  - Pešić, Miloš P.
AU  - Shah, Ankita V.
AU  - Serajuddin, Abu T.M.
AU  - Verbić, Tatjana
AU  - Avdeef, Alex
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2925
AB  - Although solubility-pH data for desipramine hydrochloride (DsHCl) have been reported previously, the aim of the present study was to critically examine the aqueous solubility-pH behavior of DsHCl in buffer-free and buffered solutions, in the presence of physiologically-relevant chloride concentration, using experimental practices recommended in the recently-published “white paper” (Avdeef et al., 2016). The computer program pDISOL-X was used to design the structured experiments (pH-RSF method), to process the data, and to refine the equilibrium constants. Low-to-high and high-to-low pH assays (using HCl, H 3 PO 4 , or NaOH to adjust pH) were performed on phosphate-buffered (0.12‑0.15 M) saturated solutions of DsHCl in the pH 1.3–11.6 range. After equilibration (stirring 6 h, followed by 18 h stir-free sedimentation), filtration or centrifugation was used for phase separation. Concentration was measured using HPLC with UV/VIS detection. The 2:1 drug-phosphate solubility product (K sp 2:1 = [DsH + ] 2 [HPO 4 2− ]) was determined from data in the pH 4–9 region. The free base of desipramine was prepared and used to determine the K sp 1:1 ([DsH + ][H 2 PO 4 − ]) in chloride-free acidified suspension. In addition, phosphate-free titrations were conducted to determine the intrinsic solubility, S 0 , and the 1:1 drug-chloride solubility product, K sp DsH [rad] Cl = [DsH + ][Cl − ]. Under the assay conditions, only the phosphate-free solutions showed some supersaturation near pH max 8.0. In phosphate-containing solutions, pH max was indicated at higher pH (8.8–9.6). Oils mixed with solids were observed to form in alkaline solutions (pH > 11). Notably, soluble drug-phosphate complexes appeared to form below pH 3.9 and above pH max in saturated phosphate‑containing saline solutions. This was indicated by the systematic pH shift to higher values in the log S-pH curve in alkaline solution than expected from the Henderson-Hasselbalch equation. For pH < 3.9, saturated phosphate-containing saline solutions exhibited elevated solubility, with drug-hydrochloride as the sole precipitate. Salt solubility products, intrinsic solubility, and complexation constants, which rationalized the data, were determined. Elemental, thermogravimetric (TGA), differential scanning calorimetric (DSC), and powder X-ray diffraction (PXRD) analyses were used to characterize the precipitates isolated from suspensions at different pH.
PB  - Elsevier
T2  - European Journal of Pharmaceutical Sciences
T1  - Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates
VL  - 133
SP  - 264
EP  - 274
DO  - 10.1016/j.ejps.2019.03.014
ER  - 
@article{
author = "Marković, Olivera S. and Pešić, Miloš P. and Shah, Ankita V. and Serajuddin, Abu T.M. and Verbić, Tatjana and Avdeef, Alex",
year = "2019",
abstract = "Although solubility-pH data for desipramine hydrochloride (DsHCl) have been reported previously, the aim of the present study was to critically examine the aqueous solubility-pH behavior of DsHCl in buffer-free and buffered solutions, in the presence of physiologically-relevant chloride concentration, using experimental practices recommended in the recently-published “white paper” (Avdeef et al., 2016). The computer program pDISOL-X was used to design the structured experiments (pH-RSF method), to process the data, and to refine the equilibrium constants. Low-to-high and high-to-low pH assays (using HCl, H 3 PO 4 , or NaOH to adjust pH) were performed on phosphate-buffered (0.12‑0.15 M) saturated solutions of DsHCl in the pH 1.3–11.6 range. After equilibration (stirring 6 h, followed by 18 h stir-free sedimentation), filtration or centrifugation was used for phase separation. Concentration was measured using HPLC with UV/VIS detection. The 2:1 drug-phosphate solubility product (K sp 2:1 = [DsH + ] 2 [HPO 4 2− ]) was determined from data in the pH 4–9 region. The free base of desipramine was prepared and used to determine the K sp 1:1 ([DsH + ][H 2 PO 4 − ]) in chloride-free acidified suspension. In addition, phosphate-free titrations were conducted to determine the intrinsic solubility, S 0 , and the 1:1 drug-chloride solubility product, K sp DsH [rad] Cl = [DsH + ][Cl − ]. Under the assay conditions, only the phosphate-free solutions showed some supersaturation near pH max 8.0. In phosphate-containing solutions, pH max was indicated at higher pH (8.8–9.6). Oils mixed with solids were observed to form in alkaline solutions (pH > 11). Notably, soluble drug-phosphate complexes appeared to form below pH 3.9 and above pH max in saturated phosphate‑containing saline solutions. This was indicated by the systematic pH shift to higher values in the log S-pH curve in alkaline solution than expected from the Henderson-Hasselbalch equation. For pH < 3.9, saturated phosphate-containing saline solutions exhibited elevated solubility, with drug-hydrochloride as the sole precipitate. Salt solubility products, intrinsic solubility, and complexation constants, which rationalized the data, were determined. Elemental, thermogravimetric (TGA), differential scanning calorimetric (DSC), and powder X-ray diffraction (PXRD) analyses were used to characterize the precipitates isolated from suspensions at different pH.",
publisher = "Elsevier",
journal = "European Journal of Pharmaceutical Sciences",
title = "Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates",
volume = "133",
pages = "264-274",
doi = "10.1016/j.ejps.2019.03.014"
}
Marković, O. S., Pešić, M. P., Shah, A. V., Serajuddin, A. T.M., Verbić, T.,& Avdeef, A.. (2019). Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates. in European Journal of Pharmaceutical Sciences
Elsevier., 133, 264-274.
https://doi.org/10.1016/j.ejps.2019.03.014
Marković OS, Pešić MP, Shah AV, Serajuddin AT, Verbić T, Avdeef A. Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates. in European Journal of Pharmaceutical Sciences. 2019;133:264-274.
doi:10.1016/j.ejps.2019.03.014 .
Marković, Olivera S., Pešić, Miloš P., Shah, Ankita V., Serajuddin, Abu T.M., Verbić, Tatjana, Avdeef, Alex, "Solubility-pH profile of desipramine hydrochloride in saline phosphate buffer: Enhanced solubility due to drug-buffer aggregates" in European Journal of Pharmaceutical Sciences, 133 (2019):264-274,
https://doi.org/10.1016/j.ejps.2019.03.014 . .
7
11
12

Supplementary data for the article: Marković, O. S.; Pešić, M. P.; Shah, A. V.; Serajuddin, A. T. M.; Verbić, T. Ž.; Avdeef, A. Solubility-PH Profile of Desipramine Hydrochloride in Saline Phosphate Buffer: Enhanced Solubility Due to Drug-Buffer Aggregates. European Journal of Pharmaceutical Sciences 2019, 133, 264–274. https://doi.org/10.1016/j.ejps.2019.03.014

Marković, Olivera S.; Pešić, Miloš P.; Shah, Ankita V.; Serajuddin, Abu T.M.; Verbić, Tatjana; Avdeef, Alex

(Elsevier, 2019)

TY  - DATA
AU  - Marković, Olivera S.
AU  - Pešić, Miloš P.
AU  - Shah, Ankita V.
AU  - Serajuddin, Abu T.M.
AU  - Verbić, Tatjana
AU  - Avdeef, Alex
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2926
PB  - Elsevier
T2  - European Journal of Pharmaceutical Sciences
T1  - Supplementary data for the article: Marković, O. S.; Pešić, M. P.; Shah, A. V.; Serajuddin, A. T. M.; Verbić, T. Ž.; Avdeef, A. Solubility-PH Profile of Desipramine Hydrochloride in Saline Phosphate Buffer: Enhanced Solubility Due to Drug-Buffer Aggregates. European Journal of Pharmaceutical Sciences 2019, 133, 264–274. https://doi.org/10.1016/j.ejps.2019.03.014
DO  - 10.1016/j.ejps.2019.03.014
ER  - 
@misc{
author = "Marković, Olivera S. and Pešić, Miloš P. and Shah, Ankita V. and Serajuddin, Abu T.M. and Verbić, Tatjana and Avdeef, Alex",
year = "2019",
publisher = "Elsevier",
journal = "European Journal of Pharmaceutical Sciences",
title = "Supplementary data for the article: Marković, O. S.; Pešić, M. P.; Shah, A. V.; Serajuddin, A. T. M.; Verbić, T. Ž.; Avdeef, A. Solubility-PH Profile of Desipramine Hydrochloride in Saline Phosphate Buffer: Enhanced Solubility Due to Drug-Buffer Aggregates. European Journal of Pharmaceutical Sciences 2019, 133, 264–274. https://doi.org/10.1016/j.ejps.2019.03.014",
doi = "10.1016/j.ejps.2019.03.014"
}
Marković, O. S., Pešić, M. P., Shah, A. V., Serajuddin, A. T.M., Verbić, T.,& Avdeef, A.. (2019). Supplementary data for the article: Marković, O. S.; Pešić, M. P.; Shah, A. V.; Serajuddin, A. T. M.; Verbić, T. Ž.; Avdeef, A. Solubility-PH Profile of Desipramine Hydrochloride in Saline Phosphate Buffer: Enhanced Solubility Due to Drug-Buffer Aggregates. European Journal of Pharmaceutical Sciences 2019, 133, 264–274. https://doi.org/10.1016/j.ejps.2019.03.014. in European Journal of Pharmaceutical Sciences
Elsevier..
https://doi.org/10.1016/j.ejps.2019.03.014
Marković OS, Pešić MP, Shah AV, Serajuddin AT, Verbić T, Avdeef A. Supplementary data for the article: Marković, O. S.; Pešić, M. P.; Shah, A. V.; Serajuddin, A. T. M.; Verbić, T. Ž.; Avdeef, A. Solubility-PH Profile of Desipramine Hydrochloride in Saline Phosphate Buffer: Enhanced Solubility Due to Drug-Buffer Aggregates. European Journal of Pharmaceutical Sciences 2019, 133, 264–274. https://doi.org/10.1016/j.ejps.2019.03.014. in European Journal of Pharmaceutical Sciences. 2019;.
doi:10.1016/j.ejps.2019.03.014 .
Marković, Olivera S., Pešić, Miloš P., Shah, Ankita V., Serajuddin, Abu T.M., Verbić, Tatjana, Avdeef, Alex, "Supplementary data for the article: Marković, O. S.; Pešić, M. P.; Shah, A. V.; Serajuddin, A. T. M.; Verbić, T. Ž.; Avdeef, A. Solubility-PH Profile of Desipramine Hydrochloride in Saline Phosphate Buffer: Enhanced Solubility Due to Drug-Buffer Aggregates. European Journal of Pharmaceutical Sciences 2019, 133, 264–274. https://doi.org/10.1016/j.ejps.2019.03.014" in European Journal of Pharmaceutical Sciences (2019),
https://doi.org/10.1016/j.ejps.2019.03.014 . .
7
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12

Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action

Selaković, Života; Tran, J.P.; Kota, K.P.; Lazić, Marija; Retterer, C.; Besh, R.; Panchal, R.G.; Soloveva, V.; Sean, V.A.; Jay, W.B.; Pavić, A.; Verbić, Tatjana; Vasiljević, Branka; Kuehl, K.; Duplantier, A.J.; Bavari, S.; Mudhasani, R.; Šolaja, Bogdan A.

(Elsevier, 2019)

TY  - JOUR
AU  - Selaković, Života
AU  - Tran, J.P.
AU  - Kota, K.P.
AU  - Lazić, Marija
AU  - Retterer, C.
AU  - Besh, R.
AU  - Panchal, R.G.
AU  - Soloveva, V.
AU  - Sean, V.A.
AU  - Jay, W.B.
AU  - Pavić, A.
AU  - Verbić, Tatjana
AU  - Vasiljević, Branka
AU  - Kuehl, K.
AU  - Duplantier, A.J.
AU  - Bavari, S.
AU  - Mudhasani, R.
AU  - Šolaja, Bogdan A.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2966
AB  - Ebola virus (EBOV) causes a deadly hemorrhagic fever in humans and non-human primates. There is currently no FDA-approved vaccine or medication to counter this disease. Here, we report on the design, synthesis and anti-viral activities of two classes of compounds which show high potency against EBOV in both in vitro cell culture assays and in vivo mouse models Ebola viral disease. These compounds incorporate the structural features of cationic amphiphilic drugs (CAD), i.e they possess both a hydrophobic domain and a hydrophilic domain consisting of an ionizable amine functional group. These structural features enable easily diffusion into cells but once inside an acidic compartment their amine groups became protonated, ionized and remain trapped inside the acidic compartments such as late endosomes and lysosomes. These compounds, by virtue of their lysomotrophic functions, blocked EBOV entry. However, unlike other drugs containing a CAD moiety including chloroquine and amodiaquine, compounds reported in this study display faster kinetics of accumulation in the lysosomes, robust expansion of late endosome/lysosomes, relatively more potent suppression of lysosome fusion with other vesicular compartments and inhibition of cathepsins activities, all of which play a vital role in anti-EBOV activity. Furthermore, the diazachrysene 2 (ZSML08) that showed most potent activity against EBOV in in vitro cell culture assays also showed significant survival benefit with 100% protection in mouse models of Ebola virus disease, at a low dose of 10 mg/kg/day. Lastly, toxicity studies in vivo using zebrafish models suggest no developmental defects or toxicity associated with these compounds. Overall, these studies describe two new pharmacophores that by virtue of being potent lysosomotrophs, display potent anti-EBOV activities both in vitro and in vivo animal models of EBOV disease. © 2018 Elsevier Masson SAS
PB  - Elsevier
T2  - European Journal of Medicinal Chemistry
T1  - Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action
VL  - 162
SP  - 32
EP  - 50
DO  - 10.1016/j.ejmech.2018.10.061
UR  - Kon_1331
ER  - 
@article{
author = "Selaković, Života and Tran, J.P. and Kota, K.P. and Lazić, Marija and Retterer, C. and Besh, R. and Panchal, R.G. and Soloveva, V. and Sean, V.A. and Jay, W.B. and Pavić, A. and Verbić, Tatjana and Vasiljević, Branka and Kuehl, K. and Duplantier, A.J. and Bavari, S. and Mudhasani, R. and Šolaja, Bogdan A.",
year = "2019",
abstract = "Ebola virus (EBOV) causes a deadly hemorrhagic fever in humans and non-human primates. There is currently no FDA-approved vaccine or medication to counter this disease. Here, we report on the design, synthesis and anti-viral activities of two classes of compounds which show high potency against EBOV in both in vitro cell culture assays and in vivo mouse models Ebola viral disease. These compounds incorporate the structural features of cationic amphiphilic drugs (CAD), i.e they possess both a hydrophobic domain and a hydrophilic domain consisting of an ionizable amine functional group. These structural features enable easily diffusion into cells but once inside an acidic compartment their amine groups became protonated, ionized and remain trapped inside the acidic compartments such as late endosomes and lysosomes. These compounds, by virtue of their lysomotrophic functions, blocked EBOV entry. However, unlike other drugs containing a CAD moiety including chloroquine and amodiaquine, compounds reported in this study display faster kinetics of accumulation in the lysosomes, robust expansion of late endosome/lysosomes, relatively more potent suppression of lysosome fusion with other vesicular compartments and inhibition of cathepsins activities, all of which play a vital role in anti-EBOV activity. Furthermore, the diazachrysene 2 (ZSML08) that showed most potent activity against EBOV in in vitro cell culture assays also showed significant survival benefit with 100% protection in mouse models of Ebola virus disease, at a low dose of 10 mg/kg/day. Lastly, toxicity studies in vivo using zebrafish models suggest no developmental defects or toxicity associated with these compounds. Overall, these studies describe two new pharmacophores that by virtue of being potent lysosomotrophs, display potent anti-EBOV activities both in vitro and in vivo animal models of EBOV disease. © 2018 Elsevier Masson SAS",
publisher = "Elsevier",
journal = "European Journal of Medicinal Chemistry",
title = "Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action",
volume = "162",
pages = "32-50",
doi = "10.1016/j.ejmech.2018.10.061",
url = "Kon_1331"
}
Selaković, Ž., Tran, J.P., Kota, K.P., Lazić, M., Retterer, C., Besh, R., Panchal, R.G., Soloveva, V., Sean, V.A., Jay, W.B., Pavić, A., Verbić, T., Vasiljević, B., Kuehl, K., Duplantier, A.J., Bavari, S., Mudhasani, R.,& Šolaja, B. A.. (2019). Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action. in European Journal of Medicinal Chemistry
Elsevier., 162, 32-50.
https://doi.org/10.1016/j.ejmech.2018.10.061
Kon_1331
Selaković Ž, Tran J, Kota K, Lazić M, Retterer C, Besh R, Panchal R, Soloveva V, Sean V, Jay W, Pavić A, Verbić T, Vasiljević B, Kuehl K, Duplantier A, Bavari S, Mudhasani R, Šolaja BA. Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action. in European Journal of Medicinal Chemistry. 2019;162:32-50.
doi:10.1016/j.ejmech.2018.10.061
Kon_1331 .
Selaković, Života, Tran, J.P., Kota, K.P., Lazić, Marija, Retterer, C., Besh, R., Panchal, R.G., Soloveva, V., Sean, V.A., Jay, W.B., Pavić, A., Verbić, Tatjana, Vasiljević, Branka, Kuehl, K., Duplantier, A.J., Bavari, S., Mudhasani, R., Šolaja, Bogdan A., "Second generation of diazachrysenes: Protection of Ebola virus infected mice and mechanism of action" in European Journal of Medicinal Chemistry, 162 (2019):32-50,
https://doi.org/10.1016/j.ejmech.2018.10.061 .,
Kon_1331 .
3
9
8
9

Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061

Selaković, Života; Tran, J.P.; Kota, K.P.; Lazić, Marija; Retterer, C.; Besh, R.; Panchal, R.G.; Soloveva, V.; Sean, V.A.; Jay, W.B.; Pavić, A.; Verbić, Tatjana; Vasiljević, Branka; Kuehl, K.; Duplantier, A.J.; Bavari, S.; Mudhasani, R.; Šolaja, Bogdan A.

(2019)

TY  - DATA
AU  - Selaković, Života
AU  - Tran, J.P.
AU  - Kota, K.P.
AU  - Lazić, Marija
AU  - Retterer, C.
AU  - Besh, R.
AU  - Panchal, R.G.
AU  - Soloveva, V.
AU  - Sean, V.A.
AU  - Jay, W.B.
AU  - Pavić, A.
AU  - Verbić, Tatjana
AU  - Vasiljević, Branka
AU  - Kuehl, K.
AU  - Duplantier, A.J.
AU  - Bavari, S.
AU  - Mudhasani, R.
AU  - Šolaja, Bogdan A.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2967
T2  - European Journal of Medicinal Chemistry
T1  - Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061
ER  - 
@misc{
author = "Selaković, Života and Tran, J.P. and Kota, K.P. and Lazić, Marija and Retterer, C. and Besh, R. and Panchal, R.G. and Soloveva, V. and Sean, V.A. and Jay, W.B. and Pavić, A. and Verbić, Tatjana and Vasiljević, Branka and Kuehl, K. and Duplantier, A.J. and Bavari, S. and Mudhasani, R. and Šolaja, Bogdan A.",
year = "2019",
journal = "European Journal of Medicinal Chemistry",
title = "Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061"
}
Selaković, Ž., Tran, J.P., Kota, K.P., Lazić, M., Retterer, C., Besh, R., Panchal, R.G., Soloveva, V., Sean, V.A., Jay, W.B., Pavić, A., Verbić, T., Vasiljević, B., Kuehl, K., Duplantier, A.J., Bavari, S., Mudhasani, R.,& Šolaja, B. A.. (2019). Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061. in European Journal of Medicinal Chemistry.
Selaković Ž, Tran J, Kota K, Lazić M, Retterer C, Besh R, Panchal R, Soloveva V, Sean V, Jay W, Pavić A, Verbić T, Vasiljević B, Kuehl K, Duplantier A, Bavari S, Mudhasani R, Šolaja BA. Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061. in European Journal of Medicinal Chemistry. 2019;..
Selaković, Života, Tran, J.P., Kota, K.P., Lazić, Marija, Retterer, C., Besh, R., Panchal, R.G., Soloveva, V., Sean, V.A., Jay, W.B., Pavić, A., Verbić, Tatjana, Vasiljević, Branka, Kuehl, K., Duplantier, A.J., Bavari, S., Mudhasani, R., Šolaja, Bogdan A., "Supplementary data for article: Selaković, Ž.; Tran, J. P.; Kota, K. P.; Lazić, M.; Retterer, C.; Besh, R.; Panchal, R. G.; Soloveva, V.; Sean, V. A.; Jay, W. B.; et al. Second Generation of Diazachrysenes: Protection of Ebola Virus Infected Mice and Mechanism of Action. European Journal of Medicinal Chemistry 2019, 162, 32–50. https://doi.org/10.1016/j.ejmech.2018.10.061" in European Journal of Medicinal Chemistry (2019).

Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity

Božinović, Nina S.; Ajdačić, Vladimir; Lazić, Jelena O.; Lecerf, Maxime; Daventure, Victoria; Nikodinović-Runić, Jasmina; Opsenica, Igor; Dimitrov, Jordan D.

(American Chemical Society, 2019)

TY  - JOUR
AU  - Božinović, Nina S.
AU  - Ajdačić, Vladimir
AU  - Lazić, Jelena O.
AU  - Lecerf, Maxime
AU  - Daventure, Victoria
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
AU  - Dimitrov, Jordan D.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3793
AB  - In a healthy immune repertoire, there exists a fraction of polyreactive antibodies that can bind to a variety of unrelated self- and foreign antigens. Apart from naturally polyreactive antibodies, in every healthy individual, there is a fraction of antibody that can gain polyreactivity upon exposure to porphyrin cofactor heme. Molecular mechanisms and biological significance of the appearance of cryptic polyreactivity are not well understood. It is believed that heme acts as an interfacial cofactor between the antibody and the newly recognized antigens. To further test this claim and gain insight into the types of interactions involved in heme binding, we herein investigated the influence of a group of aromatic guanylhydrazone molecules on the heme-induced antibody polyreactivity. From the analysis of SAR and the results of UV-vis absorbance spectroscopy, it was concluded that the most probable mechanism by which the studied molecules inhibit heme-mediated polyreactivity of the antibody is the direct binding to heme, thus preventing heme from binding to antibody and/or antigen. The inhibitory capacity of the most potent compounds was substantially higher than that of chloroquine, a well-known heme binder. Some of the guanylhydrazone molecules were able to induce polyreactivity of the studied antibody themselves, possibly by a mechanism similar to heme. Results described here point to the conclusion that heme indeed must bind to an antibody to induce its polyreactivity, and that both π-stacking interactions and iron coordination contribute to the binding affinity, while certain structures, such as guanylhydrazones, can interfere with these processes.
PB  - American Chemical Society
T2  - ACS Omega
T1  - Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity
VL  - 4
IS  - 24
SP  - 20450
EP  - 20458
DO  - 10.1021/acsomega.9b01548
ER  - 
@article{
author = "Božinović, Nina S. and Ajdačić, Vladimir and Lazić, Jelena O. and Lecerf, Maxime and Daventure, Victoria and Nikodinović-Runić, Jasmina and Opsenica, Igor and Dimitrov, Jordan D.",
year = "2019",
abstract = "In a healthy immune repertoire, there exists a fraction of polyreactive antibodies that can bind to a variety of unrelated self- and foreign antigens. Apart from naturally polyreactive antibodies, in every healthy individual, there is a fraction of antibody that can gain polyreactivity upon exposure to porphyrin cofactor heme. Molecular mechanisms and biological significance of the appearance of cryptic polyreactivity are not well understood. It is believed that heme acts as an interfacial cofactor between the antibody and the newly recognized antigens. To further test this claim and gain insight into the types of interactions involved in heme binding, we herein investigated the influence of a group of aromatic guanylhydrazone molecules on the heme-induced antibody polyreactivity. From the analysis of SAR and the results of UV-vis absorbance spectroscopy, it was concluded that the most probable mechanism by which the studied molecules inhibit heme-mediated polyreactivity of the antibody is the direct binding to heme, thus preventing heme from binding to antibody and/or antigen. The inhibitory capacity of the most potent compounds was substantially higher than that of chloroquine, a well-known heme binder. Some of the guanylhydrazone molecules were able to induce polyreactivity of the studied antibody themselves, possibly by a mechanism similar to heme. Results described here point to the conclusion that heme indeed must bind to an antibody to induce its polyreactivity, and that both π-stacking interactions and iron coordination contribute to the binding affinity, while certain structures, such as guanylhydrazones, can interfere with these processes.",
publisher = "American Chemical Society",
journal = "ACS Omega",
title = "Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity",
volume = "4",
number = "24",
pages = "20450-20458",
doi = "10.1021/acsomega.9b01548"
}
Božinović, N. S., Ajdačić, V., Lazić, J. O., Lecerf, M., Daventure, V., Nikodinović-Runić, J., Opsenica, I.,& Dimitrov, J. D.. (2019). Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. in ACS Omega
American Chemical Society., 4(24), 20450-20458.
https://doi.org/10.1021/acsomega.9b01548
Božinović NS, Ajdačić V, Lazić JO, Lecerf M, Daventure V, Nikodinović-Runić J, Opsenica I, Dimitrov JD. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. in ACS Omega. 2019;4(24):20450-20458.
doi:10.1021/acsomega.9b01548 .
Božinović, Nina S., Ajdačić, Vladimir, Lazić, Jelena O., Lecerf, Maxime, Daventure, Victoria, Nikodinović-Runić, Jasmina, Opsenica, Igor, Dimitrov, Jordan D., "Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity" in ACS Omega, 4, no. 24 (2019):20450-20458,
https://doi.org/10.1021/acsomega.9b01548 . .
1
1
1
1

Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548

Božinović, Nina S.; Ajdačić, Vladimir; Lazić, Jelena O.; Lecerf, Maxime; Daventure, Victoria; Nikodinović-Runić, Jasmina; Opsenica, Igor; Dimitrov, Jordan D.

(American Chemical Society, 2019)

TY  - DATA
AU  - Božinović, Nina S.
AU  - Ajdačić, Vladimir
AU  - Lazić, Jelena O.
AU  - Lecerf, Maxime
AU  - Daventure, Victoria
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
AU  - Dimitrov, Jordan D.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3794
PB  - American Chemical Society
T2  - ACS Omega
T1  - Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548
ER  - 
@misc{
author = "Božinović, Nina S. and Ajdačić, Vladimir and Lazić, Jelena O. and Lecerf, Maxime and Daventure, Victoria and Nikodinović-Runić, Jasmina and Opsenica, Igor and Dimitrov, Jordan D.",
year = "2019",
publisher = "American Chemical Society",
journal = "ACS Omega",
title = "Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548"
}
Božinović, N. S., Ajdačić, V., Lazić, J. O., Lecerf, M., Daventure, V., Nikodinović-Runić, J., Opsenica, I.,& Dimitrov, J. D.. (2019). Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548. in ACS Omega
American Chemical Society..
Božinović NS, Ajdačić V, Lazić JO, Lecerf M, Daventure V, Nikodinović-Runić J, Opsenica I, Dimitrov JD. Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548. in ACS Omega. 2019;..
Božinović, Nina S., Ajdačić, Vladimir, Lazić, Jelena O., Lecerf, Maxime, Daventure, Victoria, Nikodinović-Runić, Jasmina, Opsenica, Igor, Dimitrov, Jordan D., "Supplementary data for article: Božinović, N.; Ajdačić, V.; Lazic, J.; Lecerf, M.; Daventure, V.; Nikodinovic-Runic, J.; Opsenica, I. M.; Dimitrov, J. D. Aromatic Guanylhydrazones for the Control of Heme-Induced Antibody Polyreactivity. ACS Omega 2019, 4 (24), 20450–20458. https://doi.org/10.1021/acsomega.9b01548" in ACS Omega (2019).