Jakovljević, Katarina

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  • Jakovljević, Katarina (8)

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Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies

Jakovljević, Katarina; Joksović, Milan D.; Botta, Bruno; Jovanović, Ljiljana S.; Avdović, Edina; Marković, Zoran; Mihailović, Vladimir; Andrić, Marijana; Trifunović, Snežana S.; Marković, Violeta

(Elsevier, 2019)

TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksović, Milan D.
AU  - Botta, Bruno
AU  - Jovanović, Ljiljana S.
AU  - Avdović, Edina
AU  - Marković, Zoran
AU  - Mihailović, Vladimir
AU  - Andrić, Marijana
AU  - Trifunović, Snežana S.
AU  - Marković, Violeta
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3738
AB  - A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole amide derivative 3a were prepared to compare the effects of the structural changes on the radical-scavenging activity. The obtained compounds were examined for their antioxidative potential by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. In addition, selected compounds were studied by density functional theory (DFT) and cyclic voltammetry experiments. The tested compounds showed high potential to scavenging DPPH radical and ABTS radical cation compared with the referent antioxidants ascorbic acid and nordihydroguaiaretic acid (NDGA). On the basis of the calculated thermodynamic parameters, it can be concluded that the sequential proton loss electron transfer (SPLET) mechanism represents the most probable reaction path in a polar solvent for DPPH radical–scavenging activity. On the other hand, the single electron transfer followed by proton transfer (SET-PT) can be a likely mechanistic pathway in the case of an ABTS radical cation.
PB  - Elsevier
T2  - Comptes Rendus Chimie
T1  - Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies
VL  - 22
IS  - 8
SP  - 585
EP  - 598
DO  - 10.1016/j.crci.2019.06.001
ER  - 
@article{
author = "Jakovljević, Katarina and Joksović, Milan D. and Botta, Bruno and Jovanović, Ljiljana S. and Avdović, Edina and Marković, Zoran and Mihailović, Vladimir and Andrić, Marijana and Trifunović, Snežana S. and Marković, Violeta",
year = "2019",
abstract = "A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole amide derivative 3a were prepared to compare the effects of the structural changes on the radical-scavenging activity. The obtained compounds were examined for their antioxidative potential by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. In addition, selected compounds were studied by density functional theory (DFT) and cyclic voltammetry experiments. The tested compounds showed high potential to scavenging DPPH radical and ABTS radical cation compared with the referent antioxidants ascorbic acid and nordihydroguaiaretic acid (NDGA). On the basis of the calculated thermodynamic parameters, it can be concluded that the sequential proton loss electron transfer (SPLET) mechanism represents the most probable reaction path in a polar solvent for DPPH radical–scavenging activity. On the other hand, the single electron transfer followed by proton transfer (SET-PT) can be a likely mechanistic pathway in the case of an ABTS radical cation.",
publisher = "Elsevier",
journal = "Comptes Rendus Chimie",
title = "Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies",
volume = "22",
number = "8",
pages = "585-598",
doi = "10.1016/j.crci.2019.06.001"
}
Jakovljević, K., Joksović, M. D., Botta, B., Jovanović, L. S., Avdović, E., Marković, Z., Mihailović, V., Andrić, M., Trifunović, S. S.,& Marković, V.. (2019). Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies. in Comptes Rendus Chimie
Elsevier., 22(8), 585-598.
https://doi.org/10.1016/j.crci.2019.06.001
Jakovljević K, Joksović MD, Botta B, Jovanović LS, Avdović E, Marković Z, Mihailović V, Andrić M, Trifunović SS, Marković V. Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies. in Comptes Rendus Chimie. 2019;22(8):585-598.
doi:10.1016/j.crci.2019.06.001 .
Jakovljević, Katarina, Joksović, Milan D., Botta, Bruno, Jovanović, Ljiljana S., Avdović, Edina, Marković, Zoran, Mihailović, Vladimir, Andrić, Marijana, Trifunović, Snežana S., Marković, Violeta, "Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis, antioxidant activity, and computational and electrochemical studies" in Comptes Rendus Chimie, 22, no. 8 (2019):585-598,
https://doi.org/10.1016/j.crci.2019.06.001 . .
4
4
5

Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001

Jakovljević, Katarina; Joksović, Milan D.; Botta, Bruno; Jovanović, Ljiljana S.; Avdović, Edina; Marković, Zoran; Mihailović, Vladimir; Andrić, Marijana; Trifunović, Snežana S.; Marković, Violeta

(Elsevier, 2019)

TY  - DATA
AU  - Jakovljević, Katarina
AU  - Joksović, Milan D.
AU  - Botta, Bruno
AU  - Jovanović, Ljiljana S.
AU  - Avdović, Edina
AU  - Marković, Zoran
AU  - Mihailović, Vladimir
AU  - Andrić, Marijana
AU  - Trifunović, Snežana S.
AU  - Marković, Violeta
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3739
PB  - Elsevier
T2  - Comptes Rendus Chimie
T1  - Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001
ER  - 
@misc{
author = "Jakovljević, Katarina and Joksović, Milan D. and Botta, Bruno and Jovanović, Ljiljana S. and Avdović, Edina and Marković, Zoran and Mihailović, Vladimir and Andrić, Marijana and Trifunović, Snežana S. and Marković, Violeta",
year = "2019",
publisher = "Elsevier",
journal = "Comptes Rendus Chimie",
title = "Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001"
}
Jakovljević, K., Joksović, M. D., Botta, B., Jovanović, L. S., Avdović, E., Marković, Z., Mihailović, V., Andrić, M., Trifunović, S. S.,& Marković, V.. (2019). Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001. in Comptes Rendus Chimie
Elsevier..
Jakovljević K, Joksović MD, Botta B, Jovanović LS, Avdović E, Marković Z, Mihailović V, Andrić M, Trifunović SS, Marković V. Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001. in Comptes Rendus Chimie. 2019;..
Jakovljević, Katarina, Joksović, Milan D., Botta, Bruno, Jovanović, Ljiljana S., Avdović, Edina, Marković, Zoran, Mihailović, Vladimir, Andrić, Marijana, Trifunović, Snežana S., Marković, Violeta, "Supplementary data for the article: Jakovljević, K.; Joksović, M. D.; Botta, B.; Jovanović, L. S.; Avdović, E.; Marković, Z.; Mihailović, V.; Andrić, M.; Trifunović, S.; Marković, V. Novel 1,3,4-Thiadiazole Conjugates Derived from Protocatechuic Acid: Synthesis, Antioxidant Activity, and Computational and Electrochemical Studies. Comptes Rendus Chimie 2019, 22 (8), 585–598. https://doi.org/10.1016/j.crci.2019.06.001" in Comptes Rendus Chimie (2019).

Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies

Jakovljević, Katarina; Joksović, Milan D.; Matić, Ivana Z.; Petrović, Nina; Stanojković, Tatjana; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksović, Ljubinka; Trifunović, Snežana S.; Marković, Violeta

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksović, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrović, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksović, Ljubinka
AU  - Trifunović, Snežana S.
AU  - Marković, Violeta
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2892
AB  - Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.
PB  - Royal Soc Chemistry, Cambridge
T2  - MedChemComm
T1  - Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies
VL  - 9
IS  - 10
SP  - 1679
EP  - 1697
DO  - 10.1039/c8md00316e
ER  - 
@article{
author = "Jakovljević, Katarina and Joksović, Milan D. and Matić, Ivana Z. and Petrović, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksović, Ljubinka and Trifunović, Snežana S. and Marković, Violeta",
year = "2018",
abstract = "Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "MedChemComm",
title = "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies",
volume = "9",
number = "10",
pages = "1679-1697",
doi = "10.1039/c8md00316e"
}
Jakovljević, K., Joksović, M. D., Matić, I. Z., Petrović, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksović, L., Trifunović, S. S.,& Marković, V.. (2018). Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in MedChemComm
Royal Soc Chemistry, Cambridge., 9(10), 1679-1697.
https://doi.org/10.1039/c8md00316e
Jakovljević K, Joksović MD, Matić IZ, Petrović N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksović L, Trifunović SS, Marković V. Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in MedChemComm. 2018;9(10):1679-1697.
doi:10.1039/c8md00316e .
Jakovljević, Katarina, Joksović, Milan D., Matić, Ivana Z., Petrović, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksović, Ljubinka, Trifunović, Snežana S., Marković, Violeta, "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies" in MedChemComm, 9, no. 10 (2018):1679-1697,
https://doi.org/10.1039/c8md00316e . .
4
10
11
11

Supplementary material for the article: Jakovljević, K.; Joksović, M. D.; Matić, I. Z.; Petrović, N.; Stanojković, T.; Sladić, D.; Vujčić, M.; Janović, B.; Joksović, L.; Trifunović, S.; et al. Novel 1,3,4-Thiadiazole-Chalcone Hybrids Containing Catechol Moiety: Synthesis, Antioxidant Activity, Cytotoxicity and DNA Interaction Studies. MedChemComm 2018, 9 (10), 1679–1697. https://doi.org/10.1039/c8md00316e

Jakovljević, Katarina; Joksović, Milan D.; Matić, Ivana Z.; Petrović, Nina; Stanojković, Tatjana; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksović, Ljubinka; Trifunović, Snežana S.; Marković, Violeta

(Royal Soc Chemistry, Cambridge, 2018)

TY  - DATA
AU  - Jakovljević, Katarina
AU  - Joksović, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrović, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksović, Ljubinka
AU  - Trifunović, Snežana S.
AU  - Marković, Violeta
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3051
PB  - Royal Soc Chemistry, Cambridge
T2  - MedChemComm
T1  - Supplementary material for the article: Jakovljević, K.; Joksović, M. D.; Matić, I. Z.; Petrović, N.; Stanojković, T.; Sladić, D.;  Vujčić, M.; Janović, B.; Joksović, L.; Trifunović, S.; et al. Novel 1,3,4-Thiadiazole-Chalcone  Hybrids Containing Catechol Moiety: Synthesis, Antioxidant Activity, Cytotoxicity and  DNA Interaction Studies. MedChemComm 2018, 9 (10), 1679–1697.  https://doi.org/10.1039/c8md00316e
UR  - Kon_3420
ER  - 
@misc{
author = "Jakovljević, Katarina and Joksović, Milan D. and Matić, Ivana Z. and Petrović, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksović, Ljubinka and Trifunović, Snežana S. and Marković, Violeta",
year = "2018",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "MedChemComm",
title = "Supplementary material for the article: Jakovljević, K.; Joksović, M. D.; Matić, I. Z.; Petrović, N.; Stanojković, T.; Sladić, D.;  Vujčić, M.; Janović, B.; Joksović, L.; Trifunović, S.; et al. Novel 1,3,4-Thiadiazole-Chalcone  Hybrids Containing Catechol Moiety: Synthesis, Antioxidant Activity, Cytotoxicity and  DNA Interaction Studies. MedChemComm 2018, 9 (10), 1679–1697.  https://doi.org/10.1039/c8md00316e",
url = "Kon_3420"
}
Jakovljević, K., Joksović, M. D., Matić, I. Z., Petrović, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksović, L., Trifunović, S. S.,& Marković, V.. (2018). Supplementary material for the article: Jakovljević, K.; Joksović, M. D.; Matić, I. Z.; Petrović, N.; Stanojković, T.; Sladić, D.;  Vujčić, M.; Janović, B.; Joksović, L.; Trifunović, S.; et al. Novel 1,3,4-Thiadiazole-Chalcone  Hybrids Containing Catechol Moiety: Synthesis, Antioxidant Activity, Cytotoxicity and  DNA Interaction Studies. MedChemComm 2018, 9 (10), 1679–1697.  https://doi.org/10.1039/c8md00316e. in MedChemComm
Royal Soc Chemistry, Cambridge..
Kon_3420
Jakovljević K, Joksović MD, Matić IZ, Petrović N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksović L, Trifunović SS, Marković V. Supplementary material for the article: Jakovljević, K.; Joksović, M. D.; Matić, I. Z.; Petrović, N.; Stanojković, T.; Sladić, D.;  Vujčić, M.; Janović, B.; Joksović, L.; Trifunović, S.; et al. Novel 1,3,4-Thiadiazole-Chalcone  Hybrids Containing Catechol Moiety: Synthesis, Antioxidant Activity, Cytotoxicity and  DNA Interaction Studies. MedChemComm 2018, 9 (10), 1679–1697.  https://doi.org/10.1039/c8md00316e. in MedChemComm. 2018;.
Kon_3420 .
Jakovljević, Katarina, Joksović, Milan D., Matić, Ivana Z., Petrović, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksović, Ljubinka, Trifunović, Snežana S., Marković, Violeta, "Supplementary material for the article: Jakovljević, K.; Joksović, M. D.; Matić, I. Z.; Petrović, N.; Stanojković, T.; Sladić, D.;  Vujčić, M.; Janović, B.; Joksović, L.; Trifunović, S.; et al. Novel 1,3,4-Thiadiazole-Chalcone  Hybrids Containing Catechol Moiety: Synthesis, Antioxidant Activity, Cytotoxicity and  DNA Interaction Studies. MedChemComm 2018, 9 (10), 1679–1697.  https://doi.org/10.1039/c8md00316e" in MedChemComm (2018),
Kon_3420 .

Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies

Jakovljević, Katarina; Joksović, Milan D.; Matić, Ivana Z.; Petrović, Nina; Stanojković, Tatjana; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksović, Ljubinka; Trifunović, Snežana S.; Marković, Violeta

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksović, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrović, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksović, Ljubinka
AU  - Trifunović, Snežana S.
AU  - Marković, Violeta
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2089
AB  - Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.
PB  - Royal Soc Chemistry, Cambridge
T2  - MedChemComm
T1  - Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies
VL  - 9
IS  - 10
SP  - 1679
EP  - 1697
DO  - 10.1039/c8md00316e
UR  - Kon_3420
ER  - 
@article{
author = "Jakovljević, Katarina and Joksović, Milan D. and Matić, Ivana Z. and Petrović, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksović, Ljubinka and Trifunović, Snežana S. and Marković, Violeta",
year = "2018",
abstract = "Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "MedChemComm",
title = "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies",
volume = "9",
number = "10",
pages = "1679-1697",
doi = "10.1039/c8md00316e",
url = "Kon_3420"
}
Jakovljević, K., Joksović, M. D., Matić, I. Z., Petrović, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksović, L., Trifunović, S. S.,& Marković, V.. (2018). Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in MedChemComm
Royal Soc Chemistry, Cambridge., 9(10), 1679-1697.
https://doi.org/10.1039/c8md00316e
Kon_3420
Jakovljević K, Joksović MD, Matić IZ, Petrović N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksović L, Trifunović SS, Marković V. Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in MedChemComm. 2018;9(10):1679-1697.
doi:10.1039/c8md00316e
Kon_3420 .
Jakovljević, Katarina, Joksović, Milan D., Matić, Ivana Z., Petrović, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksović, Ljubinka, Trifunović, Snežana S., Marković, Violeta, "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies" in MedChemComm, 9, no. 10 (2018):1679-1697,
https://doi.org/10.1039/c8md00316e .,
Kon_3420 .
4
10
11
11

Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies

Milošev, Milorad Z.; Jakovljević, Katarina; Joksović, Milan D.; Stanojković, Tatjana; Matić, Ivana Z.; Perović, Milka; Tešić, Vesna; Kanazir, Selma; Mladenović, Milan; Rodić, Marko; Leovac, Vukadin M.; Trifunović, Snežana S.; Marković, Violeta

(Wiley, Hoboken, 2017)

TY  - JOUR
AU  - Milošev, Milorad Z.
AU  - Jakovljević, Katarina
AU  - Joksović, Milan D.
AU  - Stanojković, Tatjana
AU  - Matić, Ivana Z.
AU  - Perović, Milka
AU  - Tešić, Vesna
AU  - Kanazir, Selma
AU  - Mladenović, Milan
AU  - Rodić, Marko
AU  - Leovac, Vukadin M.
AU  - Trifunović, Snežana S.
AU  - Marković, Violeta
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3221
AB  - A series of 18 novel N-Mannich bases derived from 5-adamantyl-1,2,4-triazole-3-th ione was synthesized and characterized using NMR spectroscopy and X-ray diffraction technique. All derivatives were evaluated for their anticancer potential against four human cancer cell lines. Several tested compounds exerted good cytotoxic activities on K562 and HL-60 cell lines, along with pronounced selectivity, showing lower cytotoxicity against normal fibroblasts MRC-5 compared to cancer cells. The effects of compounds 5b,5e, and 5j on the cell cycle were investigated by flow cytometric analysis. It was found that these compounds cause the accumulation of cells in the subG1 and G1 phases of the cell cycle and induce caspase-dependent apoptosis, while the anti-angiogenic effects of 5b, 5e, and 5j have been confirmed in EA. hy926 cells using a tube formation assay. Further, the interaction of Bax protein with compound 5b was investigated by means of molecular modeling, applying the combined molecular docking/molecular dynamics approach.
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies
VL  - 89
IS  - 6
SP  - 943
EP  - 952
DO  - 10.1111/cbdd.12920
ER  - 
@article{
author = "Milošev, Milorad Z. and Jakovljević, Katarina and Joksović, Milan D. and Stanojković, Tatjana and Matić, Ivana Z. and Perović, Milka and Tešić, Vesna and Kanazir, Selma and Mladenović, Milan and Rodić, Marko and Leovac, Vukadin M. and Trifunović, Snežana S. and Marković, Violeta",
year = "2017",
abstract = "A series of 18 novel N-Mannich bases derived from 5-adamantyl-1,2,4-triazole-3-th ione was synthesized and characterized using NMR spectroscopy and X-ray diffraction technique. All derivatives were evaluated for their anticancer potential against four human cancer cell lines. Several tested compounds exerted good cytotoxic activities on K562 and HL-60 cell lines, along with pronounced selectivity, showing lower cytotoxicity against normal fibroblasts MRC-5 compared to cancer cells. The effects of compounds 5b,5e, and 5j on the cell cycle were investigated by flow cytometric analysis. It was found that these compounds cause the accumulation of cells in the subG1 and G1 phases of the cell cycle and induce caspase-dependent apoptosis, while the anti-angiogenic effects of 5b, 5e, and 5j have been confirmed in EA. hy926 cells using a tube formation assay. Further, the interaction of Bax protein with compound 5b was investigated by means of molecular modeling, applying the combined molecular docking/molecular dynamics approach.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies",
volume = "89",
number = "6",
pages = "943-952",
doi = "10.1111/cbdd.12920"
}
Milošev, M. Z., Jakovljević, K., Joksović, M. D., Stanojković, T., Matić, I. Z., Perović, M., Tešić, V., Kanazir, S., Mladenović, M., Rodić, M., Leovac, V. M., Trifunović, S. S.,& Marković, V.. (2017). Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies. in Chemical Biology and Drug Design
Wiley, Hoboken., 89(6), 943-952.
https://doi.org/10.1111/cbdd.12920
Milošev MZ, Jakovljević K, Joksović MD, Stanojković T, Matić IZ, Perović M, Tešić V, Kanazir S, Mladenović M, Rodić M, Leovac VM, Trifunović SS, Marković V. Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies. in Chemical Biology and Drug Design. 2017;89(6):943-952.
doi:10.1111/cbdd.12920 .
Milošev, Milorad Z., Jakovljević, Katarina, Joksović, Milan D., Stanojković, Tatjana, Matić, Ivana Z., Perović, Milka, Tešić, Vesna, Kanazir, Selma, Mladenović, Milan, Rodić, Marko, Leovac, Vukadin M., Trifunović, Snežana S., Marković, Violeta, "Mannich bases of 1,2,4-triazole-3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies" in Chemical Biology and Drug Design, 89, no. 6 (2017):943-952,
https://doi.org/10.1111/cbdd.12920 . .
8
8
9

Supplementary material for the article: Milošev, M. Z.; Jakovljević, K.; Joksović, M. D.; Stanojković, T.; Matić, I. Z.; Perović, M.; Tešić, V.; Kanazir, S.; Mladenović, M.; Rodić, M. V.; et al. Mannich Bases of 1,2,4-Triazole3-Thione Containing Adamantane Moiety: Synthesis, Preliminary Anticancer Evaluation, and Molecular Modeling Studies. Chemical Biology and Drug Design 2017, 89 (6), 943–952. https://doi.org/10.1111/cbdd.12920

Milošev, Milorad Z.; Jakovljević, Katarina; Joksović, Milan D.; Stanojković, Tatjana; Matić, Ivana Z.; Perović, Milka; Tešić, Vesna; Kanazir, Selma; Mladenović, Milan; Rodić, Marko; Leovac, Vukadin M.; Trifunović, Snežana S.; Marković, Violeta

(Wiley, Hoboken, 2017)

TY  - DATA
AU  - Milošev, Milorad Z.
AU  - Jakovljević, Katarina
AU  - Joksović, Milan D.
AU  - Stanojković, Tatjana
AU  - Matić, Ivana Z.
AU  - Perović, Milka
AU  - Tešić, Vesna
AU  - Kanazir, Selma
AU  - Mladenović, Milan
AU  - Rodić, Marko
AU  - Leovac, Vukadin M.
AU  - Trifunović, Snežana S.
AU  - Marković, Violeta
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3222
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Supplementary material for the article: Milošev, M. Z.; Jakovljević, K.; Joksović, M. D.; Stanojković, T.; Matić, I. Z.; Perović, M.; Tešić, V.; Kanazir, S.; Mladenović, M.; Rodić, M. V.; et al. Mannich Bases of 1,2,4-Triazole3-Thione Containing Adamantane Moiety: Synthesis, Preliminary Anticancer Evaluation, and Molecular Modeling Studies. Chemical Biology and Drug Design 2017, 89 (6), 943–952. https://doi.org/10.1111/cbdd.12920
ER  - 
@misc{
author = "Milošev, Milorad Z. and Jakovljević, Katarina and Joksović, Milan D. and Stanojković, Tatjana and Matić, Ivana Z. and Perović, Milka and Tešić, Vesna and Kanazir, Selma and Mladenović, Milan and Rodić, Marko and Leovac, Vukadin M. and Trifunović, Snežana S. and Marković, Violeta",
year = "2017",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Supplementary material for the article: Milošev, M. Z.; Jakovljević, K.; Joksović, M. D.; Stanojković, T.; Matić, I. Z.; Perović, M.; Tešić, V.; Kanazir, S.; Mladenović, M.; Rodić, M. V.; et al. Mannich Bases of 1,2,4-Triazole3-Thione Containing Adamantane Moiety: Synthesis, Preliminary Anticancer Evaluation, and Molecular Modeling Studies. Chemical Biology and Drug Design 2017, 89 (6), 943–952. https://doi.org/10.1111/cbdd.12920"
}
Milošev, M. Z., Jakovljević, K., Joksović, M. D., Stanojković, T., Matić, I. Z., Perović, M., Tešić, V., Kanazir, S., Mladenović, M., Rodić, M., Leovac, V. M., Trifunović, S. S.,& Marković, V.. (2017). Supplementary material for the article: Milošev, M. Z.; Jakovljević, K.; Joksović, M. D.; Stanojković, T.; Matić, I. Z.; Perović, M.; Tešić, V.; Kanazir, S.; Mladenović, M.; Rodić, M. V.; et al. Mannich Bases of 1,2,4-Triazole3-Thione Containing Adamantane Moiety: Synthesis, Preliminary Anticancer Evaluation, and Molecular Modeling Studies. Chemical Biology and Drug Design 2017, 89 (6), 943–952. https://doi.org/10.1111/cbdd.12920. in Chemical Biology and Drug Design
Wiley, Hoboken..
Milošev MZ, Jakovljević K, Joksović MD, Stanojković T, Matić IZ, Perović M, Tešić V, Kanazir S, Mladenović M, Rodić M, Leovac VM, Trifunović SS, Marković V. Supplementary material for the article: Milošev, M. Z.; Jakovljević, K.; Joksović, M. D.; Stanojković, T.; Matić, I. Z.; Perović, M.; Tešić, V.; Kanazir, S.; Mladenović, M.; Rodić, M. V.; et al. Mannich Bases of 1,2,4-Triazole3-Thione Containing Adamantane Moiety: Synthesis, Preliminary Anticancer Evaluation, and Molecular Modeling Studies. Chemical Biology and Drug Design 2017, 89 (6), 943–952. https://doi.org/10.1111/cbdd.12920. in Chemical Biology and Drug Design. 2017;..
Milošev, Milorad Z., Jakovljević, Katarina, Joksović, Milan D., Stanojković, Tatjana, Matić, Ivana Z., Perović, Milka, Tešić, Vesna, Kanazir, Selma, Mladenović, Milan, Rodić, Marko, Leovac, Vukadin M., Trifunović, Snežana S., Marković, Violeta, "Supplementary material for the article: Milošev, M. Z.; Jakovljević, K.; Joksović, M. D.; Stanojković, T.; Matić, I. Z.; Perović, M.; Tešić, V.; Kanazir, S.; Mladenović, M.; Rodić, M. V.; et al. Mannich Bases of 1,2,4-Triazole3-Thione Containing Adamantane Moiety: Synthesis, Preliminary Anticancer Evaluation, and Molecular Modeling Studies. Chemical Biology and Drug Design 2017, 89 (6), 943–952. https://doi.org/10.1111/cbdd.12920" in Chemical Biology and Drug Design (2017).

Mannich bases of 1,2,4-triazole--3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies

Milošev, Milorad Z.; Jakovljević, Katarina; Joksović, Milan D.; Stanojković, Tatjana; Matić, Ivana Z.; Perović, Milka; Tešić, Vesna; Kanazir, Selma; Mladenović, Milan; Rodić, Marko; Leovac, Vukadin M.; Trifunović, Snežana S.; Marković, Violeta

(Wiley, Hoboken, 2017)

TY  - JOUR
AU  - Milošev, Milorad Z.
AU  - Jakovljević, Katarina
AU  - Joksović, Milan D.
AU  - Stanojković, Tatjana
AU  - Matić, Ivana Z.
AU  - Perović, Milka
AU  - Tešić, Vesna
AU  - Kanazir, Selma
AU  - Mladenović, Milan
AU  - Rodić, Marko
AU  - Leovac, Vukadin M.
AU  - Trifunović, Snežana S.
AU  - Marković, Violeta
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2482
AB  - A series of 18 novel N-Mannich bases derived from 5-adamantyl-1,2,4-triazole-3-th ione was synthesized and characterized using NMR spectroscopy and X-ray diffraction technique. All derivatives were evaluated for their anticancer potential against four human cancer cell lines. Several tested compounds exerted good cytotoxic activities on K562 and HL-60 cell lines, along with pronounced selectivity, showing lower cytotoxicity against normal fibroblasts MRC-5 compared to cancer cells. The effects of compounds 5b,5e, and 5j on the cell cycle were investigated by flow cytometric analysis. It was found that these compounds cause the accumulation of cells in the subG1 and G1 phases of the cell cycle and induce caspase-dependent apoptosis, while the anti-angiogenic effects of 5b, 5e, and 5j have been confirmed in EA. hy926 cells using a tube formation assay. Further, the interaction of Bax protein with compound 5b was investigated by means of molecular modeling, applying the combined molecular docking/molecular dynamics approach.
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Mannich bases of 1,2,4-triazole--3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies
VL  - 89
IS  - 6
SP  - 943
EP  - 952
DO  - 10.1111/cbdd.12920
UR  - Kon_3298
ER  - 
@article{
author = "Milošev, Milorad Z. and Jakovljević, Katarina and Joksović, Milan D. and Stanojković, Tatjana and Matić, Ivana Z. and Perović, Milka and Tešić, Vesna and Kanazir, Selma and Mladenović, Milan and Rodić, Marko and Leovac, Vukadin M. and Trifunović, Snežana S. and Marković, Violeta",
year = "2017",
abstract = "A series of 18 novel N-Mannich bases derived from 5-adamantyl-1,2,4-triazole-3-th ione was synthesized and characterized using NMR spectroscopy and X-ray diffraction technique. All derivatives were evaluated for their anticancer potential against four human cancer cell lines. Several tested compounds exerted good cytotoxic activities on K562 and HL-60 cell lines, along with pronounced selectivity, showing lower cytotoxicity against normal fibroblasts MRC-5 compared to cancer cells. The effects of compounds 5b,5e, and 5j on the cell cycle were investigated by flow cytometric analysis. It was found that these compounds cause the accumulation of cells in the subG1 and G1 phases of the cell cycle and induce caspase-dependent apoptosis, while the anti-angiogenic effects of 5b, 5e, and 5j have been confirmed in EA. hy926 cells using a tube formation assay. Further, the interaction of Bax protein with compound 5b was investigated by means of molecular modeling, applying the combined molecular docking/molecular dynamics approach.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Mannich bases of 1,2,4-triazole--3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies",
volume = "89",
number = "6",
pages = "943-952",
doi = "10.1111/cbdd.12920",
url = "Kon_3298"
}
Milošev, M. Z., Jakovljević, K., Joksović, M. D., Stanojković, T., Matić, I. Z., Perović, M., Tešić, V., Kanazir, S., Mladenović, M., Rodić, M., Leovac, V. M., Trifunović, S. S.,& Marković, V.. (2017). Mannich bases of 1,2,4-triazole--3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies. in Chemical Biology and Drug Design
Wiley, Hoboken., 89(6), 943-952.
https://doi.org/10.1111/cbdd.12920
Kon_3298
Milošev MZ, Jakovljević K, Joksović MD, Stanojković T, Matić IZ, Perović M, Tešić V, Kanazir S, Mladenović M, Rodić M, Leovac VM, Trifunović SS, Marković V. Mannich bases of 1,2,4-triazole--3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies. in Chemical Biology and Drug Design. 2017;89(6):943-952.
doi:10.1111/cbdd.12920
Kon_3298 .
Milošev, Milorad Z., Jakovljević, Katarina, Joksović, Milan D., Stanojković, Tatjana, Matić, Ivana Z., Perović, Milka, Tešić, Vesna, Kanazir, Selma, Mladenović, Milan, Rodić, Marko, Leovac, Vukadin M., Trifunović, Snežana S., Marković, Violeta, "Mannich bases of 1,2,4-triazole--3-thione containing adamantane moiety: Synthesis, preliminary anticancer evaluation, and molecular modeling studies" in Chemical Biology and Drug Design, 89, no. 6 (2017):943-952,
https://doi.org/10.1111/cbdd.12920 .,
Kon_3298 .
8
8
9