Terzić-Jovanović, Nataša

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orcid::0000-0002-4127-525X
  • Terzić-Jovanović, Nataša (22)
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Author's Bibliography

Aminoquinolines afford resistance to cerebral malaria in susceptible mice

Srbljanović, Jelena; Bobić, Branko; Štajner, Tijana; Uzelac, Aleksandra; Opsenica, Igor; Terzić-Jovanović, Nataša; Bauman, Neda; Šolaja, Bogdan A.; Đurković-Đaković, Olgica

(Elsevier, 2020)

TY  - JOUR
AU  - Srbljanović, Jelena
AU  - Bobić, Branko
AU  - Štajner, Tijana
AU  - Uzelac, Aleksandra
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Bauman, Neda
AU  - Šolaja, Bogdan A.
AU  - Đurković-Đaković, Olgica
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4054
AB  - ObjectivesMalaria treatment is impeded by increasing resistance to conventional antimalarial drugs. Here we explored the activity of ten novel benzothiophene, thiophene and benzene aminoquinolines.MethodsIn vitro testing was performed by the lactate dehydrogenase assay in chloroquine (CQ)-sensitive Plasmodium falciparum strain 3D7 and CQ-resistant (CQR) P. falciparum strain Dd2. In vivo activity was evaluated by a modified Thompson test using C57BL/6 mice infected with Plasmodium berghei ANKA strain.ResultsNine of the ten compounds had a lower 50% inhibitory concentration (IC50) than CQ against the CQR strain Dd2. Five of these compounds that were available for in vivo evaluation were shown to be non-toxic. All five compounds administered at a dose of 160mg/kg/day for 3 days prolonged the survival of treated compared with untreated mice. Untreated control mice died by Day 7 with a mean parasitaemia of 15%. Among treated mice, a dichotomous outcome was observed, with a two-third majority of treated mice dying by Day 17 with a low mean parasitaemia of 5%, whilst one-third survived longer with a mean hyperparasitaemia of 70%; specifically, five of these mice survived a mean of 25 days, whilst two even survived past Day 31.ConclusionsThe significant antimalarial potential of this aminoquinoline series is illustrated by its excellent in vitro activity against the CQR P. falciparum strain and significant in vivo activity. Interestingly, compounds ClAQ7, ClAQ9 and ClAQ11 were able to confer resistance to cerebral malaria and afford a switch to hyperparasitaemia to mice prone to the neurological syndrome.
PB  - Elsevier
T2  - Journal of Global Antimicrobial Resistance
T2  - Journal of Global Antimicrobial Resistance
T1  - Aminoquinolines afford resistance to cerebral malaria in susceptible mice
VL  - 23
SP  - 20
EP  - 25
DO  - 10.1016/j.jgar.2020.07.027
ER  - 
@article{
author = "Srbljanović, Jelena and Bobić, Branko and Štajner, Tijana and Uzelac, Aleksandra and Opsenica, Igor and Terzić-Jovanović, Nataša and Bauman, Neda and Šolaja, Bogdan A. and Đurković-Đaković, Olgica",
year = "2020",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/4054",
abstract = "ObjectivesMalaria treatment is impeded by increasing resistance to conventional antimalarial drugs. Here we explored the activity of ten novel benzothiophene, thiophene and benzene aminoquinolines.MethodsIn vitro testing was performed by the lactate dehydrogenase assay in chloroquine (CQ)-sensitive Plasmodium falciparum strain 3D7 and CQ-resistant (CQR) P. falciparum strain Dd2. In vivo activity was evaluated by a modified Thompson test using C57BL/6 mice infected with Plasmodium berghei ANKA strain.ResultsNine of the ten compounds had a lower 50% inhibitory concentration (IC50) than CQ against the CQR strain Dd2. Five of these compounds that were available for in vivo evaluation were shown to be non-toxic. All five compounds administered at a dose of 160mg/kg/day for 3 days prolonged the survival of treated compared with untreated mice. Untreated control mice died by Day 7 with a mean parasitaemia of 15%. Among treated mice, a dichotomous outcome was observed, with a two-third majority of treated mice dying by Day 17 with a low mean parasitaemia of 5%, whilst one-third survived longer with a mean hyperparasitaemia of 70%; specifically, five of these mice survived a mean of 25 days, whilst two even survived past Day 31.ConclusionsThe significant antimalarial potential of this aminoquinoline series is illustrated by its excellent in vitro activity against the CQR P. falciparum strain and significant in vivo activity. Interestingly, compounds ClAQ7, ClAQ9 and ClAQ11 were able to confer resistance to cerebral malaria and afford a switch to hyperparasitaemia to mice prone to the neurological syndrome.",
publisher = "Elsevier",
journal = "Journal of Global Antimicrobial Resistance, Journal of Global Antimicrobial Resistance",
title = "Aminoquinolines afford resistance to cerebral malaria in susceptible mice",
volume = "23",
pages = "20-25",
doi = "10.1016/j.jgar.2020.07.027"
}
Srbljanović, J., Bobić, B., Štajner, T., Uzelac, A., Opsenica, I., Terzić-Jovanović, N., Bauman, N., Šolaja, B. A.,& Đurković-Đaković, O. (2020). Aminoquinolines afford resistance to cerebral malaria in susceptible mice.
Journal of Global Antimicrobial Resistance
Elsevier., 23, 20-25.
https://doi.org/10.1016/j.jgar.2020.07.027
Srbljanović J, Bobić B, Štajner T, Uzelac A, Opsenica I, Terzić-Jovanović N, Bauman N, Šolaja BA, Đurković-Đaković O. Aminoquinolines afford resistance to cerebral malaria in susceptible mice. Journal of Global Antimicrobial Resistance. 2020;23:20-25
Srbljanović Jelena, Bobić Branko, Štajner Tijana, Uzelac Aleksandra, Opsenica Igor, Terzić-Jovanović Nataša, Bauman Neda, Šolaja Bogdan A., Đurković-Đaković Olgica, "Aminoquinolines afford resistance to cerebral malaria in susceptible mice" Journal of Global Antimicrobial Resistance, 23 (2020):20-25,
https://doi.org/10.1016/j.jgar.2020.07.027 .
1
1

Human serum albumin binding of certain antimalarials

Marković, Olivera S.; Cvijetić, Ilija; Zlatović, Mario; Opsenica, Igor; Konstantinović, Jelena M.; Terzić-Jovanović, Nataša; Šolaja, Bogdan A.; Verbić, Tatjana

(Pergamon-Elsevier Science Ltd, Oxford, 2018)

TY  - JOUR
AU  - Marković, Olivera S.
AU  - Cvijetić, Ilija
AU  - Zlatović, Mario
AU  - Opsenica, Igor
AU  - Konstantinović, Jelena M.
AU  - Terzić-Jovanović, Nataša
AU  - Šolaja, Bogdan A.
AU  - Verbić, Tatjana
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2085
AB  - Interactions between eight in-house synthesized aminoquinolines, along with well-known chloroquine, and human serum albumin (HSA) have been studied by fluorescence spectroscopy. The synthesized aminoquinolines, despite being structurally diverse, were found to be very potent antimalarials. Fluorescence measurements indicate that three compounds having additional thiophene or benzothiophene substructure bind more strongly to HSA than other studied compounds. Competitive binding experiments indicate that these three compounds bind significantly stronger to warfarin compared to diazepam binding site. Fluorescence quenching at three temperatures (20, 25, and 37 degrees C) was analyzed using classical Stern-Volmer equation, and a static quenching mechanism was proposed. The enthalpy and entropy changes upon sulphur-containing compound-HSA interactions were calculated using Van't Hoff equation. Positive values of enthalpy and entropy changes indicate that non-specific, hydrophobic interactions are the main contributors to HSA-compound interaction. Molecular docking and calculated lipophilicity descriptors indicate the same, pointing out that the increased lipophilicity of sulphur-containing compounds might be a reason for their better binding to HSA. Obtained results might contribute to design of novel derivatives with improved-pharmacokinetic properties and drug efficacy. (C) 2017 Elsevier B.V. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy
T1  - Human serum albumin binding of certain antimalarials
VL  - 192
SP  - 128
EP  - 139
DO  - 10.1016/j.saa.2017.10.061
ER  - 
@article{
author = "Marković, Olivera S. and Cvijetić, Ilija and Zlatović, Mario and Opsenica, Igor and Konstantinović, Jelena M. and Terzić-Jovanović, Nataša and Šolaja, Bogdan A. and Verbić, Tatjana",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2085",
abstract = "Interactions between eight in-house synthesized aminoquinolines, along with well-known chloroquine, and human serum albumin (HSA) have been studied by fluorescence spectroscopy. The synthesized aminoquinolines, despite being structurally diverse, were found to be very potent antimalarials. Fluorescence measurements indicate that three compounds having additional thiophene or benzothiophene substructure bind more strongly to HSA than other studied compounds. Competitive binding experiments indicate that these three compounds bind significantly stronger to warfarin compared to diazepam binding site. Fluorescence quenching at three temperatures (20, 25, and 37 degrees C) was analyzed using classical Stern-Volmer equation, and a static quenching mechanism was proposed. The enthalpy and entropy changes upon sulphur-containing compound-HSA interactions were calculated using Van't Hoff equation. Positive values of enthalpy and entropy changes indicate that non-specific, hydrophobic interactions are the main contributors to HSA-compound interaction. Molecular docking and calculated lipophilicity descriptors indicate the same, pointing out that the increased lipophilicity of sulphur-containing compounds might be a reason for their better binding to HSA. Obtained results might contribute to design of novel derivatives with improved-pharmacokinetic properties and drug efficacy. (C) 2017 Elsevier B.V. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy",
title = "Human serum albumin binding of certain antimalarials",
volume = "192",
pages = "128-139",
doi = "10.1016/j.saa.2017.10.061"
}
Marković, O. S., Cvijetić, I., Zlatović, M., Opsenica, I., Konstantinović, J. M., Terzić-Jovanović, N., Šolaja, B. A.,& Verbić, T. (2018). Human serum albumin binding of certain antimalarials.
Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy
Pergamon-Elsevier Science Ltd, Oxford., 192, 128-139.
https://doi.org/10.1016/j.saa.2017.10.061
Marković OS, Cvijetić I, Zlatović M, Opsenica I, Konstantinović JM, Terzić-Jovanović N, Šolaja BA, Verbić T. Human serum albumin binding of certain antimalarials. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy. 2018;192:128-139
Marković Olivera S., Cvijetić Ilija, Zlatović Mario, Opsenica Igor, Konstantinović Jelena M., Terzić-Jovanović Nataša, Šolaja Bogdan A., Verbić Tatjana, "Human serum albumin binding of certain antimalarials" Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy, 192 (2018):128-139,
https://doi.org/10.1016/j.saa.2017.10.061 .
10
10
10

Supplementary data for the article: Marković, O. S.; Cvijetić, I. N.; Zlatović, M. V.; Opsenica, I. M.; Konstantinović, J. M.; Terzić Jovanović, N. V.; Šolaja, B. A.; Verbić, T. Ž. Human Serum Albumin Binding of Certain Antimalarials. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 2018, 192, 128–139. https://doi.org/10.1016/j.saa.2017.10.061

Marković, Olivera S.; Cvijetić, Ilija; Zlatović, Mario; Opsenica, Igor; Konstantinović, Jelena M.; Terzić-Jovanović, Nataša; Šolaja, Bogdan A.; Verbić, Tatjana

(Pergamon-Elsevier Science Ltd, Oxford, 2018)

TY  - BOOK
AU  - Marković, Olivera S.
AU  - Cvijetić, Ilija
AU  - Zlatović, Mario
AU  - Opsenica, Igor
AU  - Konstantinović, Jelena M.
AU  - Terzić-Jovanović, Nataša
AU  - Šolaja, Bogdan A.
AU  - Verbić, Tatjana
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2913
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy
T1  - Supplementary data for the article: Marković, O. S.; Cvijetić, I. N.; Zlatović, M. V.; Opsenica, I. M.; Konstantinović, J. M.; Terzić Jovanović, N. V.; Šolaja, B. A.; Verbić, T. Ž. Human Serum Albumin Binding of Certain Antimalarials. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 2018, 192, 128–139. https://doi.org/10.1016/j.saa.2017.10.061
ER  - 
@book{
author = "Marković, Olivera S. and Cvijetić, Ilija and Zlatović, Mario and Opsenica, Igor and Konstantinović, Jelena M. and Terzić-Jovanović, Nataša and Šolaja, Bogdan A. and Verbić, Tatjana",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2913",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy",
title = "Supplementary data for the article: Marković, O. S.; Cvijetić, I. N.; Zlatović, M. V.; Opsenica, I. M.; Konstantinović, J. M.; Terzić Jovanović, N. V.; Šolaja, B. A.; Verbić, T. Ž. Human Serum Albumin Binding of Certain Antimalarials. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 2018, 192, 128–139. https://doi.org/10.1016/j.saa.2017.10.061"
}
Marković, O. S., Cvijetić, I., Zlatović, M., Opsenica, I., Konstantinović, J. M., Terzić-Jovanović, N., Šolaja, B. A.,& Verbić, T. (2018). Supplementary data for the article: Marković, O. S.; Cvijetić, I. N.; Zlatović, M. V.; Opsenica, I. M.; Konstantinović, J. M.; Terzić Jovanović, N. V.; Šolaja, B. A.; Verbić, T. Ž. Human Serum Albumin Binding of Certain Antimalarials. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 2018, 192, 128–139. https://doi.org/10.1016/j.saa.2017.10.061.
Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy
Pergamon-Elsevier Science Ltd, Oxford..
Marković OS, Cvijetić I, Zlatović M, Opsenica I, Konstantinović JM, Terzić-Jovanović N, Šolaja BA, Verbić T. Supplementary data for the article: Marković, O. S.; Cvijetić, I. N.; Zlatović, M. V.; Opsenica, I. M.; Konstantinović, J. M.; Terzić Jovanović, N. V.; Šolaja, B. A.; Verbić, T. Ž. Human Serum Albumin Binding of Certain Antimalarials. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 2018, 192, 128–139. https://doi.org/10.1016/j.saa.2017.10.061. Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy. 2018;
Marković Olivera S., Cvijetić Ilija, Zlatović Mario, Opsenica Igor, Konstantinović Jelena M., Terzić-Jovanović Nataša, Šolaja Bogdan A., Verbić Tatjana, "Supplementary data for the article: Marković, O. S.; Cvijetić, I. N.; Zlatović, M. V.; Opsenica, I. M.; Konstantinović, J. M.; Terzić Jovanović, N. V.; Šolaja, B. A.; Verbić, T. Ž. Human Serum Albumin Binding of Certain Antimalarials. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy 2018, 192, 128–139. https://doi.org/10.1016/j.saa.2017.10.061" Spectrochimica Acta. Part A: Molecular and Biomolecular Spectroscopy (2018)

Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice

Konstantinović, Jelena M.; Selaković, Milica; Orsini, Stefania; Bogojević, Katarina; D'Alessandro, Sarah; Scaccabarozzi, Diletta; Terzić-Jovanović, Nataša; Gradoni, Luigi; Basilico, Nicoletta; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2018)

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Selaković, Milica
AU  - Orsini, Stefania
AU  - Bogojević, Katarina
AU  - D'Alessandro, Sarah
AU  - Scaccabarozzi, Diletta
AU  - Terzić-Jovanović, Nataša
AU  - Gradoni, Luigi
AU  - Basilico, Nicoletta
AU  - Šolaja, Bogdan A.
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2948
AB  - In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50  lt  1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50  lt  1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.
PB  - Amer Chemical Soc, Washington
T2  - ACS Medicinal Chemistry Letters
T1  - Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice
VL  - 9
IS  - 7
SP  - 629
EP  - 634
DO  - 10.1021/acsmedchemlett.8b00053
ER  - 
@article{
author = "Konstantinović, Jelena M. and Selaković, Milica and Orsini, Stefania and Bogojević, Katarina and D'Alessandro, Sarah and Scaccabarozzi, Diletta and Terzić-Jovanović, Nataša and Gradoni, Luigi and Basilico, Nicoletta and Šolaja, Bogdan A.",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2948",
abstract = "In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50  lt  1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50  lt  1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS Medicinal Chemistry Letters",
title = "Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice",
volume = "9",
number = "7",
pages = "629-634",
doi = "10.1021/acsmedchemlett.8b00053"
}
Konstantinović, J. M., Selaković, M., Orsini, S., Bogojević, K., D'Alessandro, S., Scaccabarozzi, D., Terzić-Jovanović, N., Gradoni, L., Basilico, N.,& Šolaja, B. A. (2018). Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice.
ACS Medicinal Chemistry Letters
Amer Chemical Soc, Washington., 9(7), 629-634.
https://doi.org/10.1021/acsmedchemlett.8b00053
Konstantinović JM, Selaković M, Orsini S, Bogojević K, D'Alessandro S, Scaccabarozzi D, Terzić-Jovanović N, Gradoni L, Basilico N, Šolaja BA. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice. ACS Medicinal Chemistry Letters. 2018;9(7):629-634
Konstantinović Jelena M., Selaković Milica, Orsini Stefania, Bogojević Katarina, D'Alessandro Sarah, Scaccabarozzi Diletta, Terzić-Jovanović Nataša, Gradoni Luigi, Basilico Nicoletta, Šolaja Bogdan A., "Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice" ACS Medicinal Chemistry Letters, 9, no. 7 (2018):629-634,
https://doi.org/10.1021/acsmedchemlett.8b00053 .
1
7
5
7

Supplementary data for the article: Konstantinović, J.; Videnović, M.; Orsini, S.; Bogojević, K.; D’Alessandro, S.; Scaccabarozzi, D.; Terzić Jovanović, N.; Gradoni, L.; Basilico, N.; Šolaja, B. A. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania Infantum Infected Mice. ACS Medicinal Chemistry Letters 2018, 9 (7), 629–634. https://doi.org/10.1021/acsmedchemlett.8b00053

Konstantinović, Jelena M.; Selaković, Milica; Orsini, Stefania; Bogojević, Katarina; D'Alessandro, Sarah; Scaccabarozzi, Diletta; Terzić-Jovanović, Nataša; Gradoni, Luigi; Basilico, Nicoletta; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2018)

TY  - BOOK
AU  - Konstantinović, Jelena M.
AU  - Selaković, Milica
AU  - Orsini, Stefania
AU  - Bogojević, Katarina
AU  - D'Alessandro, Sarah
AU  - Scaccabarozzi, Diletta
AU  - Terzić-Jovanović, Nataša
AU  - Gradoni, Luigi
AU  - Basilico, Nicoletta
AU  - Šolaja, Bogdan A.
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2949
PB  - Amer Chemical Soc, Washington
T2  - ACS Medicinal Chemistry Letters
T1  - Supplementary data for the article: Konstantinović, J.; Videnović, M.; Orsini, S.; Bogojević, K.; D’Alessandro, S.; Scaccabarozzi, D.; Terzić Jovanović, N.; Gradoni, L.; Basilico, N.; Šolaja, B. A. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania Infantum Infected Mice. ACS Medicinal Chemistry Letters 2018, 9 (7), 629–634. https://doi.org/10.1021/acsmedchemlett.8b00053
ER  - 
@book{
author = "Konstantinović, Jelena M. and Selaković, Milica and Orsini, Stefania and Bogojević, Katarina and D'Alessandro, Sarah and Scaccabarozzi, Diletta and Terzić-Jovanović, Nataša and Gradoni, Luigi and Basilico, Nicoletta and Šolaja, Bogdan A.",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2949",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS Medicinal Chemistry Letters",
title = "Supplementary data for the article: Konstantinović, J.; Videnović, M.; Orsini, S.; Bogojević, K.; D’Alessandro, S.; Scaccabarozzi, D.; Terzić Jovanović, N.; Gradoni, L.; Basilico, N.; Šolaja, B. A. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania Infantum Infected Mice. ACS Medicinal Chemistry Letters 2018, 9 (7), 629–634. https://doi.org/10.1021/acsmedchemlett.8b00053"
}
Konstantinović, J. M., Selaković, M., Orsini, S., Bogojević, K., D'Alessandro, S., Scaccabarozzi, D., Terzić-Jovanović, N., Gradoni, L., Basilico, N.,& Šolaja, B. A. (2018). Supplementary data for the article: Konstantinović, J.; Videnović, M.; Orsini, S.; Bogojević, K.; D’Alessandro, S.; Scaccabarozzi, D.; Terzić Jovanović, N.; Gradoni, L.; Basilico, N.; Šolaja, B. A. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania Infantum Infected Mice. ACS Medicinal Chemistry Letters 2018, 9 (7), 629–634. https://doi.org/10.1021/acsmedchemlett.8b00053.
ACS Medicinal Chemistry Letters
Amer Chemical Soc, Washington..
Konstantinović JM, Selaković M, Orsini S, Bogojević K, D'Alessandro S, Scaccabarozzi D, Terzić-Jovanović N, Gradoni L, Basilico N, Šolaja BA. Supplementary data for the article: Konstantinović, J.; Videnović, M.; Orsini, S.; Bogojević, K.; D’Alessandro, S.; Scaccabarozzi, D.; Terzić Jovanović, N.; Gradoni, L.; Basilico, N.; Šolaja, B. A. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania Infantum Infected Mice. ACS Medicinal Chemistry Letters 2018, 9 (7), 629–634. https://doi.org/10.1021/acsmedchemlett.8b00053. ACS Medicinal Chemistry Letters. 2018;
Konstantinović Jelena M., Selaković Milica, Orsini Stefania, Bogojević Katarina, D'Alessandro Sarah, Scaccabarozzi Diletta, Terzić-Jovanović Nataša, Gradoni Luigi, Basilico Nicoletta, Šolaja Bogdan A., "Supplementary data for the article: Konstantinović, J.; Videnović, M.; Orsini, S.; Bogojević, K.; D’Alessandro, S.; Scaccabarozzi, D.; Terzić Jovanović, N.; Gradoni, L.; Basilico, N.; Šolaja, B. A. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania Infantum Infected Mice. ACS Medicinal Chemistry Letters 2018, 9 (7), 629–634. https://doi.org/10.1021/acsmedchemlett.8b00053" ACS Medicinal Chemistry Letters (2018)

Supplementary data for the article: Konstantinović, J.; Kiris, E.; Kota, K. P.; Kugelman-Tonos, J.; Videnović, M.; Cazares, L. H.; Terzić Jovanović, N.; Verbić, T. Ž.; Andjelković, B.; Duplantier, A. J.; et al. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. Journal of Medicinal Chemistry 2018, 61 (4), 1595–1608. https://doi.org/10.1021/acs.jmedchem.7b01710

Konstantinović, Jelena M.; Kiris, Erkan; Kota, Krishna P.; Kugelman-Tonos, Johanny; Selaković, Milica; Cazares, Lisa H.; Terzić-Jovanović, Nataša; Verbić, Tatjana; Anđelković, Boban D.; Duplantier, Allen J.; Bavari, Sina; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2018)

TY  - BOOK
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Selaković, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan A.
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3039
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Supplementary data for the article: Konstantinović, J.; Kiris, E.; Kota, K. P.; Kugelman-Tonos, J.; Videnović, M.; Cazares, L. H.; Terzić Jovanović, N.; Verbić, T. Ž.; Andjelković, B.; Duplantier, A. J.; et al. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. Journal of Medicinal Chemistry 2018, 61 (4), 1595–1608. https://doi.org/10.1021/acs.jmedchem.7b01710
ER  - 
@book{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Selaković, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan A.",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3039",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Supplementary data for the article: Konstantinović, J.; Kiris, E.; Kota, K. P.; Kugelman-Tonos, J.; Videnović, M.; Cazares, L. H.; Terzić Jovanović, N.; Verbić, T. Ž.; Andjelković, B.; Duplantier, A. J.; et al. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. Journal of Medicinal Chemistry 2018, 61 (4), 1595–1608. https://doi.org/10.1021/acs.jmedchem.7b01710"
}
Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Selaković, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B. A. (2018). Supplementary data for the article: Konstantinović, J.; Kiris, E.; Kota, K. P.; Kugelman-Tonos, J.; Videnović, M.; Cazares, L. H.; Terzić Jovanović, N.; Verbić, T. Ž.; Andjelković, B.; Duplantier, A. J.; et al. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. Journal of Medicinal Chemistry 2018, 61 (4), 1595–1608. https://doi.org/10.1021/acs.jmedchem.7b01710.
Journal of Medicinal Chemistry
Amer Chemical Soc, Washington..
Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Selaković M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja BA. Supplementary data for the article: Konstantinović, J.; Kiris, E.; Kota, K. P.; Kugelman-Tonos, J.; Videnović, M.; Cazares, L. H.; Terzić Jovanović, N.; Verbić, T. Ž.; Andjelković, B.; Duplantier, A. J.; et al. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. Journal of Medicinal Chemistry 2018, 61 (4), 1595–1608. https://doi.org/10.1021/acs.jmedchem.7b01710. Journal of Medicinal Chemistry. 2018;
Konstantinović Jelena M., Kiris Erkan, Kota Krishna P., Kugelman-Tonos Johanny, Selaković Milica, Cazares Lisa H., Terzić-Jovanović Nataša, Verbić Tatjana, Anđelković Boban D., Duplantier Allen J., Bavari Sina, Šolaja Bogdan A., "Supplementary data for the article: Konstantinović, J.; Kiris, E.; Kota, K. P.; Kugelman-Tonos, J.; Videnović, M.; Cazares, L. H.; Terzić Jovanović, N.; Verbić, T. Ž.; Andjelković, B.; Duplantier, A. J.; et al. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. Journal of Medicinal Chemistry 2018, 61 (4), 1595–1608. https://doi.org/10.1021/acs.jmedchem.7b01710" Journal of Medicinal Chemistry (2018)

New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model

Konstantinović, Jelena M.; Kiris, Erkan; Kota, Krishna P.; Kugelman-Tonos, Johanny; Selaković, Milica; Cazares, Lisa H.; Terzić-Jovanović, Nataša; Verbić, Tatjana; Anđelković, Boban D.; Duplantier, Allen J.; Bavari, Sina; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2018)

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Selaković, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan A.
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2099
AB  - The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model
VL  - 61
IS  - 4
SP  - 1595
EP  - 1608
DO  - 10.1021/acs.jmedchem.7b01710
ER  - 
@article{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Selaković, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan A.",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2099",
abstract = "The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model",
volume = "61",
number = "4",
pages = "1595-1608",
doi = "10.1021/acs.jmedchem.7b01710"
}
Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Selaković, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B. A. (2018). New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model.
Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 61(4), 1595-1608.
https://doi.org/10.1021/acs.jmedchem.7b01710
Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Selaković M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja BA. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. Journal of Medicinal Chemistry. 2018;61(4):1595-1608
Konstantinović Jelena M., Kiris Erkan, Kota Krishna P., Kugelman-Tonos Johanny, Selaković Milica, Cazares Lisa H., Terzić-Jovanović Nataša, Verbić Tatjana, Anđelković Boban D., Duplantier Allen J., Bavari Sina, Šolaja Bogdan A., "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model" Journal of Medicinal Chemistry, 61, no. 4 (2018):1595-1608,
https://doi.org/10.1021/acs.jmedchem.7b01710 .
3
3
3

Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice

Konstantinović, Jelena M.; Selaković, Milica; Orsini, Stefania; Bogojević, Katarina; D'Alessandro, Sarah; Scaccabarozzi, Diletta; Terzić-Jovanović, Nataša; Gradoni, Luigi; Basilico, Nicoletta; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2018)

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Selaković, Milica
AU  - Orsini, Stefania
AU  - Bogojević, Katarina
AU  - D'Alessandro, Sarah
AU  - Scaccabarozzi, Diletta
AU  - Terzić-Jovanović, Nataša
AU  - Gradoni, Luigi
AU  - Basilico, Nicoletta
AU  - Šolaja, Bogdan A.
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2209
AB  - In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50  lt  1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50  lt  1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.
PB  - Amer Chemical Soc, Washington
T2  - ACS Medicinal Chemistry Letters
T1  - Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice
VL  - 9
IS  - 7
SP  - 629
EP  - 634
DO  - 10.1021/acsmedchemlett.8b00053
ER  - 
@article{
author = "Konstantinović, Jelena M. and Selaković, Milica and Orsini, Stefania and Bogojević, Katarina and D'Alessandro, Sarah and Scaccabarozzi, Diletta and Terzić-Jovanović, Nataša and Gradoni, Luigi and Basilico, Nicoletta and Šolaja, Bogdan A.",
year = "2018",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2209",
abstract = "In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50  lt  1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50  lt  1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.",
publisher = "Amer Chemical Soc, Washington",
journal = "ACS Medicinal Chemistry Letters",
title = "Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice",
volume = "9",
number = "7",
pages = "629-634",
doi = "10.1021/acsmedchemlett.8b00053"
}
Konstantinović, J. M., Selaković, M., Orsini, S., Bogojević, K., D'Alessandro, S., Scaccabarozzi, D., Terzić-Jovanović, N., Gradoni, L., Basilico, N.,& Šolaja, B. A. (2018). Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice.
ACS Medicinal Chemistry Letters
Amer Chemical Soc, Washington., 9(7), 629-634.
https://doi.org/10.1021/acsmedchemlett.8b00053
Konstantinović JM, Selaković M, Orsini S, Bogojević K, D'Alessandro S, Scaccabarozzi D, Terzić-Jovanović N, Gradoni L, Basilico N, Šolaja BA. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice. ACS Medicinal Chemistry Letters. 2018;9(7):629-634
Konstantinović Jelena M., Selaković Milica, Orsini Stefania, Bogojević Katarina, D'Alessandro Sarah, Scaccabarozzi Diletta, Terzić-Jovanović Nataša, Gradoni Luigi, Basilico Nicoletta, Šolaja Bogdan A., "Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice" ACS Medicinal Chemistry Letters, 9, no. 7 (2018):629-634,
https://doi.org/10.1021/acsmedchemlett.8b00053 .
1
7
5
7

Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy

Srbljanović, Jelena; Štajner, Tijana; Konstantinović, Jelena M.; Terzić-Jovanović, Nataša; Uzelac, Aleksandra; Bobić, Branko; Šolaja, Bogdan A.; Đurković-Đaković, Olgica

(Elsevier Science Bv, Amsterdam, 2017)

TY  - JOUR
AU  - Srbljanović, Jelena
AU  - Štajner, Tijana
AU  - Konstantinović, Jelena M.
AU  - Terzić-Jovanović, Nataša
AU  - Uzelac, Aleksandra
AU  - Bobić, Branko
AU  - Šolaja, Bogdan A.
AU  - Đurković-Đaković, Olgica
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2514
AB  - Malaria remains a major disease in the developing world and globally is the most important parasitic disease causing significant morbidity and mortality. Because of widespread resistance to conventional antimalarials, including chloroquine (CQ), new drugs are urgently needed. Here we report on the antimalarial efficacy, both in vitro and in vivo, of a series of aminoquinoline derivatives with adamantane or benzothiophene as a carrier. In vitro efficacy was evaluated by a lactate dehydrogenase (LDH) assay in cultures of a CQ-sensitive (3D7) and CQ-resistant (Dd2) strain of Plasmodium falcipanim. Of a series of 26 screened compounds, 12 that exerted a growth inhibition rate of  gt = 5% were further examined in vitro to determine the 50% inhibitory concentration (IC50) values. Nine compounds shown in preliminary experiments to be non-toxic in vivo were evaluated in C57BL/6 mice infected with Plasmodium herghei ANKA strain using a modified Thompson test. All nine compounds examined in vivo prolonged the survival of treated versus untreated mice, four of which afforded  gt = 60% survival. Most notably, two of these compounds, both with the adamantane carrier, afforded complete cure (100% survival and parasite clearance). Interestingly, one of these compounds had no in vitro effect against the CQ resistant P. falciparum strain. Better in vivo compared with in vitro results suggest a role for compound metabolites rather than the compounds themselves. The results presented here point to adamantane as a carrier that enhances the antimalarial potential of aminoquinolines.
PB  - Elsevier Science Bv, Amsterdam
T2  - International Journal of Antimicrobial Agents
T1  - Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy
VL  - 50
IS  - 3
SP  - 461
EP  - 466
DO  - 10.1016/j.ijantimicag.2017.06.002
ER  - 
@article{
author = "Srbljanović, Jelena and Štajner, Tijana and Konstantinović, Jelena M. and Terzić-Jovanović, Nataša and Uzelac, Aleksandra and Bobić, Branko and Šolaja, Bogdan A. and Đurković-Đaković, Olgica",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2514",
abstract = "Malaria remains a major disease in the developing world and globally is the most important parasitic disease causing significant morbidity and mortality. Because of widespread resistance to conventional antimalarials, including chloroquine (CQ), new drugs are urgently needed. Here we report on the antimalarial efficacy, both in vitro and in vivo, of a series of aminoquinoline derivatives with adamantane or benzothiophene as a carrier. In vitro efficacy was evaluated by a lactate dehydrogenase (LDH) assay in cultures of a CQ-sensitive (3D7) and CQ-resistant (Dd2) strain of Plasmodium falcipanim. Of a series of 26 screened compounds, 12 that exerted a growth inhibition rate of  gt = 5% were further examined in vitro to determine the 50% inhibitory concentration (IC50) values. Nine compounds shown in preliminary experiments to be non-toxic in vivo were evaluated in C57BL/6 mice infected with Plasmodium herghei ANKA strain using a modified Thompson test. All nine compounds examined in vivo prolonged the survival of treated versus untreated mice, four of which afforded  gt = 60% survival. Most notably, two of these compounds, both with the adamantane carrier, afforded complete cure (100% survival and parasite clearance). Interestingly, one of these compounds had no in vitro effect against the CQ resistant P. falciparum strain. Better in vivo compared with in vitro results suggest a role for compound metabolites rather than the compounds themselves. The results presented here point to adamantane as a carrier that enhances the antimalarial potential of aminoquinolines.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "International Journal of Antimicrobial Agents",
title = "Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy",
volume = "50",
number = "3",
pages = "461-466",
doi = "10.1016/j.ijantimicag.2017.06.002"
}
Srbljanović, J., Štajner, T., Konstantinović, J. M., Terzić-Jovanović, N., Uzelac, A., Bobić, B., Šolaja, B. A.,& Đurković-Đaković, O. (2017). Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy.
International Journal of Antimicrobial Agents
Elsevier Science Bv, Amsterdam., 50(3), 461-466.
https://doi.org/10.1016/j.ijantimicag.2017.06.002
Srbljanović J, Štajner T, Konstantinović JM, Terzić-Jovanović N, Uzelac A, Bobić B, Šolaja BA, Đurković-Đaković O. Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy. International Journal of Antimicrobial Agents. 2017;50(3):461-466
Srbljanović Jelena, Štajner Tijana, Konstantinović Jelena M., Terzić-Jovanović Nataša, Uzelac Aleksandra, Bobić Branko, Šolaja Bogdan A., Đurković-Đaković Olgica, "Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy" International Journal of Antimicrobial Agents, 50, no. 3 (2017):461-466,
https://doi.org/10.1016/j.ijantimicag.2017.06.002 .
1
2
2
3

Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy

Srbljanović, Jelena; Štajner, Tijana; Konstantinović, Jelena M.; Terzić-Jovanović, Nataša; Uzelac, Aleksandra; Bobić, Branko; Šolaja, Bogdan A.; Đurković-Đaković, Olgica

(Elsevier Science Bv, Amsterdam, 2017)

TY  - JOUR
AU  - Srbljanović, Jelena
AU  - Štajner, Tijana
AU  - Konstantinović, Jelena M.
AU  - Terzić-Jovanović, Nataša
AU  - Uzelac, Aleksandra
AU  - Bobić, Branko
AU  - Šolaja, Bogdan A.
AU  - Đurković-Đaković, Olgica
PY  - 2017
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3214
AB  - Malaria remains a major disease in the developing world and globally is the most important parasitic disease causing significant morbidity and mortality. Because of widespread resistance to conventional antimalarials, including chloroquine (CQ), new drugs are urgently needed. Here we report on the antimalarial efficacy, both in vitro and in vivo, of a series of aminoquinoline derivatives with adamantane or benzothiophene as a carrier. In vitro efficacy was evaluated by a lactate dehydrogenase (LDH) assay in cultures of a CQ-sensitive (3D7) and CQ-resistant (Dd2) strain of Plasmodium falcipanim. Of a series of 26 screened compounds, 12 that exerted a growth inhibition rate of  gt = 5% were further examined in vitro to determine the 50% inhibitory concentration (IC50) values. Nine compounds shown in preliminary experiments to be non-toxic in vivo were evaluated in C57BL/6 mice infected with Plasmodium herghei ANKA strain using a modified Thompson test. All nine compounds examined in vivo prolonged the survival of treated versus untreated mice, four of which afforded  gt = 60% survival. Most notably, two of these compounds, both with the adamantane carrier, afforded complete cure (100% survival and parasite clearance). Interestingly, one of these compounds had no in vitro effect against the CQ resistant P. falciparum strain. Better in vivo compared with in vitro results suggest a role for compound metabolites rather than the compounds themselves. The results presented here point to adamantane as a carrier that enhances the antimalarial potential of aminoquinolines.
PB  - Elsevier Science Bv, Amsterdam
T2  - International Journal of Antimicrobial Agents
T1  - Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy
VL  - 50
IS  - 3
SP  - 461
EP  - 466
DO  - 10.1016/j.ijantimicag.2017.06.002
ER  - 
@article{
author = "Srbljanović, Jelena and Štajner, Tijana and Konstantinović, Jelena M. and Terzić-Jovanović, Nataša and Uzelac, Aleksandra and Bobić, Branko and Šolaja, Bogdan A. and Đurković-Đaković, Olgica",
year = "2017",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3214",
abstract = "Malaria remains a major disease in the developing world and globally is the most important parasitic disease causing significant morbidity and mortality. Because of widespread resistance to conventional antimalarials, including chloroquine (CQ), new drugs are urgently needed. Here we report on the antimalarial efficacy, both in vitro and in vivo, of a series of aminoquinoline derivatives with adamantane or benzothiophene as a carrier. In vitro efficacy was evaluated by a lactate dehydrogenase (LDH) assay in cultures of a CQ-sensitive (3D7) and CQ-resistant (Dd2) strain of Plasmodium falcipanim. Of a series of 26 screened compounds, 12 that exerted a growth inhibition rate of  gt = 5% were further examined in vitro to determine the 50% inhibitory concentration (IC50) values. Nine compounds shown in preliminary experiments to be non-toxic in vivo were evaluated in C57BL/6 mice infected with Plasmodium herghei ANKA strain using a modified Thompson test. All nine compounds examined in vivo prolonged the survival of treated versus untreated mice, four of which afforded  gt = 60% survival. Most notably, two of these compounds, both with the adamantane carrier, afforded complete cure (100% survival and parasite clearance). Interestingly, one of these compounds had no in vitro effect against the CQ resistant P. falciparum strain. Better in vivo compared with in vitro results suggest a role for compound metabolites rather than the compounds themselves. The results presented here point to adamantane as a carrier that enhances the antimalarial potential of aminoquinolines.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "International Journal of Antimicrobial Agents",
title = "Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy",
volume = "50",
number = "3",
pages = "461-466",
doi = "10.1016/j.ijantimicag.2017.06.002"
}
Srbljanović, J., Štajner, T., Konstantinović, J. M., Terzić-Jovanović, N., Uzelac, A., Bobić, B., Šolaja, B. A.,& Đurković-Đaković, O. (2017). Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy.
International Journal of Antimicrobial Agents
Elsevier Science Bv, Amsterdam., 50(3), 461-466.
https://doi.org/10.1016/j.ijantimicag.2017.06.002
Srbljanović J, Štajner T, Konstantinović JM, Terzić-Jovanović N, Uzelac A, Bobić B, Šolaja BA, Đurković-Đaković O. Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy. International Journal of Antimicrobial Agents. 2017;50(3):461-466
Srbljanović Jelena, Štajner Tijana, Konstantinović Jelena M., Terzić-Jovanović Nataša, Uzelac Aleksandra, Bobić Branko, Šolaja Bogdan A., Đurković-Đaković Olgica, "Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy" International Journal of Antimicrobial Agents, 50, no. 3 (2017):461-466,
https://doi.org/10.1016/j.ijantimicag.2017.06.002 .
1
2
2
3

Derivati diaminoalkiladamantana sa supstituisanim hinolinima kao inhibitori parazita Plasmodium falciparum i botulinum neurotoksina

Terzić-Jovanović, Nataša

(Универзитет у Београду, Хемијски факултет, 2017)

TY  - BOOK
AU  - Terzić-Jovanović, Nataša
PY  - 2017
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=4958
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:15580/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=48952591
UR  - http://nardus.mpn.gov.rs/123456789/8116
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2730
AB  - Rezime: Malarija je jedna od najrasprostranjenijih bolesti, koja preti približno polovinisvetske populacije i koja je u zemljama u razvoju glavni uzrok smrtnosti dece uzrasta do5 godina. Nagli razvoj rezistentnih formi parazita na postojeće antimalarike stvarapotrebu za razvojem novih lekova. Jedna od strategija za razvoj novih lekova, kojom sesmanjuju troškovi i skraćuje vreme potrebno za pronalazak novih aktivnih supstanci jehemijska modifikacaja postojećih hinolinskih antimalarika poznatog mehanizmadejstva.U okviru ove doktorske teze izvršena je sinteza serije aminohinolinskih derivatakod koje su adamantanski fragmenti preko amido-aminskih i diaminskih premostnihnizova povezani sa različito supstituisanim hinolinskim jezgrima. Određena jeantimalarijska aktivnost svih sintetisanih jedinjenja. Rezultati bioloških testova potvrdilisu antimalarijsku aktivnost, a dodatno je utvrđena i inhibitorna aktivnost pojedinihderivata prema botulinum neurotoksinu tipa A (BoNT/A LC).Botulinum neurotoksini (BoNTs) sa letalnom dozom (LC50) od 1-5 ng/kg telesnetežine su najsmrtonosniji otrovi poznati čoveku. Zbog svoje velike toksičnosti, lakoćeproizvodnje i transporta svrstavaju se od Centra za kontrolu i prevenciju bolesti SAD uA kategoriju agenasa sa najvećim rizikom za korišćenje u bioterorizmu. Nepostojanjeodobrenog farmakološkog pristupa za tretman intoksikacije, stvara veliku potrebu zarazvojem inhibitora BoNT.U toku rada dobijeni su sledeći rezultati:(i) Sintetisano je osam amido-adamantanskih aminohinolina (99a-d i 100a-d).Svi sintetisani amidni derivati poseduju nedovoljno dobru in vitro antimalarijskuaktivnost (IC50 = 6 - 1400 nM). Na osnovu indeksa rezistencije (IR) uočena je višaaktivnost amido-adamantanskih aminohinolina prema CQS soju (D6) u poređenju saCQR (W2) i multirezistentnim (TM91C235) sojem. Najaktivnije jedinjenje iz ove serije pokazuje in vitro aktivnost prema CQS soju D6, 100a: IC90(D6) = 157 nM osam putanižu od aktivnosti CQ (IC90(D6) = 20 nM)...
AB  - Malaria is one of the most devastating diseases which threatens half theworld's population and remains a major cause of mortality among children aged < 5years in developing countries. The wide-spread resistance of various strains to currentantimalarials potentiates the need for development of new drugs. One of the strategiesfor the development of new therapeutics, that reduces costs and shortens the timeneeded for the discovery of new active substances, is chemical modification ofquinoline-based drugs with known mechanism of action.Antimalarial and BoNT/ LC inhibitory activities of variously substituted 4-aminoquinolines coupled to adamantane carrier were described within this PhD thesis.Botulinum neurotoxins (BoNTs) are the most potent of known toxins (LC50 = 1-5 ng/kg). Due to ease of production, spreading and lethality BoNTs are listed ascategory A biothreat agens by the U.S. Centers for Disease Control and Prevention(CDC). The absence of an approved pharmacological approach for the treatment ofintoxication, creates an urgent need to develop inhibitors BoNT.The results are summarized as follows:(i) Eight derivatives with an amide functionality linking the 4,7-ACQ moietyto adamantane (99a-d and 100a-d) were synthesized. All synthesized compounds arepoorly active (IC50 = 6 - 1400 nM). Analysis of the resistance index (RI) showed thatcompounds are more active against D6 strain than against the CQ-resistant W2 andmultidrug resistant TM91C235 strain. The most active amide within the series is eighttimes less active (100a: IC90 (D6) = 157 nM) against the CQ- sensitive D6 strain thanCQ (IC90 (D6) = 20 nM).(ii) The series of ten aminoquinoline derivatives in which the adamantanefragment is connected to quinoline core through unbranched diamine linker wassynthesized (106a-d, 106i, 107a-107i and 107i). Eight out of ten synthetic derivatives exhibited better IC90 activity against CQ-sensitive D6 strain compared to CQ (1), sevenare more potent against multi-resistant C235 strain and one against MFQ-sensitive W2...strain than MFQ (14).
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Derivati diaminoalkiladamantana sa supstituisanim hinolinima kao inhibitori parazita Plasmodium falciparum i botulinum neurotoksina
ER  - 
@phdthesis{
author = "Terzić-Jovanović, Nataša",
year = "2017",
url = "http://eteze.bg.ac.rs/application/showtheses?thesesId=4958, https://fedorabg.bg.ac.rs/fedora/get/o:15580/bdef:Content/download, http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=48952591, http://nardus.mpn.gov.rs/123456789/8116, http://cherry.chem.bg.ac.rs/handle/123456789/2730",
abstract = "Rezime: Malarija je jedna od najrasprostranjenijih bolesti, koja preti približno polovinisvetske populacije i koja je u zemljama u razvoju glavni uzrok smrtnosti dece uzrasta do5 godina. Nagli razvoj rezistentnih formi parazita na postojeće antimalarike stvarapotrebu za razvojem novih lekova. Jedna od strategija za razvoj novih lekova, kojom sesmanjuju troškovi i skraćuje vreme potrebno za pronalazak novih aktivnih supstanci jehemijska modifikacaja postojećih hinolinskih antimalarika poznatog mehanizmadejstva.U okviru ove doktorske teze izvršena je sinteza serije aminohinolinskih derivatakod koje su adamantanski fragmenti preko amido-aminskih i diaminskih premostnihnizova povezani sa različito supstituisanim hinolinskim jezgrima. Određena jeantimalarijska aktivnost svih sintetisanih jedinjenja. Rezultati bioloških testova potvrdilisu antimalarijsku aktivnost, a dodatno je utvrđena i inhibitorna aktivnost pojedinihderivata prema botulinum neurotoksinu tipa A (BoNT/A LC).Botulinum neurotoksini (BoNTs) sa letalnom dozom (LC50) od 1-5 ng/kg telesnetežine su najsmrtonosniji otrovi poznati čoveku. Zbog svoje velike toksičnosti, lakoćeproizvodnje i transporta svrstavaju se od Centra za kontrolu i prevenciju bolesti SAD uA kategoriju agenasa sa najvećim rizikom za korišćenje u bioterorizmu. Nepostojanjeodobrenog farmakološkog pristupa za tretman intoksikacije, stvara veliku potrebu zarazvojem inhibitora BoNT.U toku rada dobijeni su sledeći rezultati:(i) Sintetisano je osam amido-adamantanskih aminohinolina (99a-d i 100a-d).Svi sintetisani amidni derivati poseduju nedovoljno dobru in vitro antimalarijskuaktivnost (IC50 = 6 - 1400 nM). Na osnovu indeksa rezistencije (IR) uočena je višaaktivnost amido-adamantanskih aminohinolina prema CQS soju (D6) u poređenju saCQR (W2) i multirezistentnim (TM91C235) sojem. Najaktivnije jedinjenje iz ove serije pokazuje in vitro aktivnost prema CQS soju D6, 100a: IC90(D6) = 157 nM osam putanižu od aktivnosti CQ (IC90(D6) = 20 nM)..., Malaria is one of the most devastating diseases which threatens half theworld's population and remains a major cause of mortality among children aged < 5years in developing countries. The wide-spread resistance of various strains to currentantimalarials potentiates the need for development of new drugs. One of the strategiesfor the development of new therapeutics, that reduces costs and shortens the timeneeded for the discovery of new active substances, is chemical modification ofquinoline-based drugs with known mechanism of action.Antimalarial and BoNT/ LC inhibitory activities of variously substituted 4-aminoquinolines coupled to adamantane carrier were described within this PhD thesis.Botulinum neurotoxins (BoNTs) are the most potent of known toxins (LC50 = 1-5 ng/kg). Due to ease of production, spreading and lethality BoNTs are listed ascategory A biothreat agens by the U.S. Centers for Disease Control and Prevention(CDC). The absence of an approved pharmacological approach for the treatment ofintoxication, creates an urgent need to develop inhibitors BoNT.The results are summarized as follows:(i) Eight derivatives with an amide functionality linking the 4,7-ACQ moietyto adamantane (99a-d and 100a-d) were synthesized. All synthesized compounds arepoorly active (IC50 = 6 - 1400 nM). Analysis of the resistance index (RI) showed thatcompounds are more active against D6 strain than against the CQ-resistant W2 andmultidrug resistant TM91C235 strain. The most active amide within the series is eighttimes less active (100a: IC90 (D6) = 157 nM) against the CQ- sensitive D6 strain thanCQ (IC90 (D6) = 20 nM).(ii) The series of ten aminoquinoline derivatives in which the adamantanefragment is connected to quinoline core through unbranched diamine linker wassynthesized (106a-d, 106i, 107a-107i and 107i). Eight out of ten synthetic derivatives exhibited better IC90 activity against CQ-sensitive D6 strain compared to CQ (1), sevenare more potent against multi-resistant C235 strain and one against MFQ-sensitive W2...strain than MFQ (14).",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Derivati diaminoalkiladamantana sa supstituisanim hinolinima kao inhibitori parazita Plasmodium falciparum i botulinum neurotoksina"
}
Terzić-Jovanović, N. (2017). Derivati diaminoalkiladamantana sa supstituisanim hinolinima kao inhibitori parazita Plasmodium falciparum i botulinum neurotoksina.
Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
Terzić-Jovanović N. Derivati diaminoalkiladamantana sa supstituisanim hinolinima kao inhibitori parazita Plasmodium falciparum i botulinum neurotoksina. Универзитет у Београду. 2017;
Terzić-Jovanović Nataša, "Derivati diaminoalkiladamantana sa supstituisanim hinolinima kao inhibitori parazita Plasmodium falciparum i botulinum neurotoksina" Универзитет у Београду (2017)

Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?

Terzić-Jovanović, Nataša; Konstantinović, Jelena M.; Tot, Mikloš; Burojević, Jovana; Đurković-Đaković, Olgica; Srbljanović, Jelena; Štajner, Tijana; Verbić, Tatjana; Zlatović, Mario; Machado, Marta; Albuquerque, Ines S.; Prudencio, Miguel; Sciotii, Richard J.; Pečić, Stevan; D'Alessandro, Sarah; Taramelli, Donatella; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2016)

TY  - JOUR
AU  - Terzić-Jovanović, Nataša
AU  - Konstantinović, Jelena M.
AU  - Tot, Mikloš
AU  - Burojević, Jovana
AU  - Đurković-Đaković, Olgica
AU  - Srbljanović, Jelena
AU  - Štajner, Tijana
AU  - Verbić, Tatjana
AU  - Zlatović, Mario
AU  - Machado, Marta
AU  - Albuquerque, Ines S.
AU  - Prudencio, Miguel
AU  - Sciotii, Richard J.
AU  - Pečić, Stevan
AU  - D'Alessandro, Sarah
AU  - Taramelli, Donatella
AU  - Šolaja, Bogdan A.
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/2036
AB  - The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 mu M and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 mu M). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 +/- 0.37 mu M). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?
VL  - 59
IS  - 1
SP  - 264
EP  - 281
DO  - 10.1021/acs.jmedchem.5b01374
ER  - 
@article{
author = "Terzić-Jovanović, Nataša and Konstantinović, Jelena M. and Tot, Mikloš and Burojević, Jovana and Đurković-Đaković, Olgica and Srbljanović, Jelena and Štajner, Tijana and Verbić, Tatjana and Zlatović, Mario and Machado, Marta and Albuquerque, Ines S. and Prudencio, Miguel and Sciotii, Richard J. and Pečić, Stevan and D'Alessandro, Sarah and Taramelli, Donatella and Šolaja, Bogdan A.",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/2036",
abstract = "The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 mu M and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 mu M). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 +/- 0.37 mu M). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?",
volume = "59",
number = "1",
pages = "264-281",
doi = "10.1021/acs.jmedchem.5b01374"
}
Terzić-Jovanović, N., Konstantinović, J. M., Tot, M., Burojević, J., Đurković-Đaković, O., Srbljanović, J., Štajner, T., Verbić, T., Zlatović, M., Machado, M., Albuquerque, I. S., Prudencio, M., Sciotii, R. J., Pečić, S., D'Alessandro, S., Taramelli, D.,& Šolaja, B. A. (2016). Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?.
Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 59(1), 264-281.
https://doi.org/10.1021/acs.jmedchem.5b01374
Terzić-Jovanović N, Konstantinović JM, Tot M, Burojević J, Đurković-Đaković O, Srbljanović J, Štajner T, Verbić T, Zlatović M, Machado M, Albuquerque IS, Prudencio M, Sciotii RJ, Pečić S, D'Alessandro S, Taramelli D, Šolaja BA. Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?. Journal of Medicinal Chemistry. 2016;59(1):264-281
Terzić-Jovanović Nataša, Konstantinović Jelena M., Tot Mikloš, Burojević Jovana, Đurković-Đaković Olgica, Srbljanović Jelena, Štajner Tijana, Verbić Tatjana, Zlatović Mario, Machado Marta, Albuquerque Ines S., Prudencio Miguel, Sciotii Richard J., Pečić Stevan, D'Alessandro Sarah, Taramelli Donatella, Šolaja Bogdan A., "Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?" Journal of Medicinal Chemistry, 59, no. 1 (2016):264-281,
https://doi.org/10.1021/acs.jmedchem.5b01374 .
1
19
16
20

Supplementary data for the article: Terzić, N.; Konstantinović, J.; Tot, M.; Burojević, J.; Djurković-Djaković, O.; Srbljanović, J.; Štajner, T.; Verbić, T.; Zlatović, M.; Machado, M.; et al. Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials? Journal of Medicinal Chemistry 2016, 59 (1), 264–281. https://doi.org/10.1021/acs.jmedchem.5b01374

Terzić-Jovanović, Nataša; Konstantinović, Jelena M.; Tot, Mikloš; Burojević, Jovana; Đurković-Đaković, Olgica; Srbljanović, Jelena; Štajner, Tijana; Verbić, Tatjana; Zlatović, Mario; Machado, Marta; Albuquerque, Ines S.; Prudencio, Miguel; Sciotii, Richard J.; Pečić, Stevan; D'Alessandro, Sarah; Taramelli, Donatella; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2016)

TY  - BOOK
AU  - Terzić-Jovanović, Nataša
AU  - Konstantinović, Jelena M.
AU  - Tot, Mikloš
AU  - Burojević, Jovana
AU  - Đurković-Đaković, Olgica
AU  - Srbljanović, Jelena
AU  - Štajner, Tijana
AU  - Verbić, Tatjana
AU  - Zlatović, Mario
AU  - Machado, Marta
AU  - Albuquerque, Ines S.
AU  - Prudencio, Miguel
AU  - Sciotii, Richard J.
AU  - Pečić, Stevan
AU  - D'Alessandro, Sarah
AU  - Taramelli, Donatella
AU  - Šolaja, Bogdan A.
PY  - 2016
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3606
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Supplementary data for the article: Terzić, N.; Konstantinović, J.; Tot, M.; Burojević, J.; Djurković-Djaković, O.; Srbljanović, J.; Štajner, T.; Verbić, T.; Zlatović, M.; Machado, M.; et al. Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials? Journal of Medicinal Chemistry 2016, 59 (1), 264–281. https://doi.org/10.1021/acs.jmedchem.5b01374
ER  - 
@book{
author = "Terzić-Jovanović, Nataša and Konstantinović, Jelena M. and Tot, Mikloš and Burojević, Jovana and Đurković-Đaković, Olgica and Srbljanović, Jelena and Štajner, Tijana and Verbić, Tatjana and Zlatović, Mario and Machado, Marta and Albuquerque, Ines S. and Prudencio, Miguel and Sciotii, Richard J. and Pečić, Stevan and D'Alessandro, Sarah and Taramelli, Donatella and Šolaja, Bogdan A.",
year = "2016",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/3606",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Supplementary data for the article: Terzić, N.; Konstantinović, J.; Tot, M.; Burojević, J.; Djurković-Djaković, O.; Srbljanović, J.; Štajner, T.; Verbić, T.; Zlatović, M.; Machado, M.; et al. Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials? Journal of Medicinal Chemistry 2016, 59 (1), 264–281. https://doi.org/10.1021/acs.jmedchem.5b01374"
}
Terzić-Jovanović, N., Konstantinović, J. M., Tot, M., Burojević, J., Đurković-Đaković, O., Srbljanović, J., Štajner, T., Verbić, T., Zlatović, M., Machado, M., Albuquerque, I. S., Prudencio, M., Sciotii, R. J., Pečić, S., D'Alessandro, S., Taramelli, D.,& Šolaja, B. A. (2016). Supplementary data for the article: Terzić, N.; Konstantinović, J.; Tot, M.; Burojević, J.; Djurković-Djaković, O.; Srbljanović, J.; Štajner, T.; Verbić, T.; Zlatović, M.; Machado, M.; et al. Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials? Journal of Medicinal Chemistry 2016, 59 (1), 264–281. https://doi.org/10.1021/acs.jmedchem.5b01374.
Journal of Medicinal Chemistry
Amer Chemical Soc, Washington..
Terzić-Jovanović N, Konstantinović JM, Tot M, Burojević J, Đurković-Đaković O, Srbljanović J, Štajner T, Verbić T, Zlatović M, Machado M, Albuquerque IS, Prudencio M, Sciotii RJ, Pečić S, D'Alessandro S, Taramelli D, Šolaja BA. Supplementary data for the article: Terzić, N.; Konstantinović, J.; Tot, M.; Burojević, J.; Djurković-Djaković, O.; Srbljanović, J.; Štajner, T.; Verbić, T.; Zlatović, M.; Machado, M.; et al. Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials? Journal of Medicinal Chemistry 2016, 59 (1), 264–281. https://doi.org/10.1021/acs.jmedchem.5b01374. Journal of Medicinal Chemistry. 2016;
Terzić-Jovanović Nataša, Konstantinović Jelena M., Tot Mikloš, Burojević Jovana, Đurković-Đaković Olgica, Srbljanović Jelena, Štajner Tijana, Verbić Tatjana, Zlatović Mario, Machado Marta, Albuquerque Ines S., Prudencio Miguel, Sciotii Richard J., Pečić Stevan, D'Alessandro Sarah, Taramelli Donatella, Šolaja Bogdan A., "Supplementary data for the article: Terzić, N.; Konstantinović, J.; Tot, M.; Burojević, J.; Djurković-Djaković, O.; Srbljanović, J.; Štajner, T.; Verbić, T.; Zlatović, M.; Machado, M.; et al. Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials? Journal of Medicinal Chemistry 2016, 59 (1), 264–281. https://doi.org/10.1021/acs.jmedchem.5b01374" Journal of Medicinal Chemistry (2016)

Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters

Šegan, Sandra B.; Terzić-Jovanović, Nataša; Milojković-Opsenica, Dušanka; Trifković, Jelena; Šolaja, Bogdan A.; Opsenica, Dejan M.

(Elsevier Science Bv, Amsterdam, 2014)

TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Terzić-Jovanović, Nataša
AU  - Milojković-Opsenica, Dušanka
AU  - Trifković, Jelena
AU  - Šolaja, Bogdan A.
AU  - Opsenica, Dejan M.
PY  - 2014
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1795
AB  - The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO). (c) 2014 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Bv, Amsterdam
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters
VL  - 97
SP  - 178
EP  - 183
DO  - 10.1016/j.jpba.2014.04.029
ER  - 
@article{
author = "Šegan, Sandra B. and Terzić-Jovanović, Nataša and Milojković-Opsenica, Dušanka and Trifković, Jelena and Šolaja, Bogdan A. and Opsenica, Dejan M.",
year = "2014",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1795",
abstract = "The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO). (c) 2014 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Bv, Amsterdam",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters",
volume = "97",
pages = "178-183",
doi = "10.1016/j.jpba.2014.04.029"
}
Šegan, S. B., Terzić-Jovanović, N., Milojković-Opsenica, D., Trifković, J., Šolaja, B. A.,& Opsenica, D. M. (2014). Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters.
Journal of Pharmaceutical and Biomedical Analysis
Elsevier Science Bv, Amsterdam., 97, 178-183.
https://doi.org/10.1016/j.jpba.2014.04.029
Šegan SB, Terzić-Jovanović N, Milojković-Opsenica D, Trifković J, Šolaja BA, Opsenica DM. Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. Journal of Pharmaceutical and Biomedical Analysis. 2014;97:178-183
Šegan Sandra B., Terzić-Jovanović Nataša, Milojković-Opsenica Dušanka, Trifković Jelena, Šolaja Bogdan A., Opsenica Dejan M., "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters" Journal of Pharmaceutical and Biomedical Analysis, 97 (2014):178-183,
https://doi.org/10.1016/j.jpba.2014.04.029 .
7
9
9

An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes

Cvijetić, Ilija; Zizak, Zeljko P.; Stanojković, Tatjana; Juranić, Zorica D.; Terzić-Jovanović, Nataša; Opsenica, Igor; Opsenica, Dejan M.; Juranić, Ivan O.; Drakulić, Branko J.

(Elsevier France-Editions Scientifiques Medicales Elsevier, Paris, 2010)

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Zizak, Zeljko P.
AU  - Stanojković, Tatjana
AU  - Juranić, Zorica D.
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Igor
AU  - Opsenica, Dejan M.
AU  - Juranić, Ivan O.
AU  - Drakulić, Branko J.
PY  - 2010
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1120
AB  - An alignment-free 3D QSAR study on antiproliferative activity of the thirty-three 1,2,4,5-tetraoxane derivatives toward two human dedifferentiated cell lines was reported. GRIND methodology, where descriptors are derived from GRID molecular interaction fields (MIF), were used It was found that pharmacophoric pattern attributed to the most potent derivatives Include amido NH of the primary or secondary amide, and the acetoxy fragments at positions 7 and 12 of steroid core which are, along with the tetraoxane ring, common for all studied compounds. Independently, simple multiple regression model obtained by using the whole-molecular properties, confirmed that the hydrophobicity and the H-bond donor properties are the main parameters influencing potency of compounds toward human cervix carcinoma (HeLa) and human malignant melanoma (FemX) cell lines Corollary, similar structural motifs are found to be Important for the potency toward both examined cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes
VL  - 45
IS  - 10
SP  - 4570
EP  - 4577
DO  - 10.1016/j.ejmech.2010.07.019
ER  - 
@article{
author = "Cvijetić, Ilija and Zizak, Zeljko P. and Stanojković, Tatjana and Juranić, Zorica D. and Terzić-Jovanović, Nataša and Opsenica, Igor and Opsenica, Dejan M. and Juranić, Ivan O. and Drakulić, Branko J.",
year = "2010",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/1120",
abstract = "An alignment-free 3D QSAR study on antiproliferative activity of the thirty-three 1,2,4,5-tetraoxane derivatives toward two human dedifferentiated cell lines was reported. GRIND methodology, where descriptors are derived from GRID molecular interaction fields (MIF), were used It was found that pharmacophoric pattern attributed to the most potent derivatives Include amido NH of the primary or secondary amide, and the acetoxy fragments at positions 7 and 12 of steroid core which are, along with the tetraoxane ring, common for all studied compounds. Independently, simple multiple regression model obtained by using the whole-molecular properties, confirmed that the hydrophobicity and the H-bond donor properties are the main parameters influencing potency of compounds toward human cervix carcinoma (HeLa) and human malignant melanoma (FemX) cell lines Corollary, similar structural motifs are found to be Important for the potency toward both examined cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes",
volume = "45",
number = "10",
pages = "4570-4577",
doi = "10.1016/j.ejmech.2010.07.019"
}
Cvijetić, I., Zizak, Z. P., Stanojković, T., Juranić, Z. D., Terzić-Jovanović, N., Opsenica, I., Opsenica, D. M., Juranić, I. O.,& Drakulić, B. J. (2010). An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes.
European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 45(10), 4570-4577.
https://doi.org/10.1016/j.ejmech.2010.07.019
Cvijetić I, Zizak ZP, Stanojković T, Juranić ZD, Terzić-Jovanović N, Opsenica I, Opsenica DM, Juranić IO, Drakulić BJ. An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes. European Journal of Medicinal Chemistry. 2010;45(10):4570-4577
Cvijetić Ilija, Zizak Zeljko P., Stanojković Tatjana, Juranić Zorica D., Terzić-Jovanović Nataša, Opsenica Igor, Opsenica Dejan M., Juranić Ivan O., Drakulić Branko J., "An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes" European Journal of Medicinal Chemistry, 45, no. 10 (2010):4570-4577,
https://doi.org/10.1016/j.ejmech.2010.07.019 .
16
16
17

Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A

Šolaja, Bogdan A.; Opsenica, Dejan M.; Smith, Kirsten S.; Milhous, Wilbur K.; Terzić-Jovanović, Nataša; Opsenica, Igor; Burnett, James C.; Nuss, Jon; Gussio, Rick; Bavari, Sina

(Amer Chemical Soc, Washington, 2008)

TY  - JOUR
AU  - Šolaja, Bogdan A.
AU  - Opsenica, Dejan M.
AU  - Smith, Kirsten S.
AU  - Milhous, Wilbur K.
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Igor
AU  - Burnett, James C.
AU  - Nuss, Jon
AU  - Gussio, Rick
AU  - Bavari, Sina
PY  - 2008
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/961
AB  - We report on the initial result of the coupling of 4-amino7-chloroquinoline with steroidal and adamantane constituents to provide small molecules with excellent in vitro antimalarial activities (IC90 (W2) down to 6.74 nM). The same entities also inhibit the botulinum neurotoxin serotype A light chain metalloprotease at low nlicromolar levels (7-3 1 yM). Interestingly. structural features imparting increased antimalarial activity also provide increased inetalloprotease inhibition, thus allowing for simultaneous compound optimizations against distinct targets.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A
VL  - 51
IS  - 15
SP  - 4388
EP  - 4391
DO  - 10.1021/jm800737y
ER  - 
@article{
author = "Šolaja, Bogdan A. and Opsenica, Dejan M. and Smith, Kirsten S. and Milhous, Wilbur K. and Terzić-Jovanović, Nataša and Opsenica, Igor and Burnett, James C. and Nuss, Jon and Gussio, Rick and Bavari, Sina",
year = "2008",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/961",
abstract = "We report on the initial result of the coupling of 4-amino7-chloroquinoline with steroidal and adamantane constituents to provide small molecules with excellent in vitro antimalarial activities (IC90 (W2) down to 6.74 nM). The same entities also inhibit the botulinum neurotoxin serotype A light chain metalloprotease at low nlicromolar levels (7-3 1 yM). Interestingly. structural features imparting increased antimalarial activity also provide increased inetalloprotease inhibition, thus allowing for simultaneous compound optimizations against distinct targets.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A",
volume = "51",
number = "15",
pages = "4388-4391",
doi = "10.1021/jm800737y"
}
Šolaja, B. A., Opsenica, D. M., Smith, K. S., Milhous, W. K., Terzić-Jovanović, N., Opsenica, I., Burnett, J. C., Nuss, J., Gussio, R.,& Bavari, S. (2008). Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A.
Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 51(15), 4388-4391.
https://doi.org/10.1021/jm800737y
Šolaja BA, Opsenica DM, Smith KS, Milhous WK, Terzić-Jovanović N, Opsenica I, Burnett JC, Nuss J, Gussio R, Bavari S. Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A. Journal of Medicinal Chemistry. 2008;51(15):4388-4391
Šolaja Bogdan A., Opsenica Dejan M., Smith Kirsten S., Milhous Wilbur K., Terzić-Jovanović Nataša, Opsenica Igor, Burnett James C., Nuss Jon, Gussio Rick, Bavari Sina, "Novel 4-aminoquinolines active against chloroquine-resistant and sensitive P. falciparum strains that also inhibit botulinum serotype A" Journal of Medicinal Chemistry, 51, no. 15 (2008):4388-4391,
https://doi.org/10.1021/jm800737y .
3
41
45
49

Mixed tetraoxanes containing the acetone subunit as antimalarials

Opsenica, Dejan M.; Terzić-Jovanović, Nataša; Smith, Philip L.; Yang, Youngsun; Anova, Lalaine; Smith, Kirsten S.; Šolaja, Bogdan A.

(Pergamon-Elsevier Science Ltd, Oxford, 2008)

TY  - JOUR
AU  - Opsenica, Dejan M.
AU  - Terzić-Jovanović, Nataša
AU  - Smith, Philip L.
AU  - Yang, Youngsun
AU  - Anova, Lalaine
AU  - Smith, Kirsten S.
AU  - Šolaja, Bogdan A.
PY  - 2008
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/957
AB  - Eleven new tetraoxanes possessing cholic acid-derived carrier and isopropylidene moiety were synthesized and were tested in vitro and in vivo. In vitro screening revealed that nine of them were more potent against CQ-resistant W2 than CQ-susceptible D6 strain and that two of them were equally or more potent than artemisinin and mefloquine against multi- drug resistant TM91C235 strain. Amine 8 cured all mice at the dose of 160 mg/kg/day, while the anilide 9 exhibited MCD  lt = 20 mg/kg/day. The diol 13 was most potent antiproliferative with GI(50), TGI, LC50 MG_MID 0.98 mu M, 3.80 mu M, 11.22 mu M, respectively. All tested compounds showed no toxic effects. (c) 2008 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry
T1  - Mixed tetraoxanes containing the acetone subunit as antimalarials
VL  - 16
IS  - 14
SP  - 7039
EP  - 7045
DO  - 10.1016/j.bmc.2008.05.017
ER  - 
@article{
author = "Opsenica, Dejan M. and Terzić-Jovanović, Nataša and Smith, Philip L. and Yang, Youngsun and Anova, Lalaine and Smith, Kirsten S. and Šolaja, Bogdan A.",
year = "2008",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/957",
abstract = "Eleven new tetraoxanes possessing cholic acid-derived carrier and isopropylidene moiety were synthesized and were tested in vitro and in vivo. In vitro screening revealed that nine of them were more potent against CQ-resistant W2 than CQ-susceptible D6 strain and that two of them were equally or more potent than artemisinin and mefloquine against multi- drug resistant TM91C235 strain. Amine 8 cured all mice at the dose of 160 mg/kg/day, while the anilide 9 exhibited MCD  lt = 20 mg/kg/day. The diol 13 was most potent antiproliferative with GI(50), TGI, LC50 MG_MID 0.98 mu M, 3.80 mu M, 11.22 mu M, respectively. All tested compounds showed no toxic effects. (c) 2008 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry",
title = "Mixed tetraoxanes containing the acetone subunit as antimalarials",
volume = "16",
number = "14",
pages = "7039-7045",
doi = "10.1016/j.bmc.2008.05.017"
}
Opsenica, D. M., Terzić-Jovanović, N., Smith, P. L., Yang, Y., Anova, L., Smith, K. S.,& Šolaja, B. A. (2008). Mixed tetraoxanes containing the acetone subunit as antimalarials.
Bioorganic and Medicinal Chemistry
Pergamon-Elsevier Science Ltd, Oxford., 16(14), 7039-7045.
https://doi.org/10.1016/j.bmc.2008.05.017
Opsenica DM, Terzić-Jovanović N, Smith PL, Yang Y, Anova L, Smith KS, Šolaja BA. Mixed tetraoxanes containing the acetone subunit as antimalarials. Bioorganic and Medicinal Chemistry. 2008;16(14):7039-7045
Opsenica Dejan M., Terzić-Jovanović Nataša, Smith Philip L., Yang Youngsun, Anova Lalaine, Smith Kirsten S., Šolaja Bogdan A., "Mixed tetraoxanes containing the acetone subunit as antimalarials" Bioorganic and Medicinal Chemistry, 16, no. 14 (2008):7039-7045,
https://doi.org/10.1016/j.bmc.2008.05.017 .
13
15
15

Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives

Terzić-Jovanović, Nataša; Opsenica, Dejan M.; Milić, Dragana; Tinant, Bernard; Smith, Kirsten S.; Milhous, Wilbur K.; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2007)

TY  - JOUR
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan M.
AU  - Milić, Dragana
AU  - Tinant, Bernard
AU  - Smith, Kirsten S.
AU  - Milhous, Wilbur K.
AU  - Šolaja, Bogdan A.
PY  - 2007
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/882
AB  - The synthesis of deoxycholic acid (DCA)- and cholic acid (CA)-derived mixed tetraoxanes revealed that N-(2-dimethylamino)ethyl derivatives are potent antimalarials in vitro and in vivo. The tetraoxanes presented in this paper are dual inhibitors: besides curing mice in vivo without observed toxic effects, they kill cancer cell lines at very low concentrations. For example, DCA and CA derivatives 16 and 25 cured 3/5 (160 mg/kg/day) and 2/5 (40 mg/kg/day, MTD  gt 960 mg/kg), respectively, and they were extremely active against melanoma LOX IMVI cancer, LC50 = 22 nM and 69 nM, respectively.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives
VL  - 50
IS  - 21
SP  - 5118
EP  - 5127
DO  - 10.1021/jm070684m
ER  - 
@article{
author = "Terzić-Jovanović, Nataša and Opsenica, Dejan M. and Milić, Dragana and Tinant, Bernard and Smith, Kirsten S. and Milhous, Wilbur K. and Šolaja, Bogdan A.",
year = "2007",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/882",
abstract = "The synthesis of deoxycholic acid (DCA)- and cholic acid (CA)-derived mixed tetraoxanes revealed that N-(2-dimethylamino)ethyl derivatives are potent antimalarials in vitro and in vivo. The tetraoxanes presented in this paper are dual inhibitors: besides curing mice in vivo without observed toxic effects, they kill cancer cell lines at very low concentrations. For example, DCA and CA derivatives 16 and 25 cured 3/5 (160 mg/kg/day) and 2/5 (40 mg/kg/day, MTD  gt 960 mg/kg), respectively, and they were extremely active against melanoma LOX IMVI cancer, LC50 = 22 nM and 69 nM, respectively.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives",
volume = "50",
number = "21",
pages = "5118-5127",
doi = "10.1021/jm070684m"
}
Terzić-Jovanović, N., Opsenica, D. M., Milić, D., Tinant, B., Smith, K. S., Milhous, W. K.,& Šolaja, B. A. (2007). Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives.
Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 50(21), 5118-5127.
https://doi.org/10.1021/jm070684m
Terzić-Jovanović N, Opsenica DM, Milić D, Tinant B, Smith KS, Milhous WK, Šolaja BA. Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives. Journal of Medicinal Chemistry. 2007;50(21):5118-5127
Terzić-Jovanović Nataša, Opsenica Dejan M., Milić Dragana, Tinant Bernard, Smith Kirsten S., Milhous Wilbur K., Šolaja Bogdan A., "Deoxycholic acid-derived tetraoxane antimalarials and antiproliferatives" Journal of Medicinal Chemistry, 50, no. 21 (2007):5118-5127,
https://doi.org/10.1021/jm070684m .
60
71
75

Tetraoxane antimalarials and their reaction with Fe(II)

Opsenica, Igor; Terzić-Jovanović, Nataša; Opsenica, Dejan M.; Angelovski, Goran; Lehnig, Manfred; Eilbracht, Peter; Tinant, Bernard; Juranić, Zorica D.; Smith, Kirsten S.; Yang, Young S.; Diaz, Damaris S.; Smith, Philip L.; Milhous, Wilbur K.; Dokovic, Dejan; Šolaja, Bogdan A.

(Amer Chemical Soc, Washington, 2006)

TY  - JOUR
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan M.
AU  - Angelovski, Goran
AU  - Lehnig, Manfred
AU  - Eilbracht, Peter
AU  - Tinant, Bernard
AU  - Juranić, Zorica D.
AU  - Smith, Kirsten S.
AU  - Yang, Young S.
AU  - Diaz, Damaris S.
AU  - Smith, Philip L.
AU  - Milhous, Wilbur K.
AU  - Dokovic, Dejan
AU  - Šolaja, Bogdan A.
PY  - 2006
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/783
AB  - Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Tetraoxane antimalarials and their reaction with Fe(II)
VL  - 49
IS  - 13
SP  - 3790
EP  - 3799
DO  - 10.1021/jm050966r
ER  - 
@article{
author = "Opsenica, Igor and Terzić-Jovanović, Nataša and Opsenica, Dejan M. and Angelovski, Goran and Lehnig, Manfred and Eilbracht, Peter and Tinant, Bernard and Juranić, Zorica D. and Smith, Kirsten S. and Yang, Young S. and Diaz, Damaris S. and Smith, Philip L. and Milhous, Wilbur K. and Dokovic, Dejan and Šolaja, Bogdan A.",
year = "2006",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/783",
abstract = "Mixed tetraoxanes 5a and 13 synthesized from cholic acid and 4-oxocyclohexanecarboxylic acid were as active as artemisinin against chloroquine-susceptible, chloroquine-resistant, and multidrug-resistant Plasmodium falciparum strains (IC50, IC90). Most active 13 is metabolically stable in in vitro metabolism studies. In vivo studies on tetraoxanes with a C(4'') methyl group afforded compound 15, which cured 4/5 mice at 600 and 200 mg, kg(-1), day(-1), and 2/5 mice at 50 mg, kg(-1), day(-1), showing no toxic effects. Tetraoxane 19 was an extremely active antiproliferative with LC50 of 17 nM and maximum tolerated dose of 400 mg/kg. In Fe(II)-induced scission of tetraoxane antimalarials only RO center dot radicals were detected by EPR experiments. This finding and the indication of Fe(IV)=O species led us to propose that RO center dot radicals are probably capable of inducing the parasite's death. Our results suggest that C radicals are possibly not the only lethal species derived from peroxide prodrug antimalarials, as currently believed.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Tetraoxane antimalarials and their reaction with Fe(II)",
volume = "49",
number = "13",
pages = "3790-3799",
doi = "10.1021/jm050966r"
}
Opsenica, I., Terzić-Jovanović, N., Opsenica, D. M., Angelovski, G., Lehnig, M., Eilbracht, P., Tinant, B., Juranić, Z. D., Smith, K. S., Yang, Y. S., Diaz, D. S., Smith, P. L., Milhous, W. K., Dokovic, D.,& Šolaja, B. A. (2006). Tetraoxane antimalarials and their reaction with Fe(II).
Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 49(13), 3790-3799.
https://doi.org/10.1021/jm050966r
Opsenica I, Terzić-Jovanović N, Opsenica DM, Angelovski G, Lehnig M, Eilbracht P, Tinant B, Juranić ZD, Smith KS, Yang YS, Diaz DS, Smith PL, Milhous WK, Dokovic D, Šolaja BA. Tetraoxane antimalarials and their reaction with Fe(II). Journal of Medicinal Chemistry. 2006;49(13):3790-3799
Opsenica Igor, Terzić-Jovanović Nataša, Opsenica Dejan M., Angelovski Goran, Lehnig Manfred, Eilbracht Peter, Tinant Bernard, Juranić Zorica D., Smith Kirsten S., Yang Young S., Diaz Damaris S., Smith Philip L., Milhous Wilbur K., Dokovic Dejan, Šolaja Bogdan A., "Tetraoxane antimalarials and their reaction with Fe(II)" Journal of Medicinal Chemistry, 49, no. 13 (2006):3790-3799,
https://doi.org/10.1021/jm050966r .
44
55
57

Reductive cleavage of 1,2,4,5-tetraoxane antimalarials

Šolaja, Bogdan A.; Terzić-Jovanović, Nataša; Smith, K; Opsenica, Dejan M.; Smith, PL; Milhous, WK

(Amer Chemical Soc, Washington, 2005)

TY  - CONF
AU  - Šolaja, Bogdan A.
AU  - Terzić-Jovanović, Nataša
AU  - Smith, K
AU  - Opsenica, Dejan M.
AU  - Smith, PL
AU  - Milhous, WK
PY  - 2005
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/774
PB  - Amer Chemical Soc, Washington
C3  - ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
T1  - Reductive cleavage of 1,2,4,5-tetraoxane antimalarials
VL  - 230
ER  - 
@conference{
author = "Šolaja, Bogdan A. and Terzić-Jovanović, Nataša and Smith, K and Opsenica, Dejan M. and Smith, PL and Milhous, WK",
year = "2005",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/774",
publisher = "Amer Chemical Soc, Washington",
journal = "ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY",
title = "Reductive cleavage of 1,2,4,5-tetraoxane antimalarials",
volume = "230"
}
Šolaja, B. A., Terzić-Jovanović, N., Smith, K., Opsenica, D. M., Smith, P.,& Milhous, W. (2005). Reductive cleavage of 1,2,4,5-tetraoxane antimalarials.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY
Amer Chemical Soc, Washington., 230.
Šolaja BA, Terzić-Jovanović N, Smith K, Opsenica DM, Smith P, Milhous W. Reductive cleavage of 1,2,4,5-tetraoxane antimalarials. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY. 2005;230
Šolaja Bogdan A., Terzić-Jovanović Nataša, Smith K, Opsenica Dejan M., Smith PL, Milhous WK, "Reductive cleavage of 1,2,4,5-tetraoxane antimalarials" ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 230 (2005)

7,8,15,16-tetraoxa-dispiro[5.2.5.2]hexadecane-3-carboxylic acid derivatives and their antimalarial activity

Opsenica, Igor; Terzić-Jovanović, Nataša; Opsenica, Dejan M.; Milhous, WK; Šolaja, Bogdan A.

(Serbian Chemical Soc, Belgrade, 2004)

TY  - JOUR
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Dejan M.
AU  - Milhous, WK
AU  - Šolaja, Bogdan A.
PY  - 2004
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/680
AB  - Several C2 symmetrical mixed tetraoxanes were prepared starting from a gemdihydroperoxide and a ketone. The obtained tetraoxanes showed pronounced antimalarial activity against P falciparum chloroquine resistant W2 and chloroquine susceptible D6 strains, with N-(2-dimethylamino)ethyl-7,8,15,16-tetraoxa-dispiro[5.2.5.2]hexadecaric-3-carboxamide being as active as artermisinin.
AB  - U ovom radu prikazana je sinteza serije C2 mešovitih tetraoksana polazeći od gem-dihidroperoksida cikloheksanona. Dobijenim derivatima ispitana je in vitro aktivnost prema W2 i D6 sojevima P. falciparum. Utvrđeno je da derivat N-(2-dimetilamino)etil 7,8,15,16-tetraoksa-dispiroŠ5.2.5.2Ćheksadekan-3-karboksamid pokazuje aktivnost vrlo blisku aktivnosti poznatog antimalarika artemizinina.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - 7,8,15,16-tetraoxa-dispiro[5.2.5.2]hexadecane-3-carboxylic acid derivatives and their antimalarial activity
T1  - Antimalarijska aktivnost derivata 7,8,15,16-tetraoksa-dispiro5.2.5.2heksadekan-3-karboksilne kiseline
VL  - 69
IS  - 11
SP  - 919
EP  - 922
DO  - 10.2298/JSC0411919O
ER  - 
@article{
author = "Opsenica, Igor and Terzić-Jovanović, Nataša and Opsenica, Dejan M. and Milhous, WK and Šolaja, Bogdan A.",
year = "2004",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/680",
abstract = "Several C2 symmetrical mixed tetraoxanes were prepared starting from a gemdihydroperoxide and a ketone. The obtained tetraoxanes showed pronounced antimalarial activity against P falciparum chloroquine resistant W2 and chloroquine susceptible D6 strains, with N-(2-dimethylamino)ethyl-7,8,15,16-tetraoxa-dispiro[5.2.5.2]hexadecaric-3-carboxamide being as active as artermisinin., U ovom radu prikazana je sinteza serije C2 mešovitih tetraoksana polazeći od gem-dihidroperoksida cikloheksanona. Dobijenim derivatima ispitana je in vitro aktivnost prema W2 i D6 sojevima P. falciparum. Utvrđeno je da derivat N-(2-dimetilamino)etil 7,8,15,16-tetraoksa-dispiroŠ5.2.5.2Ćheksadekan-3-karboksamid pokazuje aktivnost vrlo blisku aktivnosti poznatog antimalarika artemizinina.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "7,8,15,16-tetraoxa-dispiro[5.2.5.2]hexadecane-3-carboxylic acid derivatives and their antimalarial activity, Antimalarijska aktivnost derivata 7,8,15,16-tetraoksa-dispiro5.2.5.2heksadekan-3-karboksilne kiseline",
volume = "69",
number = "11",
pages = "919-922",
doi = "10.2298/JSC0411919O"
}
Opsenica, I., Terzić-Jovanović, N., Opsenica, D. M., Milhous, W.,& Šolaja, B. A. (2004). Antimalarijska aktivnost derivata 7,8,15,16-tetraoksa-dispiro5.2.5.2heksadekan-3-karboksilne kiseline.
Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 69(11), 919-922.
https://doi.org/10.2298/JSC0411919O
Opsenica I, Terzić-Jovanović N, Opsenica DM, Milhous W, Šolaja BA. Antimalarijska aktivnost derivata 7,8,15,16-tetraoksa-dispiro5.2.5.2heksadekan-3-karboksilne kiseline. Journal of the Serbian Chemical Society. 2004;69(11):919-922
Opsenica Igor, Terzić-Jovanović Nataša, Opsenica Dejan M., Milhous WK, Šolaja Bogdan A., "Antimalarijska aktivnost derivata 7,8,15,16-tetraoksa-dispiro5.2.5.2heksadekan-3-karboksilne kiseline" Journal of the Serbian Chemical Society, 69, no. 11 (2004):919-922,
https://doi.org/10.2298/JSC0411919O .
3
9
15
14

Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity

Šolaja, Bogdan A.; Terzić-Jovanović, Nataša; Pocsfalvi, G; Gerena, L; Tinant, B; Opsenica, Dejan M.; Milhous, WK

(Amer Chemical Soc, Washington, 2002)

TY  - JOUR
AU  - Šolaja, Bogdan A.
AU  - Terzić-Jovanović, Nataša
AU  - Pocsfalvi, G
AU  - Gerena, L
AU  - Tinant, B
AU  - Opsenica, Dejan M.
AU  - Milhous, WK
PY  - 2002
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/500
AB  - Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 muM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further transformed into corresponding acids and amides.
PB  - Amer Chemical Soc, Washington
T2  - Journal of Medicinal Chemistry
T1  - Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity
VL  - 45
IS  - 16
SP  - 3331
EP  - 3336
DO  - 10.1021/jm020891g
ER  - 
@article{
author = "Šolaja, Bogdan A. and Terzić-Jovanović, Nataša and Pocsfalvi, G and Gerena, L and Tinant, B and Opsenica, Dejan M. and Milhous, WK",
year = "2002",
url = "http://cherry.chem.bg.ac.rs/handle/123456789/500",
abstract = "Mixed 1,2,4,5-tetraoxanes possessing simple spirocycloalkane and spirocholic acid-derived substituents were prepared and shown to have significantly higher in vitro antimalarial activity than bis-substituted tetraoxanes. Out of 41 synthesized tetraoxanes, 12 were in vitro more potent against Plasmodium falciparum chloroquine-resistant W2 clone than artemisinin, and the most potent one was 2.4 times as active as arteether. In addition, 9 compounds exhibit higher activity than chloroquine against P. falciparum chloroquine-susceptible D6 clone. Cytotoxicity was assessed for most active compounds against the Vero cell line, showing a cytotoxicity/antimalarial potency ratio of 1/(1400-9500). For the first time, tetraoxanes were screened against Mycobacterium tuberculosis with MICs as low as 4.73 muM against H37Rv strain. Mixed tetraoxanes were synthesized in a simple procedure from cholic acid methyl esters by direct coupling of steroidal gem-dihydroperoxide to simple ketones and further transformed into corresponding acids and amides.",
publisher = "Amer Chemical Soc, Washington",
journal = "Journal of Medicinal Chemistry",
title = "Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity",
volume = "45",
number = "16",
pages = "3331-3336",
doi = "10.1021/jm020891g"
}
Šolaja, B. A., Terzić-Jovanović, N., Pocsfalvi, G., Gerena, L., Tinant, B., Opsenica, D. M.,& Milhous, W. (2002). Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity.
Journal of Medicinal Chemistry
Amer Chemical Soc, Washington., 45(16), 3331-3336.
https://doi.org/10.1021/jm020891g
Šolaja BA, Terzić-Jovanović N, Pocsfalvi G, Gerena L, Tinant B, Opsenica DM, Milhous W. Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity. Journal of Medicinal Chemistry. 2002;45(16):3331-3336
Šolaja Bogdan A., Terzić-Jovanović Nataša, Pocsfalvi G, Gerena L, Tinant B, Opsenica Dejan M., Milhous WK, "Mixed steroidal 1,2,4,5-tetraoxanes: Antimalarial and antimycobacterial activity" Journal of Medicinal Chemistry, 45, no. 16 (2002):3331-3336,
https://doi.org/10.1021/jm020891g .
3
87
103
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