Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes

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info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172016/RS//

Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes (en)
Синтеза, моделовање, физичко-хемијске и биолошке особине органских једињења и одговарајућих комплекса метала (sr)
Sinteza, modelovanje, fizičko-hemijske i biološke osobine organskih jedinjenja i odgovarajućih kompleksa metala (sr_RS)
Authors

Publications

Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study

Maksimović, Jelena P.; Tosović, Jelena; Pagnacco, Maja

(Chemical Society of Japan, 2020)

TY  - JOUR
AU  - Maksimović, Jelena P.
AU  - Tosović, Jelena
AU  - Pagnacco, Maja
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3776
AB  - The pyrocatechol inhibitory effect on the oscillatory Bray-Liebhafsky (BL) reaction is reported. Obtained results are compared with those available in the literature (R. Cervellati et al, Helvetica Chimica Acta 2001) for Briggs-Rauscher (BR) reaction with pyrocatechol addition. The two orders of magnitude larger calibration curve slope obtained in BR in comparison to BL reaction, suggests that different reactions are responsible for inhibitory effects in these systems. The potential explanation of pyrocatechol behavior is given by employing the ultraviolet-visible (UV/VIS) spectroscopy, density functional theory, and coupled cluster computational methods. The last two were employed for the first time to discover potential candidates among unstable chemical species HIO, HIO2, I2O, HOO•, HO•, IO•, IO2•, and I• of the BL (and BR) system for reaction with pyrocatechol. The calculated reaction rate constants for the hydrogen atom transfer reactions between pyrocatechol and free radical intermediates indicate the following order of reactivity: HO• > IO• > HOO• > IO2•. The same order of reactivity is also observed in the case of a thermodynamic investigation. In addition, kinetic insight indicates that the inhibitory behavior of pyrocatechol could not be explained with one particular chemical reaction in the BL (or in the BR) oscillatory system.
PB  - Chemical Society of Japan
T2  - Bulletin of the Chemical Society of Japan
T1  - Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study
VL  - 93
IS  - 5
SP  - 676
EP  - 684
DO  - 10.1246/bcsj.20190296
ER  - 
@article{
author = "Maksimović, Jelena P. and Tosović, Jelena and Pagnacco, Maja",
year = "2020",
abstract = "The pyrocatechol inhibitory effect on the oscillatory Bray-Liebhafsky (BL) reaction is reported. Obtained results are compared with those available in the literature (R. Cervellati et al, Helvetica Chimica Acta 2001) for Briggs-Rauscher (BR) reaction with pyrocatechol addition. The two orders of magnitude larger calibration curve slope obtained in BR in comparison to BL reaction, suggests that different reactions are responsible for inhibitory effects in these systems. The potential explanation of pyrocatechol behavior is given by employing the ultraviolet-visible (UV/VIS) spectroscopy, density functional theory, and coupled cluster computational methods. The last two were employed for the first time to discover potential candidates among unstable chemical species HIO, HIO2, I2O, HOO•, HO•, IO•, IO2•, and I• of the BL (and BR) system for reaction with pyrocatechol. The calculated reaction rate constants for the hydrogen atom transfer reactions between pyrocatechol and free radical intermediates indicate the following order of reactivity: HO• > IO• > HOO• > IO2•. The same order of reactivity is also observed in the case of a thermodynamic investigation. In addition, kinetic insight indicates that the inhibitory behavior of pyrocatechol could not be explained with one particular chemical reaction in the BL (or in the BR) oscillatory system.",
publisher = "Chemical Society of Japan",
journal = "Bulletin of the Chemical Society of Japan",
title = "Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study",
volume = "93",
number = "5",
pages = "676-684",
doi = "10.1246/bcsj.20190296"
}
Maksimović, J. P., Tosović, J.,& Pagnacco, M.. (2020). Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study. in Bulletin of the Chemical Society of Japan
Chemical Society of Japan., 93(5), 676-684.
https://doi.org/10.1246/bcsj.20190296
Maksimović JP, Tosović J, Pagnacco M. Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study. in Bulletin of the Chemical Society of Japan. 2020;93(5):676-684.
doi:10.1246/bcsj.20190296 .
Maksimović, Jelena P., Tosović, Jelena, Pagnacco, Maja, "Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study" in Bulletin of the Chemical Society of Japan, 93, no. 5 (2020):676-684,
https://doi.org/10.1246/bcsj.20190296 . .
4
3
5

Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study

Maksimović, Jelena P.; Tosović, Jelena; Pagnacco, Maja

(Chemical Society of Japan, 2020)

TY  - JOUR
AU  - Maksimović, Jelena P.
AU  - Tosović, Jelena
AU  - Pagnacco, Maja
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3853
AB  - The pyrocatechol inhibitory effect on the oscillatory Bray-Liebhafsky (BL) reaction is reported. Obtained results are compared with those available in the literature (R. Cervellati et al, Helvetica Chimica Acta 2001) for Briggs-Rauscher (BR) reaction with pyrocatechol addition. The two orders of magnitude larger calibration curve slope obtained in BR in comparison to BL reaction, suggests that different reactions are responsible for inhibitory effects in these systems. The potential explanation of pyrocatechol behavior is given by employing the ultraviolet-visible (UV/VIS) spectroscopy, density functional theory, and coupled cluster computational methods. The last two were employed for the first time to discover potential candidates among unstable chemical species HIO, HIO2, I2O, HOO•, HO•, IO•, IO2•, and I• of the BL (and BR) system for reaction with pyrocatechol. The calculated reaction rate constants for the hydrogen atom transfer reactions between pyrocatechol and free radical intermediates indicate the following order of reactivity: HO• > IO• > HOO• > IO2•. The same order of reactivity is also observed in the case of a thermodynamic investigation. In addition, kinetic insight indicates that the inhibitory behavior of pyrocatechol could not be explained with one particular chemical reaction in the BL (or in the BR) oscillatory system.
PB  - Chemical Society of Japan
T2  - Bulletin of the Chemical Society of Japan
T1  - Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study
VL  - 93
IS  - 5
SP  - 676
EP  - 684
DO  - 10.1246/bcsj.20190296
ER  - 
@article{
author = "Maksimović, Jelena P. and Tosović, Jelena and Pagnacco, Maja",
year = "2020",
abstract = "The pyrocatechol inhibitory effect on the oscillatory Bray-Liebhafsky (BL) reaction is reported. Obtained results are compared with those available in the literature (R. Cervellati et al, Helvetica Chimica Acta 2001) for Briggs-Rauscher (BR) reaction with pyrocatechol addition. The two orders of magnitude larger calibration curve slope obtained in BR in comparison to BL reaction, suggests that different reactions are responsible for inhibitory effects in these systems. The potential explanation of pyrocatechol behavior is given by employing the ultraviolet-visible (UV/VIS) spectroscopy, density functional theory, and coupled cluster computational methods. The last two were employed for the first time to discover potential candidates among unstable chemical species HIO, HIO2, I2O, HOO•, HO•, IO•, IO2•, and I• of the BL (and BR) system for reaction with pyrocatechol. The calculated reaction rate constants for the hydrogen atom transfer reactions between pyrocatechol and free radical intermediates indicate the following order of reactivity: HO• > IO• > HOO• > IO2•. The same order of reactivity is also observed in the case of a thermodynamic investigation. In addition, kinetic insight indicates that the inhibitory behavior of pyrocatechol could not be explained with one particular chemical reaction in the BL (or in the BR) oscillatory system.",
publisher = "Chemical Society of Japan",
journal = "Bulletin of the Chemical Society of Japan",
title = "Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study",
volume = "93",
number = "5",
pages = "676-684",
doi = "10.1246/bcsj.20190296"
}
Maksimović, J. P., Tosović, J.,& Pagnacco, M.. (2020). Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study. in Bulletin of the Chemical Society of Japan
Chemical Society of Japan., 93(5), 676-684.
https://doi.org/10.1246/bcsj.20190296
Maksimović JP, Tosović J, Pagnacco M. Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study. in Bulletin of the Chemical Society of Japan. 2020;93(5):676-684.
doi:10.1246/bcsj.20190296 .
Maksimović, Jelena P., Tosović, Jelena, Pagnacco, Maja, "Insight into the Origin of Pyrocatechol Inhibition on Oscillating Bray-Liebhafsky Reaction: Combined Experimental and Theoretical Study" in Bulletin of the Chemical Society of Japan, 93, no. 5 (2020):676-684,
https://doi.org/10.1246/bcsj.20190296 . .
4
3
5

The Briggs-Rauscher reaction as an unusual detector for a different type of bronzes

Maksimović, Tijana; Maksimović, Jelena; Mudrinić, Tihana; Nedić, Zoran; Joksović, Ljubinka; Mojović, Zorica; Pagnacco, Maja

(Institute of Technical Sciences of SASA, 2019)

TY  - CONF
AU  - Maksimović, Tijana
AU  - Maksimović, Jelena
AU  - Mudrinić, Tihana
AU  - Nedić, Zoran
AU  - Joksović, Ljubinka
AU  - Mojović, Zorica
AU  - Pagnacco, Maja
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6969
AB  - The Briggs-Rauscher (BR) reaction is an oscillating reaction in which the oxidation of malonic acid (CH2(COOH)2) in the presence of hydrogen peroxide (H2O2) and potassium iodate (KIO3) is catalyzed with a metal ion (usually manganese ion (Mn2+)) in an acid solution (HClO4). It is well known that the BR reaction represents a chemical system that is extremely sensitive to the addition of different types of analytes. Every change in oscillatory dynamics, caused by analyte addition, can be used for the assessment of analyte concentration, as well as its potential antiradical activities. The basic idea of this work is to use the oscillatory reaction, as an unusual and novel system for distinguishing different types of insoluble materials such as bronzes, specifically phosphate tungsten bronze (PWB) and phosphate molybdenum bronze (PMoB). Regarding the results obtained, the increasing mass of PWB leads to a significant decrease of BR oscillatory time, while the addition of PMoB has not affected the BR reaction dynamics. The obtained different behavior of PWB and PMoB introduced the BR reaction as a systemdetector for these two types of bronzes. In order to investigate the mechanism of bronzes action in BR oscillatory reaction, the pH and electric conductivity measurements, as well as inductively coupled plasma and the cyclic voltammetry measurements were done. This work extends the practical aspect of the BR reaction for the examination of solid materials. Furthermore, the obtained results open a new section of oscillatory reaction usage in material science and catalysis in general.
PB  - Institute of Technical Sciences of SASA
C3  - Program and the Book of Abstracts - Eighteenth Young Researchers’ Conference - Materials Science and Engineering, December 4-6 2019,  Belgrade, Serbia
T1  - The Briggs-Rauscher reaction as an unusual detector for a different type of bronzes
SP  - 49
EP  - 49
UR  - https://hdl.handle.net/21.15107/rcub_cer_6969
ER  - 
@conference{
author = "Maksimović, Tijana and Maksimović, Jelena and Mudrinić, Tihana and Nedić, Zoran and Joksović, Ljubinka and Mojović, Zorica and Pagnacco, Maja",
year = "2019",
abstract = "The Briggs-Rauscher (BR) reaction is an oscillating reaction in which the oxidation of malonic acid (CH2(COOH)2) in the presence of hydrogen peroxide (H2O2) and potassium iodate (KIO3) is catalyzed with a metal ion (usually manganese ion (Mn2+)) in an acid solution (HClO4). It is well known that the BR reaction represents a chemical system that is extremely sensitive to the addition of different types of analytes. Every change in oscillatory dynamics, caused by analyte addition, can be used for the assessment of analyte concentration, as well as its potential antiradical activities. The basic idea of this work is to use the oscillatory reaction, as an unusual and novel system for distinguishing different types of insoluble materials such as bronzes, specifically phosphate tungsten bronze (PWB) and phosphate molybdenum bronze (PMoB). Regarding the results obtained, the increasing mass of PWB leads to a significant decrease of BR oscillatory time, while the addition of PMoB has not affected the BR reaction dynamics. The obtained different behavior of PWB and PMoB introduced the BR reaction as a systemdetector for these two types of bronzes. In order to investigate the mechanism of bronzes action in BR oscillatory reaction, the pH and electric conductivity measurements, as well as inductively coupled plasma and the cyclic voltammetry measurements were done. This work extends the practical aspect of the BR reaction for the examination of solid materials. Furthermore, the obtained results open a new section of oscillatory reaction usage in material science and catalysis in general.",
publisher = "Institute of Technical Sciences of SASA",
journal = "Program and the Book of Abstracts - Eighteenth Young Researchers’ Conference - Materials Science and Engineering, December 4-6 2019,  Belgrade, Serbia",
title = "The Briggs-Rauscher reaction as an unusual detector for a different type of bronzes",
pages = "49-49",
url = "https://hdl.handle.net/21.15107/rcub_cer_6969"
}
Maksimović, T., Maksimović, J., Mudrinić, T., Nedić, Z., Joksović, L., Mojović, Z.,& Pagnacco, M.. (2019). The Briggs-Rauscher reaction as an unusual detector for a different type of bronzes. in Program and the Book of Abstracts - Eighteenth Young Researchers’ Conference - Materials Science and Engineering, December 4-6 2019,  Belgrade, Serbia
Institute of Technical Sciences of SASA., 49-49.
https://hdl.handle.net/21.15107/rcub_cer_6969
Maksimović T, Maksimović J, Mudrinić T, Nedić Z, Joksović L, Mojović Z, Pagnacco M. The Briggs-Rauscher reaction as an unusual detector for a different type of bronzes. in Program and the Book of Abstracts - Eighteenth Young Researchers’ Conference - Materials Science and Engineering, December 4-6 2019,  Belgrade, Serbia. 2019;:49-49.
https://hdl.handle.net/21.15107/rcub_cer_6969 .
Maksimović, Tijana, Maksimović, Jelena, Mudrinić, Tihana, Nedić, Zoran, Joksović, Ljubinka, Mojović, Zorica, Pagnacco, Maja, "The Briggs-Rauscher reaction as an unusual detector for a different type of bronzes" in Program and the Book of Abstracts - Eighteenth Young Researchers’ Conference - Materials Science and Engineering, December 4-6 2019,  Belgrade, Serbia (2019):49-49,
https://hdl.handle.net/21.15107/rcub_cer_6969 .

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

Jakovljević, Katarina; Joksovic, Milan D.; Matić, Ivana Z.; Petrovic, Nina; Stanojković, Tatjana; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksovic, Ljubinka; Trifunović, Snežana; Markovic, Violeta

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksovic, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrovic, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Trifunović, Snežana
AU  - Markovic, Violeta
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2379
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3136
AB  - Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.
PB  - Royal Soc Chemistry, Cambridge
T2  - Medchemcomm
T1  - Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies
VL  - 9
IS  - 10
SP  - 1679
EP  - 1697
DO  - 10.1039/c8md00316e
ER  - 
@article{
author = "Jakovljević, Katarina and Joksovic, Milan D. and Matić, Ivana Z. and Petrovic, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Trifunović, Snežana and Markovic, Violeta",
year = "2018",
abstract = "Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies",
volume = "9",
number = "10",
pages = "1679-1697",
doi = "10.1039/c8md00316e"
}
Jakovljević, K., Joksovic, M. D., Matić, I. Z., Petrovic, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Trifunović, S.,& Markovic, V.. (2018). Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm
Royal Soc Chemistry, Cambridge., 9(10), 1679-1697.
https://doi.org/10.1039/c8md00316e
Jakovljević K, Joksovic MD, Matić IZ, Petrovic N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksovic L, Trifunović S, Markovic V. Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm. 2018;9(10):1679-1697.
doi:10.1039/c8md00316e .
Jakovljević, Katarina, Joksovic, Milan D., Matić, Ivana Z., Petrovic, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Trifunović, Snežana, Markovic, Violeta, "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies" in Medchemcomm, 9, no. 10 (2018):1679-1697,
https://doi.org/10.1039/c8md00316e . .
4
25
15
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Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"

Jakovljević, Katarina; Joksovic, Milan D.; Matić, Ivana Z.; Petrovic, Nina; Stanojković, Tatjana; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksovic, Ljubinka; Trifunović, Snežana; Markovic, Violeta

(Royal Society of Chemistry, Cambridge, 2018)

TY  - DATA
AU  - Jakovljević, Katarina
AU  - Joksovic, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrovic, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Trifunović, Snežana
AU  - Markovic, Violeta
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4534
AB  - Copies of 1H and 13C NMR spectra for 5a-m
PB  - Royal Society of Chemistry, Cambridge
T2  - Medchemcomm
T1  - Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"
UR  - https://hdl.handle.net/21.15107/rcub_cer_4534
ER  - 
@misc{
author = "Jakovljević, Katarina and Joksovic, Milan D. and Matić, Ivana Z. and Petrovic, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Trifunović, Snežana and Markovic, Violeta",
year = "2018",
abstract = "Copies of 1H and 13C NMR spectra for 5a-m",
publisher = "Royal Society of Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"",
url = "https://hdl.handle.net/21.15107/rcub_cer_4534"
}
Jakovljević, K., Joksovic, M. D., Matić, I. Z., Petrovic, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Trifunović, S.,& Markovic, V.. (2018). Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies". in Medchemcomm
Royal Society of Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cer_4534
Jakovljević K, Joksovic MD, Matić IZ, Petrovic N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksovic L, Trifunović S, Markovic V. Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies". in Medchemcomm. 2018;.
https://hdl.handle.net/21.15107/rcub_cer_4534 .
Jakovljević, Katarina, Joksovic, Milan D., Matić, Ivana Z., Petrovic, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Trifunović, Snežana, Markovic, Violeta, "Supplementary Information for: "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies"" in Medchemcomm (2018),
https://hdl.handle.net/21.15107/rcub_cer_4534 .

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

Jakovljević, Katarina; Joksovic, Milan D.; Matić, Ivana Z.; Petrovic, Nina; Stanojković, Tatjana; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksovic, Ljubinka; Trifunović, Snežana; Markovic, Violeta

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Jakovljević, Katarina
AU  - Joksovic, Milan D.
AU  - Matić, Ivana Z.
AU  - Petrovic, Nina
AU  - Stanojković, Tatjana
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Trifunović, Snežana
AU  - Markovic, Violeta
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2379
AB  - Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.
PB  - Royal Soc Chemistry, Cambridge
T2  - Medchemcomm
T1  - Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies
VL  - 9
IS  - 10
SP  - 1679
EP  - 1697
DO  - 10.1039/c8md00316e
ER  - 
@article{
author = "Jakovljević, Katarina and Joksovic, Milan D. and Matić, Ivana Z. and Petrovic, Nina and Stanojković, Tatjana and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Trifunović, Snežana and Markovic, Violeta",
year = "2018",
abstract = "Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxidant and cytotoxic effects on human acute promyelocytic leukemia HL-60 cells. Several compounds exerted good cytotoxic activities on cervical adenocarcinoma HeLa cells. The treatment of HeLa cells with IC50 and double IC50 concentrations of the compounds 5a, 5c, 5f, and 5m induced a statistically significant increase in the percentage of cells within a subG1 cell cycle phase. The examined compounds caused G2/M cell cycle arrest in HeLa cells. Each of these compounds triggered apoptosis in HeLa cells through activation of caspase-3, the main effector caspase, caspase-8, which is involved in the extrinsic apoptotic pathway, and caspase-9, which is involved in the intrinsic apoptotic pathway. All of the examined compounds decreased the expression levels of MMP2 in HeLa cells and levels of protumorigenic miR-133b. Compounds 5a and 5m lowered the expression level of oncogenic miR-21 in HeLa cells. In addition, compounds 5a, 5f, and 5m decreased the expression levels of oncogenic miR-155 while the treatment of HeLa cells with compounds 5a, 5c, and 5f increased expression of tumor-suppressive miR-206. Observed effects of these compounds on expression levels of four examined miRNAs suggest their prominent cancer-suppressive activity. An investigation by absorption and fluorescence spectroscopy showed more efficient calf thymus DNA binding activity of the compound 5m in comparison to other tested compounds. Results of a pUC19 plasmid cleavage study and comet assay showed DNA damaging activities of compounds 5a and 5c.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Medchemcomm",
title = "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies",
volume = "9",
number = "10",
pages = "1679-1697",
doi = "10.1039/c8md00316e"
}
Jakovljević, K., Joksovic, M. D., Matić, I. Z., Petrovic, N., Stanojković, T., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Trifunović, S.,& Markovic, V.. (2018). Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm
Royal Soc Chemistry, Cambridge., 9(10), 1679-1697.
https://doi.org/10.1039/c8md00316e
Jakovljević K, Joksovic MD, Matić IZ, Petrovic N, Stanojković T, Sladić D, Vujčić M, Janović B, Joksovic L, Trifunović S, Markovic V. Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies. in Medchemcomm. 2018;9(10):1679-1697.
doi:10.1039/c8md00316e .
Jakovljević, Katarina, Joksovic, Milan D., Matić, Ivana Z., Petrovic, Nina, Stanojković, Tatjana, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Trifunović, Snežana, Markovic, Violeta, "Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies" in Medchemcomm, 9, no. 10 (2018):1679-1697,
https://doi.org/10.1039/c8md00316e . .
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Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure

Konovalov, Bata; Zivkovic, Marija D.; Milovanovic, Jelena Z.; Đorđević, Dragana B.; Arsenijevic, Aleksandar N.; Vasic, Ivana R.; Janjić, Goran; Franich, Andjela; Manojlović, Dragan; Škrivanj, Sandra; Milovanovic, Marija Z.; Đuran, Miloš; Rajkovic, Snezana

(Royal Soc Chemistry, Cambridge, 2018)

TY  - JOUR
AU  - Konovalov, Bata
AU  - Zivkovic, Marija D.
AU  - Milovanovic, Jelena Z.
AU  - Đorđević, Dragana B.
AU  - Arsenijevic, Aleksandar N.
AU  - Vasic, Ivana R.
AU  - Janjić, Goran
AU  - Franich, Andjela
AU  - Manojlović, Dragan
AU  - Škrivanj, Sandra
AU  - Milovanovic, Marija Z.
AU  - Đuran, Miloš
AU  - Rajkovic, Snezana
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2353
AB  - The synthesis, spectroscopic characterization, cytotoxic activity and DNA binding evaluation of seven new dinuclear platinum(ii) complexes Pt1-Pt7, with the general formula [{Pt(L)Cl}(2)(-1,5-nphe)](ClO4)(2) (1,5-nphe is 1,5-naphthyridine; while L is two ammines (Pt1) or one bidentate coordinated diamine: ethylenediamine (Pt2), (+/-)-1,2-propylenediamine (Pt3), trans-(+/-)-1,2-diaminocyclohexane (Pt4), 1,3-propylenediamine (Pt5), 2,2-dimethyl-1,3-propylenediamine (Pt6), and 1,3-pentanediamine (Pt7)), were reported. In vitro cytotoxic activity of these complexes was evaluated against three tumor cell lines, murine colon carcinoma (CT26), murine mammary carcinoma (4T1) and murine lung cancer (LLC1) and two normal cell lines, murine mesenchymal stem cells (MSC) and human fibroblast (MRC-5) cells. The results of the MTT assay indicate that all investigated complexes have almost no cytotoxic effects on 4T1 and very low cytotoxicity toward LLC1 cell lines. In contrast to the effects on LLC1 and 4T1 cells, complexes Pt1 and Pt2 had significant cytotoxic activity toward CT26 cells. Complex Pt1 had a much lower IC50 value for activity on CT26 cells compared with cisplatin. In comparison with cisplatin, all dinuclear Pt1-Pt7 complexes showed lower cytotoxicity toward normal MSC and MRC-5 cells. In order to measure the amount of platinum(ii) complexes taken up by the cells, we quantified the cellular platinum content using inductively coupled plasma mass spectrometry (ICP-QMS). Molecular docking studies performed to evaluate the potential binding mode of dinuclear platinum(ii) complexes Pt1-Pt7 and their aqua derivatives W1-W7, respectively, at the double stranded DNA showed that groove spanning and backbone tracking are the most stable binding modes.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure
VL  - 47
IS  - 42
SP  - 15091
EP  - 15102
DO  - 10.1039/c8dt01946k
ER  - 
@article{
author = "Konovalov, Bata and Zivkovic, Marija D. and Milovanovic, Jelena Z. and Đorđević, Dragana B. and Arsenijevic, Aleksandar N. and Vasic, Ivana R. and Janjić, Goran and Franich, Andjela and Manojlović, Dragan and Škrivanj, Sandra and Milovanovic, Marija Z. and Đuran, Miloš and Rajkovic, Snezana",
year = "2018",
abstract = "The synthesis, spectroscopic characterization, cytotoxic activity and DNA binding evaluation of seven new dinuclear platinum(ii) complexes Pt1-Pt7, with the general formula [{Pt(L)Cl}(2)(-1,5-nphe)](ClO4)(2) (1,5-nphe is 1,5-naphthyridine; while L is two ammines (Pt1) or one bidentate coordinated diamine: ethylenediamine (Pt2), (+/-)-1,2-propylenediamine (Pt3), trans-(+/-)-1,2-diaminocyclohexane (Pt4), 1,3-propylenediamine (Pt5), 2,2-dimethyl-1,3-propylenediamine (Pt6), and 1,3-pentanediamine (Pt7)), were reported. In vitro cytotoxic activity of these complexes was evaluated against three tumor cell lines, murine colon carcinoma (CT26), murine mammary carcinoma (4T1) and murine lung cancer (LLC1) and two normal cell lines, murine mesenchymal stem cells (MSC) and human fibroblast (MRC-5) cells. The results of the MTT assay indicate that all investigated complexes have almost no cytotoxic effects on 4T1 and very low cytotoxicity toward LLC1 cell lines. In contrast to the effects on LLC1 and 4T1 cells, complexes Pt1 and Pt2 had significant cytotoxic activity toward CT26 cells. Complex Pt1 had a much lower IC50 value for activity on CT26 cells compared with cisplatin. In comparison with cisplatin, all dinuclear Pt1-Pt7 complexes showed lower cytotoxicity toward normal MSC and MRC-5 cells. In order to measure the amount of platinum(ii) complexes taken up by the cells, we quantified the cellular platinum content using inductively coupled plasma mass spectrometry (ICP-QMS). Molecular docking studies performed to evaluate the potential binding mode of dinuclear platinum(ii) complexes Pt1-Pt7 and their aqua derivatives W1-W7, respectively, at the double stranded DNA showed that groove spanning and backbone tracking are the most stable binding modes.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure",
volume = "47",
number = "42",
pages = "15091-15102",
doi = "10.1039/c8dt01946k"
}
Konovalov, B., Zivkovic, M. D., Milovanovic, J. Z., Đorđević, D. B., Arsenijevic, A. N., Vasic, I. R., Janjić, G., Franich, A., Manojlović, D., Škrivanj, S., Milovanovic, M. Z., Đuran, M.,& Rajkovic, S.. (2018). Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 47(42), 15091-15102.
https://doi.org/10.1039/c8dt01946k
Konovalov B, Zivkovic MD, Milovanovic JZ, Đorđević DB, Arsenijevic AN, Vasic IR, Janjić G, Franich A, Manojlović D, Škrivanj S, Milovanovic MZ, Đuran M, Rajkovic S. Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure. in Dalton Transactions. 2018;47(42):15091-15102.
doi:10.1039/c8dt01946k .
Konovalov, Bata, Zivkovic, Marija D., Milovanovic, Jelena Z., Đorđević, Dragana B., Arsenijevic, Aleksandar N., Vasic, Ivana R., Janjić, Goran, Franich, Andjela, Manojlović, Dragan, Škrivanj, Sandra, Milovanovic, Marija Z., Đuran, Miloš, Rajkovic, Snezana, "Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure" in Dalton Transactions, 47, no. 42 (2018):15091-15102,
https://doi.org/10.1039/c8dt01946k . .
21
11
18

In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands

Pantelic, Nebojsa; Zmejkovski, Bojana; Kolundzija, Branka; Crnogorac, Marija Dordic; Vujic, Jelena M.; Dojčinović, Biljana; Trifunovic, Srecko R.; Stanojković, Tatjana; Sabo, Tibor; Kaluđerović, Goran N.

(Elsevier Science Inc, New York, 2017)

TY  - JOUR
AU  - Pantelic, Nebojsa
AU  - Zmejkovski, Bojana
AU  - Kolundzija, Branka
AU  - Crnogorac, Marija Dordic
AU  - Vujic, Jelena M.
AU  - Dojčinović, Biljana
AU  - Trifunovic, Srecko R.
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2248
AB  - Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands
VL  - 172
SP  - 55
EP  - 66
DO  - 10.1016/j.jinorgbio.2017.04.001
ER  - 
@article{
author = "Pantelic, Nebojsa and Zmejkovski, Bojana and Kolundzija, Branka and Crnogorac, Marija Dordic and Vujic, Jelena M. and Dojčinović, Biljana and Trifunovic, Srecko R. and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
abstract = "Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands",
volume = "172",
pages = "55-66",
doi = "10.1016/j.jinorgbio.2017.04.001"
}
Pantelic, N., Zmejkovski, B., Kolundzija, B., Crnogorac, M. D., Vujic, J. M., Dojčinović, B., Trifunovic, S. R., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2017). In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 172, 55-66.
https://doi.org/10.1016/j.jinorgbio.2017.04.001
Pantelic N, Zmejkovski B, Kolundzija B, Crnogorac MD, Vujic JM, Dojčinović B, Trifunovic SR, Stanojković T, Sabo T, Kaluđerović GN. In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry. 2017;172:55-66.
doi:10.1016/j.jinorgbio.2017.04.001 .
Pantelic, Nebojsa, Zmejkovski, Bojana, Kolundzija, Branka, Crnogorac, Marija Dordic, Vujic, Jelena M., Dojčinović, Biljana, Trifunovic, Srecko R., Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran N., "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N '-ethylenediamine bidentate ester ligands" in Journal of Inorganic Biochemistry, 172 (2017):55-66,
https://doi.org/10.1016/j.jinorgbio.2017.04.001 . .
1
12
8
14

In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands

Pantelić, Nebojša Đ.; Zmejkovski, Bojana; Kolundžija, Branka; Crnogorac, Marija Đorđić; Vujić, Jelena M.; Dojčinović, Biljana; Trifunović, Srećko R.; Stanojković, Tatjana; Sabo, Tibor; Kaluđerović, Goran N.

(Elsevier, 2017)

TY  - JOUR
AU  - Pantelić, Nebojša Đ.
AU  - Zmejkovski, Bojana
AU  - Kolundžija, Branka
AU  - Crnogorac, Marija Đorđić
AU  - Vujić, Jelena M.
AU  - Dojčinović, Biljana
AU  - Trifunović, Srećko R.
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2931
AB  - Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.
PB  - Elsevier
T2  - Journal of Inorganic Biochemistry
T1  - In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands
VL  - 172
SP  - 55
EP  - 66
DO  - 10.1016/j.jinorgbio.2017.04.001
ER  - 
@article{
author = "Pantelić, Nebojša Đ. and Zmejkovski, Bojana and Kolundžija, Branka and Crnogorac, Marija Đorđić and Vujić, Jelena M. and Dojčinović, Biljana and Trifunović, Srećko R. and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2017",
abstract = "Four novel gold(III) complexes of general formulae [AuCl2{(S,S)-R(2)eddl}]PF6 (R(2)eddl = O,O'-dialkyl-(S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoate, R= n-Pr, n-Bu, n-Pe, i-Bu; 1-4, respectively), were synthesized and characterized by elemental analysis, UV/Vis, IR, and NMR spectroscopy, as well as high resolution mass spectrometry. Density functional theory calculations pointed out that (R,R)-N,N'-configuration diastereoisomers were energetically the most favorable. Duo to high cytotoxic activity complex 3 was chosen for stability study in DMSO, no decomposition occurs within 24 h, and for the reaction with ascorbic acid in which was reduced immediately. Additionally, 3 interacts with bovine serum albumin (BSA) as proven by UV/Vis spectroscopy. In vitro antitumor activity was determined against human cervix adenocarcinoma (HeLa), human myelogenous leukemia (K562), and human melanoma (Fem-x) cancer cell lines, as well as against non-cancerous human embryonic lung fibroblast cells MRC-5. The highest activity was observed against K562 cells (IC50: 5.04-6.51 mu M). Selectivity indices showed that these complexes are less toxic than cisplatin. 3 had a similar viability kinetics on HeLa cells as cisplatin. Drug accumulation studies in HeLa cells showed that the total gold uptake increased much faster than that of cisplatin pointing out that 3 more efficiently enters the cells than cisplatin. Furthermore, morphological and cell cycle analysis reveal that gold(III) complexes induced apoptosis in time- and dose-dependent manner.",
publisher = "Elsevier",
journal = "Journal of Inorganic Biochemistry",
title = "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands",
volume = "172",
pages = "55-66",
doi = "10.1016/j.jinorgbio.2017.04.001"
}
Pantelić, N. Đ., Zmejkovski, B., Kolundžija, B., Crnogorac, M. Đ., Vujić, J. M., Dojčinović, B., Trifunović, S. R., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2017). In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry
Elsevier., 172, 55-66.
https://doi.org/10.1016/j.jinorgbio.2017.04.001
Pantelić NĐ, Zmejkovski B, Kolundžija B, Crnogorac MĐ, Vujić JM, Dojčinović B, Trifunović SR, Stanojković T, Sabo T, Kaluđerović GN. In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands. in Journal of Inorganic Biochemistry. 2017;172:55-66.
doi:10.1016/j.jinorgbio.2017.04.001 .
Pantelić, Nebojša Đ., Zmejkovski, Bojana, Kolundžija, Branka, Crnogorac, Marija Đorđić, Vujić, Jelena M., Dojčinović, Biljana, Trifunović, Srećko R., Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran N., "In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands" in Journal of Inorganic Biochemistry, 172 (2017):55-66,
https://doi.org/10.1016/j.jinorgbio.2017.04.001 . .
1
12
8
14

Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O-Diethyl Ester of Ethylenediamine-N,N-Di-2-(4-Methyl)Pentanoic Acid

Pantelic, Nebojsa; Zmejkovski, Bojana; Markovic, Dragana D; Vujic, Jelena M; Stanojković, Tatjana; Sabo, Tibor; Kaluđerović, Goran N.

(MDPI, 2016)

TY  - JOUR
AU  - Pantelic, Nebojsa
AU  - Zmejkovski, Bojana
AU  - Markovic, Dragana D
AU  - Vujic, Jelena M
AU  - Stanojković, Tatjana
AU  - Sabo, Tibor
AU  - Kaluđerović, Goran N.
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1938
AB  - A novel gold(III) complex, [AuCl2{(S,S)-Et(2)eddl}]PF6, ((S,S)-Et(2)eddl = O,O-diethyl ester of ethylenediamine-N,N-di-2-(4-methyl)pentanoic acid) was synthesized and characterized by IR, 1D (H-1 and C-13), and 2D (H,H-COSY and H,H-NOESY) NMR spectroscopy, mass spectrometry, and elemental analysis. Density functional theory calculations confirmed that (R,R)-N,N diastereoisomer was energetically the most stable isomer. In vitro antitumor action of ligand precursor [(S,S)-H(2)Et(2)eddl]Cl-2 and corresponding gold(III) complex was determined against tumor cell lines: human adenocarcinoma (HeLa), human colon carcinoma (LS174), human breast cancer (MCF7), non-small cell lung carcinoma cell line (A549), and non-cancerous cell line human embryonic lung fibroblast (MRC-5) using microculture tetrazolium test (MTT) assay. The results indicate that both ligand precursor and gold(III) complex have showed very good to moderate cytotoxic activity against all tested malignant cell lines. The highest activity was expressed by [AuCl2{(S,S)-Et(2)eddl}]PF6 against the LS174 cells, with IC50 value of 7.4 +/- 1.2 mu M.
PB  - MDPI
T2  - Metals
T1  - Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O-Diethyl Ester of Ethylenediamine-N,N-Di-2-(4-Methyl)Pentanoic Acid
VL  - 6
IS  - 9
DO  - 10.3390/met6090226
ER  - 
@article{
author = "Pantelic, Nebojsa and Zmejkovski, Bojana and Markovic, Dragana D and Vujic, Jelena M and Stanojković, Tatjana and Sabo, Tibor and Kaluđerović, Goran N.",
year = "2016",
abstract = "A novel gold(III) complex, [AuCl2{(S,S)-Et(2)eddl}]PF6, ((S,S)-Et(2)eddl = O,O-diethyl ester of ethylenediamine-N,N-di-2-(4-methyl)pentanoic acid) was synthesized and characterized by IR, 1D (H-1 and C-13), and 2D (H,H-COSY and H,H-NOESY) NMR spectroscopy, mass spectrometry, and elemental analysis. Density functional theory calculations confirmed that (R,R)-N,N diastereoisomer was energetically the most stable isomer. In vitro antitumor action of ligand precursor [(S,S)-H(2)Et(2)eddl]Cl-2 and corresponding gold(III) complex was determined against tumor cell lines: human adenocarcinoma (HeLa), human colon carcinoma (LS174), human breast cancer (MCF7), non-small cell lung carcinoma cell line (A549), and non-cancerous cell line human embryonic lung fibroblast (MRC-5) using microculture tetrazolium test (MTT) assay. The results indicate that both ligand precursor and gold(III) complex have showed very good to moderate cytotoxic activity against all tested malignant cell lines. The highest activity was expressed by [AuCl2{(S,S)-Et(2)eddl}]PF6 against the LS174 cells, with IC50 value of 7.4 +/- 1.2 mu M.",
publisher = "MDPI",
journal = "Metals",
title = "Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O-Diethyl Ester of Ethylenediamine-N,N-Di-2-(4-Methyl)Pentanoic Acid",
volume = "6",
number = "9",
doi = "10.3390/met6090226"
}
Pantelic, N., Zmejkovski, B., Markovic, D. D., Vujic, J. M., Stanojković, T., Sabo, T.,& Kaluđerović, G. N.. (2016). Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O-Diethyl Ester of Ethylenediamine-N,N-Di-2-(4-Methyl)Pentanoic Acid. in Metals
MDPI., 6(9).
https://doi.org/10.3390/met6090226
Pantelic N, Zmejkovski B, Markovic DD, Vujic JM, Stanojković T, Sabo T, Kaluđerović GN. Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O-Diethyl Ester of Ethylenediamine-N,N-Di-2-(4-Methyl)Pentanoic Acid. in Metals. 2016;6(9).
doi:10.3390/met6090226 .
Pantelic, Nebojsa, Zmejkovski, Bojana, Markovic, Dragana D, Vujic, Jelena M, Stanojković, Tatjana, Sabo, Tibor, Kaluđerović, Goran N., "Synthesis, Characterization, and Cytotoxicity of a Novel Gold(III) Complex with O,O-Diethyl Ester of Ethylenediamine-N,N-Di-2-(4-Methyl)Pentanoic Acid" in Metals, 6, no. 9 (2016),
https://doi.org/10.3390/met6090226 . .
10
5
9

Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies

Markovic, Violeta; Debeljak, Nevena; Stanojković, Tatjana; Kolundzija, Branka; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Tanic, Nikola; Perovic, Milka; Tesic, Vesna; Antic, Jadranka; Joksovic, Milan D.

(Elsevier France-Editions Scientifiques Medicales Elsevier, Paris, 2015)

TY  - JOUR
AU  - Markovic, Violeta
AU  - Debeljak, Nevena
AU  - Stanojković, Tatjana
AU  - Kolundzija, Branka
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Tanic, Nikola
AU  - Perovic, Milka
AU  - Tesic, Vesna
AU  - Antic, Jadranka
AU  - Joksovic, Milan D.
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1745
AB  - Novel anthraquinone based chalcone compounds were synthesized starting from 1-acetylanthraquinone in a Claisen-Schmidt reaction and evaluated for their anticancer potential against three human cancer cell lines. Compounds 4a, 4b and 4j showed promising activity in inhibition of HeLa cells with IC50 values ranging from 2.36 to 2.73 mu M and low cytotoxicity against healthy MRC-5 cell lines. The effects that compounds produces on the cell cycle were investigated by flow cytometry. It was found that 4a, 4b and 4j cause the accumulation of cells in the S and G2/M phases in a dose-dependent manner and induce caspase-dependent apoptosis. All of three compounds exhibit calf thymus DNA-binding activity. The determined binding constants by absorption titrations (2.65 x 10(3) M-1, 1.36 x 10(3) M(-1)and 2.51 x 10(3) M-1 of 4a/CT-DNA, 4b/CT-DNA and 4j/CT-DNA, respectively) together with fluorescence displacement analysis designate 4a, 4b and 4j as strong minor groove binders, but no cleavage of plasmid DNA was observed.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies
VL  - 89
SP  - 401
EP  - 410
DO  - 10.1016/j.ejmech.2014.10.055
ER  - 
@article{
author = "Markovic, Violeta and Debeljak, Nevena and Stanojković, Tatjana and Kolundzija, Branka and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Tanic, Nikola and Perovic, Milka and Tesic, Vesna and Antic, Jadranka and Joksovic, Milan D.",
year = "2015",
abstract = "Novel anthraquinone based chalcone compounds were synthesized starting from 1-acetylanthraquinone in a Claisen-Schmidt reaction and evaluated for their anticancer potential against three human cancer cell lines. Compounds 4a, 4b and 4j showed promising activity in inhibition of HeLa cells with IC50 values ranging from 2.36 to 2.73 mu M and low cytotoxicity against healthy MRC-5 cell lines. The effects that compounds produces on the cell cycle were investigated by flow cytometry. It was found that 4a, 4b and 4j cause the accumulation of cells in the S and G2/M phases in a dose-dependent manner and induce caspase-dependent apoptosis. All of three compounds exhibit calf thymus DNA-binding activity. The determined binding constants by absorption titrations (2.65 x 10(3) M-1, 1.36 x 10(3) M(-1)and 2.51 x 10(3) M-1 of 4a/CT-DNA, 4b/CT-DNA and 4j/CT-DNA, respectively) together with fluorescence displacement analysis designate 4a, 4b and 4j as strong minor groove binders, but no cleavage of plasmid DNA was observed.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies",
volume = "89",
pages = "401-410",
doi = "10.1016/j.ejmech.2014.10.055"
}
Markovic, V., Debeljak, N., Stanojković, T., Kolundzija, B., Sladić, D., Vujčić, M., Janović, B., Tanic, N., Perovic, M., Tesic, V., Antic, J.,& Joksovic, M. D.. (2015). Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 89, 401-410.
https://doi.org/10.1016/j.ejmech.2014.10.055
Markovic V, Debeljak N, Stanojković T, Kolundzija B, Sladić D, Vujčić M, Janović B, Tanic N, Perovic M, Tesic V, Antic J, Joksovic MD. Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies. in European Journal of Medicinal Chemistry. 2015;89:401-410.
doi:10.1016/j.ejmech.2014.10.055 .
Markovic, Violeta, Debeljak, Nevena, Stanojković, Tatjana, Kolundzija, Branka, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Tanic, Nikola, Perovic, Milka, Tesic, Vesna, Antic, Jadranka, Joksovic, Milan D., "Anthraquinone-chalcone hybrids: Synthesis, preliminary antiproliferative evaluation and DNA-interaction studies" in European Journal of Medicinal Chemistry, 89 (2015):401-410,
https://doi.org/10.1016/j.ejmech.2014.10.055 . .
37
32
41

Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity

Kolundzija, Branka; Markovic, Violeta; Stanojković, Tatjana; Joksovic, Ljubinka; Matić, Ivana Z.; Todorović, Nina; Nikolić, Marijana; Joksovic, Milan D.

(Oxford : Pergamon-Elsevier Science Ltd, 2014)

TY  - JOUR
AU  - Kolundzija, Branka
AU  - Markovic, Violeta
AU  - Stanojković, Tatjana
AU  - Joksovic, Ljubinka
AU  - Matić, Ivana Z.
AU  - Todorović, Nina
AU  - Nikolić, Marijana
AU  - Joksovic, Milan D.
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1523
AB  - A new class of imine derivatives of hybrid chalcone analogues containing anthraquinone scaffold was synthesized and evaluated for their in vitro cytotoxic activity against HeLa, LS174, and A549 cancer cells. The compound 5n with furan ring linked to imino group showed potent activity against all target cells with IC50 values ranging from 1.76 to 6.11 mu M. A mode of action study suggested that compounds induced changes typical for apoptosis in HeLa cells. The most active compounds inhibited tubulogenesis and 5h was found to exhibit a strong anti-angiogenic effect.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Bioorganic and Medicinal Chemistry Letters
T1  - Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity
VL  - 24
IS  - 1
SP  - 65
EP  - 71
DO  - 10.1016/j.bmcl.2013.11.075
ER  - 
@article{
author = "Kolundzija, Branka and Markovic, Violeta and Stanojković, Tatjana and Joksovic, Ljubinka and Matić, Ivana Z. and Todorović, Nina and Nikolić, Marijana and Joksovic, Milan D.",
year = "2014",
abstract = "A new class of imine derivatives of hybrid chalcone analogues containing anthraquinone scaffold was synthesized and evaluated for their in vitro cytotoxic activity against HeLa, LS174, and A549 cancer cells. The compound 5n with furan ring linked to imino group showed potent activity against all target cells with IC50 values ranging from 1.76 to 6.11 mu M. A mode of action study suggested that compounds induced changes typical for apoptosis in HeLa cells. The most active compounds inhibited tubulogenesis and 5h was found to exhibit a strong anti-angiogenic effect.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Bioorganic and Medicinal Chemistry Letters",
title = "Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity",
volume = "24",
number = "1",
pages = "65-71",
doi = "10.1016/j.bmcl.2013.11.075"
}
Kolundzija, B., Markovic, V., Stanojković, T., Joksovic, L., Matić, I. Z., Todorović, N., Nikolić, M.,& Joksovic, M. D.. (2014). Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity. in Bioorganic and Medicinal Chemistry Letters
Oxford : Pergamon-Elsevier Science Ltd., 24(1), 65-71.
https://doi.org/10.1016/j.bmcl.2013.11.075
Kolundzija B, Markovic V, Stanojković T, Joksovic L, Matić IZ, Todorović N, Nikolić M, Joksovic MD. Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity. in Bioorganic and Medicinal Chemistry Letters. 2014;24(1):65-71.
doi:10.1016/j.bmcl.2013.11.075 .
Kolundzija, Branka, Markovic, Violeta, Stanojković, Tatjana, Joksovic, Ljubinka, Matić, Ivana Z., Todorović, Nina, Nikolić, Marijana, Joksovic, Milan D., "Novel anthraquinone based chalcone analogues containing an imine fragment: Synthesis, cytotoxicity and anti-angiogenic activity" in Bioorganic and Medicinal Chemistry Letters, 24, no. 1 (2014):65-71,
https://doi.org/10.1016/j.bmcl.2013.11.075 . .
40
32
44

Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate

Markovic, Violeta; Marković, Svetlana; Janicijevic, Ana; Rodić, Marko V.; Leovac, Vukadin; Todorović, Nina; Trifunović, Snežana; Joksovic, Milan D.

(Springer/Plenum Publishers, New York, 2013)

TY  - JOUR
AU  - Markovic, Violeta
AU  - Marković, Svetlana
AU  - Janicijevic, Ana
AU  - Rodić, Marko V.
AU  - Leovac, Vukadin
AU  - Todorović, Nina
AU  - Trifunović, Snežana
AU  - Joksovic, Milan D.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1225
AB  - A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate
VL  - 24
IS  - 6
SP  - 2127
EP  - 2136
DO  - 10.1007/s11224-013-0223-3
ER  - 
@article{
author = "Markovic, Violeta and Marković, Svetlana and Janicijevic, Ana and Rodić, Marko V. and Leovac, Vukadin and Todorović, Nina and Trifunović, Snežana and Joksovic, Milan D.",
year = "2013",
abstract = "A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate",
volume = "24",
number = "6",
pages = "2127-2136",
doi = "10.1007/s11224-013-0223-3"
}
Markovic, V., Marković, S., Janicijevic, A., Rodić, M. V., Leovac, V., Todorović, N., Trifunović, S.,& Joksovic, M. D.. (2013). Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry
Springer/Plenum Publishers, New York., 24(6), 2127-2136.
https://doi.org/10.1007/s11224-013-0223-3
Markovic V, Marković S, Janicijevic A, Rodić MV, Leovac V, Todorović N, Trifunović S, Joksovic MD. Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry. 2013;24(6):2127-2136.
doi:10.1007/s11224-013-0223-3 .
Markovic, Violeta, Marković, Svetlana, Janicijevic, Ana, Rodić, Marko V., Leovac, Vukadin, Todorović, Nina, Trifunović, Snežana, Joksovic, Milan D., "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate" in Structural Chemistry, 24, no. 6 (2013):2127-2136,
https://doi.org/10.1007/s11224-013-0223-3 . .
1
1
1

Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group

Markovic, Violeta; Janicijevic, Ana; Stanojković, Tatjana; Kolundzija, Branka; Sladić, Dušan; Vujčić, Miroslava; Janović, Barbara; Joksovic, Ljubinka; Djurdjevic, Predrag T.; Todorović, Nina; Trifunović, Snežana; Joksovic, Milan D.

(Elsevier France-Editions Scientifiques Medicales Elsevier, Paris, 2013)

TY  - JOUR
AU  - Markovic, Violeta
AU  - Janicijevic, Ana
AU  - Stanojković, Tatjana
AU  - Kolundzija, Branka
AU  - Sladić, Dušan
AU  - Vujčić, Miroslava
AU  - Janović, Barbara
AU  - Joksovic, Ljubinka
AU  - Djurdjevic, Predrag T.
AU  - Todorović, Nina
AU  - Trifunović, Snežana
AU  - Joksovic, Milan D.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1343
AB  - A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group
VL  - 64
SP  - 228
EP  - 238
DO  - 10.1016/j.ejmech.2013.03.071
ER  - 
@article{
author = "Markovic, Violeta and Janicijevic, Ana and Stanojković, Tatjana and Kolundzija, Branka and Sladić, Dušan and Vujčić, Miroslava and Janović, Barbara and Joksovic, Ljubinka and Djurdjevic, Predrag T. and Todorović, Nina and Trifunović, Snežana and Joksovic, Milan D.",
year = "2013",
abstract = "A series of novel anthraquinone thiosemicarbazone derivatives in a tautomerizable keto-imine form was synthesized and tested for their in vitro cytotoxic activity against human cancer cells (HeLa, MDA-MB-361, MDA-MB-453, K562, A549) and human normal MRC-5 cells. Several compounds efficiently inhibited cancer cell growth at micromolar concentrations, especially against K562 and HeLa cells. As determined by flow cytometric analysis, anthraquinone thiosemicarbazone caused significant increase in the number of sub-G1 phase of HeLa cells and apoptosis in a concentration-dependent manner. Also, inhibition of caspase-3, -8, and -9 with specific caspase inhibitors reduced the apoptosis mediated by the tested compounds in HeLa cells. All anthraquinone-thiosemicarbazones exhibit calf thymus DNA-binding activity, but no cleavage of plasmid DNA was observed.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group",
volume = "64",
pages = "228-238",
doi = "10.1016/j.ejmech.2013.03.071"
}
Markovic, V., Janicijevic, A., Stanojković, T., Kolundzija, B., Sladić, D., Vujčić, M., Janović, B., Joksovic, L., Djurdjevic, P. T., Todorović, N., Trifunović, S.,& Joksovic, M. D.. (2013). Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 64, 228-238.
https://doi.org/10.1016/j.ejmech.2013.03.071
Markovic V, Janicijevic A, Stanojković T, Kolundzija B, Sladić D, Vujčić M, Janović B, Joksovic L, Djurdjevic PT, Todorović N, Trifunović S, Joksovic MD. Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group. in European Journal of Medicinal Chemistry. 2013;64:228-238.
doi:10.1016/j.ejmech.2013.03.071 .
Markovic, Violeta, Janicijevic, Ana, Stanojković, Tatjana, Kolundzija, Branka, Sladić, Dušan, Vujčić, Miroslava, Janović, Barbara, Joksovic, Ljubinka, Djurdjevic, Predrag T., Todorović, Nina, Trifunović, Snežana, Joksovic, Milan D., "Synthesis, cytotoxic activity and DNA-interaction studies of novel anthraquinone-thiosemicarbazones with tautomerizable methylene group" in European Journal of Medicinal Chemistry, 64 (2013):228-238,
https://doi.org/10.1016/j.ejmech.2013.03.071 . .
23
16
24

Debromination of endo-(+)-3-Bromocamphor with Primary Amines

Marković, Svetlana; Markovic, Violeta; Joksovic, Milan D.; Todorović, Nina; Joksovic, Ljubinka; Divjakovic, Vladimir; Trifunović, Snežana

(Soc Brasileira Quimica, Sao Paulo, 2013)

TY  - JOUR
AU  - Marković, Svetlana
AU  - Markovic, Violeta
AU  - Joksovic, Milan D.
AU  - Todorović, Nina
AU  - Joksovic, Ljubinka
AU  - Divjakovic, Vladimir
AU  - Trifunović, Snežana
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1222
AB  - Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.
PB  - Soc Brasileira Quimica, Sao Paulo
T2  - Journal of the Brazilian Chemical Society
T1  - Debromination of endo-(+)-3-Bromocamphor with Primary Amines
VL  - 24
IS  - 7
SP  - 1099
DO  - 10.5935/0103-5053.20130144
ER  - 
@article{
author = "Marković, Svetlana and Markovic, Violeta and Joksovic, Milan D. and Todorović, Nina and Joksovic, Ljubinka and Divjakovic, Vladimir and Trifunović, Snežana",
year = "2013",
abstract = "Reductive debromination of endo-(+)-3-bromocamphor with different primary amines followed by imine formation was investigated. This reaction requires simple experimental procedure without any organic solvent, metal or conventional reducing agent. A strong influence of amine polarity on the efficacy of debromination process was observed, and ethanolamine and ethylene diamine having sufficiently high boiling points can debrominate 3-bromocamphor giving corresponding camphanimines in good isolated yields. The mechanisms of debromination of 3-bromocamphor with ethanolamine and n-hexylamine were investigated at the B3LYP/6-311+G(d,p) level of theory. The radical mechanism was revealed, and it was shown that the reaction with more polar ethanolamine is energetically more favorable.",
publisher = "Soc Brasileira Quimica, Sao Paulo",
journal = "Journal of the Brazilian Chemical Society",
title = "Debromination of endo-(+)-3-Bromocamphor with Primary Amines",
volume = "24",
number = "7",
pages = "1099",
doi = "10.5935/0103-5053.20130144"
}
Marković, S., Markovic, V., Joksovic, M. D., Todorović, N., Joksovic, L., Divjakovic, V.,& Trifunović, S.. (2013). Debromination of endo-(+)-3-Bromocamphor with Primary Amines. in Journal of the Brazilian Chemical Society
Soc Brasileira Quimica, Sao Paulo., 24(7), 1099.
https://doi.org/10.5935/0103-5053.20130144
Marković S, Markovic V, Joksovic MD, Todorović N, Joksovic L, Divjakovic V, Trifunović S. Debromination of endo-(+)-3-Bromocamphor with Primary Amines. in Journal of the Brazilian Chemical Society. 2013;24(7):1099.
doi:10.5935/0103-5053.20130144 .
Marković, Svetlana, Markovic, Violeta, Joksovic, Milan D., Todorović, Nina, Joksovic, Ljubinka, Divjakovic, Vladimir, Trifunović, Snežana, "Debromination of endo-(+)-3-Bromocamphor with Primary Amines" in Journal of the Brazilian Chemical Society, 24, no. 7 (2013):1099,
https://doi.org/10.5935/0103-5053.20130144 . .
3
3
3

Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands

Vujic, Jelena M.; Kaluđerović, Goran N.; Zmejkovski, Bojana; Milovanovic, Marija; Volarevic, Vladislav; Arsenijevic, Nebojsa; Stanojković, Tatjana; Trifunovic, Srecko R.

(Elsevier Science Sa, Lausanne, 2012)

TY  - JOUR
AU  - Vujic, Jelena M.
AU  - Kaluđerović, Goran N.
AU  - Zmejkovski, Bojana
AU  - Milovanovic, Marija
AU  - Volarevic, Vladislav
AU  - Arsenijevic, Nebojsa
AU  - Stanojković, Tatjana
AU  - Trifunovic, Srecko R.
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/969
AB  - Synthesis of four new platinum(IV) complexes 1-4, with bidentate N,N'-ligand precursors O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoic acid dihydrochloride [(S,S)-H(4)eddl]Cl-2 were reported. The composition of the novel platinum complexes was determined by elemental analysis and characterizations were performed by infrared, H-1 and C-13 NMR spectroscopy. DFT calculations indicate formation one (R,R) from three possible diastereoisomers (S,S; R,S). Complexes 1-4 displayed potent anticancer activity. IC50 values range from 0.74 to 70 mu M, against tested cell lines, except for CLL cells. The antitumoral activity of 2-4 was found to be considerably stronger to Jurkat and K562. Cell cycle analysis of cell lines showed G1 arrest in the presence of analyzed complexes.
PB  - Elsevier Science Sa, Lausanne
T2  - Inorganica Chimica Acta
T1  - Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands
VL  - 390
SP  - 123
EP  - 128
DO  - 10.1016/j.ica.2012.03.048
ER  - 
@article{
author = "Vujic, Jelena M. and Kaluđerović, Goran N. and Zmejkovski, Bojana and Milovanovic, Marija and Volarevic, Vladislav and Arsenijevic, Nebojsa and Stanojković, Tatjana and Trifunovic, Srecko R.",
year = "2012",
abstract = "Synthesis of four new platinum(IV) complexes 1-4, with bidentate N,N'-ligand precursors O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoic acid dihydrochloride [(S,S)-H(4)eddl]Cl-2 were reported. The composition of the novel platinum complexes was determined by elemental analysis and characterizations were performed by infrared, H-1 and C-13 NMR spectroscopy. DFT calculations indicate formation one (R,R) from three possible diastereoisomers (S,S; R,S). Complexes 1-4 displayed potent anticancer activity. IC50 values range from 0.74 to 70 mu M, against tested cell lines, except for CLL cells. The antitumoral activity of 2-4 was found to be considerably stronger to Jurkat and K562. Cell cycle analysis of cell lines showed G1 arrest in the presence of analyzed complexes.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Inorganica Chimica Acta",
title = "Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands",
volume = "390",
pages = "123-128",
doi = "10.1016/j.ica.2012.03.048"
}
Vujic, J. M., Kaluđerović, G. N., Zmejkovski, B., Milovanovic, M., Volarevic, V., Arsenijevic, N., Stanojković, T.,& Trifunovic, S. R.. (2012). Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands. in Inorganica Chimica Acta
Elsevier Science Sa, Lausanne., 390, 123-128.
https://doi.org/10.1016/j.ica.2012.03.048
Vujic JM, Kaluđerović GN, Zmejkovski B, Milovanovic M, Volarevic V, Arsenijevic N, Stanojković T, Trifunovic SR. Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands. in Inorganica Chimica Acta. 2012;390:123-128.
doi:10.1016/j.ica.2012.03.048 .
Vujic, Jelena M., Kaluđerović, Goran N., Zmejkovski, Bojana, Milovanovic, Marija, Volarevic, Vladislav, Arsenijevic, Nebojsa, Stanojković, Tatjana, Trifunovic, Srecko R., "Stereospecific ligands and their complexes. Part X: Synthesis, characterization and in vitro antitumoral activity of platinum(IV) complexes with O,O '-dialkyl-(S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoate ligands" in Inorganica Chimica Acta, 390 (2012):123-128,
https://doi.org/10.1016/j.ica.2012.03.048 . .
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Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones

Markovic, Violeta; Erić, Slavica; Stanojković, Tatjana; Gligorijević, Nevenka; Arandelovic, Sandra; Todorović, Nina; Trifunović, Snežana; Manojlović, Nedeljko; Jelić, Ratomir; Joksovic, Milan D.

(Oxford : Pergamon-Elsevier Science Ltd, 2011)

TY  - JOUR
AU  - Markovic, Violeta
AU  - Erić, Slavica
AU  - Stanojković, Tatjana
AU  - Gligorijević, Nevenka
AU  - Arandelovic, Sandra
AU  - Todorović, Nina
AU  - Trifunović, Snežana
AU  - Manojlović, Nedeljko
AU  - Jelić, Ratomir
AU  - Joksovic, Milan D.
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/791
AB  - Twenty five 4-aminomethylidene derivatives obtained from 3-phenyl-2-pyrazolin-5-one and 1,3-diphenyl-2-pyrazolin-5-one were synthesized and tested for their antiproliferative activity against human breast cancer MDA-MB-361 and MDA-MB-453 cell lines. The compounds derived from 1,3-diphenyl-2-pyrazolin-5-one exhibited the most remarkable activity in the treatment of both cell lines. In vitro antiproliferative activities were accompanied by an important apoptotic fraction of both cell lines; also, compounds inhibited key endothelial cell functions implicated in invasion and angiogenesis. QSAR methods were performed in order to analyze the influence of structural features of the compounds investigated on the antiproliferative potential on MDA-MB-361 and MDA-MB-453 cancer cells. One-parameter heuristic analysis was performed and different whole molecule and fragmental descriptors were considered for rationalization of mechanism of interaction of these compounds with active place of hypothetical target included in tumorigenesis.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Bioorganic and Medicinal Chemistry Letters
T1  - Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones
VL  - 21
IS  - 15
SP  - 4416
EP  - 4421
DO  - 10.1016/j.bmcl.2011.06.025
ER  - 
@article{
author = "Markovic, Violeta and Erić, Slavica and Stanojković, Tatjana and Gligorijević, Nevenka and Arandelovic, Sandra and Todorović, Nina and Trifunović, Snežana and Manojlović, Nedeljko and Jelić, Ratomir and Joksovic, Milan D.",
year = "2011",
abstract = "Twenty five 4-aminomethylidene derivatives obtained from 3-phenyl-2-pyrazolin-5-one and 1,3-diphenyl-2-pyrazolin-5-one were synthesized and tested for their antiproliferative activity against human breast cancer MDA-MB-361 and MDA-MB-453 cell lines. The compounds derived from 1,3-diphenyl-2-pyrazolin-5-one exhibited the most remarkable activity in the treatment of both cell lines. In vitro antiproliferative activities were accompanied by an important apoptotic fraction of both cell lines; also, compounds inhibited key endothelial cell functions implicated in invasion and angiogenesis. QSAR methods were performed in order to analyze the influence of structural features of the compounds investigated on the antiproliferative potential on MDA-MB-361 and MDA-MB-453 cancer cells. One-parameter heuristic analysis was performed and different whole molecule and fragmental descriptors were considered for rationalization of mechanism of interaction of these compounds with active place of hypothetical target included in tumorigenesis.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Bioorganic and Medicinal Chemistry Letters",
title = "Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones",
volume = "21",
number = "15",
pages = "4416-4421",
doi = "10.1016/j.bmcl.2011.06.025"
}
Markovic, V., Erić, S., Stanojković, T., Gligorijević, N., Arandelovic, S., Todorović, N., Trifunović, S., Manojlović, N., Jelić, R.,& Joksovic, M. D.. (2011). Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones. in Bioorganic and Medicinal Chemistry Letters
Oxford : Pergamon-Elsevier Science Ltd., 21(15), 4416-4421.
https://doi.org/10.1016/j.bmcl.2011.06.025
Markovic V, Erić S, Stanojković T, Gligorijević N, Arandelovic S, Todorović N, Trifunović S, Manojlović N, Jelić R, Joksovic MD. Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones. in Bioorganic and Medicinal Chemistry Letters. 2011;21(15):4416-4421.
doi:10.1016/j.bmcl.2011.06.025 .
Markovic, Violeta, Erić, Slavica, Stanojković, Tatjana, Gligorijević, Nevenka, Arandelovic, Sandra, Todorović, Nina, Trifunović, Snežana, Manojlović, Nedeljko, Jelić, Ratomir, Joksovic, Milan D., "Antiproliferative activity and QSAR studies of a series of new 4-aminomethylidene derivatives of some pyrazol-5-ones" in Bioorganic and Medicinal Chemistry Letters, 21, no. 15 (2011):4416-4421,
https://doi.org/10.1016/j.bmcl.2011.06.025 . .
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Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoic acid

Vujic, Jelena M.; Kaluđerović, Goran N.; Milovanovic, Marija; Zmejkovski, Bojana; Volarevic, Vladislav; Zivic, Danijela; Durdevic, Predrag; Arsenijevic, Nebojsa; Trifunovic, Srecko R.

(Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux, 2011)

TY  - JOUR
AU  - Vujic, Jelena M.
AU  - Kaluđerović, Goran N.
AU  - Milovanovic, Marija
AU  - Zmejkovski, Bojana
AU  - Volarevic, Vladislav
AU  - Zivic, Danijela
AU  - Durdevic, Predrag
AU  - Arsenijevic, Nebojsa
AU  - Trifunovic, Srecko R.
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/838
AB  - Platinum(II) complexes (1-4) with bidentate N,N'-ligands, O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoic acid were synthesized and characterized by IR, (1)H NMR and (13)C NMR spectroscopy and elemental analysis. DFT calculations were performed for the complexes and it was found that only one diastereoisomer could be formed. Cytotoxic activity of complexes 1-4 was determined against chronic lymphocytic leukemia cells (CLL) and compared to the activity of ligand precursors L1 center dot 2HCl-L4 center dot 2HCl and corresponding palladium(II) complexes, [PdCl(2)L] (L = L1-L4). The complexes were found to exhibit significantly higher antitumor activities than cisplatin on CLL cells. Cytotoxic effect of platinum(II) complexes on CLL cells was higher compared to corresponding palladium(II) complexes. In addition the mode of cell death induced by platinum(II) complexes was determined.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoic acid
VL  - 46
IS  - 9
SP  - 4559
EP  - 4565
DO  - 10.1016/j.ejmech.2011.07.034
ER  - 
@article{
author = "Vujic, Jelena M. and Kaluđerović, Goran N. and Milovanovic, Marija and Zmejkovski, Bojana and Volarevic, Vladislav and Zivic, Danijela and Durdevic, Predrag and Arsenijevic, Nebojsa and Trifunovic, Srecko R.",
year = "2011",
abstract = "Platinum(II) complexes (1-4) with bidentate N,N'-ligands, O,O'-dialkyl esters (alkyl = ethyl, n-propyl, n-butyl and n-pentyl), of (S,S)-ethylenediamine-N,N'-di-2-(4-methyl)pentanoic acid were synthesized and characterized by IR, (1)H NMR and (13)C NMR spectroscopy and elemental analysis. DFT calculations were performed for the complexes and it was found that only one diastereoisomer could be formed. Cytotoxic activity of complexes 1-4 was determined against chronic lymphocytic leukemia cells (CLL) and compared to the activity of ligand precursors L1 center dot 2HCl-L4 center dot 2HCl and corresponding palladium(II) complexes, [PdCl(2)L] (L = L1-L4). The complexes were found to exhibit significantly higher antitumor activities than cisplatin on CLL cells. Cytotoxic effect of platinum(II) complexes on CLL cells was higher compared to corresponding palladium(II) complexes. In addition the mode of cell death induced by platinum(II) complexes was determined.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoic acid",
volume = "46",
number = "9",
pages = "4559-4565",
doi = "10.1016/j.ejmech.2011.07.034"
}
Vujic, J. M., Kaluđerović, G. N., Milovanovic, M., Zmejkovski, B., Volarevic, V., Zivic, D., Durdevic, P., Arsenijevic, N.,& Trifunovic, S. R.. (2011). Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoic acid. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 46(9), 4559-4565.
https://doi.org/10.1016/j.ejmech.2011.07.034
Vujic JM, Kaluđerović GN, Milovanovic M, Zmejkovski B, Volarevic V, Zivic D, Durdevic P, Arsenijevic N, Trifunovic SR. Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoic acid. in European Journal of Medicinal Chemistry. 2011;46(9):4559-4565.
doi:10.1016/j.ejmech.2011.07.034 .
Vujic, Jelena M., Kaluđerović, Goran N., Milovanovic, Marija, Zmejkovski, Bojana, Volarevic, Vladislav, Zivic, Danijela, Durdevic, Predrag, Arsenijevic, Nebojsa, Trifunovic, Srecko R., "Stereospecific ligands and their complexes. Part VII. Synthesis, characterization and in vitro antitumoral activity of platinum(II) complexes with O,O '-dialkyl esters of (S,S)-ethylenediamine-N,N '-di-2-(4-methyl)pentanoic acid" in European Journal of Medicinal Chemistry, 46, no. 9 (2011):4559-4565,
https://doi.org/10.1016/j.ejmech.2011.07.034 . .
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