Novaković, Irena

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orcid::0000-0001-9881-1204
  • Novaković, Irena (4)
  • Novaković, Irena T (1)
  • Novaković, Irena T. (1)
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Author's Bibliography

Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone

Đorđević Aleksić, Jelena; Kolarević, Stoimir; Jovanović Marić, Jovana; Oalđe Pavlović, Mariana; Sladić, Dušan; Novaković, Irena; Vuković-Gačić, Branka

(National Library of Serbia, 2022)

TY  - JOUR
AU  - Đorđević Aleksić, Jelena
AU  - Kolarević, Stoimir
AU  - Jovanović Marić, Jovana
AU  - Oalđe Pavlović, Mariana
AU  - Sladić, Dušan
AU  - Novaković, Irena
AU  - Vuković-Gačić, Branka
PY  - 2022
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/2018
AB  - Biological activity of 2-tert-butyl-1,4-benzoquinone (TBQ) and its derivatives, 2-tert-butyl-5-(2-propylthio)-1,4-benzoquinone, 2-tert-butyl-5- -(propylthio)-1,4-benzoquinone, 2-tert-butyl-5,6-(ethylenedithio)-1,4-benzoquinone, 2-tert-butyl-5-(phenylthio)-1,4-benzoquinone and 2-tert-butyl-6-(phenylthio)- 1,4-benzoquinone, were tested for their antioxidant, antibacterial, toxic, cytotoxic and genotoxic potential. Using the DPPH test, all derivatives showed good antioxidant activity, better than ascorbic acid, and the 2-tert- -butyl-5-(propylthio)-1,4-benzoquinone derivative showed the strongest effect. Better antibacterial potential was observed against Gram-positive bacteria in the broth microdilution method in which the 2-tert-butyl-5-(phenylthio)-1,4- -benzoquinone derivative showed the strongest activity (MIC = 15.6 μM). The results of toxicity tests, using the Brine shrimp test, indicated that the derivatives lose their toxic potential compared to TBQ, except for 2-tert-butyl-6- -(phenylthio)-1,4-benzoquinone, which showed a 3 times stronger effect. Cytotoxicity was assessed by the MTT assay in 24 and 72 h treatments in MRC-5, HS 294T and A549 cell lines in threefold decreasing gradient (11, 33 and 100 μM). Modifications potentiate the cytotoxic effect, and the strongest effect was observed with the 2-tert-butyl-5,6-(ethylendithio)-1,4-benzoquinone derivative. In addition, the genotoxic potential was examined in the MRC-5 cell line using the comet assay. All tested derivatives of TBQ showed a genotoxic effect at all applied subtoxic concentrations. In general, the chemical modifications of TBQ enhanced its biological activity.
PB  - National Library of Serbia
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone
EP  - 1258
IS  - 11
SP  - 1245
VL  - 87
DO  - 10.2298/JSC220304044D
ER  - 
@article{
author = "Đorđević Aleksić, Jelena and Kolarević, Stoimir and Jovanović Marić, Jovana and Oalđe Pavlović, Mariana and Sladić, Dušan and Novaković, Irena and Vuković-Gačić, Branka",
year = "2022",
abstract = "Biological activity of 2-tert-butyl-1,4-benzoquinone (TBQ) and its derivatives, 2-tert-butyl-5-(2-propylthio)-1,4-benzoquinone, 2-tert-butyl-5- -(propylthio)-1,4-benzoquinone, 2-tert-butyl-5,6-(ethylenedithio)-1,4-benzoquinone, 2-tert-butyl-5-(phenylthio)-1,4-benzoquinone and 2-tert-butyl-6-(phenylthio)- 1,4-benzoquinone, were tested for their antioxidant, antibacterial, toxic, cytotoxic and genotoxic potential. Using the DPPH test, all derivatives showed good antioxidant activity, better than ascorbic acid, and the 2-tert- -butyl-5-(propylthio)-1,4-benzoquinone derivative showed the strongest effect. Better antibacterial potential was observed against Gram-positive bacteria in the broth microdilution method in which the 2-tert-butyl-5-(phenylthio)-1,4- -benzoquinone derivative showed the strongest activity (MIC = 15.6 μM). The results of toxicity tests, using the Brine shrimp test, indicated that the derivatives lose their toxic potential compared to TBQ, except for 2-tert-butyl-6- -(phenylthio)-1,4-benzoquinone, which showed a 3 times stronger effect. Cytotoxicity was assessed by the MTT assay in 24 and 72 h treatments in MRC-5, HS 294T and A549 cell lines in threefold decreasing gradient (11, 33 and 100 μM). Modifications potentiate the cytotoxic effect, and the strongest effect was observed with the 2-tert-butyl-5,6-(ethylendithio)-1,4-benzoquinone derivative. In addition, the genotoxic potential was examined in the MRC-5 cell line using the comet assay. All tested derivatives of TBQ showed a genotoxic effect at all applied subtoxic concentrations. In general, the chemical modifications of TBQ enhanced its biological activity.",
publisher = "National Library of Serbia",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone",
pages = "1258-1245",
number = "11",
volume = "87",
doi = "10.2298/JSC220304044D"
}
Đorđević Aleksić, J., Kolarević, S., Jovanović Marić, J., Oalđe Pavlović, M., Sladić, D., Novaković, I.,& Vuković-Gačić, B.. (2022). Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone. in Journal of the Serbian Chemical Society
National Library of Serbia., 87(11), 1245-1258.
https://doi.org/10.2298/JSC220304044D
Đorđević Aleksić J, Kolarević S, Jovanović Marić J, Oalđe Pavlović M, Sladić D, Novaković I, Vuković-Gačić B. Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone. in Journal of the Serbian Chemical Society. 2022;87(11):1245-1258.
doi:10.2298/JSC220304044D .
Đorđević Aleksić, Jelena, Kolarević, Stoimir, Jovanović Marić, Jovana, Oalđe Pavlović, Mariana, Sladić, Dušan, Novaković, Irena, Vuković-Gačić, Branka, "Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone" in Journal of the Serbian Chemical Society, 87, no. 11 (2022):1245-1258,
https://doi.org/10.2298/JSC220304044D . .

Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives.

Đorđević Aleksić, Jelena; Kolarević, Stoimir; Jovanović Marić, Jovana; Novaković, Irena; Sladić, Dušan; Vuković-Gačić, Branka

(Federation of European Microbiological Societies - FEMS, 2020)

TY  - CONF
AU  - Đorđević Aleksić, Jelena
AU  - Kolarević, Stoimir
AU  - Jovanović Marić, Jovana
AU  - Novaković, Irena
AU  - Sladić, Dušan
AU  - Vuković-Gačić, Branka
PY  - 2020
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/2155
AB  - Background: Biologically active compounds, originating from a variety of natural sources: plants, animals and microor- ganisms, have great potential for use as antimicrobial agents. Avarol, a compound originating from the Mediterranean sponge Disidea avara, exhibits a number of biological activities including antimicrobial activity. Considering that, avarol was taken as a model for the synthesis of 2-tert-butyl-1,4-benzoquinone (TBQ) derivatives.
Objectives: TBQ was chosen because of its similar chemical structure with avarol who showed strong biological activity but is more accessible and economical than avarol. By selecting the thiol group, we aimed at combining the action of two strong functional groups of natural origin, quinones and thiols, which both have antimicrobial activity.
Methods: In this work antimicrobial activity of TBQ and its derivatives: 2-tert-butyl-5-(isopropylthio)-1.4-benzoqui- none, 2-tert-butyl-5-(propylthio)-1.4-benzoquinone, 2-tert-butyl-5,6-(ethylendithio)-1.4-benzoquinone, 2-tert-bu- tyl-5-(phenylthio)-1.4-benzoquinone and 2-tert-butyl-6-(phenylthio)-1.4-benzoquinone was evaluated by the MIC mi- crodilution method on 7 different ATCC bacterial strains.
Results: All compounds tested showed stronger antimicrobial activity against Gram positive bacterial strains (Entero- coccus faecalis, Staphylococcus aureus, Bacillus spp.). A strong antimicrobial effect (MIC value less than 100μM) was shown by 2-tert-butyl-5,6- (ethylendithio)-1,4-benzoquinone, 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone deriva- tives and 2-tert-butyl-6-(phenylthio)-1,4-benzoquinone against S.aureus. TBQ, 2-tert-butyl-5-(isopropylthio)-1,4-ben- zoquinone, 2-tert-butyl-5, 6-(ethylendithio)-1,4-benzoquinone and 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone showed strong antimicrobial effect against Bacillus spp. According to our results, chemical modifications of TBQ in- crease its antimicrobial activity while derivative 2-tert-butyl-5,6-(ethylendithio)-1.4-benzoquinone is the best candi- date for further testing.
PB  - Federation of European Microbiological Societies - FEMS
C3  - FEMS Online Conference on Microbiology 2020
T1  - Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives.
SP  - 223
UR  - https://hdl.handle.net/21.15107/rcub_rimsi_2155
ER  - 
@conference{
author = "Đorđević Aleksić, Jelena and Kolarević, Stoimir and Jovanović Marić, Jovana and Novaković, Irena and Sladić, Dušan and Vuković-Gačić, Branka",
year = "2020",
abstract = "Background: Biologically active compounds, originating from a variety of natural sources: plants, animals and microor- ganisms, have great potential for use as antimicrobial agents. Avarol, a compound originating from the Mediterranean sponge Disidea avara, exhibits a number of biological activities including antimicrobial activity. Considering that, avarol was taken as a model for the synthesis of 2-tert-butyl-1,4-benzoquinone (TBQ) derivatives.
Objectives: TBQ was chosen because of its similar chemical structure with avarol who showed strong biological activity but is more accessible and economical than avarol. By selecting the thiol group, we aimed at combining the action of two strong functional groups of natural origin, quinones and thiols, which both have antimicrobial activity.
Methods: In this work antimicrobial activity of TBQ and its derivatives: 2-tert-butyl-5-(isopropylthio)-1.4-benzoqui- none, 2-tert-butyl-5-(propylthio)-1.4-benzoquinone, 2-tert-butyl-5,6-(ethylendithio)-1.4-benzoquinone, 2-tert-bu- tyl-5-(phenylthio)-1.4-benzoquinone and 2-tert-butyl-6-(phenylthio)-1.4-benzoquinone was evaluated by the MIC mi- crodilution method on 7 different ATCC bacterial strains.
Results: All compounds tested showed stronger antimicrobial activity against Gram positive bacterial strains (Entero- coccus faecalis, Staphylococcus aureus, Bacillus spp.). A strong antimicrobial effect (MIC value less than 100μM) was shown by 2-tert-butyl-5,6- (ethylendithio)-1,4-benzoquinone, 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone deriva- tives and 2-tert-butyl-6-(phenylthio)-1,4-benzoquinone against S.aureus. TBQ, 2-tert-butyl-5-(isopropylthio)-1,4-ben- zoquinone, 2-tert-butyl-5, 6-(ethylendithio)-1,4-benzoquinone and 2-tert-butyl-5-(phenylthio)-1.4-benzoquinone showed strong antimicrobial effect against Bacillus spp. According to our results, chemical modifications of TBQ in- crease its antimicrobial activity while derivative 2-tert-butyl-5,6-(ethylendithio)-1.4-benzoquinone is the best candi- date for further testing.",
publisher = "Federation of European Microbiological Societies - FEMS",
journal = "FEMS Online Conference on Microbiology 2020",
title = "Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives.",
pages = "223",
url = "https://hdl.handle.net/21.15107/rcub_rimsi_2155"
}
Đorđević Aleksić, J., Kolarević, S., Jovanović Marić, J., Novaković, I., Sladić, D.,& Vuković-Gačić, B.. (2020). Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives.. in FEMS Online Conference on Microbiology 2020
Federation of European Microbiological Societies - FEMS., 223.
https://hdl.handle.net/21.15107/rcub_rimsi_2155
Đorđević Aleksić J, Kolarević S, Jovanović Marić J, Novaković I, Sladić D, Vuković-Gačić B. Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives.. in FEMS Online Conference on Microbiology 2020. 2020;:223.
https://hdl.handle.net/21.15107/rcub_rimsi_2155 .
Đorđević Aleksić, Jelena, Kolarević, Stoimir, Jovanović Marić, Jovana, Novaković, Irena, Sladić, Dušan, Vuković-Gačić, Branka, "Antimicrobial activity of 2-tert-butyl-1.4-benzoquinone and its selected alkylthio and arylthio derivatives." in FEMS Online Conference on Microbiology 2020 (2020):223,
https://hdl.handle.net/21.15107/rcub_rimsi_2155 .

Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models

Kolarević, Stoimir; Milovanović, Dragana; Kracun-Kolarević, Margareta; Kostić-Vuković, Jovana; Sunjog, Karolina; Martinović, Rajko; Đorđević Aleksić, Jelena; Novaković, Irena; Sladic, Dusan; Vukovic-Gacic, Branka

(Taylor & Francis Ltd, Abingdon, 2019)

TY  - JOUR
AU  - Kolarević, Stoimir
AU  - Milovanović, Dragana
AU  - Kracun-Kolarević, Margareta
AU  - Kostić-Vuković, Jovana
AU  - Sunjog, Karolina
AU  - Martinović, Rajko
AU  - Đorđević Aleksić, Jelena
AU  - Novaković, Irena
AU  - Sladic, Dusan
AU  - Vukovic-Gacic, Branka
PY  - 2019
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1274
AB  - In this study, mutagenic and genotoxic potential of anti-tumor compounds avarol, avarone, and its derivatives 3 '-methoxyavarone, 4 '-(methylamino)avarone and 3 '-(methylamino)avarone was evaluated and compared to cytostatics commonly used in chemotherapy (5-fluorouracil, etoposid, and cisplatin). Mutagenic potential of selected hydroquinone and quinones was assessed in prokaryotic model by the SOS/umuC assay in Salmonella typhimurium TA1535/pSK1002. Genotoxic potential was also assessed in eukaryotic models using comet assay in human fetal lung cell line (MRC-5), human adenocarcinoma epithelial cell line (A549), and in human peripheral blood cells (HPBC). The results indicated that avarol and avarone do not exert mutagenic/genotoxic potential. Among the studied avarone derivatives, mutagenic potential was detected by SOS/umuC test for 3 '-(methylamino)avarone, but only after metabolic activation. The results of comet assay indicated that 3 '-methoxyavarone and 3 '-(methylamino)avarone have a significant impact on the level of DNA damage in the MRC-5 cell line. Genotoxic potential was not observed in A549 cells or HPBC probably due to a different uptake rate for the compounds and lower in metabolism rate within these cells.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Drug and Chemical Toxicology
T1  - Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models
EP  - 139
IS  - 2
SP  - 130
VL  - 42
DO  - 10.1080/01480545.2017.1413108
ER  - 
@article{
author = "Kolarević, Stoimir and Milovanović, Dragana and Kracun-Kolarević, Margareta and Kostić-Vuković, Jovana and Sunjog, Karolina and Martinović, Rajko and Đorđević Aleksić, Jelena and Novaković, Irena and Sladic, Dusan and Vukovic-Gacic, Branka",
year = "2019",
abstract = "In this study, mutagenic and genotoxic potential of anti-tumor compounds avarol, avarone, and its derivatives 3 '-methoxyavarone, 4 '-(methylamino)avarone and 3 '-(methylamino)avarone was evaluated and compared to cytostatics commonly used in chemotherapy (5-fluorouracil, etoposid, and cisplatin). Mutagenic potential of selected hydroquinone and quinones was assessed in prokaryotic model by the SOS/umuC assay in Salmonella typhimurium TA1535/pSK1002. Genotoxic potential was also assessed in eukaryotic models using comet assay in human fetal lung cell line (MRC-5), human adenocarcinoma epithelial cell line (A549), and in human peripheral blood cells (HPBC). The results indicated that avarol and avarone do not exert mutagenic/genotoxic potential. Among the studied avarone derivatives, mutagenic potential was detected by SOS/umuC test for 3 '-(methylamino)avarone, but only after metabolic activation. The results of comet assay indicated that 3 '-methoxyavarone and 3 '-(methylamino)avarone have a significant impact on the level of DNA damage in the MRC-5 cell line. Genotoxic potential was not observed in A549 cells or HPBC probably due to a different uptake rate for the compounds and lower in metabolism rate within these cells.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Drug and Chemical Toxicology",
title = "Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models",
pages = "139-130",
number = "2",
volume = "42",
doi = "10.1080/01480545.2017.1413108"
}
Kolarević, S., Milovanović, D., Kracun-Kolarević, M., Kostić-Vuković, J., Sunjog, K., Martinović, R., Đorđević Aleksić, J., Novaković, I., Sladic, D.,& Vukovic-Gacic, B.. (2019). Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models. in Drug and Chemical Toxicology
Taylor & Francis Ltd, Abingdon., 42(2), 130-139.
https://doi.org/10.1080/01480545.2017.1413108
Kolarević S, Milovanović D, Kracun-Kolarević M, Kostić-Vuković J, Sunjog K, Martinović R, Đorđević Aleksić J, Novaković I, Sladic D, Vukovic-Gacic B. Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models. in Drug and Chemical Toxicology. 2019;42(2):130-139.
doi:10.1080/01480545.2017.1413108 .
Kolarević, Stoimir, Milovanović, Dragana, Kracun-Kolarević, Margareta, Kostić-Vuković, Jovana, Sunjog, Karolina, Martinović, Rajko, Đorđević Aleksić, Jelena, Novaković, Irena, Sladic, Dusan, Vukovic-Gacic, Branka, "Evaluation of genotoxic potential of avarol, avarone, and its methoxy and methylamino derivatives in prokaryotic and eukaryotic test models" in Drug and Chemical Toxicology, 42, no. 2 (2019):130-139,
https://doi.org/10.1080/01480545.2017.1413108 . .
2
9
5
7

Antioxidant Activity of Selected Polyphenolics in Yeast Cells: The Case Study of Montenegrin Merlot Wine

Đorđević, Neda O.; Todorović, Nevena; Novaković, Irena T.; Pezo, Lato; Pejin, Boris; Maras, Vesna; Tešević, Vele; Pajović, Snežana B.

(MDPI, Basel, 2018)

TY  - JOUR
AU  - Đorđević, Neda O.
AU  - Todorović, Nevena
AU  - Novaković, Irena T.
AU  - Pezo, Lato
AU  - Pejin, Boris
AU  - Maras, Vesna
AU  - Tešević, Vele
AU  - Pajović, Snežana B.
PY  - 2018
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1155
AB  - Screens of antioxidant activity (AA) of various natural products have been a focus of the research community worldwide. This work aimed to differentiate selected samples of Merlot wines originated from Montenegro, with regard to phenolic profile and antioxidant capacity studied by survival rate, total sulfhydryl groups and activities of glutathione peroxidase (GPx), glutathione reductase and catalase in H2O2-stressed Saccharomyces cerevisiae cells. In this study, DPPH assay was also performed. Higher total phenolic content leads to an enhanced AA under both conditions. The same trend was observed for catechin and gallic acid, the most abundant phenolics in the examined wine samples. Finally, the findings of an Artificial Neural Network (ANN) model were in a good agreement (r(2) = 0.978) with the experimental data. All tested samples exhibited a protective effect in H2O2-stressed yeast cells. Pre-treatment with examined wines increased survival in H2O2-stressed cells and shifted antioxidative defense towards GPx-mediated defense. Finally, sensitivity analysis of obtained ANN model highlights the complexity of the impact that variations in the concentrations of specific phenolic components have on the antioxidant defense system.
PB  - MDPI, Basel
T2  - Molecules
T1  - Antioxidant Activity of Selected Polyphenolics in Yeast Cells: The Case Study of Montenegrin Merlot Wine
IS  - 8
VL  - 23
DO  - 10.3390/molecules23081971
ER  - 
@article{
author = "Đorđević, Neda O. and Todorović, Nevena and Novaković, Irena T. and Pezo, Lato and Pejin, Boris and Maras, Vesna and Tešević, Vele and Pajović, Snežana B.",
year = "2018",
abstract = "Screens of antioxidant activity (AA) of various natural products have been a focus of the research community worldwide. This work aimed to differentiate selected samples of Merlot wines originated from Montenegro, with regard to phenolic profile and antioxidant capacity studied by survival rate, total sulfhydryl groups and activities of glutathione peroxidase (GPx), glutathione reductase and catalase in H2O2-stressed Saccharomyces cerevisiae cells. In this study, DPPH assay was also performed. Higher total phenolic content leads to an enhanced AA under both conditions. The same trend was observed for catechin and gallic acid, the most abundant phenolics in the examined wine samples. Finally, the findings of an Artificial Neural Network (ANN) model were in a good agreement (r(2) = 0.978) with the experimental data. All tested samples exhibited a protective effect in H2O2-stressed yeast cells. Pre-treatment with examined wines increased survival in H2O2-stressed cells and shifted antioxidative defense towards GPx-mediated defense. Finally, sensitivity analysis of obtained ANN model highlights the complexity of the impact that variations in the concentrations of specific phenolic components have on the antioxidant defense system.",
publisher = "MDPI, Basel",
journal = "Molecules",
title = "Antioxidant Activity of Selected Polyphenolics in Yeast Cells: The Case Study of Montenegrin Merlot Wine",
number = "8",
volume = "23",
doi = "10.3390/molecules23081971"
}
Đorđević, N. O., Todorović, N., Novaković, I. T., Pezo, L., Pejin, B., Maras, V., Tešević, V.,& Pajović, S. B.. (2018). Antioxidant Activity of Selected Polyphenolics in Yeast Cells: The Case Study of Montenegrin Merlot Wine. in Molecules
MDPI, Basel., 23(8).
https://doi.org/10.3390/molecules23081971
Đorđević NO, Todorović N, Novaković IT, Pezo L, Pejin B, Maras V, Tešević V, Pajović SB. Antioxidant Activity of Selected Polyphenolics in Yeast Cells: The Case Study of Montenegrin Merlot Wine. in Molecules. 2018;23(8).
doi:10.3390/molecules23081971 .
Đorđević, Neda O., Todorović, Nevena, Novaković, Irena T., Pezo, Lato, Pejin, Boris, Maras, Vesna, Tešević, Vele, Pajović, Snežana B., "Antioxidant Activity of Selected Polyphenolics in Yeast Cells: The Case Study of Montenegrin Merlot Wine" in Molecules, 23, no. 8 (2018),
https://doi.org/10.3390/molecules23081971 . .
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Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues

Filipović, Nenad R.; Elshaflu, Hana; Grubisic, Sonja; Jovanović, Ljiljana S.; Rodic, Marko; Novaković, Irena; Malešević, Aleksandar; Đorđević, Ivana S.; Li, Haidong; Sojic, Neso; Marinković, Aleksandar; Todorović, Tamara R.

(Royal Soc Chemistry, Cambridge, 2017)

TY  - JOUR
AU  - Filipović, Nenad R.
AU  - Elshaflu, Hana
AU  - Grubisic, Sonja
AU  - Jovanović, Ljiljana S.
AU  - Rodic, Marko
AU  - Novaković, Irena
AU  - Malešević, Aleksandar
AU  - Đorđević, Ivana S.
AU  - Li, Haidong
AU  - Sojic, Neso
AU  - Marinković, Aleksandar
AU  - Todorović, Tamara R.
PY  - 2017
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/1036
AB  - The first Co(III) complexes with (1,3-selenazol-2-yl)hydrazones as an unexplored class of ligands were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. The novel ligands act as NNN tridentate chelators forming octahedral Co(III) complexes. The impact of structural changes on ligands' periphery as well as that of isosteric replacement of sulphur with selenium on the electrochemical and electronic absorption features of complexes are explored. To support the experimental data, density functional theory (DFT) calculations were also conducted. Theoretical NMR chemical shifts, the relative energies and natural bond orbital (NBO) analysis are calculated within the DFT approach, while the singlet excited state energies and HOMO-LUMO energy gap were calculated with time-dependent density functional theory (TD-DFT). The electrophilic f(-) and nucleophilic f(+) Fukui functions are well adapted to find the electrophile and nucleophile centres in the molecules. Both (1,3-selenazol-2-yl)- and (1,3-thiazol-2-yl) hydrazone Co(III) complexes showed potent antimicrobial and antioxidant activity. A significant difference among them was a smaller cytotoxicity of selenium compounds.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues
EP  - 2924
IS  - 9
SP  - 2910
VL  - 46
DO  - 10.1039/c6dt04785h
ER  - 
@article{
author = "Filipović, Nenad R. and Elshaflu, Hana and Grubisic, Sonja and Jovanović, Ljiljana S. and Rodic, Marko and Novaković, Irena and Malešević, Aleksandar and Đorđević, Ivana S. and Li, Haidong and Sojic, Neso and Marinković, Aleksandar and Todorović, Tamara R.",
year = "2017",
abstract = "The first Co(III) complexes with (1,3-selenazol-2-yl)hydrazones as an unexplored class of ligands were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. The novel ligands act as NNN tridentate chelators forming octahedral Co(III) complexes. The impact of structural changes on ligands' periphery as well as that of isosteric replacement of sulphur with selenium on the electrochemical and electronic absorption features of complexes are explored. To support the experimental data, density functional theory (DFT) calculations were also conducted. Theoretical NMR chemical shifts, the relative energies and natural bond orbital (NBO) analysis are calculated within the DFT approach, while the singlet excited state energies and HOMO-LUMO energy gap were calculated with time-dependent density functional theory (TD-DFT). The electrophilic f(-) and nucleophilic f(+) Fukui functions are well adapted to find the electrophile and nucleophile centres in the molecules. Both (1,3-selenazol-2-yl)- and (1,3-thiazol-2-yl) hydrazone Co(III) complexes showed potent antimicrobial and antioxidant activity. A significant difference among them was a smaller cytotoxicity of selenium compounds.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues",
pages = "2924-2910",
number = "9",
volume = "46",
doi = "10.1039/c6dt04785h"
}
Filipović, N. R., Elshaflu, H., Grubisic, S., Jovanović, L. S., Rodic, M., Novaković, I., Malešević, A., Đorđević, I. S., Li, H., Sojic, N., Marinković, A.,& Todorović, T. R.. (2017). Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 46(9), 2910-2924.
https://doi.org/10.1039/c6dt04785h
Filipović NR, Elshaflu H, Grubisic S, Jovanović LS, Rodic M, Novaković I, Malešević A, Đorđević IS, Li H, Sojic N, Marinković A, Todorović TR. Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues. in Dalton Transactions. 2017;46(9):2910-2924.
doi:10.1039/c6dt04785h .
Filipović, Nenad R., Elshaflu, Hana, Grubisic, Sonja, Jovanović, Ljiljana S., Rodic, Marko, Novaković, Irena, Malešević, Aleksandar, Đorđević, Ivana S., Li, Haidong, Sojic, Neso, Marinković, Aleksandar, Todorović, Tamara R., "Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues" in Dalton Transactions, 46, no. 9 (2017):2910-2924,
https://doi.org/10.1039/c6dt04785h . .
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Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA

Vujcic, Miroslava T; Tufegdžić, Srđan J.; Novaković, Irena T; Đikanović, Daniela; Gasic, Miroslav J; Sladic, Dusan

(Elsevier, Amsterdam, 2013)

TY  - JOUR
AU  - Vujcic, Miroslava T
AU  - Tufegdžić, Srđan J.
AU  - Novaković, Irena T
AU  - Đikanović, Daniela
AU  - Gasic, Miroslav J
AU  - Sladic, Dusan
PY  - 2013
UR  - http://rimsi.imsi.bg.ac.rs/handle/123456789/734
AB  - The interactions of avarone, a quinone from the marine sponge Dysideaavara, and the methylamino derivatives of avarone (2), 3'-(methylamino)avarone (3) and 4'-(methylamino)avarone (4) with calf thymus DNA (CT-DNA) were studied. Agarose gel electrophoreticanalysis showed that binding of the quinones quenched fluorescence of ethidium bromide (EB). The extent of fluorescence quenching of intercalator EB by competitive displacement from EB-CT-DNA system and of groove binder Hoechst 33258 (H) from H-CT-DNA system with the quinones was analyzed by fluorescence spectroscopy. The obtained results demonstrated that the quinones reduced binding of both the intercalator EB and the minor groove binder H, indicating possible degradation of DNA. The substituent on the quinone moiety determined the extent of DNA damaging effect of the quinone, which was the most extensive with 3'-(methylamino)avarone and the least extensive with its regioisomer 4'-(methylamino)avarone. The results were confirmed by the observed hyperchromic effects in UV-visible spectra measured after interactions of the derivatives with CT-DNA.
PB  - Elsevier, Amsterdam
T2  - International Journal of Biological Macromolecules
T1  - Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA
EP  - 410
SP  - 405
VL  - 62
DO  - 10.1016/j.ijbiomac.2013.09.013
ER  - 
@article{
author = "Vujcic, Miroslava T and Tufegdžić, Srđan J. and Novaković, Irena T and Đikanović, Daniela and Gasic, Miroslav J and Sladic, Dusan",
year = "2013",
abstract = "The interactions of avarone, a quinone from the marine sponge Dysideaavara, and the methylamino derivatives of avarone (2), 3'-(methylamino)avarone (3) and 4'-(methylamino)avarone (4) with calf thymus DNA (CT-DNA) were studied. Agarose gel electrophoreticanalysis showed that binding of the quinones quenched fluorescence of ethidium bromide (EB). The extent of fluorescence quenching of intercalator EB by competitive displacement from EB-CT-DNA system and of groove binder Hoechst 33258 (H) from H-CT-DNA system with the quinones was analyzed by fluorescence spectroscopy. The obtained results demonstrated that the quinones reduced binding of both the intercalator EB and the minor groove binder H, indicating possible degradation of DNA. The substituent on the quinone moiety determined the extent of DNA damaging effect of the quinone, which was the most extensive with 3'-(methylamino)avarone and the least extensive with its regioisomer 4'-(methylamino)avarone. The results were confirmed by the observed hyperchromic effects in UV-visible spectra measured after interactions of the derivatives with CT-DNA.",
publisher = "Elsevier, Amsterdam",
journal = "International Journal of Biological Macromolecules",
title = "Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA",
pages = "410-405",
volume = "62",
doi = "10.1016/j.ijbiomac.2013.09.013"
}
Vujcic, M. T., Tufegdžić, S. J., Novaković, I. T., Đikanović, D., Gasic, M. J.,& Sladic, D.. (2013). Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA. in International Journal of Biological Macromolecules
Elsevier, Amsterdam., 62, 405-410.
https://doi.org/10.1016/j.ijbiomac.2013.09.013
Vujcic MT, Tufegdžić SJ, Novaković IT, Đikanović D, Gasic MJ, Sladic D. Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA. in International Journal of Biological Macromolecules. 2013;62:405-410.
doi:10.1016/j.ijbiomac.2013.09.013 .
Vujcic, Miroslava T, Tufegdžić, Srđan J., Novaković, Irena T, Đikanović, Daniela, Gasic, Miroslav J, Sladic, Dusan, "Studies on the interactions of bioactive quinone avarone and its methylamino derivatives with calf thymus DNA" in International Journal of Biological Macromolecules, 62 (2013):405-410,
https://doi.org/10.1016/j.ijbiomac.2013.09.013 . .
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