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 . .