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Title: | Synthesis and biological activity of alkylthio and arylthio Derivatives of tert-butylquinone | Authors: | Đorđević, J. Kolarević, S. Jovanović Marić, J. Oalđe Pavlović, M. Sadić, D. Novaković, I. Vuković-Gačić, B. |
Keywords: | TBQ toxicity;MTT assay;Antimicrobial activity;Antioxidant activity;Comet test | Issue Date: | 30-Sep-2022 | Rank: | M23 | Publisher: | Serbian Chemical Society | Journal: | Journal of the Serbian Chemical Society | 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. |
URI: | https://biore.bio.bg.ac.rs/handle/123456789/4714 | DOI: | 10.2298/JSC220304044D |
Appears in Collections: | Journal Article |
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