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Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone
dc.creator | Đorđević Aleksić, Jelena | |
dc.creator | Kolarević, Stoimir | |
dc.creator | Jovanović Marić, Jovana | |
dc.creator | Oalđe Pavlović, Mariana | |
dc.creator | Sladić, Dušan | |
dc.creator | Novaković, Irena | |
dc.creator | Vuković-Gačić, Branka | |
dc.date.accessioned | 2023-07-21T08:28:24Z | |
dc.date.available | 2023-07-21T08:28:24Z | |
dc.date.issued | 2022 | |
dc.identifier.issn | 0352-5139 | |
dc.identifier.uri | http://rimsi.imsi.bg.ac.rs/handle/123456789/2018 | |
dc.description.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. | sr |
dc.language.iso | en | sr |
dc.publisher | National Library of Serbia | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200168/RS// | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200178/RS// | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200007/RS// | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200053/RS// | sr |
dc.relation | info:eu-repo/grantAgreement/MESTD/inst-2020/200026/RS// | sr |
dc.rights | openAccess | sr |
dc.rights.uri | https://creativecommons.org/licenses/by-nc-nd/4.0/ | |
dc.source | Journal of the Serbian Chemical Society | sr |
dc.subject | TBQ; toxicity; MTT assay; antibacterial activity; antioxidant activity; comet test | sr |
dc.title | Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone | sr |
dc.type | article | sr |
dc.rights.license | BY-NC-ND | sr |
dc.rights.holder | Serbian Chemical Society | sr |
dc.citation.epage | 1258 | |
dc.citation.issue | 11 | |
dc.citation.rank | M23 | |
dc.citation.spage | 1245 | |
dc.citation.volume | 87 | |
dc.identifier.doi | 10.2298/JSC220304044D | |
dc.identifier.fulltext | http://rimsi.imsi.bg.ac.rs/bitstream/id/5290/0352-51392200044D.pdf | |
dc.type.version | publishedVersion | sr |