Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone: Scientific paper

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

doi:10.2298/JSC220304044D

PDF (2.578 kB) Supplementary Material (5.27 MB)

Published: Sep 30, 2022

Updated: 30.09.2022

DOI: https://doi.org/10.2298/JSC220304044D

Keywords:

TBQ toxicity MTT assay antimicrobial activity antioxidant activity comet test

Jelena Đorđević

University of Belgrade, Institute for Multidisciplinary Research, Kneza Višeslava 1, 11030 Belgrade, Serbia

https://orcid.org/0000-0003-1771-8353

Stoimir Kolarević

University of Belgrade, Institute for Biological Research “Siniša Stanković”, National Institute of Republic of Serbia, Bulevar despota Stefana 142, 11060 Belgrade, Serbia

https://orcid.org/0000-0002-6938-8803

Jovana Jovanović Marić

University of Belgrade, Institute for Biological Research “Siniša Stanković”, National Institute of Republic of Serbia, Bulevar despota Stefana 142, 11060 Belgrade, Serbia

https://orcid.org/0000-0003-1635-7787

Mariana Oalđe Pavlović

University of Belgrade, Chair of Plant Morphology and Systematics, Faculty of Biology, Studentski trg 16, 11158 Belgrade, Serbia

https://orcid.org/0000-0001-9338-7811

Dušan Sladić

University of Belgrade, Faculty of Chemistry, Studentski trg 12-16, 11158 Belgrade, Serbia

https://orcid.org/0000-0002-1000-9813

Irena Novakovic

University of Belgrade, Institute for Chemistry, Technology and Metallurgy, National Institute of Republic of Serbia, Njegoševa 12, Belgrade, Serbia

https://orcid.org/0000-0001-9881-1204

Branka Vuković-Gačić

University of Belgrade, Centre for Genotoxicology and Ecogenotoxicology, Faculty of Biology, Studentski trg 16, 11158 Belgrade, Serbia

https://orcid.org/0000-0001-8767-1912

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.

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How to Cite

[1]

J. Đorđević, “Synthesis and biological activity of alkylthio and arylthio derivatives of tert-butylquinone: Scientific paper”, J. Serb. Chem. Soc., vol. 87, no. 11, pp. 1245–1258, Sep. 2022.

Issue

Vol. 87 No. 11 (2022)

Section

Biochemistry & Biotechnology

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution license 4.0 that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.

Funding data

Ministarstvo Prosvete, Nauke i Tehnološkog Razvoja
Grant numbers 451-03-9/2021-14/200053;451-03-9/2021-14/200007;451-03-68/2022-14/200178;451-03-9/2021-14/200168;451-03-68/2022-14/200026

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