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Biological Activity of Newly Synthesized Benzimidazole and Benzothizole 2,5‐Disubstituted Furane Derivatives

Racané, Livio; Zlatar, Ivo; Perin, Nataša; Cindrić, Maja; Radovanović, Vedrana; Banjanac, Mihailo; Shanmugam, Suresh; Radić Stojković, Marijana; Brajša, Karmen; Hranjec, Marijana (2021) Biological Activity of Newly Synthesized Benzimidazole and Benzothizole 2,5‐Disubstituted Furane Derivatives. Molecules, 26 . pp. 4935-4956. ISSN 1420-3049

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Newly designed and synthesized cyano, amidino and acrylonitrile 2, 5‐disubstituted furane derivatives with either benzimidazole/benzothiazole nuclei have been evaluated for antitumor and antimicrobial activity. For potential antitumor activity, the compounds were tested in 2D and 3D cell culture methods on three human lung cancer cell lines, A549, HCC827 and NCI‐H358, with MTS cytotoxicity and BrdU proliferation assays in vitro. Compounds 5, 6, 8, 9 and 15 have been proven to be compounds with potential antitumor activity with high potential to stop the proliferation of cells. In general, benzothiazole derivatives were more active in comparison to benzimidazole derivatives. Antimicrobial activity was evaluated with Broth microdilution testing (according to CLSI (Clinical Laboratory Standards Institute) guidelines) on Gram‐negative Escherichia coli and Gram‐positive Staphylococcus aureus. Additionally, Saccharomyces cerevisiae was included in testing as a eukaryotic model organism. Compounds 5, 6, 8, 9 and 15 showed the most promising antibacterial activity. In general, the compounds showed antitumor activity, higher in 2D assays in comparison with 3D assays, on all three cell lines in both assays. In natural conditions, compounds with such an activity profile (less toxic but still effective against tumor growth) could be promising new antitumor drugs. Some of the tested compounds showed antimicrobial activity. In contrast to ctDNA, the presence of nitro group or chlorine in selected furane‐benzothiazole structures did not influence the binding mode with AT‐DNA. All compounds dominantly bound inside the minor groove of AT‐DNA either in form of monomers or dimer and higher‐order aggregates.

Item Type: Article
Uncontrolled Keywords: amidines ; acrylonitriles ; benzimidazoles ; benzothiazoles ; furanes ; antitumor activity ; DNA binding
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
Project titleProject leaderProject codeProject type
Istraživanje antioksidativnog djelovanja benzazolskog skeleta u dizajnu novih antitumorskih agensaHranjec, MarijanaIP-2018-01-4379HRZZ
Molekularno prepoznavanje DNA:RNA hibridnih i višelančanih struktura u bioanalitičkim i in vitro sustavimaRadić Stojković, MarijanaIP-2018-01-4694HRZZ
Depositing User: Marijana Radić Stojković
Date Deposited: 18 Aug 2021 08:14
DOI: 10.3390/molecules26164935

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