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Article

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

1
Department of Applied Chemistry, Faculty of Textile Technology, University of Zagreb, Prilaz baruna Filipovića 28a, 10000 Zagreb, Croatia
2
Pharmacology In Vitro, Fidelta Ltd., Prilaz baruna Filipovića 29, 10000 Zagreb, Croatia
3
Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia
4
Division of Organic Chemistry and Biochemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, Croatia
*
Authors to whom correspondence should be addressed.
These authors contributed equally.
Academic Editor: René Csuk
Molecules 2021, 26(16), 4935; https://doi.org/10.3390/molecules26164935
Received: 14 July 2021 / Revised: 5 August 2021 / Accepted: 11 August 2021 / Published: 14 August 2021
(This article belongs to the Special Issue Ligand Binding to DNA and RNA)
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. View Full-Text
Keywords: amidines; acrylonitriles; benzimidazoles; benzothiazoles; furanes; antitumor activity; DNA binding amidines; acrylonitriles; benzimidazoles; benzothiazoles; furanes; antitumor activity; DNA binding
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MDPI and ACS Style

Racané, L.; Zlatar, I.; Perin, N.; Cindrić, M.; Radovanović, V.; Banjanac, M.; Shanmugam, S.; Stojković, M.R.; Brajša, K.; Hranjec, M. Biological Activity of Newly Synthesized Benzimidazole and Benzothizole 2,5-Disubstituted Furane Derivatives. Molecules 2021, 26, 4935. https://doi.org/10.3390/molecules26164935

AMA Style

Racané L, Zlatar I, Perin N, Cindrić M, Radovanović V, Banjanac M, Shanmugam S, Stojković MR, Brajša K, Hranjec M. Biological Activity of Newly Synthesized Benzimidazole and Benzothizole 2,5-Disubstituted Furane Derivatives. Molecules. 2021; 26(16):4935. https://doi.org/10.3390/molecules26164935

Chicago/Turabian Style

Racané, Livio, Ivo Zlatar, Nataša Perin, Maja Cindrić, Vedrana Radovanović, Mihailo Banjanac, Suresh Shanmugam, Marijana R. Stojković, Karmen Brajša, and Marijana Hranjec. 2021. "Biological Activity of Newly Synthesized Benzimidazole and Benzothizole 2,5-Disubstituted Furane Derivatives" Molecules 26, no. 16: 4935. https://doi.org/10.3390/molecules26164935

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