Unsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity

Copper(II) complexes with 1,1,1-trifluoro-4-(4-methoxyphenyl)butan-2,4-dione (HL1) were synthesized and characterized by elemental analysis, FT-IR spectroscopy, and single crystal X-ray diffraction. The biological properties of HL1 and cis-[Cu...

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Autores principales:	Liliya A. Khamidullina, Igor S. Puzyrev, Gennady L. Burygin, Pavel V. Dorovatovskii, Yan V. Zubavichus, Anna V. Mitrofanova, Victor N. Khrustalev, Tatiana V. Timofeeva, Pavel A. Slepukhin, Polina D. Tobysheva, Alexander V. Pestov, Euro Solari, Alexander G. Tskhovrebov, Valentine G. Nenajdenko
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	copper(II) diketonates cytotoxic activity antimicrobial activity anticancer agents Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/af26447aeb60433a929bcb5b78c9029e
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spelling	oai:doaj.org-article:af26447aeb60433a929bcb5b78c9029e2021-11-11T18:28:29ZUnsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity10.3390/molecules262164661420-3049https://doaj.org/article/af26447aeb60433a929bcb5b78c9029e2021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6466https://doaj.org/toc/1420-3049Copper(II) complexes with 1,1,1-trifluoro-4-(4-methoxyphenyl)butan-2,4-dione (H<b>L1</b>) were synthesized and characterized by elemental analysis, FT-IR spectroscopy, and single crystal X-ray diffraction. The biological properties of H<b>L1</b> and <i>cis</i>-[Cu(<b>L1</b>)<sub>2</sub>(DMSO)] (<b>3</b>) were examined against Gram-positive and Gram-negative bacteria and opportunistic unicellular fungi. The cytotoxicity was estimated towards the HeLa and Vero cell lines. Complex <b>3</b> demonstrated antibacterial activity towards <i>S. aureus</i> comparable to that of streptomycin, lower antifungal activity than the ligand H<b>L1</b> and moderate cytotoxicity. The bioactivity was compared with the activity of compounds of similar structures. The effect of changing the position of the methoxy group at the aromatic ring in the ligand moiety of the complexes on their antimicrobial and cytotoxic activity was explored. We propose that complex <b>3</b> has lower bioavailability and reduced bioactivity than expected due to strong intermolecular contacts. In addition, molecular docking studies provided theoretical information on the interactions of tested compounds with ribonucleotide reductase subunit R2, as well as the chaperones Hsp70 and Hsp90, which are important biomolecular targets for antitumor and antimicrobial drug search and design. The obtained results revealed that the complexes displayed enhanced affinity over organic ligands. Taken together, the copper(II) complexes with the trifluoromethyl methoxyphenyl-substituted β-diketones could be considered as promising anticancer agents with antibacterial properties.Liliya A. KhamidullinaIgor S. PuzyrevGennady L. BuryginPavel V. DorovatovskiiYan V. ZubavichusAnna V. MitrofanovaVictor N. KhrustalevTatiana V. TimofeevaPavel A. SlepukhinPolina D. TobyshevaAlexander V. PestovEuro SolariAlexander G. TskhovrebovValentine G. NenajdenkoMDPI AGarticlecopper(II)diketonatescytotoxic activityantimicrobial activityanticancer agentsOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6466, p 6466 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	copper(II) diketonates cytotoxic activity antimicrobial activity anticancer agents Organic chemistry QD241-441
spellingShingle	copper(II) diketonates cytotoxic activity antimicrobial activity anticancer agents Organic chemistry QD241-441 Liliya A. Khamidullina Igor S. Puzyrev Gennady L. Burygin Pavel V. Dorovatovskii Yan V. Zubavichus Anna V. Mitrofanova Victor N. Khrustalev Tatiana V. Timofeeva Pavel A. Slepukhin Polina D. Tobysheva Alexander V. Pestov Euro Solari Alexander G. Tskhovrebov Valentine G. Nenajdenko Unsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity
description	Copper(II) complexes with 1,1,1-trifluoro-4-(4-methoxyphenyl)butan-2,4-dione (H<b>L1</b>) were synthesized and characterized by elemental analysis, FT-IR spectroscopy, and single crystal X-ray diffraction. The biological properties of H<b>L1</b> and <i>cis</i>-[Cu(<b>L1</b>)<sub>2</sub>(DMSO)] (<b>3</b>) were examined against Gram-positive and Gram-negative bacteria and opportunistic unicellular fungi. The cytotoxicity was estimated towards the HeLa and Vero cell lines. Complex <b>3</b> demonstrated antibacterial activity towards <i>S. aureus</i> comparable to that of streptomycin, lower antifungal activity than the ligand H<b>L1</b> and moderate cytotoxicity. The bioactivity was compared with the activity of compounds of similar structures. The effect of changing the position of the methoxy group at the aromatic ring in the ligand moiety of the complexes on their antimicrobial and cytotoxic activity was explored. We propose that complex <b>3</b> has lower bioavailability and reduced bioactivity than expected due to strong intermolecular contacts. In addition, molecular docking studies provided theoretical information on the interactions of tested compounds with ribonucleotide reductase subunit R2, as well as the chaperones Hsp70 and Hsp90, which are important biomolecular targets for antitumor and antimicrobial drug search and design. The obtained results revealed that the complexes displayed enhanced affinity over organic ligands. Taken together, the copper(II) complexes with the trifluoromethyl methoxyphenyl-substituted β-diketones could be considered as promising anticancer agents with antibacterial properties.
format	article
author	Liliya A. Khamidullina Igor S. Puzyrev Gennady L. Burygin Pavel V. Dorovatovskii Yan V. Zubavichus Anna V. Mitrofanova Victor N. Khrustalev Tatiana V. Timofeeva Pavel A. Slepukhin Polina D. Tobysheva Alexander V. Pestov Euro Solari Alexander G. Tskhovrebov Valentine G. Nenajdenko
author_facet	Liliya A. Khamidullina Igor S. Puzyrev Gennady L. Burygin Pavel V. Dorovatovskii Yan V. Zubavichus Anna V. Mitrofanova Victor N. Khrustalev Tatiana V. Timofeeva Pavel A. Slepukhin Polina D. Tobysheva Alexander V. Pestov Euro Solari Alexander G. Tskhovrebov Valentine G. Nenajdenko
author_sort	Liliya A. Khamidullina
title	Unsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity
title_short	Unsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity
title_full	Unsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity
title_fullStr	Unsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity
title_full_unstemmed	Unsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity
title_sort	unsymmetrical trifluoromethyl methoxyphenyl β-diketones: effect of the position of methoxy group and coordination at cu(ii) on biological activity
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/af26447aeb60433a929bcb5b78c9029e
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Unsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity

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