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Please use this identifier to cite or link to this item: http://elar.urfu.ru/handle/10995/112211
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dc.contributor.authorKhamidullina, L. A.en
dc.contributor.authorPuzyrev, I. S.en
dc.contributor.authorBurygin, G. L.en
dc.contributor.authorDorovatovskii, P. V.en
dc.contributor.authorZubavichus, Y. V.en
dc.contributor.authorMitrofanova, A. V.en
dc.contributor.authorKhrustalev, V. N.en
dc.contributor.authorTimofeeva, T. V.en
dc.contributor.authorSlepukhin, P. A.en
dc.contributor.authorTobysheva, P. D.en
dc.contributor.authorPestov, A. V.en
dc.contributor.authorSolari, E.en
dc.contributor.authorTskhovrebov, A. G.en
dc.contributor.authorNenajdenko, V. G.en
dc.date.accessioned2022-05-12T08:30:40Z-
dc.date.available2022-05-12T08:30:40Z-
dc.date.issued2021-
dc.identifier.citationUnsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity / L. A. Khamidullina, I. S. Puzyrev, G. L. Burygin et al. // Molecules. — 2021. — Vol. 26. — Iss. 21. — 6466.en
dc.identifier.issn1420-3049-
dc.identifier.otherAll Open Access, Gold, Green3
dc.identifier.urihttp://elar.urfu.ru/handle/10995/112211-
dc.description.abstractCopper(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(L1)2 (DMSO)] (3) 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 3 demonstrated antibacterial activity towards S. aureus comparable to that of streptomycin, lower antifungal activity than the ligand HL1 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 3 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. © 2021, MDPI. All rights reserved.en
dc.description.sponsorshipThis work was funded by RFBR and Sverdlovsk region (project numbers 20-43-660042 and 20-53-00006) and supported by the basic theme of the Russian Academy of Sciences (state registration no. AAAA-A19-119011790132-7 and project no. AAAA-A19-119012490006-1). XRD experiments and analytical studies were carried out using the equipment of the Center for Joint Use “Spectroscopy and Analysis of Organic Compounds” at the Postovsky Institute of Organic Synthesis UB RAS. X-ray study was supported by the U.S. National Science Foundation (Grant DMR-1523611 PREM). The cytotoxicity assay was carried out at the “Simbioz” Center for the Collective Use of Research Equipment in the Field of Physical–Chemical Biology and Nanobiotechnology at IBPPM RAS. This work has been supported by the RUDN University Strategic Academic Leadership Program.en
dc.format.mimetypeapplication/pdfen
dc.language.isoenen
dc.publisherMDPIen1
dc.publisherMDPI AGen
dc.rightsinfo:eu-repo/semantics/openAccessen
dc.sourceMolecules2
dc.sourceMoleculesen
dc.subjectANTICANCER AGENTSen
dc.subjectANTIMICROBIAL ACTIVITYen
dc.subjectCOPPER(II)en
dc.subjectCYTOTOXIC ACTIVITYen
dc.subjectDIKETONATESen
dc.subjectANTIINFECTIVE AGENTen
dc.subjectANTINEOPLASTIC AGENTen
dc.subjectCOORDINATION COMPOUNDen
dc.subjectCOPPERen
dc.subjectKETONEen
dc.subjectANIMALen
dc.subjectCELL PROLIFERATIONen
dc.subjectCELL SURVIVALen
dc.subjectCHEMICAL STRUCTUREen
dc.subjectCHEMISTRYen
dc.subjectCHLOROCEBUS AETHIOPSen
dc.subjectDOSE RESPONSEen
dc.subjectDRUG EFFECTen
dc.subjectDRUG SCREENINGen
dc.subjectESCHERICHIA COLIen
dc.subjectHELA CELL LINEen
dc.subjectHUMANen
dc.subjectMICROBIAL SENSITIVITY TESTen
dc.subjectMOLECULAR DOCKINGen
dc.subjectSTAPHYLOCOCCUS AUREUSen
dc.subjectSTRUCTURE ACTIVITY RELATIONen
dc.subjectSYNTHESISen
dc.subjectVERO CELL LINEen
dc.subjectANIMALSen
dc.subjectANTI-BACTERIAL AGENTSen
dc.subjectANTINEOPLASTIC AGENTSen
dc.subjectCELL PROLIFERATIONen
dc.subjectCELL SURVIVALen
dc.subjectCHLOROCEBUS AETHIOPSen
dc.subjectCOORDINATION COMPLEXESen
dc.subjectCOPPERen
dc.subjectDOSE-RESPONSE RELATIONSHIP, DRUGen
dc.subjectDRUG SCREENING ASSAYS, ANTITUMORen
dc.subjectESCHERICHIA COLIen
dc.subjectHELA CELLSen
dc.subjectHUMANSen
dc.subjectKETONESen
dc.subjectMICROBIAL SENSITIVITY TESTSen
dc.subjectMOLECULAR DOCKING SIMULATIONen
dc.subjectMOLECULAR STRUCTUREen
dc.subjectSTAPHYLOCOCCUS AUREUSen
dc.subjectSTRUCTURE-ACTIVITY RELATIONSHIPen
dc.subjectVERO CELLSen
dc.titleUnsymmetrical Trifluoromethyl Methoxyphenyl β-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activityen
dc.typeArticleen
dc.typeinfo:eu-repo/semantics/articleen
dc.typeinfo:eu-repo/semantics/publishedVersionen
dc.identifier.rsi47522602-
dc.identifier.doi10.3390/molecules26216466-
dc.identifier.scopus85118401056-
local.contributor.employeeKhamidullina, L.A., Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 Sofia Kovalevskaya Street, Ekaterinburg, 620137, Russian Federation, Institute of Natural Sciences and Mathematics, Ural Federal University, 19 Mira Street, Ekaterinburg, 620002, Russian Federation; Puzyrev, I.S., Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 Sofia Kovalevskaya Street, Ekaterinburg, 620137, Russian Federation; Burygin, G.L., Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov, 410049, Russian Federation; Dorovatovskii, P.V., NRC “Kurchatov Institute”, 1 Acad. Kurchatov Sq., Moscow, 123182, Russian Federation; Zubavichus, Y.V., Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 5 Lavrentiev Ave., Novosibirsk, 630090, Russian Federation; Mitrofanova, A.V., Department of Inorganic Chemistry, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklay Street, Moscow, 117198, Russian Federation; Khrustalev, V.N., Department of Inorganic Chemistry, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklay Street, Moscow, 117198, Russian Federation, Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prosp., Moscow, 119991, Russian Federation; Timofeeva, T.V., Department of Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, United States; Slepukhin, P.A., Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 Sofia Kovalevskaya Street, Ekaterinburg, 620137, Russian Federation; Tobysheva, P.D., Institute of Natural Sciences and Mathematics, Ural Federal University, 19 Mira Street, Ekaterinburg, 620002, Russian Federation; Pestov, A.V., Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 Sofia Kovalevskaya Street, Ekaterinburg, 620137, Russian Federation, Institute of Natural Sciences and Mathematics, Ural Federal University, 19 Mira Street, Ekaterinburg, 620002, Russian Federation; Solari, E., Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, CH 1015, Switzerland; Tskhovrebov, A.G., Department of Inorganic Chemistry, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklay Street, Moscow, 117198, Russian Federation; Nenajdenko, V.G., Chemistry Department, Lomonosov Moscow State University, 1/3 Leninskie Gory, Moscow, 119991, Russian Federationen
local.issue21-
local.volume26-
dc.identifier.wos000726978400001-
local.contributor.departmentPostovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 Sofia Kovalevskaya Street, Ekaterinburg, 620137, Russian Federation; Institute of Natural Sciences and Mathematics, Ural Federal University, 19 Mira Street, Ekaterinburg, 620002, Russian Federation; Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov, 410049, Russian Federation; NRC “Kurchatov Institute”, 1 Acad. Kurchatov Sq., Moscow, 123182, Russian Federation; Boreskov Institute of Catalysis, Siberian Branch of the Russian Academy of Sciences, 5 Lavrentiev Ave., Novosibirsk, 630090, Russian Federation; Department of Inorganic Chemistry, Peoples’ Friendship University of Russia (RUDN University), 6 Miklukho-Maklay Street, Moscow, 117198, Russian Federation; Zelinsky Institute of Organic Chemistry RAS, 47 Leninsky Prosp., Moscow, 119991, Russian Federation; Department of Chemistry, New Mexico Highlands University, Las Vegas, NM 87701, United States; Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), Lausanne, CH 1015, Switzerland; Chemistry Department, Lomonosov Moscow State University, 1/3 Leninskie Gory, Moscow, 119991, Russian Federationen
local.identifier.pure28887392-
local.description.order6466-
local.identifier.eid2-s2.0-85118401056-
local.identifier.wosWOS:000726978400001-
local.identifier.pmid34770875-
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