Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity

By reacting a series of 2,6-diacetylpyridine bis-hydrazones containing pyrimidine (H2L1), benzimidazole (H2L2) and phthalazine (H2L3) heterocyclic fragments with copper(ii) chloride and bromide, a variety of pentacoordinated complexes of the composition [Cu(H2L1)X]X, [Cu(HL2)X] and [Cu(HL3)X], where...

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Autori principali:	Demidov, O. P., Демидов, О. П.
Natura:	Статья
Lingua:	English
Pubblicazione:	2024
Soggetti:	Mammals Molecular dynamics Cell culture Chelation Chlorine compounds Coordination reactions Copper compounds Crystal structure Cyclic voltammetry Electron spin resonance spectroscopy
Accesso online:	https://dspace.ncfu.ru/handle/20.500.12258/26813
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spelling	ir-20.500.12258-268132024-02-29T09:38:35Z Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity Demidov, O. P. Демидов, О. П. Mammals Molecular dynamics Cell culture Chelation Chlorine compounds Coordination reactions Copper compounds Crystal structure Cyclic voltammetry Electron spin resonance spectroscopy By reacting a series of 2,6-diacetylpyridine bis-hydrazones containing pyrimidine (H2L1), benzimidazole (H2L2) and phthalazine (H2L3) heterocyclic fragments with copper(ii) chloride and bromide, a variety of pentacoordinated complexes of the composition [Cu(H2L1)X]X, [Cu(HL2)X] and [Cu(HL3)X], where X = Cl-, Br-, are formed. The properties and structure of the compounds were studied by means of NMR, IR, UV-vis, ESR, and X-ray absorption spectroscopy, cyclic voltammetry and X-Ray single crystal diffraction methods. It was shown that complexes of the cationic type [Cu(H2L1)X]X have an asymmetric structure with a distorted square-pyramidal geometry of the coordination unit. The coordination polyhedron of metal chelates [Cu(HL2)X] and [Cu(HL3)X] is an almost ideal square pyramid. Investigations of the cytotoxic activity of the obtained compounds in vitro on human hepatocellular carcinoma (HepG2) and non-tumor human lung fibroblast (MRC-5) cell lines demonstrated that complexes show higher activity compared with the well-known anticancer agent cisplatin. In addition, metal chelates [Cu(H2L1)Cl]Cl, [Cu(HL2)Cl], [Cu(HL2)Br] and [Cu(HL3)Cl] were less toxic to non-tumor cells MRC-5. A study of the binding of complexes to bovine serum albumin (BSA) protein using fluorescence spectroscopy showed that copper complexes are strongly bound to BSA. To study the mechanism of interaction of the complexes with the DNA of cancer cells, molecular dynamics simulation of the compound [Cu(HL3)Cl] was carried out. It was shown that the complex enters into p-stacking interactions predominantly with adenine and thymine bases. 2024-02-29T09:37:09Z 2024-02-29T09:37:09Z 2024 Статья Kapustina, A.A., Tupolova, Y.P., Popov, L.D., Vlasenko, V.G., Gishko, K.B., Berejnaya, A.G., Shcherbatykh, A.A., Golubeva, Y.A., Klyushova, L.S., Lider, E.V., Lazarenko, V.A., Demidov, O.P., Knyazev, P.A., Bachurin, S.S., Nalbandyan, V.B., Shcherbakov, I.N. Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity // Dalton Transactions. - 2024. - 53 (7). - pp. 3330-3347. - DOI: 10.1039/d3dt03750a http://hdl.handle.net/20.500.12258/26813 en Dalton Transactions application/pdf application/pdf
institution	СКФУ
collection	Репозиторий
language	English
topic	Mammals Molecular dynamics Cell culture Chelation Chlorine compounds Coordination reactions Copper compounds Crystal structure Cyclic voltammetry Electron spin resonance spectroscopy
spellingShingle	Mammals Molecular dynamics Cell culture Chelation Chlorine compounds Coordination reactions Copper compounds Crystal structure Cyclic voltammetry Electron spin resonance spectroscopy Demidov, O. P. Демидов, О. П. Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity
description	By reacting a series of 2,6-diacetylpyridine bis-hydrazones containing pyrimidine (H2L1), benzimidazole (H2L2) and phthalazine (H2L3) heterocyclic fragments with copper(ii) chloride and bromide, a variety of pentacoordinated complexes of the composition [Cu(H2L1)X]X, [Cu(HL2)X] and [Cu(HL3)X], where X = Cl-, Br-, are formed. The properties and structure of the compounds were studied by means of NMR, IR, UV-vis, ESR, and X-ray absorption spectroscopy, cyclic voltammetry and X-Ray single crystal diffraction methods. It was shown that complexes of the cationic type [Cu(H2L1)X]X have an asymmetric structure with a distorted square-pyramidal geometry of the coordination unit. The coordination polyhedron of metal chelates [Cu(HL2)X] and [Cu(HL3)X] is an almost ideal square pyramid. Investigations of the cytotoxic activity of the obtained compounds in vitro on human hepatocellular carcinoma (HepG2) and non-tumor human lung fibroblast (MRC-5) cell lines demonstrated that complexes show higher activity compared with the well-known anticancer agent cisplatin. In addition, metal chelates [Cu(H2L1)Cl]Cl, [Cu(HL2)Cl], [Cu(HL2)Br] and [Cu(HL3)Cl] were less toxic to non-tumor cells MRC-5. A study of the binding of complexes to bovine serum albumin (BSA) protein using fluorescence spectroscopy showed that copper complexes are strongly bound to BSA. To study the mechanism of interaction of the complexes with the DNA of cancer cells, molecular dynamics simulation of the compound [Cu(HL3)Cl] was carried out. It was shown that the complex enters into p-stacking interactions predominantly with adenine and thymine bases.
format	Статья
author	Demidov, O. P. Демидов, О. П.
author_facet	Demidov, O. P. Демидов, О. П.
author_sort	Demidov, O. P.
title	Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity
title_short	Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity
title_full	Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity
title_fullStr	Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity
title_full_unstemmed	Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity
title_sort	copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity
publishDate	2024
url	https://dspace.ncfu.ru/handle/20.500.12258/26813
work_keys_str_mv	AT demidovop copperiicoordinationcompoundsbasedonbishydrazonesof26diacetylpyridinesynthesisstructureandcytotoxicactivity AT demidovop copperiicoordinationcompoundsbasedonbishydrazonesof26diacetylpyridinesynthesisstructureandcytotoxicactivity
_version_	1809808870973898752

Copper(ii) coordination compounds based on bis-hydrazones of 2,6-diacetylpyridine: synthesis, structure, and cytotoxic activity

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