Copper(II) Furancarboxylate Complexes with 5-Nitro-1,10-Phenanthroline as Promising Biological Agents

K. A. Koshenskova; Кошенскова К. А.; D. E. Baravikov; Баравиков Д. Е.; Yu. V. Nelyubina; Нелюбина Ю. В.; P. V. Primakov; Примаков П. В.; V. O. Shender; Шендер В. О.; I. K. Maljants; Мальянц И. К.; O. B. Bekker; Беккер О. Б.; T. M. Aliev; Алиев Т. М.; E. A. Borodin; Бородин Е. А.; D. D. Kotel’nikov; Котельников Д. Д.; N. Yu. Leusova; Леусова Н. Ю.; S. N. Mantrov; Мантров С. Н.; M. A. Kiskin; Кискин М. А.; I. L. Eremenko; Еременко И. Л.; I. A. Lutsenko; Луценко И. А.

doi:10.31857/S0132344X23600212

Copper(II) Furancarboxylate Complexes with 5-Nitro-1,10-Phenanthroline as Promising Biological Agents

Authors: Koshenskova K.A.¹, Baravikov D.E.¹^,2, Nelyubina Y.V.³, Primakov P.V.³, Shender V.O.⁴, Maljants I.K.⁴, Bekker O.B.⁵, Aliev T.M.³, Borodin E.A.⁶, Kotel’nikov D.D.⁶, Leusova N.Y.⁷, Mantrov S.N.², Kiskin M.A.¹, Eremenko I.L.¹^,3, Lutsenko I.A.¹
Affiliations:
1. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia
2. Mendeleev University of Chemical Technology of Russia, Moscow, Russia
3. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia
4. Lopukhin Federal Research and Clinical Center of Physical Chemical Medicine, Federal Medical Biological Agency, Moscow, Russia
5. Vavilov Institute of General Genetics, Russian Academy of Sciences, Moscow, Russia
6. Amur State Medical Academy, Blagoveshchensk, Russia
7. Institute of Geology and Nature Management, Far East Branch, Russian Academy of Sciences, Blagoveshchensk, Russia
Issue: Vol 49, No 10 (2023)
Pages: 632-643
Section: Articles
URL: https://rjonco.com/0132-344X/article/view/667474
DOI: https://doi.org/10.31857/S0132344X23600212
EDN: https://elibrary.ru/MYGCWR
ID: 667474

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Abstract

The reaction of copper(II) acetate with 2-furancarboxylic (HFur)/5-nitro-2-furancarboxylic (HNfur) acids and 5-nitro-1,10-phenanthroline (Nphen) in methanol resulted in the formation of the binuclear coordination compounds [Cu2(L)4(Nphen)2]·X (L = Fur (I), Nfur (II); X = H2O (I)), which were structurally studied by direct X-ray diffraction (CCDC no. 2244205 (I) and 2244206 (II)). According to X-ray diffraction data, the coordination environment of the central metal ion in I and II is composed of two nitrogen atoms of Nphen and three oxygen atoms of the acid anions, which thus form the {CuN2O3} tetragonal pyramid in which the copper coordination number is five. Intermolecular hydrogen bonds and stacking interactions between the Nphen aromatic rings provide supramolecular stabilization of I and II. A characteristic feature of supramolecular organization of II is the presence of a coordination bond between the Cu2+ cation and oxygen of the Nphen NO2- group of parallel chains. A biological activity assay for complexes I and II concerning the cytotoxic properties against a human ovarian adenocarcinoma cell line (SKOV3) and the mycobacterial strain Mycolicibacterium smegmatis showed an efficient suppression of cell viability. The results of mathematical modeling of the probability of Cu2+ binding to amino acid residues of M. smegmatis proteins suggested the affinity of the Cu(II) ion to a number of amino acids in polypeptide sites. It was shown that metal ion binding in mycobacterial proteins is more characteristic of histidine- and glutamic acid-containing moieties.

Keywords

copper(II), coordination compounds, furancarboxylates, 5-nitro-1, 10-phenanthroline, crystal structure, biological activity, Mycolicibacterium smegmatis, SKOV3, mathematical modeling

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