An unusual iminoacylation of 2-amino pyridyl thiazole: Synthesis, X-ray crystallography and DFT study of copper(II) amidine complexes and their cytotoxicity, DNA binding and cleavage study
authors Bera, P; Brandao, P; Mondal, G; Santra, A; Jana, A; Mokhamatam, RB; Manna, SK; Mandal, TK; Bera, P
nationality International
journal POLYHEDRON
author keywords Pyridyl-thiazole; Amidine complexes; X-ray crystallography; Cytotoxicity; DNA cleavage
keywords DENSITY FUNCTIONALS; NICKEL-COMPLEXES; SCHIFF-BASE; DERIVATIVES; DISCOVERY; CHEMISTRY; ACETONITRILE; POTENT; REACTIVITY; INSERTION
abstract Insertion of acetonitrile in the exocyclic NH2 group of the thiazole unit of 2-amino-4-(2-pyridyl)thiazole (HL) in the presence of copper chloride results in the formation of the monomeric amidine complex [Cu (LC(Me)=NH))Cl-2] (1). The same reaction of HL and copper(II) perchlorate yields the complex [Cu(HL)(2)] (ClO4)(2) (2), without acetonitrile insertion. However, the presence of a spacer donor, e.g. pyrazine, in the reaction medium results in the formation of a dinuclear amidine derivative, [(ClO4)(LC(MeNH}Cu(pyrazine)Cu(LC(Me)=NH)(ClO4)] (ClO4)(2) (3). Complexes 1 and 3 are the first examples of copper assisted iminoacylation of 2-amino pyridylthiazole derivatives, confirming a nitrile to amidine transformation. The new complexes were characterized by single crystal X-ray crystallography, cyclic voltammetry and a DFT study. The complexes have a potential cytotoxic effect in human monocytic cells (U937) with IC50 values ranging from 0.84 to 4.5 01. Significant necrotic activities are ascertained by a lactate dehydrogenase (LDH) enzyme release assay. The interaction with calf thymus (CT) DNA shows the binding constant (Kb) values are 104 M-1. The chemical nuclease activity of 1, 2 and 3 result in 65, 99 and 80% relaxation of supercoiled DNA at 10 jAM in the presence of glutathione (GSH, 1 mM), respectively. The study with radical scavengers proved that a hydroxyl or singlet oxygen-like species is responsible for the DNA degradation. (C) 2018 Elsevier Ltd. All rights reserved.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0277-5387
year published 2019
volume 159
beginning page 436
ending page 445
digital object identifier (doi) 10.1016/j.poly.2018.11.069
web of science category Chemistry, Inorganic & Nuclear; Crystallography
subject category Chemistry; Crystallography
unique article identifier WOS:000458228000049
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journal analysis (jcr 2019):
journal impact factor 2.343
5 year journal impact factor 1.894
category normalized journal impact factor percentile 60.363
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