Copper(II) Schiff base complexes: Synthetic and medicinal perspective

Kumari, Pratima; Choudhary, Manshu; Kumar, Aman; Yadav, Pragati; Singh, Bijender; Kataria, Ramesh; Kumar, Vinod

doi:10.1016/j.inoche.2023.111409

Cited by 5 publications

(1 citation statement)

References 134 publications

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“…Among the copper complexes, those formed by Schiff bases have been the object of extensive study. These compounds have attracted considerable interest in the scientific community due to their interesting properties, particularly those related to their biological and pharmacological action and possible use in medicine [1][2][3][4][5][6][7][8][57][58][59][60][61][62][63]. For example, hesperetin Schiff bases containing benzohydrazide (HHSB or L 1 H 3 ), isoniazid (HIN or L 2 H 3 ), and thiosemicarbazide (HTSC or L 3 H 3 ) and their complexes with copper(II) have been investigated in analytical/spectral studies, and biological action in vitro such as cytotoxicity against human cancer cells, genotoxicity, and antimicrobial activity was ascertained by this and other groups [64][65][66].…”

Section: Introductionmentioning

confidence: 99%

Experimental and Computational Studies on the Interaction of DNA with Hesperetin Schiff Base CuII Complexes

Pisanu,

Sykula,

Sciortino

et al. 2024

IJMS

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The interactions with calf thymus DNA (CT-DNA) of three Schiff bases formed by the condensation of hesperetin with benzohydrazide (HHSB or L1H3), isoniazid (HIN or L2H3), or thiosemicarbazide (HTSC or L3H3) and their CuII complexes (CuHHSB, CuHIN, and CuHTSC with the general formula [CuLnH2(AcO)]) were evaluated in aqueous solution both experimentally and theoretically. UV–Vis studies indicate that the ligands and complexes exhibit hypochromism, which suggests helical ordering in the DNA helix. The intrinsic binding constants (Kb) of the Cu compounds with CT-DNA, in the range (2.3–9.2) × 106, from CuHTSC to CuHHSB, were higher than other copper-based potential drugs, suggesting that π–π stacking interaction due to the presence of the aromatic rings favors the binding. Thiazole orange (TO) assays confirmed that ligands and Cu complexes displace TO from the DNA binding site, quenching the fluorescence emission. DFT calculations allow for an assessment of the equilibrium between [Cu(LnH2)(AcO)] and [Cu(LnH2)(H2O)]+, the tautomer that binds CuII, amido (am) and not imido (im), and the coordination mode of HTSC (O−, N, S), instead of (O−, N, NH2). The docking studies indicate that the intercalative is preferred over the minor groove binding to CT-DNA with the order [Cu(L1H2am)(AcO)] > [Cu(L2H2am)(AcO)] ≈ TO ≈ L1H3 > [Cu(L3H2am)(AcO)], in line with the experimental Kb constants, obtained from the UV–Vis spectroscopy. Moreover, dockings predict that the binding strength of [Cu(L1H2am)(AcO)] is larger than [Cu(L1H2am)(H2O)]+. Overall, the results suggest that when different enantiomers, tautomers, and donor sets are possible for a metal complex, a computational approach should be recommended to predict the type and strength of binding to DNA and, in general, to macromolecules.

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