DNA binding and cleavage activity of three new copper (II) complexes of chiral N-salicyl-β-amino alcohol Schiff bases

Turgay Tunç, Nadir Demirel, Mahmut Emir, Aslıhan Günel, Mehmet Çolak, Nurcan Karacan

Abstract


Abstract. Three new copper(II) complexes (1-3) with general formula [Cu(HL)CH3COO] of N-salicyl-β-amino alcohol Schiff bases containing, (S)-(+)-phenyl glycinol, (1S, 2R)-2-amino-1, 2-diphenylethanol and 1, 1, 3-triphenyl-(R)-(+)-2-amino propanol, were synthesized.  Their structures were characterized by FTIR, LCMS, magnetic moment, molar conductance and elemental analysis data. DFT calculations proposed distorted square planar geometries for the complexes. The calculated IR spectra are in good agreement with the experimental IR spectra, confirming the proposed structures. Their interactions with calf thymus DNA were investigated and their binding constants Kb were found. Gel electrophoresis reveals that all complexes display significant nuclease activity against supercoiled pentry/d-topo plasmid DNA.

 

Resumen. Tres nuevos complejos de cobre (II) (1-3) con la fórmula general [Cu (HL) CH

3COO] de N-salicil-β-amino alcohol Schiff bases que contienen, (S) - (+) - fenilglicinol, (1S, 2R). Se sintetizaron -2-amino-1, 2-difeniletanol y 1, 1, 3-trifenil- (R) - (+) - 2-amino propanol. Sus estructuras se caracterizaron por FTIR, LCMS, momento magnético, conductancia molar y datos de análisis elemental. Los cálculos de DFT propusieron geometrías planas cuadradas distorsionadas para los complejos. Los espectros de IR calculados están en buena concordancia con los espectros de IR experimentales, confirmando las estructuras propuestas. Se investigaron sus interacciones con el ADN del timo de ternera y se encontraron sus constantes de unión Kb. La electroforesis en gel revela que todos los complejos muestran una actividad nucleasa significativa contra el ADN plasmídico pentry / d-topo superenrollado.

 


Keywords


Copper (II) complexes; DFT calculations; DNA binding; DNA cleavage; Schiff base complexes.

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DOI: http://dx.doi.org/10.29356/jmcs.v62i3.424

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Journal of the Mexican Chemical Society (J. Mex. Chem. Soc.) Vol 62, No 2 (2018). Quarterly publication (April-June). Edited and distributed by Sociedad Química de México, A.C. Barranca del Muerto 26, Col. Crédito Constructor, Del. Benito Juárez, C.P. 03940, Mexico City. Phone: +5255 56626837; +5255 56626823 Contact: soquimex@sqm.org.mx http://www.sqm.org.mx Editor-in-Chief: Ignacio González-Martínez. Indexed Journal. Certificate of reserved rights for recurrent publications under digital distribution granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 04-2018-091118040000-203. Certificate of lawful title and content: Under procedure. ISSN-e granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 2594-0317. ISSN granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 1870-249X. Postal registration of printed matter deposited by editors or agents granted by SEPOMEX: IM09-0312 Copyright © Sociedad Química de México, A.C. Total or partial reproduction is prohibited without written permission of the right holder. The Figures/schemes quality and the general contents of this publication are full responsibility of the authors. Updated December 12th, 2018 by Adriana Vázquez (editorial assistant, e-mail: editor.jmcs@gmail.com), J. Mex. Chem. Soc., Sociedad Química de México, A.C.