Metal–azasterol complexes: Synthesis, characterization, interaction studies with DNA and TrxR and Biological Evaluation

Gonzalo Visbal, Angel Rubén Higuera-Padilla, Luana Pereira Borba-Santos, Wanderley de Souza, Sonia Rozental, Maribel Navarro

Abstract


A new azasterol 22-hydrazine-imidazolin-2-yl-chol-5-ene-3β-ol (AH3) and their derivatives [Au(AH3)Cl] (1) and [Cu(AH3)2(H2O)2](NO3)2 (2) were synthesized and characterized by a combination of elemental analyses, 1H and 13C -NMR, UV-vis and infrared spectroscopies. The interactions with two targets DNA and TrxR were investigated. The results from these studies suggested that these metal-azasterol complexes interact with DNA most probably by covalent binding. Complex 1 showed also the ability to strongly inhibit TrxR. Additionally, their activities against yeast cells of Sporothrix spp. were evaluated; finding that complex 1 was the most active, even better than itraconazole.

Keywords


Azasterol; gold; copper; DNA; thiorredoxin reductase; Sporothrix spp.

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Copyright (c) 2017 Gonzalo Visbal, Angel Rubén Higuera-Padilla, Luana Pereira Borba-Santos, Wanderley de Souza, Sonia Rozental, Maribel Navarro

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Journal of the Mexican Chemical Society (J. Mex. Chem. Soc.) Quarterly publication. Editor-in-Chief: Ignacio González-Martínez. Indexed Journal. Certificate of reserved rights granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 04-2005-052710530600-102. Certificate of lawful title and content: Under procedure. 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 responsability of the authors. 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