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.) Vol 61, No 3 (2017). Quarterly publication (July-September). 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 granted by the Instituto Nacional del Derecho de Autor (INDAUTOR): 04-2005-052710530600-102. 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 October 26th, 2017 by Adriana Vázquez (editorial assistant, e-mail: editor.jmcs@gmail.com), J. Mex. Chem. Soc., Sociedad Química de México, A.C.