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Molecules 2015, 20(6), 9929-9948; doi:10.3390/molecules20069929

Potential Amoebicidal Activity of Hydrazone Derivatives: Synthesis, Characterization, Electrochemical Behavior, Theoretical Study and Evaluation of the Biological Activity

1
Departamento de Inmunología, Instituto de Investigaciones Biomédicas, Universidad Nacional Autónoma de México, Avenida Universidad 3000, 04510 Mexico City, Mexico
2
Laboratorio de Química Inorgánica Medicinal, Departamento de Química Inorgánica y Nuclear, Facultad de Química, Universidad Nacional Autónoma de México, Avenida Universidad 3000, 04510 Mexico City, Mexico
3
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, 72570 Puebla, Mexico
4
Facultad de Química, Universidad Nacional Autónoma de México, Avenida Universidad 3000, 04510 Mexico City, Mexico
5
Departamento de Electroquímica, Centro de Investigación y Desarrollo Tecnológico en Electroquímica, S.C., Parque Tecnológico Querétaro, Sanfandila, Pedro de Escobedo, C.P. 76703 Querétaro, México
6
Department of Medicinal Chemistry, College of Pharmacy, University of Utah, 2000 East 30 South Skaggs 201, Salt Lake City, UT 84112, USA
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editor: Christophe Dardonville
Received: 18 March 2015 / Accepted: 24 April 2015 / Published: 29 May 2015
(This article belongs to the Special Issue Antiparasitic Agents)
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Abstract

Four new hydrazones were synthesized by the condensation of the selected hydrazine and the appropriate nitrobenzaldehyde. A complete characterization was done employing 1H- and 13C-NMR, electrochemical techniques and theoretical studies. After the characterization and electrochemical analysis of each compound, amoebicidal activity was tested in vitro against the HM1:IMSS strain of Entamoeba histolytica. The results showed the influence of the nitrobenzene group and the hydrazone linkage on the amoebicidal activity. meta-Nitro substituted compound 2 presents a promising amoebicidal activity with an IC50 = 0.84 μM, which represents a 7-fold increase in cell growth inhibition potency with respect to metronidazole (IC50 = 6.3 μM). Compounds 1, 3, and 4 show decreased amoebicidal activity, with IC50 values of 7, 75 and 23 µM, respectively, as a function of the nitro group position on the aromatic ring. The observed differences in the biological activity could be explained not only by the redox potential of the molecules, but also by their capacity to participate in the formation of intra- and intermolecular hydrogen bonds. Redox potentials as well as the amoebicidal activity can be described with parameters obtained from the DFT analysis. View Full-Text
Keywords: hydrazone; amoebicidal activity; ROS production; electrochemistry; DFT; hydrogen bonds; Entamoeba histolytica hydrazone; amoebicidal activity; ROS production; electrochemistry; DFT; hydrogen bonds; Entamoeba histolytica
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Toledano-Magaña, Y.; García-Ramos, J.C.; Navarro-Olivarria, M.; Flores-Alamo, M.; Manzanera-Estrada, M.; Ortiz-Frade, L.; Galindo-Murillo, R.; Ruiz-Azuara, L.; Meléndrez-Luevano, R.M.; Cabrera-Vivas, B.M. Potential Amoebicidal Activity of Hydrazone Derivatives: Synthesis, Characterization, Electrochemical Behavior, Theoretical Study and Evaluation of the Biological Activity. Molecules 2015, 20, 9929-9948.

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