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

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العنوان: Potential Amoebicidal Activity of Hydrazone Derivatives: Synthesis, Characterization, Electrochemical Behavior, Theoretical Study and Evaluation of the Biological Activity
المؤلفون: Mayra Manzanera-Estrada, Luis Ortiz-Frade, Rodrigo Galindo-Murillo, Yanis Toledano-Magaña, Marcos Flores-Alamo, Ruth Meléndrez-Luevano, Lena Ruiz-Azuara, Blanca M. Cabrera-Vivas, Marisol Navarro-Olivarria, Juan Carlos García-Ramos
المصدر: Molecules, Vol 20, Iss 6, Pp 9929-9948 (2015)
Molecules
Volume 20
Issue 6
Pages 9929-9948
بيانات النشر: MDPI AG, 2015.
سنة النشر: 2015
مصطلحات موضوعية: amoebicidal activity, Hydrazine, Pharmaceutical Science, Hydrazone, Redox, DFT, Article, Analytical Chemistry, Nitrobenzene, lcsh:QD241-441, Inhibitory Concentration 50, Structure-Activity Relationship, chemistry.chemical_compound, hydrazone, lcsh:Organic chemistry, Metronidazole, Drug Discovery, Organic chemistry, Molecule, Amebicides, Physical and Theoretical Chemistry, ROS production, Nitrobenzenes, Entamoeba histolytica, chemistry.chemical_classification, Hydrogen bond, Organic Chemistry, Hydrazones, Hydrogen Bonding, Biological activity, Electrochemical Techniques, Combinatorial chemistry, Hydrazines, chemistry, electrochemistry, Chemistry (miscellaneous), Benzaldehydes, hydrogen bonds, Nitro, Quantum Theory, Molecular Medicine, Oxidation-Reduction
الوصف: 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.
وصف الملف: application/pdf
اللغة: English
تدمد: 1420-3049
URL الوصول: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::a98ee25ae4111fa8f86b3786d3a125fb
http://www.mdpi.com/1420-3049/20/6/9929
Rights: OPEN
رقم الانضمام: edsair.doi.dedup.....a98ee25ae4111fa8f86b3786d3a125fb
قاعدة البيانات: OpenAIRE
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