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Molecules 2017, 22(7), 1060; doi:10.3390/molecules22071060

In silico Study of the Pharmacologic Properties and Cytotoxicity Pathways in Cancer Cells of Various Indolylquinone Analogues of Perezone

1
Departamento de Ciencias Químicas, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, Estado de México, C.P. 54740, México
2
Instituto de Ciencias Biomédicas, Universidad Autónoma de Ciudad Juárez, Henry Dunant #4600, Ciudad Juárez 32310, México
3
Instituto de Ingeniería y tecnología, Universidad Autónoma de Ciudad Juárez, Ave. Del Charro 450 Norte, Ciudad Juárez 32310, México
*
Author to whom correspondence should be addressed.
Received: 30 May 2017 / Revised: 16 June 2017 / Accepted: 19 June 2017 / Published: 25 June 2017
(This article belongs to the Special Issue The Biomedical Importance of Indoles and Their Derivatives)
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Abstract

Several indolylquinone analogues of perezone, a natural sesquiterpene quinone, were characterized in this work by theoretical methods. In addition, some physicochemical, toxicological and metabolic properties were predicted using bioinformatics software. The predicted physicochemical properties are in agreement with the solubility and cLogP values, the penetration across the cell membrane, and absorption values, as well as with a possible apoptosis-activated mechanism of cytotoxic action. The toxicological predictions suggest no mutagenic, tumorigenic or reproductive effects of the four target molecules. Complementarily, the results of a performed docking study show high scoring values and hydrogen bonding values in agreement with the cytotoxicity IC50 value ranking, i.e: indolylmenadione > indolylperezone > indolylplumbagine > indolylisoperezone. Consequently, it is possible to suggest an appropriate apoptotic pathway for each compound. Finally, potential metabolic pathways of the molecules were proposed. View Full-Text
Keywords: indolylquinones; perezone; apoptosis; cancer; quantum chemistry calculations; docking study; chemioinformatics tools indolylquinones; perezone; apoptosis; cancer; quantum chemistry calculations; docking study; chemioinformatics tools
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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

Escobedo-González, R.; Vargas-Requena, C.L.; Moyers-Montoya, E.; Aceves-Hernández, J.M.; Nicolás-Vázquez, M.I.; Miranda-Ruvalcaba, R. In silico Study of the Pharmacologic Properties and Cytotoxicity Pathways in Cancer Cells of Various Indolylquinone Analogues of Perezone. Molecules 2017, 22, 1060.

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