Design and Synthesis of a Diaza-bicyclo-naphthalen-oxiranyl-methanone Derivative. Theoretical Analysis of Their Interaction with Cytochrome P450-17A1

Figueroa-Valverde, Lauro; Francisco, Diaz Cedillo; Marcela, Rosas-Nexticapa; Virginia, Mateu-Armand; Elizabeth, Montano-Tapia; Maria, Lopez-Ramos; Elodia, García-Cervera; Eduardo, Pool Gómez; Lenin, Hau-Heredia; Alondra, Alfonso-Jimenez; Jhair, Cabrera-Tuz

doi:10.22034/chemm.2018.147492.1083

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	Design and Synthesis of a Diaza-bicyclo-naphthalen-oxiranyl-methanone Derivative. Theoretical Analysis of Their Interaction with Cytochrome P450-17A1
Article 4, Volume 3, Issue 2. pp. 145-275, March and April 2019, Page 194-210 PDF (1.15 MB)
Document Type: Original Article
DOI: 10.22034/chemm.2018.147492.1083
Authors
Lauro Figueroa-Valverde ¹; Diaz Cedillo Francisco²; Rosas-Nexticapa Marcela³; Mateu-Armand Virginia³; Montano-Tapia Elizabeth³; Lopez-Ramos Maria¹; García-Cervera Elodia¹; Pool Gómez Eduardo¹; Hau-Heredia Lenin¹; Alfonso-Jimenez Alondra¹; Cabrera-Tuz Jhair¹
¹Laboratory of Pharmaco-Chemistry at the Faculty of Chemical Biological Sciences of the University Autonomous of Campeche, Av. Agustín Melgar s/n, Col Buenavista C.P.24039 Campeche Cam., México
²Escuela Nacional de Ciencias Biológicas del Instituto Politécnico Nacional. Prol. Carpio y Plan de Ayala s/n Col. Santo Tomas, México, D.F. C.P. 11340
³Facultad de Nutrición, Universidad Veracruzana. Médicos y Odontólogos s/n, 91010, Xalapa, Veracruz. México
Receive Date: 04 September 2018, Revise Date: 22 September 2018, Accept Date: 25 October 2018
Abstract
Several agents have been used for the treatment of prostate cancer such as flutamide, galeterone, abiraterone and others; however, some of these drugs can produce some secondary effects. The aim of this study was to synthesize a diaza-bicyclo-naphthalen-oxiranyl-methanone derivative using some chemical tools. The structure of all compounds involved in this study was confirmed by spectroscopy and spectrometry data. In addition, the theoretical interaction of diaza-bicyclo-naphthalen-oxiranyl-methanone derivative with the cytochrome P450-17A₁ enzyme (3RUK) was evaluated in a docking model using some drugs such as galeterone and abiraterone as controls. The results showed that diaza-bicyclo-naphthalen-oxiranyl-methanone could interact with different types of amino acid residues involving 3RUK protein surface as compared to both galeterone and abiraterone. This phenomenon may be due to the differences in the chemical structure of compounds. All these data indicate that diaza-bicyclo-naphthalen-oxiranyl-methanone derivative could change the biological activity of cytochrome P450-17A₁ enzyme which may be translated as good candidates for prostate cancer.
Graphical Abstract

Keywords
Diaza-bicyclo-naphthalen-oxiranyl-methanone; Derivative; Prostate cancer; Cytochrome P450 17A1; Docking
Main Subjects
Applied Chemistry


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