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Title: Identification and in silico prediction of metabolites of the model compound, tebufenozide by human CYP3A4 and CYP2C19.
Authors: Shirotani, Naoki
Togawa, Moe
Ikushiro, Shinichi
Sakaki, Toshiyuki
Harada, Toshiyuki
Miyagawa, Hisashi
Matsui, Masayoshi
Nagahori, Hirohisa
Mikata, Kazuki
Nishioka, Kazuhiko
Hirai, Nobuhiro  kyouindb  KAKEN_id
Akamatsu, Miki  kyouindb  KAKEN_id
Author's alias: 赤松, 美紀
Issue Date: 15-Oct-2015
Publisher: Elsevier Ltd.
Journal title: Bioorganic & medicinal chemistry
Volume: 23
Issue: 20
Start page: 6594
End page: 6601
Abstract: The metabolites of tebufenozide, a model compound, formed by the yeast-expressed human CYP3A4 and CYP2C19 were identified to clarify the substrate recognition mechanism of the human cytochrome P450 (CYP) isozymes. We then determined whether tebufenozide metabolites may be predicted in silico. Hydrogen abstraction energies were calculated with the density functional theory method B3LYP/6-31G(∗). A docking simulation was performed using FRED software. Several alkyl sites of tebufenozide were hydroxylated by CYP3A4 whereas only one site was modified by CYP2C19. The accessibility of each site of tebufenozide to the reaction center of CYP enzymes and the susceptibility of each hydrogen atom for metabolism by CYP enzymes were evaluated by a docking simulation and hydrogen abstraction energy estimation, respectively.
Rights: © 2015. This manuscript version is made available under the CC-BY-NC-ND 4.0 license
The full-text file will be made open to the public on 15 October 2017 in accordance with publisher's 'Terms and Conditions for Self-Archiving'.
This is not the published version. Please cite only the published version. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。
DOI(Published Version): 10.1016/j.bmc.2015.09.019
PubMed ID: 26404412
Appears in Collections:Journal Articles

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