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(E)-2-Benzylidenecyclanones: Part XVII. An LC-MS study of microsomal transformation reactions of (E)-2-[(4'-methoxyphenyl)methylene]-benzosuberon-1-one: A cyclic chalcone analog

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Structure and stereochemistry
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Submitted   Jan 18, 2023
Published   Mar 22, 2023
Issue    Vol 4 No 2 (2022)
DOI   10.25082/JPBR.2022.02.004

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Fatemeh Kenari
Institute of Pharmaceutical Chemistry, University of Pécs, H-7624, Pécs, Hungary
Szilárd Molnár
Research Institute for Viticulture and Oenology, University of Pécs, H-7634, Hungary
Zoltán Pintér
Institute of Pharmaceutical Chemistry, University of Pécs, H-7624, Pécs, Hungary
Sobhan Bitaraf
Institute of Pharmaceutical Chemistry, University of Pécs, H-7624, Pécs, Hungary
Pál Perjési corresponding author
Institute of Pharmaceutical Chemistry, University of Pécs, H-7624, Pécs, Hungary

Abstract

Biotransformation of the antiproliferative (E)-2-[(4’-methoxyphenyl)methylene]-benzosuberon-1-one (2c) was studied using rat liver microsomes. As a result of the CYP-catalyzed transformations, one monooxygenated (2c+O) and the demethylated (2c-CH2) metabolites were identified by HPLC-MS. (E)-2-[(4’-methoxyphenyl)methylene]-benzosuberon-1-ol, the expected product of rat liver microsomal carbonyl reductase, was not found in the incubates. Microsomal GST-catalyzed reaction of the compound resulted in formation of diastereomeric GST-conjugates. Under the present HPLC conditions, the diastereomeric adducts were separated into two chromatographic peaks (2c-GSH-1 and 2c-GSH-2).

Keywords
chalcone, benzosuberone, microsome, CYP, chalcone reductase, glutathione, microsomal glutathione transferase

Article Details

How to Cite
Kenari, F., Molnár, S., Pintér, Z., Bitaraf, S., & Perjési, P. (2023). (E)-2-Benzylidenecyclanones: Part XVII. An LC-MS study of microsomal transformation reactions of (E)-2-[(4’-methoxyphenyl)methylene]-benzosuberon-1-one: A cyclic chalcone analog. Journal of Pharmaceutical and Biopharmaceutical Research, 4(2), 326-339. https://doi.org/10.25082/JPBR.2022.02.004
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This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

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