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Small Molecule Inhibitors of Retinoic Acid 4-Hydroxylase (CYP26): Synthesis and Biological Evaluation of Imidazole Methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates

Lookup NU author(s): Dr Caroline Bridgens, Professor Gareth Veal, Dr Chris RedfernORCiD, Dr Jane Renwick


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The synthesis and potent inhibitory activity of novel imidazole methyl 3-(4-(aryl-2-ylamino)phenyl)propanoates in a MCF-7 CYP26A1 microsomal assay is described. The induction of CYP26A1 mRNA was used to evaluate the ability of the compounds to enhance the biological effects of all-trans retinoic acid (ATRA) in a retinoid-responsive neuroblastoma cell line. The most promising inhibitor, 3-imidazol-1-yl-2-methyl-3-[4-(naphthalen-2-ylamino)-phenyl]-propionic acid methyl ester (20), with an IC50 of 3 nM (compared with liarozole IC50 of 540 nM and R116010 IC50 of 10 nM) was further evaluated for CYP selectivity using a panel of CYP enzymes, mutagenicity (Ames screen), and hepatic stability.

Publication metadata

Author(s): Gomaa MS, Bridgens CE, Aboraia AS, Veal GJ, Redfern CPF, Brancale A, Armstrong JL, Simons C

Publication type: Article

Publication status: Published

Journal: Journal of Medicinal Chemistry

Year: 2011

Volume: 54

Issue: 8

Pages: 2778-2791

Print publication date: 23/03/2011

ISSN (print): 0022-2623

ISSN (electronic): 1520-4804

Publisher: American Chemical Society


DOI: 10.1021/jm101583w


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Funder referenceFunder name
C7735/A9612Cancer Research UK