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Synthesis, biological evaluation, and molecular modeling investigation of new chiral fibrates with PPARalpha and PPARgamma agonist activity.

Abstract：

:Peroxisome proliferator-activated receptors (PPARs) are ligand-activated transcription factors that govern lipid and glucose homeostasis playing a central role in cardiovascular diseases, obesity, and diabetes. Medications targeted to PPARs have been established to treat hyperlipidemia (fibrates) and insulin resistance (glitazones). Thus, there is significant interest in developing new and specific ligands for these receptors. Here, we present the results of the screening of new ligands of PPARalpha and PPARgamma. Optical isomers of new chiral fibrates were synthesized and tested in cell-based assays. Compound (S)-7 showed a dual PPARalpha/gamma activity, and its stereochemistry was crucial in receptor activation. Protease protection experiments suggested that this compound binds directly to PPAR. Moreover, computational studies showed that it properly docks to PPARalpha and gamma ligand binding pockets. Interestingly, (S)-7 exhibited only a modest capacity to induce the differentiation of murine fibroblasts 3T3-L1 into adipocytes compared to rosiglitazone, a well-known PPARgamma agonist.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Pinelli A,Godio C,Laghezza A,Mitro N,Fracchiolla G,Tortorella V,Lavecchia A,Novellino E,Fruchart JC,Staels B,Crestani M,Loiodice F

doi

10.1021/jm0502844

keywords:

subject

Has Abstract

pub_date

2005-08-25 00:00:00

pages

5509-19

issue

17

eissn

0022-2623

issn

1520-4804

journal_volume

48

pub_type

杂志文章

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