Literature DB >> 24900463

Avicholic Acid: A Lead Compound from Birds on the Route to Potent TGR5 Modulators.

Roberto Pellicciari1, Antimo Gioiello1, Paola Sabbatini1, Francesco Venturoni1, Roberto Nuti1, Carolina Colliva2, Giovanni Rizzo3, Luciano Adorini3, Mark Pruzanski3, Aldo Roda2, Antonio Macchiarulo1.   

Abstract

Grounding on our former 3D QSAR studies, a knowledge-based screen of natural bile acids from diverse animal species has led to the identification of avicholic acid as a selective but weak TGR5 agonist. Chemical modifications of this compound resulted in the disclosure of 6α-ethyl-16-epi-avicholic acid that shows enhanced potency at TGR5 and FXR receptors. The synthesis, biological appraisals, and structure-activity relationships of this series of compounds are herein described. Moreover, a thorough physicochemical characterization of 6α-ethyl-16-epi-avicholic acid as compared to naturally occurring bile acids is reported and discussed.

Entities:  

Keywords:  16-epi-avicholic acid; CMC; FXR; TGR5; avicholic acid; bile acid; structure−activity relationship

Year:  2012        PMID： 24900463      PMCID： PMC4025660          DOI： 10.1021/ml200256d

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  26 in total

1.  A novel primary bile acid in the Shoebill stork and herons and its phylogenetic significance.

Authors:  L R Hagey; C D Schteingart; H-T Ton-Nu; A F Hofmann
Journal:  J Lipid Res       Date:  2002-05       Impact factor: 5.922

2.  Expression and function of the bile acid receptor GpBAR1 (TGR5) in the murine enteric nervous system.

Authors:  D P Poole; C Godfrey; F Cattaruzza; G S Cottrell; J G Kirkland; J C Pelayo; N W Bunnett; C U Corvera
Journal:  Neurogastroenterol Motil       Date:  2010-03-12       Impact factor: 3.598

3.  The G-protein-coupled bile acid receptor, Gpbar1 (TGR5), negatively regulates hepatic inflammatory response through antagonizing nuclear factor κ light-chain enhancer of activated B cells (NF-κB) in mice.

Authors:  Yan-Dong Wang; Wei-Dong Chen; Donna Yu; Barry M Forman; Wendong Huang
Journal:  Hepatology       Date:  2011-08-11       Impact factor: 17.425

4.  Back door modulation of the farnesoid X receptor: design, synthesis, and biological evaluation of a series of side chain modified chenodeoxycholic acid derivatives.

Authors:  Roberto Pellicciari; Antimo Gioiello; Gabriele Costantino; Bahman M Sadeghpour; Giovanni Rizzo; Udo Meyer; Derek J Parks; Antonio Entrena-Guadix; Stefano Fiorucci
Journal:  J Med Chem       Date:  2006-07-13       Impact factor: 7.446

Review 5.  Bile acids and the membrane bile acid receptor TGR5--connecting nutrition and metabolism.

Authors:  Charles Thomas; Johan Auwerx; Kristina Schoonjans
Journal:  Thyroid       Date:  2008-02       Impact factor: 6.568

6.  Hepatic bile acid uptake: effect of conjugation, hydroxyl and keto groups, and albumin binding.

Authors:  R Aldini; A Roda; A M Labate; G Cappelleri; E Roda; L Barbara
Journal:  J Lipid Res       Date:  1982-11       Impact factor: 5.922

Review 7.  Role of bile acids and bile acid receptors in metabolic regulation.

Authors:  Philippe Lefebvre; Bertrand Cariou; Fleur Lien; Folkert Kuipers; Bart Staels
Journal:  Physiol Rev       Date:  2009-01       Impact factor: 37.312

8.  Expression and function of the bile acid receptor TGR5 in Kupffer cells.

Authors:  Verena Keitel; Markus Donner; Stefanie Winandy; Ralf Kubitz; Dieter Häussinger
Journal:  Biochem Biophys Res Commun       Date:  2008-05-09       Impact factor: 3.575

9.  Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.

Authors:  Hiroyuki Sato; Antonio Macchiarulo; Charles Thomas; Antimo Gioiello; Mizuho Une; Alan F Hofmann; Régis Saladin; Kristina Schoonjans; Roberto Pellicciari; Johan Auwerx
Journal:  J Med Chem       Date:  2008-02-29       Impact factor: 7.446

10.  TGR5-mediated bile acid sensing controls glucose homeostasis.

Authors:  Charles Thomas; Antimo Gioiello; Lilia Noriega; Axelle Strehle; Julien Oury; Giovanni Rizzo; Antonio Macchiarulo; Hiroyasu Yamamoto; Chikage Mataki; Mark Pruzanski; Roberto Pellicciari; Johan Auwerx; Kristina Schoonjans
Journal:  Cell Metab       Date:  2009-09       Impact factor: 27.287
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  3 in total

1.  Synthesis and Biological Evaluation of Bile Acid Analogues Inhibitory to Clostridium difficile Spore Germination.

Authors:  Kristen L Stoltz; Raymond Erickson; Christopher Staley; Alexa R Weingarden; Erin Romens; Clifford J Steer; Alexander Khoruts; Michael J Sadowsky; Peter I Dosa
Journal:  J Med Chem       Date:  2017-04-12       Impact factor: 7.446

2.  Probing the Binding Site of Bile Acids in TGR5.

Authors:  Antonio Macchiarulo; Antimo Gioiello; Charles Thomas; Thijs W H Pols; Roberto Nuti; Cristina Ferrari; Nicola Giacchè; Francesca De Franco; Mark Pruzanski; Johan Auwerx; Kristina Schoonjans; Roberto Pellicciari
Journal:  ACS Med Chem Lett       Date:  2013-10-15       Impact factor: 4.345

Review 3.  Microbial Hydroxysteroid Dehydrogenases: From Alpha to Omega.

Authors:  Heidi L Doden; Jason M Ridlon
Journal:  Microorganisms       Date:  2021-02-24
  3 in total

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