Literature DB >> 18092091

Identification of productive inhibitor binding orientation in fatty acid amide hydrolase (FAAH) by QM/MM mechanistic modelling.

Alessio Lodola1, Marco Mor, Silvia Rivara, Christo Christov, Giorgio Tarzia, Daniele Piomelli, Adrian J Mulholland.   

Abstract

Modelling of the mechanism of covalent adduct formation by the inhibitor O-arylcarbamate URB524 in FAAH shows that only one of the two possible inhibitor binding orientations is consistent with the experimentally observed irreversible carbamoylation of the nucleophile serine: this is a potentially crucial insight for designing new covalent inhibitors of this promising drug target.

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Year:  2007        PMID： 18092091     DOI： 10.1039/b714136j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  15 in total

1.  Covalent inhibitors of fatty acid amide hydrolase: a rationale for the activity of piperidine and piperazine aryl ureas.

Authors:  Giulia Palermo; Davide Branduardi; Matteo Masetti; Alessio Lodola; Marco Mor; Daniele Piomelli; Andrea Cavalli; Marco De Vivo
Journal:  J Med Chem       Date:  2011-09-08       Impact factor: 7.446

Review 2.  A practical guide to modelling enzyme-catalysed reactions.

Authors:  Richard Lonsdale; Jeremy N Harvey; Adrian J Mulholland
Journal:  Chem Soc Rev       Date:  2012-01-26       Impact factor: 54.564

3.  A second generation of carbamate-based fatty acid amide hydrolase inhibitors with improved activity in vivo.

Authors:  Jason R Clapper; Federica Vacondio; Alvin R King; Andrea Duranti; Andrea Tontini; Claudia Silva; Silvano Sanchini; Giorgio Tarzia; Marco Mor; Daniele Piomelli
Journal:  ChemMedChem       Date:  2009-09       Impact factor: 3.466

4.  Biphenyl-3-yl alkylcarbamates as fatty acid amide hydrolase (FAAH) inhibitors: steric effects of N-alkyl chain on rat plasma and liver stability.

Authors:  Federica Vacondio; Claudia Silva; Alessio Lodola; Caterina Carmi; Silvia Rivara; Andrea Duranti; Andrea Tontini; Silvano Sanchini; Jason R Clapper; Daniele Piomelli; Giorgio Tarzia; Marco Mor
Journal:  Eur J Med Chem       Date:  2011-07-21       Impact factor: 6.514

5.  Multiscale Methods in Drug Design Bridge Chemical and Biological Complexity in the Search for Cures.

Authors:  Rommie E Amaro; Adrian J Mulholland
Journal:  Nat Rev Chem       Date:  2018-04-11       Impact factor: 34.035

6.  Fatty acid amide hydrolase as a potential therapeutic target for the treatment of pain and CNS disorders.

Authors:  Kay Ahn; Douglas S Johnson; Benjamin F Cravatt
Journal:  Expert Opin Drug Discov       Date:  2009-07       Impact factor: 6.098

7.  Application of a SCC-DFTB QM/MM approach to the investigation of the catalytic mechanism of fatty acid amide hydrolase.

Authors:  Luigi Capoferri; Marco Mor; Jitnapa Sirirak; Ewa Chudyk; Adrian J Mulholland; Alessio Lodola
Journal:  J Mol Model       Date:  2011-03-02       Impact factor: 1.810

8.  Synthesis and structure-activity relationship studies of O-biphenyl-3-yl carbamates as peripherally restricted fatty acid amide hydrolase inhibitors.

Authors:  Guillermo Moreno-Sanz; Andrea Duranti; Laurin Melzig; Claudio Fiorelli; Gian Filippo Ruda; Giampiero Colombano; Paola Mestichelli; Silvano Sanchini; Andrea Tontini; Marco Mor; Tiziano Bandiera; Rita Scarpelli; Giorgio Tarzia; Daniele Piomelli
Journal:  J Med Chem       Date:  2013-07-03       Impact factor: 7.446

9.  Quantum mechanics/molecular mechanics modeling of fatty acid amide hydrolase reactivation distinguishes substrate from irreversible covalent inhibitors.

Authors:  Alessio Lodola; Luigi Capoferri; Silvia Rivara; Giorgio Tarzia; Daniele Piomelli; Adrian Mulholland; Marco Mor
Journal:  J Med Chem       Date:  2013-03-07       Impact factor: 7.446

10.  Beyond picomolar affinities: quantitative aspects of noncovalent and covalent binding of drugs to proteins.

Authors:  Adam J T Smith; Xiyun Zhang; Andrew G Leach; K N Houk
Journal:  J Med Chem       Date:  2009-01-22       Impact factor: 7.446
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