Literature DB >> 24900487

β-Lactones Inhibit N-acylethanolamine Acid Amidase by S-Acylation of the Catalytic N-Terminal Cysteine.

Andrea Armirotti1, Elisa Romeo1, Stefano Ponzano1, Luisa Mengatto1, Mauro Dionisi1, Claudia Karacsonyi1, Fabio Bertozzi1, Gianpiero Garau1, Glauco Tarozzo1, Angelo Reggiani1, Tiziano Bandiera1, Giorgio Tarzia2, Marco Mor3, Daniele Piomelli4.   

Abstract

The cysteine amidase N-acylethanolamine acid amidase (NAAA) is a member of the N-terminal nucleophile class of enzymes and a potential target for anti-inflammatory drugs. We investigated the mechanism of inhibition of human NAAA by substituted β-lactones. We characterized pharmacologically a representative member of this class, ARN077, and showed, using high-resolution liquid chromatography-tandem mass spectrometry, that this compound forms a thioester bond with the N-terminal catalytic cysteine in human NAAA.

Entities:  

Keywords:  NAAA; covalent inhibitors; cysteine amidase; high resolution mass spectrometry; proteomics

Year:  2012        PMID： 24900487      PMCID： PMC4025845          DOI： 10.1021/ml300056y

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


  29 in total

1.  Molecular characterization of N-acylethanolamine-hydrolyzing acid amidase, a novel member of the choloylglycine hydrolase family with structural and functional similarity to acid ceramidase.

Authors:  Kazuhito Tsuboi; Yong-Xin Sun; Yasuo Okamoto; Nobukazu Araki; Takeharu Tonai; Natsuo Ueda
Journal:  J Biol Chem       Date:  2005-01-17       Impact factor: 5.157

2.  Biosynthesis of an endogenous cannabinoid precursor in neurons and its control by calcium and cAMP.

Authors:  H Cadas; S Gaillet; M Beltramo; L Venance; D Piomelli
Journal:  J Neurosci       Date:  1996-06-15       Impact factor: 6.167

Review 3.  The search for the palmitoylethanolamide receptor.

Authors:  Jesse LoVerme; Giovanna La Rana; Roberto Russo; Antonio Calignano; Daniele Piomelli
Journal:  Life Sci       Date:  2005-08-19       Impact factor: 5.037

4.  Antihyperalgesic effects of spinal cannabinoids.

Authors:  J D Richardson; L Aanonsen; K M Hargreaves
Journal:  Eur J Pharmacol       Date:  1998-03-19       Impact factor: 4.432

5.  Proinflammatory stimuli control N-acylphosphatidylethanolamine-specific phospholipase D expression in macrophages.

Authors:  Chenggang Zhu; Carlos Solorzano; Saurabh Sahar; Natalia Realini; Ernest Fung; Paolo Sassone-Corsi; Daniele Piomelli
Journal:  Mol Pharmacol       Date:  2011-01-13       Impact factor: 4.436

6.  Antidepressant-like activity and modulation of brain monoaminergic transmission by blockade of anandamide hydrolysis.

Authors:  G Gobbi; F R Bambico; R Mangieri; M Bortolato; P Campolongo; M Solinas; T Cassano; M G Morgese; G Debonnel; A Duranti; A Tontini; G Tarzia; M Mor; V Trezza; S R Goldberg; V Cuomo; D Piomelli
Journal:  Proc Natl Acad Sci U S A       Date:  2005-12-13       Impact factor: 11.205

7.  N-cyclohexanecarbonylpentadecylamine: a selective inhibitor of the acid amidase hydrolysing N-acylethanolamines, as a tool to distinguish acid amidase from fatty acid amide hydrolase.

Authors:  Kazuhito Tsuboi; Christine Hilligsmann; Séverine Vandevoorde; Didier M Lambert; Natsuo Ueda
Journal:  Biochem J       Date:  2004-04-01       Impact factor: 3.857

8.  Amino acid residues crucial in pH regulation and proteolytic activation of N-acylethanolamine-hydrolyzing acid amidase.

Authors:  Jun Wang; Li-Ying Zhao; Toru Uyama; Kazuhito Tsuboi; Takeharu Tonai; Natsuo Ueda
Journal:  Biochim Biophys Acta       Date:  2008-08-28

9.  The fatty acid amide hydrolase inhibitor URB597 (cyclohexylcarbamic acid 3'-carbamoylbiphenyl-3-yl ester) reduces neuropathic pain after oral administration in mice.

Authors:  Roberto Russo; Jesse Loverme; Giovanna La Rana; Timothy R Compton; Jeff Parrott; Andrea Duranti; Andrea Tontini; Marco Mor; Giorgio Tarzia; Antonio Calignano; Daniele Piomelli
Journal:  J Pharmacol Exp Ther       Date:  2007-04-05       Impact factor: 4.030

10.  A catalytically silent FAAH-1 variant drives anandamide transport in neurons.

Authors:  Jin Fu; Giovanni Bottegoni; Oscar Sasso; Rosalia Bertorelli; Walter Rocchia; Matteo Masetti; Ana Guijarro; Alessio Lodola; Andrea Armirotti; Gianpiero Garau; Tiziano Bandiera; Angelo Reggiani; Marco Mor; Andrea Cavalli; Daniele Piomelli
Journal:  Nat Neurosci       Date:  2011-11-20       Impact factor: 24.884
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  10 in total

1.  A Potent Systemically Active N-Acylethanolamine Acid Amidase Inhibitor that Suppresses Inflammation and Human Macrophage Activation.

Authors:  Alison Ribeiro; Silvia Pontis; Luisa Mengatto; Andrea Armirotti; Valerio Chiurchiù; Valeria Capurro; Annalisa Fiasella; Andrea Nuzzi; Elisa Romeo; Guillermo Moreno-Sanz; Mauro Maccarrone; Angelo Reggiani; Giorgio Tarzia; Marco Mor; Fabio Bertozzi; Tiziano Bandiera; Daniele Piomelli
Journal:  ACS Chem Biol       Date:  2015-04-15       Impact factor: 5.100

2.  Second-Generation Non-Covalent NAAA Inhibitors are Protective in a Model of Multiple Sclerosis.

Authors:  Marco Migliore; Silvia Pontis; Angel Luis Fuentes de Arriba; Natalia Realini; Esther Torrente; Andrea Armirotti; Elisa Romeo; Simona Di Martino; Debora Russo; Daniela Pizzirani; Maria Summa; Massimiliano Lanfranco; Giuliana Ottonello; Perrine Busquet; Kwang-Mook Jung; Miguel Garcia-Guzman; Roger Heim; Rita Scarpelli; Daniele Piomelli
Journal:  Angew Chem Int Ed Engl       Date:  2016-07-12       Impact factor: 15.336

3.  Activity-Based Probe for N-Acylethanolamine Acid Amidase.

Authors:  Elisa Romeo; Stefano Ponzano; Andrea Armirotti; Maria Summa; Fabio Bertozzi; Gianpiero Garau; Tiziano Bandiera; Daniele Piomelli
Journal:  ACS Chem Biol       Date:  2015-06-23       Impact factor: 5.100

4.  Peroxisome proliferator-activated receptor α mediates acute effects of palmitoylethanolamide on sensory neurons.

Authors:  Iryna A Khasabova; Yee Xiong; Lia G Coicou; Daniele Piomelli; Virginia Seybold
Journal:  J Neurosci       Date:  2012-09-12       Impact factor: 6.167

Review 5.  Advances in the discovery of N-acylethanolamine acid amidase inhibitors.

Authors:  Tiziano Bandiera; Stefano Ponzano; Daniele Piomelli
Journal:  Pharmacol Res       Date:  2014-05-04       Impact factor: 7.658

6.  Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase.

Authors:  Elisa Romeo; Silvia Pontis; Stefano Ponzano; Fabiola Bonezzi; Marco Migliore; Simona Di Martino; Maria Summa; Daniele Piomelli
Journal:  J Vis Exp       Date:  2016-11-23       Impact factor: 1.355

7.  Discovery and SAR Evolution of Pyrazole Azabicyclo[3.2.1]octane Sulfonamides as a Novel Class of Non-Covalent N-Acylethanolamine-Hydrolyzing Acid Amidase (NAAA) Inhibitors for Oral Administration.

Authors:  Paolo Di Fruscia; Anna Carbone; Giovanni Bottegoni; Francesco Berti; Francesca Giacomina; Stefano Ponzano; Chiara Pagliuca; Annalisa Fiasella; Daniela Pizzirani; Jose Antonio Ortega; Andrea Nuzzi; Glauco Tarozzo; Luisa Mengatto; Roberta Giampà; Ilaria Penna; Debora Russo; Elisa Romeo; Maria Summa; Rosalia Bertorelli; Andrea Armirotti; Sine Mandrup Bertozzi; Angelo Reggiani; Tiziano Bandiera; Fabio Bertozzi
Journal:  J Med Chem       Date:  2021-09-01       Impact factor: 7.446

8.  Antinociceptive effects of the N-acylethanolamine acid amidase inhibitor ARN077 in rodent pain models.

Authors:  Oscar Sasso; Guillermo Moreno-Sanz; Cataldo Martucci; Natalia Realini; Mauro Dionisi; Luisa Mengatto; Andrea Duranti; Glauco Tarozzo; Giorgio Tarzia; Marco Mor; Rosalia Bertorelli; Angelo Reggiani; Daniele Piomelli
Journal:  Pain       Date:  2012-11-02       Impact factor: 6.961

Review 9.  Peripheral gating of pain signals by endogenous lipid mediators.

Authors:  Daniele Piomelli; Oscar Sasso
Journal:  Nat Neurosci       Date:  2014-01-28       Impact factor: 24.884

10.  Biochemical and mass spectrometric characterization of human N-acylethanolamine-hydrolyzing acid amidase inhibition.

Authors:  Jay M West; Nikolai Zvonok; Kyle M Whitten; Subramanian K Vadivel; Anna L Bowman; Alexandros Makriyannis
Journal:  PLoS One       Date:  2012-08-31       Impact factor: 3.240
  10 in total

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