ArticleJournal of medicinal chemistry2010
Synthesis and structure-activity relationships of N-(2-oxo-3-oxetanyl)amides as N-acylethanolamine-hydrolyzing acid amidase inhibitors.
Article in Journal of medicinal chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 54 citations in OpenAlex.
- Fluorescence-Based Enzyme Activity Assay: Ascertaining the Activity and Inhibition of Endocannabinoid Hydrolytic Enzymes.International journal of molecular sciences · 2024Review
- Characterization and Preliminary In Vitro Antioxidant Activity of a New Multidrug Formulation Based on the Co-Encapsulation of Rutin and the α-Acylamino-β-Lactone NAAA Inhibitor URB894 within PLGA Nanoparticles.Antioxidants (Basel, Switzerland) · 2023Article
- α-Acylamino-β-lactoneAntioxidants (Basel, Switzerland) · 2022Article
- Synthesis, biological evaluation, and structure activity relationship (SAR) study of pyrrolidine amide derivatives asMedChemComm · 2019Article
- Molecular mechanism of activation of the immunoregulatory amidase NAAA.Proceedings of the National Academy of Sciences of the United States of America · 2018Article
- Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase.Journal of visualized experiments : JoVE · 2016Article
- Activity-Based Probe for N-Acylethanolamine Acid Amidase.ACS chemical biology · 2015Article
- Palmitoylethanolamide, a naturally occurring lipid, is an orally effective intestinal anti-inflammatory agent.British journal of pharmacology · 2015Article
- Advances in the discovery of N-acylethanolamine acid amidase inhibitors.Pharmacological research · 2014Review
- 3-Aminoazetidin-2-one derivatives as N-acylethanolamine acid amidase (NAAA) inhibitors suitable for systemic administration.ChemMedChem · 2014Article
- Mast cells, glia and neuroinflammation: partners in crime?Immunology · 2014Review
- Article
- Endogenous molecules stimulating N-acylethanolamine-hydrolyzing acid amidase (NAAA).ACS chemical neuroscience · 2012Article
- β-Lactones Inhibit N-acylethanolamine Acid Amidase by S-Acylation of the Catalytic N-Terminal Cysteine.ACS medicinal chemistry letters · 2012Article
- Mass spectrometric characterization of human N-acylethanolamine-hydrolyzing acid amidase.Journal of proteome research · 2012Article
- Design and synthesis of potent N-acylethanolamine-hydrolyzing acid amidase (NAAA) inhibitor as anti-inflammatory compounds.PloS one · 2012Article
- Biochemical and mass spectrometric characterization of human N-acylethanolamine-hydrolyzing acid amidase inhibition.PloS one · 2012Article
- A catalytic mechanism for cysteine N-terminal nucleophile hydrolases, as revealed by free energy simulations.PloS one · 2012Article
- Biphenyl-3-yl alkylcarbamates as fatty acid amide hydrolase (FAAH) inhibitors: steric effects of N-alkyl chain on rat plasma and liver stability.European journal of medicinal chemistry · 2011Article
Corrections and comments
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Authors and funding
10 authors at 3 institutions in 2 countries.
Funding
Abstract
The fatty acid ethanolamides (FAEs) are a family of bioactive lipid mediators that include the endogenous agonist of peroxisome proliferator-activated receptor-alpha, palmitoylethanolamide (PEA). FAEs are hydrolyzed intracellularly by either fatty acid amide hydrolase or N-acylethanolamine-hydrolyzing acid amidase (NAAA). Selective inhibition of NAAA by (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide [(S)-OOPP, 7a] prevents PEA degradation in mouse leukocytes and attenuates responses to proinflammatory stimuli. Starting from the structure of 7a, a series of beta-lactones was prepared and tested on recombinant rat NAAA to explore structure-activity relationships (SARs) for this class of inhibitors and improve their in vitro potency. Following the hypothesis that these compounds inhibit NAAA by acylation of the catalytic cysteine, we identified several requirements for recognition at the active site and obtained new potent inhibitors. In particular, (S)-N-(2-oxo-3-oxetanyl)biphenyl-4-carboxamide (7h) was more potent than 7a at inhibiting recombinant rat NAAA activity (7a, IC(50) = 420 nM; 7h, IC(50) = 115 nM) in vitro and at reducing carrageenan-induced leukocyte infiltration in vivo.
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