(Q27667078)

English

Fluoride-Mediated Capture of a Noncovalent Bound State of a Reversible Covalent Enzyme Inhibitor: X-ray Crystallographic Analysis of an Exceptionally Potent α-Ketoheterocycle Inhibitor of Fatty Acid Amide Hydrolase

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scholarly article

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Fluoride-Mediated Capture of a Noncovalent Bound State of a Reversible Covalent Enzyme Inhibitor: X-ray Crystallographic Analysis of an Exceptionally Potent α-Ketoheterocycle Inhibitor of Fatty Acid Amide Hydrolase (English)

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based on heuristic

inferred from title

Benjamin Cravatt

4

object named as

Benjamin F Cravatt

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author name string

Mauro Mileni

1

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Joie Garfunkle

2

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Cyrine Ezzili

3

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Raymond C Stevens

5

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Dale L Boger

6

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language of work or name

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publication date

23 March 2011

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Journal of the American Chemical Society

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133

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11

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4092-100

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Structural Insights into the Prereaction State of Pyruvate Decarboxylase from Zymomonas mobilis ,

1 reference

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20 March 2017

X-ray Crystallographic Analysis of α-Ketoheterocycle Inhibitors Bound to a Humanized Variant of Fatty Acid Amide Hydrolase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

20 March 2017

Binding and Inactivation Mechanism of a Humanized Fatty Acid Amide Hydrolase by α-Ketoheterocycle Inhibitors Revealed from Cocrystal Structures

1 reference

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20 March 2017

Discovery and Characterization of a Highly Selective FAAH Inhibitor that Reduces Inflammatory Pain

1 reference

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20 March 2017

Structure-guided inhibitor design for human FAAH by interspecies active site conversion

1 reference

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20 March 2017

Mechanism of carbamate inactivation of FAAH: implications for the design of covalent inhibitors and in vivo functional probes for enzymes

1 reference

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20 March 2017

Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling

1 reference

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20 March 2017

Molecular characterization of human and mouse fatty acid amide hydrolases

1 reference

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20 March 2017

Fatty acid amide hydrolase competitively degrades bioactive amides and esters through a nonconventional catalytic mechanism

1 reference

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20 March 2017

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

1 reference

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20 March 2017

Fatty acid amide hydrolase inhibitors. Surprising selectivity of chiral azetidine ureas

1 reference

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20 March 2017

Enzymatic pathways that regulate endocannabinoid signaling in the nervous system

1 reference

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20 March 2017

Novel mechanistic class of fatty acid amide hydrolase inhibitors with remarkable selectivity

1 reference

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20 March 2017

Identification of a high-affinity binding site involved in the transport of endocannabinoids

1 reference

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20 March 2017

Cyclohexylcarbamic acid 3'- or 4'-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modeling studies

1 reference

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20 March 2017

Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides

1 reference

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20 March 2017

Chemical characterization of a family of brain lipids that induce sleep

1 reference

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20 March 2017

Evidence for distinct roles in catalysis for residues of the serine-serine-lysine catalytic triad of fatty acid amide hydrolase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

20 March 2017

Isolation and structure of a brain constituent that binds to the cannabinoid receptor

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

7 April 2017

Modulation of anxiety through blockade of anandamide hydrolysis

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

7 April 2017

Recent advances in the discovery and evaluation of fatty acid amide hydrolase inhibitors

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Fatty acid amide signaling molecules

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Synthesis and evaluation of paracetamol esters as novel fatty acid amide hydrolase inhibitors.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Oxime carbamate--discovery of a series of novel FAAH inhibitors

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

beta-Lactams derived from a carbapenem chiron are selective inhibitors of human fatty acid amide hydrolase versus human monoacylglycerol lipase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Blockade of endocannabinoid-degrading enzymes attenuates neuropathic pain

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

The synthesis and biological evaluation of para-substituted phenolic N-alkyl carbamates as endocannabinoid hydrolyzing enzyme inhibitors.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Endocannabinoid modulation of scratching response in an acute allergenic model: a new prospective neural therapeutic target for pruritus

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Discovery of boronic acids as novel and potent inhibitors of fatty acid amide hydrolase.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Exploration of a fundamental substituent effect of alpha-ketoheterocycle enzyme inhibitors: Potent and selective inhibitors of fatty acid amide hydrolase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Optimization of the central heterocycle of alpha-ketoheterocycle inhibitors of fatty acid amide hydrolase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Fatty acid amide hydrolase inhibition enhances the anti-allodynic actions of endocannabinoids in a model of acute pain adapted for the mouse

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Synthesis and quantitative structure-activity relationship of fatty acid amide hydrolase inhibitors: modulation at the N-portion of biphenyl-3-yl alkylcarbamates.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Optimization of alpha-ketooxazole inhibitors of fatty acid amide hydrolase.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Inhibitors of proteases and amide hydrolases that employ an alpha-ketoheterocycle as a key enabling functionality

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Structure-activity relationships of alpha-ketooxazole inhibitors of fatty acid amide hydrolase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Potent and selective alpha-ketoheterocycle-based inhibitors of the anandamide and oleamide catabolizing enzyme, fatty acid amide hydrolase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Delineation of a fundamental alpha-ketoheterocycle substituent effect for use in the design of enzyme inhibitors

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serine hydrolases

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

In vitro and in vivo effects of fluoride ions on enzyme activity.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Inhibition of fatty acid amide hydrolase produces analgesia by multiple mechanisms

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Fluoride inhibition of enolase: crystal structure and thermodynamics

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Actions of the FAAH inhibitor URB597 in neuropathic and inflammatory chronic pain models

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Structure and function of fatty acid amide hydrolase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Discovery of a potent, selective, and efficacious class of reversible alpha-ketoheterocycle inhibitors of fatty acid amide hydrolase effective as analgesics

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Fatty acid amide hydrolase: an emerging therapeutic target in the endocannabinoid system

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Design, synthesis, and structure-activity relationships of alkylcarbamic acid aryl esters, a new class of fatty acid amide hydrolase inhibitors.

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Discovering potent and selective reversible inhibitors of enzymes in complex proteomes

1 reference

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29 September 2017

Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Proteins regulating the biosynthesis and inactivation of neuromodulatory fatty acid amides

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Exceptionally potent inhibitors of fatty acid amide hydrolase: the enzyme responsible for degradation of endogenous oleamide and anandamide

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

Discovery and characterization of endogenous cannabinoids

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29 September 2017

Oleamide: an endogenous sleep-inducing lipid and prototypical member of a new class of biological signaling molecules

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

29 September 2017

An endogenous sleep-inducing compound is a novel competitive inhibitor of fatty acid amide hydrolase

1 reference

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29 September 2017

Synthetic inhibitors of elastase

1 reference

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29 September 2017

Cerebrodiene: a brain lipid isolated from sleep-deprived cats

1 reference

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29 September 2017

N-acylated glycerophospholipids and their derivatives

1 reference

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29 September 2017

Benzothiophene piperazine and piperidine urea inhibitors of fatty acid amide hydrolase (FAAH)

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

2 June 2018

Clarifying the catalytic roles of conserved residues in the amidase signature family

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

2 June 2018

Chemical and mutagenic investigations of fatty acid amide hydrolase: evidence for a family of serine hydrolases with distinct catalytic properties

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

2 June 2018

Trifluoromethyl ketone inhibitors of fatty acid amide hydrolase: a probe of structural and conformational features contributing to inhibition

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

2 June 2018

Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

27 November 2018

Structure based design of novel irreversible FAAH inhibitors

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

27 November 2018

Biochemical and biological properties of 4-(3-phenyl-[1,2,4] thiadiazol-5-yl)-piperazine-1-carboxylic acid phenylamide, a mechanism-based inhibitor of fatty acid amide hydrolase

1 reference

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27 November 2018

Synthesis and evaluation of benzothiazole-based analogues as novel, potent, and selective fatty acid amide hydrolase inhibitors

1 reference

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27 November 2018

Thiadiazolopiperazinyl ureas as inhibitors of fatty acid amide hydrolase

1 reference

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27 November 2018

3-Alkenyl-2-azetidinones as fatty acid amide hydrolase inhibitors

1 reference

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27 November 2018

Novel ketooxazole based inhibitors of fatty acid amide hydrolase (FAAH).

1 reference

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27 November 2018

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1 reference

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27 November 2018

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1 reference

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27 November 2018

Fatty acid amide hydrolase inhibitors from virtual screening of the endocannabinoid system.

1 reference

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27 November 2018

Substituted 2-thioxoimidazolidin-4-ones and imidazolidine-2,4-diones as fatty acid amide hydrolase inhibitors templates

1 reference

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27 November 2018

Elucidation of fatty acid amide hydrolase inhibition by potent alpha-ketoheterocycle derivatives from Monte Carlo simulations

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

27 November 2018

Discovery of an exceptionally potent and selective class of fatty acid amide hydrolase inhibitors enlisting proteome-wide selectivity screening: concurrent optimization of enzyme inhibitor potency and selectivity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

27 November 2018

Heterocyclic sulfoxide and sulfone inhibitors of fatty acid amide hydrolase

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

27 November 2018

Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

27 November 2018

Comparative analysis of fatty acid amide hydrolase and cb(1) cannabinoid receptor expression in the mouse brain: evidence of a widespread role for fatty acid amide hydrolase in regulation of endocannabinoid signaling

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

27 November 2018

alpha-Keto heterocycle inhibitors of fatty acid amide hydrolase: carbonyl group modification and alpha-substitution

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

27 November 2018

Comparative characterization of a wild type and transmembrane domain-deleted fatty acid amide hydrolase: identification of the transmembrane domain as a site for oligomerization

1 reference

https://eutils.ncbi.nlm.nih.gov/entrez/eutils/elink.fcgi?dbfrom=pmc&linkname=pmc_refs_pubmed&retmode=json&id=3060301

27 November 2018

Fatty acid amide hydrolase substrate specificity

1 reference

https://pubmed.ncbi.nlm.nih.gov/21355555

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Peptidyl alpha-ketoheterocyclic inhibitors of human neutrophil elastase. 3. In vitro and in vivo potency of a series of peptidyl alpha-ketobenzoxazoles

1 reference

https://pubmed.ncbi.nlm.nih.gov/21355555

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Synthesis and Structure-Activity Relationships of FAAH Inhibitors: Cyclohexylcarbamic Acid Biphenyl Esters with Chemical Modulation at the Proximal Phenyl Ring

1 reference

https://pubmed.ncbi.nlm.nih.gov/21355555

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Novel inhibitors of fatty acid amide hydrolase

1 reference

https://pubmed.ncbi.nlm.nih.gov/21355555

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

The crystal structure of fluoride-inhibited cytochrome c peroxidase

1 reference

https://pubmed.ncbi.nlm.nih.gov/21355555

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

Discovery and biological activity of orally active peptidyl trifluoromethyl ketone inhibitors of human neutrophil elastase

1 reference

https://pubmed.ncbi.nlm.nih.gov/21355555

12 December 2020

based on heuristic

inferred from PubMed ID database lookup

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10.1021/JA110877Y

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