ArticleProstaglandins & other lipid mediators2018
Novel piperidine-derived amide sEH inhibitors as mediators of lipid metabolism with improved stability.
Article in Prostaglandins & other lipid mediators, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed, 29 citations in OpenAlex.
- Polynitrogen-containing compounds as multi-target sEH/FAAH inhibitors: Structure-activity relationship and pharmacological studies.Bioorganic & medicinal chemistry · 2026Article
- Synthesis and evaluation of isoquinolinyl and pyridinyl-based dual inhibitors of fatty acid amide hydrolase and soluble epoxide hydrolase to alleviate orofacial hyperalgesia in the rat.Biochemistry and biophysics reports · 2025Article
- Structure-activity relationship studies and pharmacological evaluation of 4-phenylthiazoles as dual soluble epoxide hydrolase/fatty acid amide hydrolase inhibitors.Bioorganic & medicinal chemistry · 2025Article
- Article
- Increased Soluble Epoxide Hydrolase Activity Positively Correlates with Mortality in Heart Failure Patients with Preserved Ejection Fraction: Evidence from Metabolomics.Phenomics (Cham, Switzerland) · 2023Article
- Structure-activity relationship studies of benzothiazole-phenyl analogs as multi-target ligands to alleviate pain without affecting normal behavior.Prostaglandins & other lipid mediators · 2023Article
- Further exploration of the structure-activity relationship of dual soluble epoxide hydrolase/fatty acid amide hydrolase inhibitors.Bioorganic & medicinal chemistry · 2021Article
- Species Differences in Metabolism of Soluble Epoxide Hydrolase Inhibitor, EC1728, Highlight the Importance of Clinically Relevant Screening Mechanisms in Drug Development.Molecules (Basel, Switzerland) · 2021Article
- Inhibitory Activity of Quercetin 3-Molecules (Basel, Switzerland) · 2020Article
- Inhibitory Activity of Flavonoids, Chrysoeriol and Luteolin-7-Biomolecules · 2020Article
- Dual Farnesoid X Receptor/Soluble Epoxide Hydrolase Modulators Derived from Zafirlukast.ChemMedChem · 2020Article
- Selection of Potent Inhibitors of Soluble Epoxide Hydrolase for Usage in Veterinary Medicine.Frontiers in veterinary science · 2020Article
- Article
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Authors and funding
10 authors at 3 institutions in 1 country.
Funding
Abstract
We have previously identified and reported several potent piperidine-derived amide inhibitors of the human soluble epoxide hydrolase (sEH) enzyme. The inhibition of this enzyme leads to elevated levels of epoxyeicosatrienoic acids (EETs), which are known to possess anti-inflammatory, vasodilatory, and anti-fibrotic effects. Herein, we report the synthesis of 9 analogs of the lead sEH inhibitor and the follow-up structure-activity relationship and liver microsome stability studies. Our findings show that isosteric modifications that lead to significant alterations in the steric and electronic properties at a specific position in the molecule can reduce the efficacy by up to 75-fold. On the other hand, substituting hydrogen with deuterium produces a notable increase (∼30%) in the molecules' half-lives in both rat and human microsomes, while maintaining sEH inhibition potency. These data highlight the utility of isosteric replacement for improving bioavailability, and the newly-synthesized inhibitor structures may thus, serve as a starting point for preclinical development. Our docking study reveals that in the catalytic pocket of sEH, these analogs are in proximity of the key amino acids involved in hydrolysis of EETs.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.