Inhibition of epoxide hydrolase from human, monkey, bovine, rabbit and murine liver by trans-3-phenylglycidols

Eric C. Dietze, Josefina Casas, Eiichi Kuwano, Bruce D. Hammock

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

1. 1. trans-3-Phenylglycidols were potent inhibitors of cytosolic epoxide hydrolases in all species tested. 2. 2. The order of inhibitor potency varied from species to species but trans-3-(4-nitrophenyl)glycidols were always the most potent inhibitors tested for cytosolic epoxide hydrolase. 3. 3. The S,S-enantiomer was a more potent cytosolic epoxide hydrolase inhibitor than the R,R-enantiomer when a free hydroxyl group was present. However, (2R,3R)-1-benzoyloxy-2,3-epoxy-3-(4-nitrophenyl)propane was always a better inhibitor than the (2S,3S)-enantiomer. 4. 4. All microsomal epoxide hydrolases were poorly inhibited by the trans-3-phenylglycidols, and related compounds, tested. The best new microsomal epoxide hydrolase inhibitor tested was (1S,2S)-1-phenyl-propylene oxide which gave 18-63% inhibition, at 2 mM, depending on the species tested.

Original languageEnglish (US)
Pages (from-to)309-314
Number of pages6
JournalComparative Biochemistry and Physiology -- Part B: Biochemistry and
Volume104
Issue number2
DOIs
StatePublished - 1993

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Epoxide Hydrolases
Liver
Haplorhini
Enantiomers
Rabbits
glycidol
Propane
Hydroxyl Radical
phenylglycidol

ASJC Scopus subject areas

  • Biochemistry
  • Physiology

Cite this

Inhibition of epoxide hydrolase from human, monkey, bovine, rabbit and murine liver by trans-3-phenylglycidols. / Dietze, Eric C.; Casas, Josefina; Kuwano, Eiichi; Hammock, Bruce D.

In: Comparative Biochemistry and Physiology -- Part B: Biochemistry and, Vol. 104, No. 2, 1993, p. 309-314.

Research output: Contribution to journalArticle

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AU - Hammock, Bruce D.

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AB - 1. 1. trans-3-Phenylglycidols were potent inhibitors of cytosolic epoxide hydrolases in all species tested. 2. 2. The order of inhibitor potency varied from species to species but trans-3-(4-nitrophenyl)glycidols were always the most potent inhibitors tested for cytosolic epoxide hydrolase. 3. 3. The S,S-enantiomer was a more potent cytosolic epoxide hydrolase inhibitor than the R,R-enantiomer when a free hydroxyl group was present. However, (2R,3R)-1-benzoyloxy-2,3-epoxy-3-(4-nitrophenyl)propane was always a better inhibitor than the (2S,3S)-enantiomer. 4. 4. All microsomal epoxide hydrolases were poorly inhibited by the trans-3-phenylglycidols, and related compounds, tested. The best new microsomal epoxide hydrolase inhibitor tested was (1S,2S)-1-phenyl-propylene oxide which gave 18-63% inhibition, at 2 mM, depending on the species tested.

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