Inhibition of epoxide hydrolases and glutathione S-transferases by 2-, 3-, and 4-substituted derivatives of 4′-phenylchalcone and its oxide

Toru Miyamoto, Marilyn Silva, Bruce D. Hammock

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

4′-Phenylchalcones, chalcone oxides, and related compounds were synthesized and tested as inhibitors of cytosolic epoxide hydrolase, microsomal epoxide hydrolase, and glutathione S-transferases from mouse and rat liver. Several compounds were more potent inhibitors of the cytosolic epoxide hydrolase than the parent 4′-phenylchalcone oxide while large substituents in the 4- and especially the 2-position caused a reduction in inhibition. The chalcone oxides showed selectivity as inhibitors of the cytosolic epoxide hydrolase acting on trans-stilbene oxide, while chalcones were inhibitors of cytosolic glutathione S-transferase acting on cis-stilbene oxide. Data are consistent with the hypothesis that much of the inhibition of the glutathione S-transferase is caused by the glutathione conjugate of the chalcone.

Original languageEnglish (US)
Pages (from-to)203-213
Number of pages11
JournalArchives of Biochemistry and Biophysics
Volume254
Issue number1
DOIs
StatePublished - 1987

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Epoxide Hydrolases
Carboxylesterase
Glutathione Transferase
Derivatives
Chalcones
Chalcone
Hydrolases
Liver
Glutathione
Rats
4-phenylchalcone oxide
chalcone epoxide
stilbene oxide

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

Inhibition of epoxide hydrolases and glutathione S-transferases by 2-, 3-, and 4-substituted derivatives of 4′-phenylchalcone and its oxide. / Miyamoto, Toru; Silva, Marilyn; Hammock, Bruce D.

In: Archives of Biochemistry and Biophysics, Vol. 254, No. 1, 1987, p. 203-213.

Research output: Contribution to journalArticle

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