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Inhibition of human glutathione S-transferase P1-1 by the flavonoid quercetin.

Abstract：

:In the present study, the inhibition of human glutathione S-transferase P1-1 (GSTP1-1) by the flavonoid quercetin has been investigated. The results show a time- and concentration-dependent inhibition of GSTP1-1 by quercetin. GSTP1-1 activity is completely inhibited upon 1 h incubation with 100 microM quercetin or 2 h incubation with 25 microM quercetin, whereas 1 and 10 microM quercetin inhibit GSTP1-1 activity to a significant extent reaching a maximum of 25 and 42% inhibition respectively after 2 h. Co-incubation with tyrosinase greatly enhances the rate of inactivation, whereas co-incubation with ascorbic acid or glutathione prevents this inhibition. Addition of glutathione upon complete inactivation of GSTP1-1 partially restores the activity. Inhibition studies with the GSTP1-1 mutants C47S, C101S and the double mutant C47S/C101S showed that cysteine 47 is the key residue in the interaction between quercetin and GSTP1-1. HPLC and LC-MS analysis of trypsin digested GSTP1-1 inhibited by quercetin did not show formation of a covalent bond between Cys 47 residue of the peptide fragment 45-54 and quercetin. It was demonstrated that the inability to detect the covalent quercetin-peptide adduct using LC-MS is due to the reversible nature of the adduct-formation in combination with rapid and preferential dimerization of the peptide fragment once liberated from the protein. Nevertheless, the results of the present study indicate that quinone-type oxidation products of quercetin likely act as specific active site inhibitors of GSTP1-1 by binding to cysteine 47.

journal_name

Chem Biol Interact

journal_title

Chemico-biological interactions

authors

van Zanden JJ,Ben Hamman O,van Iersel ML,Boeren S,Cnubben NH,Lo Bello M,Vervoort J,van Bladeren PJ,Rietjens IM

doi

10.1016/s0009-2797(02)00250-8

subject

Has Abstract

pub_date

2003-05-06 00:00:00

pages

139-48

issue

2

eissn

0009-2797

issn

1872-7786

pii

S0009279702002508

journal_volume

145

pub_type

杂志文章

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