Analogues of GSH in which either the gamma-glutamyl or the glycyl moiety is modified were synthesized and tested as both substrates for and inhibitors of glutathione S-transferases (GSTs) 7-7 and 8-8. Acceptor substrates for GST 7-7 were 1-chloro-2,4-dinitrobenzene (CDNB) and ethacrynic acid (ETA) and for GST 8-8 CDNB, ETA and 4-hydroxynon-trans-2-enal (HNE). The relative ability of each combination of enzyme and GSH analogue to catalyse the conjugation of all acceptor substrates was similar with the exception of the combination of GST 7-7 and gamma-L-Glu-L-Cys-L-Asp, which used CDNB but not ETA as acceptor substrate. In general, GST 7-7 was better than GST 8-8 in utilizing these analogues as substrates, and glycyl analogues were better than gamma-glutamyl analogues as both substrates and inhibitors. These results are compared with those obtained earlier with GSH analogues and GST isoenzymes 1-1, 2-2, 3-3 and 4-4 [Adang, Brussee, Meyer, Coles, Ketterer, van der Gen & Mulder (1988) Biochem. J. 255, 721-724] and the implications with respect to the nature of their active sites are discussed.
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Research Article|
December 15 1989
Interaction of rat glutathione S-transferases 7-7 and 8-8 with γ-glutamyl- or glycyl-modified glutathione analogues
A E P Adang;
A E P Adang
*Department of Organic Chemistry, University of Leiden, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
†Division of Toxicology, Center for Bio-Pharmaceutical Sciences, University of Leiden, 2300 RA Leiden, The Netherlands
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D J Meyer;
D J Meyer
‡Cancer Research Campaign Molecular Toxicology Research Group, University College and Middlesex School of Medicine, London WIP 6DB, U.K.
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J Brussee;
J Brussee
*Department of Organic Chemistry, University of Leiden, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
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A Van der Gen;
A Van der Gen
*Department of Organic Chemistry, University of Leiden, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
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B Ketterer;
B Ketterer
‡Cancer Research Campaign Molecular Toxicology Research Group, University College and Middlesex School of Medicine, London WIP 6DB, U.K.
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G J Mulder
G J Mulder
†Division of Toxicology, Center for Bio-Pharmaceutical Sciences, University of Leiden, 2300 RA Leiden, The Netherlands
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Publisher: Portland Press Ltd
Online ISSN: 1470-8728
Print ISSN: 0264-6021
© 1989 London: The Biochemical Society
1989
Biochem J (1989) 264 (3): 759–764.
Citation
A E P Adang, D J Meyer, J Brussee, A Van der Gen, B Ketterer, G J Mulder; Interaction of rat glutathione S-transferases 7-7 and 8-8 with γ-glutamyl- or glycyl-modified glutathione analogues. Biochem J 15 December 1989; 264 (3): 759–764. doi: https://doi.org/10.1042/bj2640759
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