title: Stereoselective product inhibition of glutathione S-transferase.
abstract: Isozymes 3-3 and 4-4 of rat liver glutathione S-transferase are stereoselectively inhibited by the diastereomers of 9,10-dihydro-9-glutathionyl-10-hydroxyphenanthrene, 1. The conformation of the biphenyl moiety is the same in the enzyme -1 complex as in aqueous solution with the glutathionyl and hydroxy groups in the axial positions. Isozyme 4-4 is also inhibited by the four diastereomers of 1,2-diphenyl-1-(S-glutathionyl)-2-hydroxyethane. The stereoselectivity of inhibition is modest in all cases and is manifest in both the type of inhibition as well as the magnitude of Ki.
mesh_terms: D000818:Animals; D002942:Circular Dichroism; D005978:Glutathione / Q000031:analogs & derivatives* / Q000494:pharmacology; D005982:Glutathione Transferase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D008099:Liver / Q000201:enzymology*; D008968:Molecular Conformation; D010616:Phenanthrenes / Q000494:pharmacology*; D051381:Rats; D013237:Stereoisomerism
chemical_list: D007527:Isoenzymes; D010616:Phenanthrenes; C051229:1,2-diphenyl-1-(S-glutathionyl)-2-hydroxyethane; C051228:9,10-dihydro-9-glutathionyl-10-hydroxyphenanthrene; D005982:Glutathione Transferase; D005978:Glutathione