Synthesis of 5-substituted isophthalic acids and competitive inhibition studies with bovine liver glutamate dehydrogenase.
Isophthalic acid, 5-carboxy-, 5-hydroxy-, 5-methoxy-, 5-fluoro-, 5-bromo-, 5-cyano-, and 5-methylisophthalic acid were inhibitors competitive with L-glutamate for bovine liver glutamate dehydrogenase. The extent of inhibition by the derived compounds was not much greater than that obtained with the parent compound, isophthalic acid. A plot of pKi versus pH showed the presence of an ionizable group (pKa 7.4-7.8) at the enzyme active site which interacted with the substitutent at the 5 position of the substituted isophthalates.
D000818:Animals; D001667:Binding, Competitive; D002417:Cattle; D005969:Glutamate Dehydrogenase / Q000037:antagonists & inhibitors*; D006863:Hydrogen-Ion Concentration; D008099:Liver / Q000201:enzymology*; D010795:Phthalic Acids / Q000138:chemical synthesis / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D010795:Phthalic Acids; D005969:Glutamate Dehydrogenase