PMID: 9545601Apr 18, 1998Paper

2-Methoxy-4-nitroaniline and its isomers induce cytochrome P4501A (CYP1A) enzymes with different selectivities in the rat liver

Biochimica Et Biophysica Acta
Masakuni DegawaY Yamazoe

Abstract

We reported previously that 2-methoxy-4-nitroaniline (2-MeO-4-NA) is a selective inducer of cytochrome P4501A2 (CYP1A2) in the rat liver, and its molecular size is the smallest among known CYP1A2-selective inducers. In the present study, a structure-activity relationship on the CYP1A2-selective induction has been investigated using isomeric nitroanisidines and their related chemicals. Western blot analyses revealed that the chemicals removed a substituent (amino, methoxyl or nitro group) from a 2-MeO-4-NA molecule had no capacity for inducing CYP1A enzymes in rat livers. On the other hand, isomeric nitroanisidines such as 2-MeO-4-NA, 2-MeO-5-NA and 4-MeO-2-NA induced both CYP1A2 and CYP1A1 enzymes with different selectivities. As judged from the induced levels of CYP1A proteins, 2-MeO-4-NA (CYP1A2/CYP1A1 ratio; 9.5) and 4-MeO-2-NA (0.3) were the most selective inducers of CYP1A2 and CYP1A1, respectively, among the isomeric nitroanisidines (0.44 mmol/kg) used. The induced level of CYP1A2 protein was in the order 2-MeO-4-NA > 2-MeO-5-NA > 4-MeO-2-NA, although no significant difference was observed on their CYP1A2 mRNA level. On the contrary, increases in the levels of CYP1A1 mRNA and protein were in the order 4-MeO-2-NA > 2-MeO-5...Continue Reading

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Citations

Dec 18, 2004·Environmental Science and Pollution Research International·Lillemor K GustavssonMagnus Engwall
Feb 19, 2013·Biochemical Pharmacology·Christoffer BundgaardJohn P Redrobe
Apr 14, 2006·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Kevin J CoeJ Greg Slatter
Jul 28, 2007·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Dagmar AimováMarie Stiborová

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