Induction of hepatic microsomal P450 by 4-phenylalkylpyridines in rat: chain length-dependent and sex-related differential induction of P450s

References

• Bellward G. D., Chang T., Rodriques B., McNeidl J., Maines S., Ryan D. E., Levin W., Thomas P. E. Hepatic cytochrome P-450j induction in the spontaneously diabetic BB rat. Molecular Pharmacology 1988; 33: 140–143
   PubMed Web of Science ®Google Scholar
• Bergstron F. W., Norton T. R., Seibert R. A. The alkylation of pyridines and quinolines methylated in the 2- and 4-positions. Journal of Organic Chemistry 1945; 10: 452–457
   Google Scholar
• Casazza J. P., Yun Y. P., Vefch R. L., Song B. J. Serum acetone and P450 2E levels in pregnant rats. FASEB Journal 1990; A2244(a 3178), Vol. 4
   Google Scholar
• Cason J. β-methylglutaric anhydride. Organic Syntheses 1963; 4: 630–633
   Google Scholar
• Degawa M., Hishimura T., Yoshida H., Hashimoto Y. Species, sex and organ differences in induction of a cytochrome P-450 isozyme responsible for carcinogen activation: effects of dietary heptocarcinogenic tryptophan pyrolysate components in mice and rats. Carcinogenesis 1987; 8: 1913–1918
   PubMed Web of Science ®Google Scholar
• Dong Z., Hong J., Ma Q., Li D., Bullock J., Gonzales F. S., Park S. S., Gelboin H. V., Yang C. S. Mechanism of induction of cytochrome P-450ac (P-450j) in chemically induced and spontaneous diabetic rats. Archive of Biochemistry and Biophysics 1988; 263: 29–35
   PubMed Web of Science ®Google Scholar
• Elshourbagy N. A., Guzelian P. S. Separation, purification and characterization of a novel form of hepatic cytochrome P-450 from rats treated with pregnenolone-16α-carbonitrile. Journal of Biological Chemistry 1980; 255: 1279–1285
   PubMed Web of Science ®Google Scholar
• Franklin M. R. Drug metabolizing enzyme induction by simple diaryl pyridines; 2-substituted isomers selectively increase only conjugation enzyme activities, 4-substituted isomers also induce cytochrome P450. Toxicology and Applied Pharmacology 1991; 111: 24–32
   PubMedGoogle Scholar
• Franklin M. R. Whether cytochrome P450 induction accompanies glucuronosyl and glutathione transferase induction by isomers of dipyridyl appears unrelated to dose and iron chelation properties. Journal of Biochemical Toxicology 1992; 7: 81–85
   PubMedGoogle Scholar
• Hostetler K. A., Wrighton S. A., Molowa D. T., Thomas P. E., Levin W., Guzelian P. S. Coinduction of multiple hepatic cytochrome P-450 proteins and their mRNA in rats treated with imidazole antimycotic agents. Molecular Pharmacology 1989; 35: 279–285
   PubMed Web of Science ®Google Scholar
• James M. O. Acute and subacute effects of miconazole nitrate on hepatic styrene oxide hydrolase and cytochrome P-450-dependent monooxygenase activitities in male and female AKR/J mice. Toxicology 1988; 50: 269–281
   PubMed Web of Science ®Google Scholar
• Kahl R., Friederici D. E., Kahl G. F., Ritter W., Krebs R. Clotrimazole as an inhibitor of benzo[a]pyrene metabolite-DNA adduct formation in vitro and of microsomal mono-oxytenase activity. Drug Metabolism and Disposition 1980; 8: 191–196
   PubMed Web of Science ®Google Scholar
• Kamm O., Marvel C. S. Alkyl and alkylene bromides. I. Hydrobromic acid method. Organic Syntheses 1954; 1: 25–28
   Google Scholar
• Kobayashi Y., Matsuura Y., Koatni E., Iio T., Fukuda T., Tobinaga S., Yoshida T., Kuroiwa Y. Induction of hepatic microsomal cytochrome P450 and drug-metabolizing enzymes of 4-benzylpyridine and its structurally related compounds in rats; dose- and sex-related differential induction of cytochrome P450 species. Biochemical Pharmacology 1992; 43: 2151–2159
   PubMedGoogle Scholar
• Kobayashi Y., Matsuura Y., Kotani E., Fukuda T., Aoyagi T., Tobinaga S., Yoshida T., Kuroiwa Y. Structural requirements for the induction of hepatic microsomal cytochrome P450 by imidazole- and pyridine-containing compounds in rats. Journal of Biochemistry (Tokyo) 1993; 114: 697–701
   PubMedGoogle Scholar
• Laemmli U. K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970; 227: 680–685
   PubMed Web of Science ®Google Scholar
• Lavrijsen K., Houdt J. V., Thijs D., Meuldermans W., Heykants J. Induction potential of antifungals containing an imidazole and triazole moiety. Biochemical Pharmacology 1986; 35: 1867–1878
   PubMed Web of Science ®Google Scholar
• Magdalou J., Totis M., Boiteux-Antoin A. F., Fournel-Gigleux S., Siest G., Schladt L., Oesch F. Effect of 1-benzylimidazole on cytochrome P-450 induction and on the activities of epoxide hydrolases and UDP-glucuronosyltransferase in rat liver. Biochemical Pharmacology 1988; 37: 3297–3304
   PubMed Web of Science ®Google Scholar
• Matsuura Y., Kotani E., Iio T., Fukuda T., Tobinaga S., Yoshida T., Kuroiwa Y. Structure-activity relationships in the induction of hepatic microsomal cytochrome P450 by clorimazole and its structurally related compounds in rats. Biochemcal Pharmacology 1991; 41: 1949–1956
   Google Scholar
• Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. Journal of Biological Chemistry 1964; 239: 2370–2378
   PubMed Web of Science ®Google Scholar
• Ritter J. K., Franklin M. R. High magnitude hepatic cytochrome P-450 induction by an N-substituted imidazole antimycotic, clotrimazole. Biomechanical Pharmacology 1987a; 36: 2783–2787
   Google Scholar
• Ritter J. K., Franklin M. R. Induction and inhibition of rat hepatic drug metabolism by N-substituted imidazole drugs. Drug Metabolism and Disposition 1987b; 15: 335–343
   PubMed Web of Science ®Google Scholar
• Sheete J. J., Masno J. I., Wise C. A., Estabrook R. W. Inhibition of rat liver microsomal cytochrome P-450 steroid hydroxylase reactions by imidazole antimycotic agents. Biochemical Pharmacology 1986; 35: 487–491
   Google Scholar
• Somerville L. F., Allen C. F. H. β-Benzoylpropionic acid. Organic Syntheses 1943; 2: 81–83
   Google Scholar
• Wibaut J. P., Hey J. W. Syntheses with the aid of (4-pyridylmethyl)lithium. I. Preparation of 4-alkylpyridines. Recueil des Travaux Chimiques des Pays-Bas 1953; 72: 513–521
   Google Scholar
• Wilkinson C. F., Hetnarski K. Structure-activity relationships in the effects of 1-alkylimidazoles on microsomal oxidation in vitro and in vivo. Biochemical Pharmacology 1974; 23: 2377–2386
   PubMed Web of Science ®Google Scholar
• Yang C. S., Yoo J.-S. H., Ishizaki H., Hong J. Cytochrome P-450 IIE1: roles in nitrosamine metabolism and mechanism of regulation. Drug Metabolism Review 1990; 22: 147–159
   PubMed Web of Science ®Google Scholar