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Research Article

Recalling P446. P4501A1 (CYP1A1) Opting for Clinical Application

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Pages 323-341 | Published online: 09 Oct 2008

REFERENCES

  • Alvares A. P., Schilling G., Levin W., Kuntzman R. Studies on the induction of CO-binding pigments in liver microsomes by phenobarbital and 3-methylcholanthrene. Biochem. Biophys. Res. Commun. 1967; 29: 521–526
  • Bale A. E., Nebert D. W., McBride O. W. Subchromosomal localization of the dioxin-inducible P1-450 locus (CYP1) and description of two RFLPs detected with a 3'P1-450 cDNA probe. Cytogenet. Cell Genet. 1987; 46: 574–575
  • Burke M. D., Prough R. A., Richard T. Characteristics of a microsomal cytochrome P448 mediated reaction. Drug Metabol. Dispos. 1977; 5: 1–8
  • Cammer W., Schenkman J. B., Estabrook R. W. EPR measurements of substrate interaction of cytochrome P-450. Biochem. Biophys. Res. Commun. 1966; 23: 264–268
  • Cascorbi I., Brockmöller J., Roots I. A C4887A polymorphism in exon 7 of human CYP1A1: population frequency, mutation linkages, and impact on lung cancer susceptibility. Cancer Res. 1996; 56: 4965–4969
  • Chernogolov A., Behlke J., Schunck W.-H., Roots I., Schwarz D. Human CYP1A1 allelic variants: baculovirus expression and purification, hydrodynamic, spectral, and catalytical properties and their potency in the formation of all-trans-retinoic acid. Protein Expr. Purif. 2003; 28: 259–269
  • Conney A. H. Induction of drug metabolizing enzymes: A path to the discovery of multiple cytochromes P450. Annu. Rev. Pharmacol. Toxicol. 2003; 43: 1–30
  • Conney A. H., Lu Y., Lou Y., Xie J., Huang M. Inhibitory effect of green and black tea on tumor growth. Proc. Soc. Exp. Biol. Med. 1999; 220: 229–233
  • Crofts F., Taioli E., Trachman J., Cosma G. N., Curie D., Toniolo P., Garte S. J. Functional significance of different human CYP1A1 genotypes. Carcinogenesis 1994; 15: 2961–2963
  • Drakoulis N., Cascorbi I., Brockmöller J., Gross C. R., Roots I. Polymorphisms in the human CYP1A1 gene as susceptibility factors for lung cancer: exon-7 mutation (4889 A to G), and a T to C mutation in the 3′-flanking region. Clin. Investig. 1994; 72: 240–248
  • Estabrook R. W. Discovering the functions of cytochrome P450 in drug metabolism: The role of Alfred Hildebrandt. Drug Metab. Rev. 1999; 31: 317–331
  • Estabrook R. W. A passion for P450s (Remembrances of the early history of research on cytochrome P450). Drug Metab. Disposit. 2003; 31: 1461–1473
  • Estabrook R. W., Cooper D.Y., Rosenthal O. The light-reversible carbon monoxide inhibition of the steroid C-21 hydroxylation system of the adrenal cortex. Biochem. Z. 1963; 338: 741–755
  • Estabrook R. W., Peterson J. A., Baron J., Hildebrandt A. G. The spectrophotometric measurement of turbid suspensions of cytochromes associated with drug metabolism. Methods in Pharmacology, C. F. Chignell. Appleton-Century-Crofts, New York 1972; 2: 303–350
  • Guengerich F. P. Cytochrome P450: What have we learned and what are the future issues?. Drug Metab. Rev. 2004; 36: 159–197
  • Guengerich F. P. Separation and purification of multiple forms of microsomal cytochrome P-450. Activities of different forms of cytochrome P-450 towards several compounds of environmental interest. J. Biol. Chem. 1977; 252: 3970–3979
  • Hashimoto Y., Yamano T., Mason H. S. An electron spin resonance study of microsomal electron transport. J. Biol. Chem. 1962; 237: 3843–3844
  • Haugen D. A., Coon M. J. Properties of electrophoretically homogeneous phenobarbital-inducible and β-naphthoflavone-inducible forms of liver microsomal cytochrome P-450. J. Biol. Chem. 1976; 251: 7929–7939
  • Hayashi S., Watanabe J., Nakachi K., Kawajiri K. Genetic linkage of lung cancer-associated MspI polymorphisms with amino acid replacement in the heme binding region of the human cytochrome P450IA1 gene. J. Biochem. 1991; 110: 407–411, (Tokyo).
  • Hildebrandt A. Die beschleunigte Elimination von Sulfadimethoxin bei Hunden durch Phenobarbital. MD Thesis. Medical Faculty. University Tübingen, Germany 1965
  • Hildebrandt A. G., Estabrook R. W. Spectrophotometric studies of cytochrome P-450 of liver microsomes after induction with phenobarbital and 3-methylcholanthrene. Microsomes and Drug Oxidations, J. R. Gillette, A. H. Conney, G. J. Cosmides, R. W. Estabrook, J. R. Fouts, G. J. Mannering. Academic Press Inc, New York 1969; 331–347, (1969)
  • Hildebrandt A., Remmer H., Estabrook R. W. Cytochrome P-450 in liver microsomes—one pigment or many. Biochem. Biophys. Res. Commun. 1968; 30: 607–612
  • Huang M. T., Wood A. W., Chang R. L., Yagi H., Sayer J. M., Jerina D. M., Conney A. H. Inhibitory effect of 3-hydroxybenzo(a)pyrene on the mutagenicity and tumorigenicity of (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7,8,9,10 tetrahydrobenzo(a)pyrene. Cancer Res. 1986; 46: 558–566
  • Huang C. S., Shen C. Y., Chang K. J., Hsu S. M., Chern H. D. Cytochrome P4501A1 polymorphism as a susceptibility factor for breast cancer in postmenopausal Chinese women in Taiwan. Br. J. Cancer 1999; 80: 1838–1843
  • Ishibe N., Hankinson S. E., Colditz G. A., Spiegelman D., Willett W. C., Speizer F. E., Kelsey K. T., Hunter D. J. Cigarette smoking, cytochrome P450 1A1 polymorphisms, and breast cancer risk in the Nurses' Health Study. Cancer Res. 1998; 58: 667–671
  • Jefcoate C. R. E., Gaylor J. L., Calabrese R. L. Ligand interactions with cytochrome P-450. I. Binding of primary amines. Biochemistry 1969; 8: 3455–3463
  • Jefcoate C. R. E., Gaylor J. L. Ligand interaction with hemoprotein P-450. II. Influence of phenobarbital and methylcholanthrene induction processes on P-450 spectra. Biochemistry 1969; 8: 3464–3471
  • Kawajiri K., Nakachi K., Imai K., Watanabe J., Hayashi S. The CYP1A1 gene and cancer susceptibility. Crit. Rev. Oncol. Hematol. 1993; 14: 77–87
  • Kawalek J. C., Levin W., Ryan D., Thomas P. E., Lu A. Y. H. Purification of liver microsomal cytochrome P-448 from 3-methylcholanthrene-treated rabbits. Mol. Pharmacol. 1975; 11: 874–878
  • Kinoshita T., Horie S. Studies on P-450. 3. On the absorption spectrum of P-450 in rabbit liver microsomes. J. Biochem. (Tokyo) 1967; 61: 26–34
  • Kisselev P., Schunck W. H., Roots I., Schwarz D. Association of CYP1A1 polymorphisms with differential metabolic activation of 17beta-estradiol and estrone. Cancer Res. 2005; 65: 2972–2978
  • Kisselev P., Schwarz D., Platt K. L., Schunck W. H., Roots I. Epoxidation of benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1 in reconstituted membranes. Effects of charge and nonbilayer phase propensity of the membrane. Eur. J. Biochem. 2002; 269: 1799–1805
  • Koop D. R., Morgan E. T., Tarr G. E., Coon M. J. Purification and characterization of a unique isozyme of P-450 from liver microsomes of ethanol-treated rabbits. J. Biol. Chem. 1982; 257: 8472–8480
  • Krusekopf S., Roots I. St. John's wort and its constituent hyperforin concordantly regulate expression of genes encoding enzymes involved in basic cellular pathways. Pharmacogenet. Genomics 2005; 15: 817–829
  • Krusekopf S., Roots I., Hildebrandt A. G., Kleeberg U. Time-dependent transcriptional induction of CYP1A1, CYP1A2, and CYP1B1 mRNAs by H+/K+-ATPase inhibitors and other xenobiotics. Xenobiotica 2003; 33: 107–118
  • Le Marchand L., Murphy S. P., Hankin J. H., Wilkens L. R., Kolonel L. N. Intake of flavonoids and lung cancer. J. Natl. Cancer Inst. 2000; 92: 154–160
  • Lu A. Y., Kuntzman R., West S., Jacobson M., Conney A. H. Reconstituted liver microsomal enzyme system that hydroxylates drugs, other foreign compounds, and endogenous substrates. II. Role of the cytochrome P-450 and P-448 fractions in drug and steroid hydroxylation. J. Biol. Chem. 1972; 247: 1727–1734
  • Mitrunen K., Hirvonen A. Molecular epidemiology of sporadic breast cancer. The role of polymorphic genes involved in oestrogen biosynthesis and metabolism. Mutat. Res. 2003; 544: 9–41
  • Miyake Y., Gaylor J. L., Mason H. S. Properties of a submicrosomal particle containing P‐450 and flavoprotein. J. Biol. Chem. 1968; 243: 5788–5797
  • Miyoshi Y., Noguchi S. Polymorphisms of estrogen synthesizing and metabolizing genes and breast cancer risk in Japanese women. Biomed. Pharmacother. 2003; 57: 471–481
  • Miyoshi Y., Takahashi Y., Egawa C., Noguchi S. Breast cancer risk associated with CYP1A1 genetic polymorphisms in Japanese women. Breast J. 2002; 8: 209–215
  • Nachmansohn D. Otto Heinrich Warburg. German-Jewish Pioneers in Science 1900–1933, David Nachmansohn. Springer-Verlag Berlin Heidelberg, New York 1979; 233–267
  • Nebert D. W., Gelboin H. V. Substrate-inducible microsomal aryl hydroxylase in mammalian cell culture. II. Cellular responses during enzyme induction. J. Biol. Chem. 1968; 243: 6250–6261
  • Nebert D. W. Microsomal cytochromes b5and P450during induction of aryl hydrocarbon hydroxylase activity in mammalian cell culture. J. Biol. Chem. 1970; 245: 515–527
  • Nebert D. W., Kon H. Genetic regulation of aryl hydrocarbon hydroxylase induction V. Specific changes in spin state of cytochrome P450from genetically responsive animals. J. Biol. Chem. 1973; 248: 169–178
  • Nelson D. R., Koymans L., Kamataki T., Stegman J. J., Feyereisen F., Waxman D. J., Waterman M. R., Gotoh O., Coon M. J., Estabrook R. W., Gunsalus I. C., Nebert D. W. P450 superfamily; update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 1996; 6: 1–41
  • Omura T., Sato R. The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 1964; 239: 2370–2378
  • Peisach J., Blumberg W.E. Electron paramagnetic resonance study of the high- and low-spin forms of cytochrome P-450 in liver and in liver microsomes from a methylcholanthrene-treated rabbit. Proc. Nat. Acad. Sci. 1970; 67: 172–179
  • Pickett C. B., Remus L., Jeter J., Morin J., Lu A. Y. H. Electroimmunochemical quantification of cytochrome P-450, cytochrome P-448, and epoxide hydrolase in rat liver microsomes. J. Biol. Chem. 1981; 256: 8815–8820
  • Prough R. A. Introduction: Basal and inducible expression of cytochromes P450 and related enzymes. The FASEB Journal 1999; 10: 807–808
  • Reichert R., Remmer H. Die Induktion mikrosomaler Cytochrome durch Pharmaka. Naunyn-Schmiedebergs Arch. Exp. Pharmakol. 1964; 247: 374, (Abstract).
  • Remmer H. Der beschleunigte Abbau von Pharmaka unter dem Einfluss von Luminal. Naunyn-Schmiedebergs Arch. Exp. Pharmakol. 1959; 235: 279–290
  • Remmer H., Alsleben B. Die Aktivierung der Entgiftung in den Lebermikrosomen während der Gewöhnung. Klin. Wochenschr. 1958; 36: 332–333
  • Remmer H., Schenkman J., Estabrook R. W., Sasame H., Gillette J., Narasimhulu S., Cooper D. Y., Rosenthal O. Drug interaction with hepatic cytochrome. Mol. Pharmacol. 1965; 2: 187–190
  • Saito T., Strobel H. W. Purification to homogeneity and characterization of a form of cytochrome P-450 with high specificity for benzo[α]pyrene from β-naphtoflavone-pretreated rat liver microsomes. J. Biol. Chem. 1981; 256: 984–988
  • Sandhu P., Guo Z., Baba T., Martin M. V., Tukey R. H., Guengerich F. P. Expression of modified human cytochrome P450 1A2 in Escherichia coli: stabilization, purification, spectral characterization, and catalytic activities of the enzyme. Arch. Biochem. Biophys. 1994; 309: 168–177
  • Schenkman J. B., Remmer H., Estabrook R. W. Spectral studies of drug interaction with hepatic microsomal cytochrome. Mol. Pharmacol. 1967; 3: 113–123
  • Schwarz D., Kisselev P., Cascorbi I., Schunck W. H., Roots I. Differential metabolism of benzo[a]pyrene and benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1 variants. Carcinogenesis 2001; 22: 453–459
  • Schwarz D., Kisselev P., Chernogolov A., Schunck W. H., Roots I. Human CYP1A1 variants lead to differential eicosapentaenoic acid metabolite patterns. Biochem. Bioph. Res. Co. 2005b; 336: 779–783
  • Schwarz D., Kisselev P., Ericksen S. S., Szklarz G. D., Chernogolov A., Honeck H., Schunck W. H., Roots I. Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: highly stereoselective formation of 17(R),18(S)-epoxyeicosatetraenoic acid. Biochem Pharmacol. 2004; 15: 1445–1457
  • Schwarz D., Kisselev P., Honeck H., Cascorbi I., Schunck W. H., Roots I. Co-expression of human cytochrome P4501A1 (CYP1A1) variants and human NADPH-cytochrome P450 reductase in the baculovirus/insect cell system. Xenobiotica 2001b; 31: 345–356
  • Schwarz D., Kisselev P., Roots I. St. John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1. Cancer Res. 2003; 63: 8062–8068
  • Schwarz D., Kisselev P., Roots I. CYP1A1 genotype-selective inhibition of benzo[a]pyrene activation by quercetin. Eur. J. Cancer 2005; 41: 151–158
  • Schwarz D., Kisselev P., Schunck W.-H., Chernogolov A., Boidol W., Cascorbi I., Roots I. Allelic variants of human cytochrome P4501A1 (CYP1A1): effect of T4621N and 1462V substitutions on steroid hydroxylases specificity. Pharmacogenetics 2000; 10: 519–530
  • Schwarz D., Roots I. In vitroassessment of inhibition by natural polyphenols of metabolic activation of procarcinogens by human CYP1A1. Biochem. Biophys. Res. Commun. 2003; 303: 902–907
  • Sladek N. E., Mannering G. J. Evidence for a new P-450 hemoprotein in hepatic microsomes from methylcholanthrene treated rats. Biochem. Biophys. Res. Commun. 1966; 8: 668–674
  • Spurr N. K., Gough A. C., Stevenson K., Wolf C. R. Msp-1 polymorphism detected with a cDNA probe for the P-450 I family on chromosome 15. Nucleic Acids Res. 1987; 15: 5901
  • Szklarz G. D., Paulsen M. D. Molecular modeling of cytochrome P450 1A1: enzyme-substrate interactions and substrate binding affinities. J. Biomol. Struct. Dyn. 2002; 20: 155–162
  • Tsai R., Yu C. A., Gunsalus I. C., Peisach J., Blumberg W., Orme-Johnson W. H., Beinert H. Spin-state changes in cytochrome P-450cam on binding of specific substrates. Proc. Nat. Acad. Sci. 1970; 66: 1157–1163
  • Wester M. R., Johnson E. F., Marques-Soares C., Dansette P. M., Mansuy D., Stout C. D. Structure of a substrate complex of mammalian cytochrome P450 2C5 at 2.3 A resolution: evidence for multiple substrate binding modes. Biochemistry 2003; 42: 6370–6379
  • Williams P. A., Cosme J., Sridhar V., Johnson E. F., McRee D. E. Mammalian microsomal cytochrome P450 monooxygenase: structural adaptations for membrane binding and functional diversity. Mol. Cell 2000; 5: 121–131
  • Yang K., Lamprecht S. A., Liu Y., Shinozaki H., Fan K., Leung D., Newmark H., Steele V. E., Kelloff G. J., Lipkin M. Chemoprevention studies of the flavonoids quercetin and rutin in normal and azoxymethane-treated mouse colon. Carcinogenesis 2000; 21: 1655–1660

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