Quantitative structure-activity relationships in substrates, inducers, and inhibitors of cytochrome P4501 (CYP1).

[1]  A Poland,et al.  2,3,7,8-tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity. , 1982, Annual review of pharmacology and toxicology.

[2]  A. Y. Lu,et al.  Tumor-initiating ability of the twelve monomethylbenz[a]anthracenes. , 1982, Carcinogenesis.

[3]  C. Ioannides,et al.  Induction of cytochrome P4501 as an indicator of potential chemical carcinogenesis. , 1993, Drug metabolism reviews.

[4]  C. Ioannides,et al.  CYP1 induction, binding to the hepatic aromatic hydrocarbon receptor and mutagenicity of a series of 11-alkoxy cyclopenta[a]phenanthren-17-ones: a structure activity relationship. , 1995, Toxicology.

[5]  D. Lewis,et al.  Molecular dimensions of the substrate binding site of cytochrome P-448. , 1986, Biochemical pharmacology.

[6]  D. Lewis,et al.  Molecular orbital-generated QSARs in a homologous series of alkoxyresorufins and studies of their interactive docking with P450s. , 1995, Xenobiotica; the fate of foreign compounds in biological systems.

[7]  R. Mayer,et al.  Ethoxy-, pentoxy- and benzyloxyphenoxazones and homologues: a series of substrates to distinguish between different induced cytochromes P-450. , 1985, Biochemical pharmacology.

[8]  L. Kaminsky,et al.  Metabolism of dichlorobiphenyls by hepatic microsomal cytochrome P-450. , 1980, Biochemical pharmacology.

[9]  J. Whitlock,et al.  The control of cytochrome P-450 gene expression by dioxin. , 1989, Trends in pharmacological sciences.

[10]  I. Stupans,et al.  In vitro inhibition of 3-methylcholanthrene-induced rat hepatic aryl hydrocarbon hydroxylase by 8-acyl-7-hydroxycoumarins. Structure-activity relationships and metabolite profiles. , 1984, Biochemical pharmacology.

[11]  M. J. Coon,et al.  The P450 superfamily: update on new sequences, gene mapping, accession numbers, early trivial names of enzymes, and nomenclature. , 1993, DNA and cell biology.

[12]  A. Debnath,et al.  Quantitative structure‐activity relationship investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test: 2. Mutagenicity of aromatic and heteroaromatic nitro compounds in Salmonella typhimurium TA100 , 1992, Environmental and molecular mutagenesis.

[13]  O. Hankinson,et al.  Identification of the Ah Receptor Nuclear Translocator Protein (Arnt) as a Component of the DNA Binding Form of the Ah Receptor , 1992, Science.

[14]  S. Kobayashi,et al.  Relationships between biological potency and electronic states of polychlorinated dibenzofurans and polychlorinated biphenyls. , 1992, Chemical & pharmaceutical bulletin.

[15]  C. Ioannides,et al.  Induction of the P-450 I family of proteins by polycyclic aromatic hydrocarbons: possible relationship to their carcinogenicity. , 1990, Toxicology.

[16]  D. Benford,et al.  Drug metabolism from molecules to man , 1987 .

[17]  S. Kafafi,et al.  The electronic and thermodynamic aspects of Ah receptor binding. A new structure-activity model: I. The polychlorinated dibenzo-p-dioxins. , 1992, Carcinogenesis.

[18]  P. Fu Metabolism of nitro-polycyclic aromatic hydrocarbons. , 1990, Drug metabolism reviews.

[19]  D F Lewis,et al.  A retrospective evaluation of COMPACT predictions of the outcome of NTP rodent carcinogenicity testing. , 1995, Environmental health perspectives.

[20]  C. Ioannides,et al.  Metabolic Activation of Carcinogens and Toxic Chemicals , 1988, Human toxicology.

[21]  A. Debnath,et al.  International Commission for Protection Against Environmental Mutagens and Carcinogens. The importance of the hydrophobic interaction in the mutagenicity of organic compounds. , 1994, Mutation research.

[22]  O. Hankinson The aryl hydrocarbon receptor complex. , 1995, Annual review of pharmacology and toxicology.

[23]  D. Lewis,et al.  The genotoxicity of benzanthracenes: a quantitative structure-activity study. , 1995, Mutation research.

[24]  J. Phillips Cytochrome P-450: Biochemistry and biophysics , 1990 .

[25]  C. Ioannides,et al.  Molecular orbital studies of oxygen activation and mechanisms of cytochromes P-450-mediated oxidative metabolism of xenobiotics. , 1989, Chemico-biological interactions.

[26]  C. Ioannides,et al.  Interaction with the aromatic hydrocarbon receptor, CYP1A induction, and mutagenicity of a series of diaminotoluenes: implications for their carcinogenicity. , 1996, Toxicology and applied pharmacology.

[27]  C. Ioannides,et al.  The cytochrome P450 I gene family of microsomal hemoproteins and their role in the metabolic activation of chemicals. , 1990, Drug metabolism reviews.

[28]  A. Okey,et al.  Binding of 3-methylcholanthrene and 2,3,7,8-tetrachlorodibenzo-p-dioxin to a common Ah receptor site in mouse and rat hepatic cytosols. , 1982, European journal of biochemistry.

[29]  Y. Fujii‐Kuriyama,et al.  Regulatory mechanism of gene expression of methylcholanthrene-inducible cytochrome P-450. , 1989, Drug metabolism reviews.

[30]  D. Lewis,et al.  Quantitative structure-activity relationships and COMPACT analysis of a series of food mutagens. , 1995, Food additives and contaminants.

[31]  D. Lewis,et al.  Molecular modelling of CYP1A subfamily members based on an alignment with CYP102: rationalization of CYP1A substrate specificity in terms of active site amino acid residues. , 1996, Xenobiotica; the fate of foreign compounds in biological systems.

[32]  T. Fujita,et al.  Effects of structure on binding to the 2,3,7,8-TCDD receptor protein and AHH induction--halogenated biphenyls. , 1985, Environmental health perspectives.

[33]  J. Whitlock,et al.  Regulation of cytochrome P1-450 gene expression in mouse hepatoma cells by 2,3,7,8-tetrachlorodibenzo-p-dioxin. , 1989, Drug metabolism reviews.

[34]  J. Huff,et al.  Carcinogenicity of TCDD: experimental, mechanistic, and epidemiologic evidence. , 1994, Annual review of pharmacology and toxicology.

[35]  C. Ioannides,et al.  A quantitative structure-activity relationship study on a series of 10 para-substituted toluenes binding to cytochrome P4502B4 (CYP2B4), and their hydroxylation rates. , 1995, Biochemical pharmacology.

[36]  D. Lewis,et al.  Inhibition of rat hepatic aryl hydrocarbon hydroxylase activity by a series of 7-hydroxy coumarins: QSAR studies. , 1994, Xenobiotica; the fate of foreign compounds in biological systems.

[37]  C. Ioannides,et al.  Molecular modeling of enzymes and receptors involved in carcinogenesis: QSARs and compact-3D. , 1994, Drug metabolism reviews.

[38]  S. Lamm,et al.  Comparative carcinogenicity of the PAHs as a basis for acceptable exposure levels (AELs) in drinking water. , 1989, Regulatory toxicology and pharmacology : RTP.

[39]  D. Lewis,et al.  Computer graphics analysis of the interaction of alkoxy methylenedioxybenzenes with cytochromes P4501. , 1995, Toxicology letters.

[40]  C. F. Wilkinson,et al.  Selective inhibitory interactions of alkoxymethylenedioxybenzenes towards mono-oxygenase activity in rat-hepatic microsomes. , 1985, Xenobiotica; the fate of foreign compounds in biological systems.

[41]  M. Coombs,et al.  Evaluation of the mutagenicity of compounds of known carcinogenicity, belonging to the benz[a]anthracene, chrysene, and cyclopenta[a]phenanthrene series, using Ames's test. , 1976, Cancer research.

[42]  C. Ioannides,et al.  Structural requirements for substrates of cytochromes P-450 and P-448. , 1987, Chemico-biological interactions.

[43]  J. Landers,et al.  The Ah receptor and the mechanism of dioxin toxicity. , 1991, The Biochemical journal.

[44]  A. J. Ryan,et al.  The binding to oxidised cytochromes P-450 and inhibition of mixed-function oxidases by aryl-substituted benzimidazoles and related compounds. , 1983, Chemico-biological interactions.

[45]  F. Gonzalez,et al.  Role of human cytochromes P450 in the metabolic activation of chemical carcinogens and toxins. , 1994, Drug metabolism reviews.

[46]  L. Pedersen,et al.  An Ab initio study of the relationship between nitroarene mutagenicity and electron affinity. , 1986, Molecular pharmacology.

[47]  C. Hansch,et al.  Quantitative structure-activity relationships of cytochrome P-450. , 1993, Drug metabolism reviews.

[48]  D. Smith Pharmacokinetics and pharmacodynamics in toxicology. , 1997, Xenobiotica; the fate of foreign compounds in biological systems.

[49]  D. F. Lewis Molecular orbital calculations and quantitative structure-activity relationships for some polyaromatic hydrocarbons. , 1987, Xenobiotica; the fate of foreign compounds in biological systems.

[50]  T. Fujita,et al.  Effects of substituents on the cytosolic receptor-binding avidities and aryl hydrocarbon hydroxylase induction potencies of 7-substituted 2,3-dichlorodibenzo-p-dioxins. A quantitative structure-activity relationship analysis. , 1985, Molecular pharmacology.

[51]  T. Fujita,et al.  Competitive binding of 7-substituted-2,3-dichlorodibenzo-p-dioxins with human placental ah receptor--a QSAR analysis. , 1990, Biochemical pharmacology.

[52]  D W Nebert,et al.  P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. , 1996, Pharmacogenetics.

[53]  E. Glover,et al.  Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase. , 1976, The Journal of biological chemistry.

[54]  N. Meyers,et al.  H = W. , 1964, Proceedings of the National Academy of Sciences of the United States of America.

[55]  C. Ioannides,et al.  Mutagenicity of chrysene, its methyl and benzo derivatives, and their interactions with cytochromes P-450 and the Ah-receptor; relevance to their carcinogenic potency. , 1993, Toxicology.

[56]  F. Guengerich,et al.  Studies on the structure-activity relationships for the metabolism of polybrominated biphenyls by rat liver microsomes. , 1985, Toxicology and applied pharmacology.