Microsomal Biotransformation of Benzo[<i>ghi</i>]perylene, a Mutagenic Polycyclic Aromatic Hydrocarbon without a “Classic” Bay Region
Tóm tắt
Từ khóa
Tài liệu tham khảo
Jerina D. M., 1986, Biological Reactive Intermediates III. Mechanisms of Action in Animal Models and Human Disease
LaVoie E. J., 1981, Mutagenicity of methylated fluorenes and benzofluorenes. Mutat. Res. 91, 167−176
Pahlman R., 1988, Salmonella. Mutat. Res. 207, 205−212.
LaVoie E., 1979, Polynuclear Aromatic Hydrocarbons
Andrews A. W., 1978, The relationship between carcinogenicity and mutagenicity of some polynuclear hydrocarbons. Mutat. Res. 51, 311−318
Mossanda K., 1979, Detection of mutagenic polycyclic aromatic hydrocarbons in African smoked fish. Food Cosmet. Toxicol. 17, 141−143
Platt K. L., 2002, Microsomal activation of dibenzo[def,mno]chrysene (anthanthrene), a hexacyclic aromatic hydrocarbon without a bay-region, to mutagenic metabolites. Chem. Res. Toxicol. 15, 332−342
IARC, 1983, IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Polynuclear Aromatic Compounds, Part 1, Chemical, Environmental and Experimental Data, 204
Deutsch-Wenzel R. P., 1983, J. Natl. Cancer Inst., 71
Noor Mohammad S., 1986, Indian J. Biochem. Biol., 23, 44
Hughes N. C., 1993, 32P−Postlabeling analysis of the covalent binding of benzo[ghi]perylene to DNA in vivo and in vitro. Carcinogenesis 14, 127−133
Platt K. L., 1982, K-region trans-dihydrodiols of polycyclic arenes
Cho H., 1976, J. Chem. Soc., Perkin Trans., 1
Schmassmann H., 1978, Epoxide hydratase and benzo[a]pyrene monooxygenase activities in liver, kidney and lung after treatment of rats with epoxides of widely varying structures. Biochem. Pharmacol. 27, 2237−2245
Bradford M. M., 1976, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248−254
Weems H. B., 1985, Resolution of epoxide enantiomers of polycyclic aromatic hydrocarbons by chiral stationary-phase high-performance liquid chromatography. Anal. Biochem. 148, 328−338
Ames B. N., 1975, Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test. Mutat. Res. 31, 347−363
Canter D. A., 1986, Comparative mutagenicity of aliphatic epoxides in Salmonella. Mutat. Res. 172, 105−138
Oesch F., 1971, Hepatic epoxide hydrase. Structure−activity relationships for substrates and inhibitors. Biochemistry 10, 4858−4866
Lehr R. E., 1977, J. Org. Chem., 42
Meyer V. R., 1999, Praxis der Hochleistungs-Flüssigchromatographie
Yang S. K., 1977, Enzymatic mechanism of benzo[a]pyrene conversion to phenols and diols and an improved high-pressure liquid chromatographic separation of benzo[a]pyrene derivatives. Biochemistry 16, 3680−3687
Selkirk J. K., 1975, Isolation by high-pressure liquid chromatography and characterization of benzo[a]pyrene-4,5-epoxide as a metabolite of benzo[a]pyrene. Arch. Biochem. Biophys. 168, 322−326
Platt K. L., 1987, Regio- and stereoselective metabolism of dibenz[a,h]anthracene: Identification of 12 new microsomal metabolites. Mol. Pharmacol. 32, 710−722
Van Gurp J. R., 1983, Single-step phototoxic selection procedure for isolating cells that possess aryl hydrocarbon hydroxylase. Cancer Res. 43, 6031−6038
Yang S. K., 1977, Evidence for a 2,3-epoxide as an intermediate in the microsomal metabolism of benzo[a]pyrene to 3-hydroxybenzo[a]pyrene. Biochem. Biophys. Res. Commun. 77, 1176−1182
Dewar M. J. S., 1975, The PMO Theory of Organic Chemistry
Fu P. P., 1978, Molecular orbital theoretical prediction of the isomeric products formed from reactions of arene oxides and related metabolites of polycyclic aromatic hydrocarbons. Tetrahedron 34, 857−866
Thakker D. R., 1985, Bioactivation of Foreign Compounds
Sims P., 1974, Epoxides in polycyclic aromatic hydrocarbon metabolism and carcinogenesis. Adv. Cancer Res. 20, 165−274
Jerina D. M., 1974, Arene oxides: A new aspect of drug metabolism. Science 185, 573−582
Yang S. K., 1987, Mol. Pharmacol., 32, 80
Moriarty R. M., 1975, Tetrahedron Lett., 2557−2560.
Agarwal S. K., 1990, J. Chem. Soc. Perkins Trans., 1
Jacob J., 1983, Benzo[e]pyrene metabolism in rat liver microsomes: dependence of the metabolite profile on the pretreatment of rats with various monooxygenase inducers. Carcinogenesis 4, 905−910
Lecoq S., 1991, Microsomal metabolism of dibenz[a,c]anthracene, dibenz[a,h]anthracene and dibenz[a,j]anthracene to bis-dihydrodiols and polyhydroxylated products. Chem.-Biol. Interact. 80, 261−279
Wood A. W., 1979, J. Biol. Chem., 254
Vyas K. P., 1983, Regioselectivity and stereoselectivity in the metabolism of trans-1,2-dihydroxy-1,2- 710 dihydrobenz[a]anthracene by rat liver microsomes. Mol. Pharmacol. 24, 115−123
Thakker D. R., 1986, J. Biol. Chem., 261
Nesnow, S., Davis, C., Padgett, W., George, M., Lambert, G., Meyers, F., Allison, J., Adams, L., and King, L. C. (1998) Metabolic activation of racemic and enantiomerictrans-8,9-dihydroxy-8,9-dihydrodibenzo[a,l]pyrene (dibenzo[def,p]chrysene) to dibenzo[a,l]pyrene-bis-dihydrodiols by induced rat liver microsomes and a recombinant human P450 1A1 system: The role of the K-region-derived metabolic intermediates in the formation of dibenzo[a,l]pyrene-DNA adducts.Chem. Res. Toxicol.11, 1596−1607.
Padgett, W. T., Davis, C., Lambert, G., Nelson, G. B., Ross, J. A., Yacopucci, M., and Nesnow, S. (2000) Biotransformation oftrans-4,5-dihydroxy-4,5-dihydrobenzo[a]pyrene to benzo[a]pyrene bis-diols and DNA adducts by induced rat liver microsomes.Chem. Res. Toxicol.13, 1125−1134.
Wilson N. M., 1984, Binding and metabolism of benzo[a]pyrene and 7,12-dimethylbenz[a]anthracene by seven purified forms of cytochrome P-450. Carcinogenesis 5, 1475−1483
Hall M., 1989, Carcinogenesis 10
Thomas P. E., 1983, J. Biol. Chem., 258
Oesch F., 1973, Induction, activation and inhibition of epoxide hydrase: An anomalous prevention of chlorobenzene-induced hepatotoxicity by an inhibitor of epoxide hydrase. Chem.-Biol. Interact. 6, 189−202
Shimada T., 1979, Inhibition of mono-oxygenase activities by 1,1,1-trichloropropene 2,3-oxide, an inhibitor of epoxide hydrase, in rat liver microsomes. Biochem. Pharmacol. 28, 1777−1781
Ivanetich K. M., 1982, 1,1,1-Trichloropropene-2,3-oxide: An alternate mechanism for its inhibition of cytochrome P-450. Res. Commun. Chem. Pathol. 35, 111−120
Masubuchi Y., 2001, Mechanism-based inactivation of CYP2C11 by diclofenac. Drug. Metab. Dispos. 29, 1190−1195
Owens I. S., 1979, Mutagenesis of certain benzo[a]pyrene phenols in vitro following further metabolism by mouse liver. Biochem. Pharmacol. 28, 1615−1622
Carmichael P. L., 1993, Evidence for the involvement of a bis-diol-epoxide in the metabolic activation of dibenz[a,h]anthracene to DNA-binding species in mouse skin. Cancer Res. 53, 944−948
Beach A. C., 1994, DNA adducts of the ubiquitous environmental contaminant cyclopenta[cd]pyrene. Carcinogenesis 15, 1065−1072
Abbreviations P, benzo[a]pyrene