Generation of 7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene by murine splenic macrophages

Battista, 1984, The mechanism of hydroperoxide-dependent epoxidation of 7,8-dihydroxy-7,8-dihydro-benzo(a)pyrene by rat liver microsomes, 25, 114 Baum, 1978, Occurrence and surveillance of polycyclic hydrocarbons, 45 Blanton, 1986, Immunomodulation by polycyclic aromatic hydrocarbons in mice and murine cells, Cancer Res., 46, 2735 Chen, 1984, Sequence specific binding of tetrols of BaPDE to DNA in neutral and acidic solutions, Carcinogenesis, 5, 753, 10.1093/carcin/5.6.753 Chensue, 1983, Arachidonic acid metabolism and macrophage activation, Clin. Lab. Med., 3, 677, 10.1016/S0272-2712(18)30956-9 Dean, 1983, Selective immunosuppression resulting from exposure to the carcinogenic congener of benzopyrene in B6C3F1 mice, Clin. Exp. Immunol., 52, 199 Deutsch, 1978, Regio- and stereoselectivity of various forms of cytochrome P-450 in the metabolism of benzo(a)pyrene as shown by product formation and binding to DNA, 75, 3123 Dix, 1983, Metabolism of polycyclic aromatic hydrocarbon derivatives to ultimate carcinogens during lipid peroxidation, Science, 221, 77, 10.1126/science.6304879 Dix, 1985, Hematin-catalyzed epoxidation of 7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene (BP-7,8-diol) by polyunsaturated fatty acid hydroperoxides, J. Biol. Chem., 260, 5358, 10.1016/S0021-9258(18)89029-9 Eling, 1986, Oxidation of (+)-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene by mouse keratinocytes: Evidence for peroxyl radical- and monoxygenase-dependent metabolism, Carcinogenesis, 7, 1957, 10.1093/carcin/7.12.1957 Geacintov, 1980, Kinetics of hydrolysis to tetrols and binding of benzo(a)pyrene-7,8-dihydrodiol-9,10-oxide and its tetrol derivatives to DNA. Conformation of adducts, Biochem. Biophys. Res. Commun., 92, 1335, 10.1016/0006-291X(80)90432-5 Gehan, 1975, Gehan-Wilcoxon test, 120 Gelboin, 1967, Carcinogens, enzyme induction, and gene action, Adv. Cancer Res., 10, 1, 10.1016/S0065-230X(08)60076-7 Gelboin, 1980, Benzo(a)pyrene metabolism, activation, and carcinogenesis: Role and regulation of mixed-function oxidases and related enzymes, Physiol. Rev., 60, 1107, 10.1152/physrev.1980.60.4.1107 Goujon, 1972, Genetic expression of aryl hydrocarbon hydroxylase induction. IV. Interaction of various compounds with different forms of cytochrome P-450 and the effect on benzo(a)pyrene metabolism in vitro, Mol. Pharmacol., 8, 667 Henderson, 1987, Eicosanoids and lung inflammation, Am. Rev. Respir. Dis., 135, 1176 Huberman, 1976, Identification of mutagenic metabolites of benzo(a)pyrene in mammalian cells, 73, 607 Humes, 1982, Evidence for two sources of arachidonic acid for oxidative metabolism by mouse peritoneal macrophages, J. Biol. Chem., 257, 1591, 10.1016/S0021-9258(19)68075-0 Ibanez, 1980, Physical binding of tetrols derived from BaPDE to DNA, J. Am. Chem. Soc., 102, 5661, 10.1021/ja00537a043 Jerina, 1974, Arene oxides: A new aspect of drug metabolism, Science, 185, 573, 10.1126/science.185.4151.573 Kawabata, 1987, Suppression of the in vitro humoral immune response of mouse splenocytes by benzo(a)pyrene and inhibition of benzo(a)pyrene-induced immunosuppression by α-naphthoflavone, Cancer Res., 47, 2317 Kawabata, 1989, Benzo(a)pyrene metabolism by murine spleen microsomes, Cancer Res., 49, 5816 King, 1976, (±)-7α,8β-dihydroxy-9β,10β-epoxy-7,8,9,10-tetrahydro-benzo(a)pyrene is an intermediate in the metabolism and binding to DNA of benzo(a)pyrene, 73, 2679 Ladics, 1991, Suppression of the in vitro humoral immune response of mouse splenocytes by 7,12-dimethylbenz[a]anthracene metabolites and inhibition of immunosuppression by α-naphthoflavone, Toxicol. Appl. Pharmacol., 110, 31, 10.1016/0041-008X(91)90287-O Ladics, 1992 Ladics, 1992 Laegreid, 1989, Virus-induced enhancement of arachidonate metabolism by bovine alveolar macrophages in vitro, J. Leukocyte Biol., 45, 293, 10.1002/jlb.45.4.293 Lorentzen, 1977, Benzo(a)pyrenedione/benzo(a)pyrene diol oxidation reduction couples and the generation of reactive reduced molecular oxygen, Biochemistry, 16, 1467, 10.1021/bi00626a035 Lorentzen, 1979, Toxicity of metabolic benzo(a)pyrenediones to cultured cells and the dependence upon molecular oxygen, Cancer Res., 39, 3194 Lyte, 1986, Modulation of interleukin-1 production by macrophages following benzo(a)pyrene exposure, Int. J. Immunopharmacol., 8, 377, 10.1016/0192-0561(86)90120-7 Lyte, 1987, Effect of in vivo administration of the carcinogen benzo(a)pyrene on interleukin-2 and interleukin-3 production, Int. J. Immunopharmacol., 9, 307, 10.1016/0192-0561(87)90055-5 Marnett, 1977, Prostaglandin synthetase-dependent benzo(a)pyrene oxidation: Products of the oxidation and inhibition of their formation by antioxidants, Biochem. Biophys. Res. Commun., 79, 569, 10.1016/0006-291X(77)90195-4 Mason, 1965, Oxidases, Annu. Rev. Biochem., 34, 595, 10.1146/annurev.bi.34.070165.003115 Mitchell, 1987, Differential induction of cytochrome P-450 catalyzed activities by polychlorinated biphenyls and benzo(a)pyrene in B6C3F1 mouse liver and lung, Toxicology, 43, 315, 10.1016/0300-483X(87)90090-4 Myers, 1987, Mechanisms of benzo(a)pyrene-induced modulation of antigen presentation, J. Pharmacol. Exp. Ther., 242, 399 Myers, 1988, Inhibition of IL-2 responsiveness following exposure to benzo(a)pyrene is due to alterations in accessory cell function, Int. J. Immunopharmacol., 10, 177, 10.1016/0192-0561(88)90093-8 Needleman, 1986, Arachidonic acid metabolism, Annu. Rev. Biochem., 55, 69, 10.1146/annurev.bi.55.070186.000441 Osborne, 1986, Benzopyrenes, 1 Owens, 1979, Mutagenesis of certain benzo(a)pyrene phenols in vitro following further metabolism by mouse liver, Biochem. Pharmacol., 28, 1615, 10.1016/0006-2952(79)90174-6 Panthananickal, 1981, Arachidonic acid-dependent metabolism of 7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene to polyguanylic acid-binding derivatives, Chem. Biol. Interact., 33, 239, 10.1016/0009-2797(81)90044-2 Panthananickal, 1983, Stereoselectivity of the epoxidation of 7,8-dihydrobenzo(a)pyrene by prostaglandin H synthase and cytochrome P-450 determined by the identification of polyguanylic acid adducts, J. Biol. Chem., 258, 4411, 10.1016/S0021-9258(18)32638-3 Pelkonen, 1982, Metabolism of polycyclic aromatic hydrocarbons: Etiologic role in carcinogenesis, Pharmacol. Rev., 34, 189 Pruess-Schwartz, 1989, Peroxyl radical- and cytochrome P-450-dependent metabolic activation of (+)-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene in mouse skin in vitro and in vivo, Cancer Res., 49, 1732 Samuelsson, 1978, Prostaglandins and thromboxanes, Annu. Rev. Biochem., 47, 997, 10.1146/annurev.bi.47.070178.005025 Samuelsson, 1983, Leukotrienes: Mediators of immediate hypersensitivity reactions and inflammation, Science, 220, 568, 10.1126/science.6301011 Schlosser, 1989, Metabolic activation of hydroquinone by macrophage peroxidase, Chem. Biol. Interact., 72, 191, 10.1016/0009-2797(89)90027-6 Sims, 1974, Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide, Nature, 252, 326, 10.1038/252326a0 Sivarajah, 1979, Arachidonic acid-dependent metabolism of (±)rans-7,8-dihydroxy-7,8-dihydro-benzo(a)pyrene (BP-7,8 diol) to 7,108,9 tetrols, FEBS Lett., 106, 17, 10.1016/0014-5793(79)80685-7 Sivarajah, 1981, Prostaglandin synthetase-dependent cooxidation of (±)-benzo(a)pyrene-7,8-dihydrodiol by human lung and other mammalian tissues, Cancer Res., 41, 1834 Stjernsward, 1966, Effect of noncarcinogenic and carcinogenic hydrocarbons on antibody-forming cells measured at the cellular level in vitro, J. Natl. Cancer Inst., 36, 1189 Tappel, 1973, Lipid peroxidation damage to cell components, 32, 1870 Thakker, 1976, Metabolism of benzo(a)pyrene: Conversion of (±)-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene to highly mutagenic 7,8-diol-9,10-epoxides, 73, 3381 Thakker, 1977, Stereoselective metabolism of benzo(a)pyrene and benzo(a)pyrene-7,8-dihydrodiol to diol-epoxides, Chem. Biol. Interact., 16, 281, 10.1016/0009-2797(77)90108-9 Tripp, 1985, Calcium ionophore enables soluble agonists to stimulate macrophage 5-lipoxygenase, J. Biol. Chem., 260, 5895, 10.1016/S0021-9258(18)88912-8 Urso, 1986, Suppression of humoral and cell-mediated immune responses in vitro by benzo(a)pyrene, J. Immunopharmacol., 8, 223, 10.3109/08923978609028616 White, 1984, Direct suppression of in vitro antibody production by mouse spleen cells by the carcinogen benzo(a)pyrene but not the noncarcinogenic congener benzo(a)pyrene, Cancer Res., 44, 3388 White, 1985, Immunosuppression by polycyclic aromatic hydrocarbons: A structure-activity relationship in B6C3F1 and DBA2 mice, Immunopharmacology, 9, 155, 10.1016/0162-3109(85)90011-6 Wood, 1977, Differences in mutagenicity of the optical enantiomers of the diastereomeric benzo(a)pyrene 7,8-diol-9,10-epoxides, Biochem. Biophys. Res. Commun., 77, 1389, 10.1016/S0006-291X(77)80133-2 Yang, 1976, Enzymatic conversion of benzo(a)pyrene leading predominantly to the diol-epoxide r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene through a single enantiomer of r-7,t-8-dihydroxy-7,8-dihydrobenzo(a)pyrene, 73, 2594