The Metabolism of Xenobiotics to Reactive Electrophiles in Chemical Carcinogenesis and Mutagenesis: A Collaboration with Elizabeth Cavert Miller and our Associates

References

• Sasaki T., Yoshida T. Experimentelle Erzeugung des Lebercarcinomas durch Futterung mit o-Amidoazotoluol. Virchow's Arch. Pathol. Anat. Physiol. 1935; 295: 175–200
   Google Scholar
• Kinosita R. Studies on the cancerogenic chemical substances. Trans. Jpn. Pathol. Soc. 1937; 27: 665–727
   Google Scholar
• Stevenson E. S., Dobriner K., Rhoads C. P. The metabolism of dimethylaminoazobenzene (butter yellow) in rats. Cancer Res. 1942; 2: 160–167
   Google Scholar
• Miller J. A., Baumann C. A. The determination of p-dimethylaminoazobenzene, p-monomethylaminoazobenzene, and p-aminoazobenzene in tissue. Cancer Res. 1945; 5: 157–161
   Web of Science ®Google Scholar
• Miller J. A., Miller E. C., Baumann C. A. On the methylation and demethylation of certain carcinogenic azo dyes in the rat. Cancer Res. 1945; 5: 162–168
   Web of Science ®Google Scholar
• Miller J. A., Baumann C. A. The carcinogenicity of certain azo dyes related to p-dimethylaminoazobenzene. Cancer Res. 1945; 5: 227–234
   Web of Science ®Google Scholar
• Miller J. A., Miller E. C. The carcinogenic aminoazo dyes. Adv. Cancer Res. 1953; 1: 340–396
   Google Scholar
• Miller E. C., Miller J. A. The presence and significance of bound aminoazo dyes in the livers of rats fed p-dimethylaminoazobenzene. Cancer Res. 1947; 7: 468–480
   Web of Science ®Google Scholar
• Miller E. C., Miller J. A., Sapp R. W., Weber G. M. Studies on protein-bound aminoazo dyes formed in vivo from 4-dimethylaminoazobenzene and its C-monomethyl derivatives. Cancer Res. 1949; 9: 336–343
   PubMed Web of Science ®Google Scholar
• Miller E. C., Miller J. A. In vivo combinations between carcinogens and tissue constituents and their possible role in carcinogenesis. Cancer Res. 1952; 12: 547–556
   PubMed Web of Science ®Google Scholar
• Sorof S., Cohen P. P., Miller E. C., Miller J. A. Studies on the soluble proteins from livers of rats fed aminoazo dyes. Cancer Res. 1951; 11: 383–387
   PubMed Web of Science ®Google Scholar
• Sorof S., Cohen P. P. Electrophoretic and ultracentrifugal studies on the soluble proteins of various tumors and of livers from rats fed 4-dimethylaminoazobenzene. Cancer Res. 1951; 11: 376–383
   PubMed Web of Science ®Google Scholar
• Miller E. C. Studies on the formation of protein-bound derivatives of 3,4-benzpyrene in the epidermal fraction of mouse skin. Cancer Res. 1951; 11: 100–108
   PubMed Web of Science ®Google Scholar
• Levine M., Tarver H. Studies of ethionine. III. Incorporation of ethionine into rat proteins. J. Biol. Chem. 1951; 192: 835–850
   PubMed Web of Science ®Google Scholar
• Wiest W. G., Heidelberger C. The interaction of carcinogenic hydrocarbons with tissue constituents. II. 1,2,5,6-dibenzanthracene-9,10-C14 in skin. Cancer Res. 1953; 13: 250–254
   PubMed Web of Science ®Google Scholar
• Weisburger E. K., Weisburger J. H., Morris H. P. Studies on the metabolism of 2-acetylaminofluorene-9-C14. Arch. Biochem. Biophys. 1953; 43: 474–484
   PubMed Web of Science ®Google Scholar
• Marroquin F., Farber E. The in vivo labeling of liver ribonucleic acid by p-DAB-1α-C14. Proc. Am. Assoc. Cancer Res. 1963; 4: 41
   Google Scholar
• Lin J.-K., Miller J. A., Miller E. C. Structures of hepatic nucleic acid-bound dyes in rats given the carcinogen N-methyl-4-aminoazobenzene. Cancer Res. 1975; 35: 844–850
   PubMed Web of Science ®Google Scholar
• Watson J. D., Crick F. H. C. Molecular structure of nucleic acids: A structure for deoxyribose nucleic acid. Nature (London) 1953; 171: 737–738
   PubMed Web of Science ®Google Scholar
• Wheeler G. P., Skipper H. E. Studies with mustards. III. In vivo fixation of C14 from nitrogen mustard-C14H3 in nucleic acid fractions of animal tissues. Arch. Biochem. Biophys. 1957; 72: 465–475
   PubMed Web of Science ®Google Scholar
• Miller E. C., Miller J. A. Mechanisms of chemical carcinogenesis. Nature of proximate carcinogens and interactions with macromolecules. Pharmacol. Rev. 1966; 18: 805–838
   PubMed Web of Science ®Google Scholar
• Miller E. C., Miller J. A. Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules. Cancer 1981; 47: 2327–2345
   PubMed Web of Science ®Google Scholar
• Potter V. R., Elvehjem C. A. A modified method for the study of tissue oxidations. J. Biol. Chem. 1936; 114: 495–503
   Google Scholar
• Kensler C. J., Magill J. W., Sugiura K. The metabolism of N,N-dimethyl-p-aminoazobenzene. Cancer Res. 1947; 7: 95–98
   PubMed Web of Science ®Google Scholar
• Mueller G. C., Miller J. A. The metabolism of 4-dimethylaminoazo-benzene by rat liver homogenates. J. Biol. Chem. 1948; 176: 535–544
   PubMed Web of Science ®Google Scholar
• Trager W. F. Oxidative functionalization reactions. Drugs Pharm. Sci. 1980; 10: 177–210, (Part A)
   Google Scholar
• Mueller G. C., Miller J. A. The reductive cleavage of 4-dimethylaminoazobenzene by rat liver: The intracellular distribution of the enzyme system and its requirement for triphosphopyridine nucleotide. J. Biol. Chem. 1949; 180: 1125–1136
   PubMed Web of Science ®Google Scholar
• Mueller G. C., Miller J. A. The reductive cleavage of 4-dimethylaminoazobenzene by rat liver: Reactivation of carbon dioxide-treated homogenates by riboflavin-adenine dinucleotide. J. Biol. Chem. 1950; 185: 145–154
   PubMed Web of Science ®Google Scholar
• Mueller G. C., Miller J. A. The metabolism of methylated aminoazo dyes. II. Oxidative demethylation by rat liver homogenates. J. Biol. Chem. 1953; 202: 579–587
   PubMed Web of Science ®Google Scholar
• La Du B. N., Gaudette L., Trousof N., Brodie B. B. Enzymatic dealkylation of aminopyrine (Pyramidon) and other alkylamines. J. Biol. Chem. 1955; 214: 741–752
   PubMedGoogle Scholar
• Axelrod J. The enzymatic deamination of amphetamine (Benzedrine). J. Biol. Chem. 1955; 214: 753–763
   PubMedGoogle Scholar
• Brodie B. B., Gillette J. R., La Du B. N. Enzymatic metabolism of drugs and other foreign compounds. Annu. Rev. Biochem. 1958; 27: 427–454
   PubMed Web of Science ®Google Scholar
• Brown R. R., Miller J. A., Miller E. C. The metabolism of methylated dyes. IV. Dietary factors enhancing demethylation in vitro. J. Biol. Chem. 1954; 209: 211–222
   PubMed Web of Science ®Google Scholar
• Miller E. C., Miller J. A., Conney A. H. On the mechanism of methylcholanthrene inhibition of carcinogenesis by 3α-methyl-4-dimethylaminoazobenzene. Proc. Am. Assoc. Cancer Res. 1954; 1(2)32
   Google Scholar
• Conney A. H., Miller E. C., Miller J. A. Induction of enzyme synthesis in the rat liver by 3-methylcholanthrene. Proc. Am. Assoc. Cancer Res. 1956; 2: 101
   Google Scholar
• Conney A. H., Miller E. C., Miller J. A. The metabolism of methylated dyes. V. Evidence for the induction of enzyme synthesis in the rat by 3-methylcholanthrene. Cancer Res. 1956; 16: 450–459
   PubMed Web of Science ®Google Scholar
• Conney A. H., Miller E. C., Miller J. A. Substrate-induced synthesis and other properties of benzpyrene hydroxylase in rat liver. J. Biol. Chem. 1957; 228: 753–766
   PubMed Web of Science ®Google Scholar
• Conney A. H., Gilman A. E. Puromycin inhibition of enzyme induction by 3-methylcholanthrene and phenobarbital. J. Biol. Chem. 1963; 238: 3682–3685
   PubMed Web of Science ®Google Scholar
• Gelboin H. V., Blackburn N. R. The stimulatory effect of 3-methylcholanthrene on microsomal amino acid incorporation and benzpyrene hydroxylase activity and its inhibition by actinomycin D. Biochim. Biophvs. Acta 1963; 72: 657–660
   PubMed Web of Science ®Google Scholar
• Richardson H. L., Stier A. R., Borsos-Nachtnebel E. Liver tumor inhibition and adrenal histologic responses in rats to which 3α-methyl-4-dimethylaminoazobenzene and 20-methylcholanthrene were simultaneously administered. Cancer Res. 1952; 12: 356–361
   PubMed Web of Science ®Google Scholar
• Miller E. C., Miller J. A., Brown R. R., Mac Donald J. S. On the protective effect of certain polycyclic aromatic hydrocarbons against carcinogenesis by aminoazo dyes and 2-acetylaminofluorene. Cancer Res. 1958; 18: 469–477
   PubMed Web of Science ®Google Scholar
• Conney A. H. Pharmacological implications of microsomal enzyme induction. Pharmacol. Rev. 1967; 19: 317–366
   PubMed Web of Science ®Google Scholar
• Mason H. S. Mechanisms of oxygen metabolism. Science 1957; 125: 1185–1188
   PubMed Web of Science ®Google Scholar
• Posner H. S., Mitoma C., Rothberg S., Udenfriend S. Enzymic hydroxylation of aromatic compounds. III. Studies on the mechanism of microsomal hydroxylation. Arch. Biochem. Biophys. 1961; 94: 280–290
   PubMed Web of Science ®Google Scholar
• Cooper D. Y., Estabrook R. W., Rosenthal O. The stoichiometry of C21 hydroxylation of steroids by adrenocortical microsomes. J. Biol. Chem. 1963; 238: 1320–1323
   PubMed Web of Science ®Google Scholar
• Cooper D. Y., Levin S., Harasimhulu S., Rosenthal O., Estabrook R. W. Photochemical action spectrum of the terminal oxidase of mixed-function oxidase systems. Science 1965; 147: 400–402
   PubMed Web of Science ®Google Scholar
• Coon M. J., Persson A. V. Microsomal cytochrome P-450: A central catalyst in detoxication reactions. Enzymatic Basis of Detoxication, W. B. Jakoby. Academic Press, New York 1980; Vol. 1: 117–134
   Google Scholar
• Lu A. Y. H., West S. H. Multiplicity of mammalian microsomal cytochromes P-450. Pharmacol. Rev. 1980; 31: 277–295
   Web of Science ®Google Scholar
• Wislocki P. G., Miwa G. T., Lu A. Y. H. Reactions catalyzed by the cytochrome P-450 system. Enzymatic Basis of Detoxication, W. B. Jakoby. Academic Press, New York 1980; Vol. 1: 135–182
   Google Scholar
• Weisburger E. K., Weisburger J. H. Chemistry, carcinogenicity and metabolism of 2-fluorenamine and related compounds. Adv. Cancer Res. 1956; 5: 331–431
   Web of Science ®Google Scholar
• Weisburger J. H., Weisburger E. K., Morris H. P. Urinary metabolites of the carcinogen N2-fluorenylacetamide. J. Natl. Cancer Inst. 1950; 17: 345–361
   Google Scholar
• Cramer J. W., Miller J. A., Miller E. C. N-hydroxylation: A new metabolic reaction observed in the rat with the carcinogen 2-acetylaminofluorene. J. Biol. Chem. 1960; 235: 885–888
   PubMed Web of Science ®Google Scholar
• Miller E. C., Miller J. A., Hartmann H. A. N-Hydroxy-2-acetylaminofluorene, a metabolite with increased carcinogenic activity in the rat. Cancer Res. 1961; 21: 815–824
   PubMed Web of Science ®Google Scholar
• Miller E. C., Miller J. A., Enomoto M. The comparative carcinogenicities of 2-acetylaminofluorene and its N-hydroxy metabolite in mice, hamsters, and guinea pigs. Cancer Res. 1964; 24: 2018–2032
   PubMed Web of Science ®Google Scholar
• Beland F. A., Kadlubar F. F. Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. Chemical Carcinogenesis and Mutagenesis I, C. S. Cooper, P. L. Grover. Springer-Verlag, Berlin 1990
   Google Scholar
• Poirier L. A., Miller J. A., Miller E. C., Sato K. N-Benzoyloxy-N-methyl-4-aminobenzene: Its carcinogenic activity in the rat and its reactions with proteins and nucleic acids and their constituents in vitro. Cancer Res. 1967; 27: 1600–1613
   PubMed Web of Science ®Google Scholar
• Scribner J. D., Miller J. A., Miller E. C. 3-Methylmercapto-N-methyl-4-aminoazobenzene: An alkaline-degradation product of a labile protein-bound dye in the livers of rats fed N,N-dimethyl-4-aminoazobenzene. Biochem. Biophys. Res. Commun. 1965; 20: 560–565
   PubMed Web of Science ®Google Scholar
• Lotlikar P. D., Scribner J. D., Miller J. A., Miller E. C. Reaction of esters of aromatic N-hydroxy amines and amides with methionine in vitro: A model for in vivo binding of amine carcinogens to protein. Life Sci. 1966; 5: 1263–1289
   Google Scholar
• Miller E. C., Juhl U., Miller J. A. Nucleic acid guanine: Reaction with the carcinogen N-acetoxy-2-acetylaminofluorene. Science 1966; 153: 1125–1127
   PubMed Web of Science ®Google Scholar
• Kriek E., Miller J. A., Juhl U., Miller E. C. 8-(N-Fluorenylacetamido)-guanosine, an arylamidation reaction product of guanosine and the carcinogen N-acetoxy-N-fluorenylacetamide in neutral solution. Biochemistry 1967; 6: 177–182
   PubMed Web of Science ®Google Scholar
• De Baun J. R., Rowley J. Y., Miller E. C., Miller J. A. Sulfotransferase activation of N-hydroxy-2-acetylaminofluorene in rodent livers susceptible and resistant to this carcinogen. Proc. Soc. Exp. Biol. Med. 1968; 129: 268–273
   PubMed Web of Science ®Google Scholar
• King C. M., Phillips B. Enzyme-catalyzed reactions of the carcinogen N-hydroxy-2-fluorenylacetamide with nucleic acid. Science 1968; 159: 1351–1353
   PubMed Web of Science ®Google Scholar
• De Baun J. R., Smith J. Y. R., Miller E. C., Miller J. A. Reactivity in vivo of the carcinogen N-hydroxy-2-acetylaminofluorene: Increase by sulfate ion. Science 1970; 167: 184–186
   PubMed Web of Science ®Google Scholar
• De Baun J. R., Miller E. C., Miller J. A. N-Hydroxy-2-acetylaminofluorene sulfotransferase: Its probable role in carcinogenesis and protein-(methion-S-yl) binding in rat liver. Cancer Res. 1970; 30: 577–595
   PubMed Web of Science ®Google Scholar
• Miller J. A., Miller E. C. The metabolic activation of carcinogenic aromatic amines and amides. Prog. Exp. Tumor Res. 1969; 11: 273–301
   PubMed Web of Science ®Google Scholar
• Bartsch H., Hecker E. On the metabolic activation of the carcinogen N-hydroxy-N-2-acetylaminofluorene. III. Oxidation with horseradish peroxidase to yield 2-nitrosofluorene and N-acetoxy-N-2-acetylaminofluorene. Biochim. Biophys. Acta 1971; 237: 567–578
   PubMed Web of Science ®Google Scholar
• Bartsch H., Miller J. A., Miller E. C. N-Acetoxy-N-acetylaminoarenes and nitrosoarenes. One-electron non-enzymatic and enzymatic oxidation products of various carcinogenic aromatic acethydroxamic acids. Biochim. Biophys. Acta 1972; 273: 40–51
   PubMed Web of Science ®Google Scholar
• Bartsch H., Dworkin M., Miller J. A., Miller E. C. Electrophilic N-acetoxyaminoarenes derived from carcinogenic N-hydroxy-N-acetylaminoarenes by enzymatic deacetylation and transacetylation in liver. Biochim. Biophys. Acta 1972; 286: 272–298
   PubMed Web of Science ®Google Scholar
• King C. M., Allaben W. T. Arylhydroxamic acid acetyltransferase. Enzymatic Basis of Detoxication, W. B. Jakoby. Academic Press, New York 1980; Vol. 2: 187–197
   Google Scholar
• Kriek E. On the interactions of N-2-fluorenylhydroxyamine with nucleic acids in vitro. Biochem. Biophys. Res. Commun. 1965; 20: 793–799
   PubMed Web of Science ®Google Scholar
• Tada M., Tada M. Seryl-tRNA synthetase and activation of the carcinogen 4-nitroquinoline 1-oxide. Nature (London) 1975; 255: 510–512
   PubMed Web of Science ®Google Scholar
• Miller J. A., Miller E. C. Metabolic action of carcinogenic aromatic amines and amides via N-hydroxylation and N-hydroxy esterification and its relationship to ultimate carcinogens as electrophilic reactants. Jerusalem Symp. Quantum Chem. Biochem. 1969; 1: 237–261
   Google Scholar
• Magee P. N., Montesano R., Preussmann R. N-Nitroso compounds and related carcinogens. ACS Monogr. 1976; 173: 491–625
   Google Scholar
• Mattocks A. R. Toxicity of pyrrolizidine alkaloids. Nature (London) 1968; 217: 723–728
   PubMed Web of Science ®Google Scholar
• Culvenor C. C. J., Downing D. T., Edgar J. A., Jago M. V. Pyrrolizidine alkaloids as alkylating and antimitotic agents. Ann. N.Y. Acad. Sci. 1969; 163: 837–847
   Web of Science ®Google Scholar
• Gelboin H. V. A microsome-dependent binding of benzo[a]pyrene to DNA. Cancer Res. 1969; 29: 1272–1276
   PubMed Web of Science ®Google Scholar
• Grover P. L., Sims P. Enzyme-catalyzed reactions of polycyclic hydro-carbons with deoxyribonucleic acid and protein in vitro. Biochem. J. 1969; 110: 159–160
   Web of Science ®Google Scholar
• Reynolds E. S. Liver parenchymal cell injury. IV. Pattern of incorporation of carbon and chlorine from carbon tetrachloride into chemical constituents in viro. J. Pharmacol. Exp. Ther. 1967; 155: 117–126
   PubMed Web of Science ®Google Scholar
• Butler T. C. Reduction of carbon tetrachloride in vivo and reduction of carbon tetrachloride and chloroform in vitro by tissue and tissue constituents. J. Pharmacol. Exp. Ther. 1961; 134: 311–319
   PubMed Web of Science ®Google Scholar
• Sims P., Grover P. L., Swaisland A., Pal K., Hewer A. Metabolic activation of benzo[a]pyrene proceeds by a diol-epoxide. Nature (London) 1974; 252: 326–328
   PubMed Web of Science ®Google Scholar
• Jerina D. M., Sayer J. M., Thakker D. R., Yagi H., Levin W., Wood A. W., Conney A. H. Carcinogenicity of polycyclic aromatic hydrocarbons: The bay-region theory. Carcinogenesis: Fundamental Mechanisms and Environmental Effects, B. Pullman, P. O. P.'O Ts, H. Gelboin. Reidel Publ., Dordrecht 1980; 1–12
   Google Scholar
• Rogan E. G., Devanesan P. D., Rama Krishna N. V. S., Higginbottom S. H., Padmavathi N. S., Chapman K., Cavalieri E. L., Jeong H., Jankowiak R., Small G. J. Identification and quantification of benzo[a]pyrene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 1993; 6: 356–363
   PubMed Web of Science ®Google Scholar
• Chakravarti D., Pelling J. C., Cavalieri E. L., Rogan E. G. Relating aromatic hydrocarbon-induced DNA adducts and c-H-ras mutations in mouse skin papillomas: The role of apurinic sites. Proc. Natl. Acad. Sci. USA 1995; 92: 10422–10426
   PubMed Web of Science ®Google Scholar
• Swenson D. H., Lin J.-K., Miller E. C., Miller J. A. Aflatoxin B1-2,3-oxide as a probable intermediate in the covalent binding of aflatoxins B1 and B2 to rat liver DNA and microsomal RNA in viro. Cancer Res. 1977; 37: 172–181
   PubMed Web of Science ®Google Scholar
• Martin C. N., Garner R. C. Aflatoxin B-oxide generated by chemical or enzymatic oxidation of aflatoxin B1 causes guanine substitution in nucleic acids. Nature (London) 1977; 267: 863–865
   PubMed Web of Science ®Google Scholar
• Lin J.-K., Miller J. A., Miller E. C. 2,3-Dihydro-2(guan-7-yl)-3-hydroxyaflatoxin B1, a major acid hydrolysis product of aflatoxin B1-DNA or -RNA adducts formed in hepatic microsome-mediated reactions and in rat liver in viro. Cancer Res. 1977; 37: 4430–4438
   PubMed Web of Science ®Google Scholar
• Essigmann J. M., Croy R. G., Nazdan R. G., Busby W. F., Jr., Buchi V. N. G., Wogan G. N. Structural identification of the major DNA adduct formed by aflatoxin B1 in vitro. Proc. Natl. Acad. Sci. USA 1977; 74: 1870–1874
   PubMed Web of Science ®Google Scholar
• Zadela F., Croisy A., Barbin A., Malavielle C., Tomatis L., Bartsch H. Carcinogenicity of chloroethylene oxide, an ultimate reactive metabolite of vinyl chloride and bis(chlrormethyl)ether after subcutaneous administration and in initiation-promotion experiments in mice. Cancer Res. 1980; 40: 352–356
   PubMed Web of Science ®Google Scholar
• Scherer E., Steward A. P., Emmelot P. Formation of precancerous islands in rat liver and modification of DNA by ethyl carbamate: Implications for its metabolism. Dev. Toxicol. Environ. Sci. 1980; 8: 249–254
   PubMedGoogle Scholar
• Ribovich M. L., Miller J. A., Miller E. C., Timmins L. G. Labeled 1,N6-ethenoadenosine and 3,N4-ethenocytidine in hepatic RNA of mice given ethyl-1,2[3H] or ethyl-1-[14C]ethyl carbamate (urethan). Carcinogenesis 1982; 3: 539–546
   PubMed Web of Science ®Google Scholar
• Leithauser M. T., Liem A., Stewart B. C., Miller E. C., Miller J. A. 1,N6-Ethenoadenosine formation, mutagenicity, and murine tumor induction as indicators of the generation of an electrophilic epoxide metabolite of the closely related carcinogens ethyl carbamate (urethene) and vinyl carbamate. Carcinogenesis 1990; 11: 463–473
   PubMed Web of Science ®Google Scholar
• Park K.-K., Surh Y.-J., Stewart B. C., Miller J. A. Synthesis and properties of vinyl carbamate epoxide, a possible ultimate electrophilic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate. Biochem. Biophys. Res. Commun. 1990; 169: 1094–1098
   PubMed Web of Science ®Google Scholar
• Park K.-K., Liem A., Stewart B. C., Miller J. A. Vinyl carbamate epoxide, a major strong electrophilic, mutagenic, and carcinogenic metabolite of vinyl carbamate and ethyl carbamate (urethane). Carcinogenesis 1993; 14: 441–450
   PubMed Web of Science ®Google Scholar
• Phillips D. H., Miller J. A., Miller E. C., Adams B. The N2-atom of guanine and the N6-atom of adenine residues as sites for covalent binding of metabolically activated 1α-hydroxysafrole to mouse liver DNA in viro. Cancer Res. 1981; 41: 2664–2671
   PubMed Web of Science ®Google Scholar
• Phillips D. H., Miller J. A., Miller E. C., Adams B. Structures of the DNA adducts formed in mouse liver after administration of the proximate carcinogen 1α-hydroxy estragole. Cancer Res. 1981; 41: 176–181
   PubMed Web of Science ®Google Scholar
• Boberg E. W., Miller E. C., Miller J. A., Poland A. Strong evidence from studies with brachymorphic mice and pentachlorophenol that 1α-sulfooxysafrole is the major electrophilic and carcinogenic metabolite of 1α-hydroxysafrole in mouse liver. Cancer Res. 1983; 43: 5163–5173
   PubMed Web of Science ®Google Scholar
• Surh Y.-J., Lai C.-C., Miller J. A., Miller E. C. Hepatic DNA and RNA adduct formation from the carcinogen 7-hydroxymethyl-12-methylbenz[a]anthracene and its electrophilic sulfuric acid ester metabolite in preweanling rats and mice. Biochem. Biophys. Res. Commun. 1987; 144: 576–582
   PubMed Web of Science ®Google Scholar
• Surh Y.-J., Liem A., Miller E. C., Miller J. A. Metabolic activation of 6-hydroxymethylbenzo[a]pyrene: Formation of an electrophilic sulfuric acid ester and benzylic DNA adducts in rat liver in vivo and in reactions in vitro. Carcinogenesis 1989; 10: 1519–1528
   PubMed Web of Science ®Google Scholar
• Surh Y.-J., Liem A., Miller E. C., Miller J. A. The strong hepatocarcinogenicity of an electrophilic and mutagenic metabolite 6-sulfooxymethylbenzo[a]pyrene and its formation of benzylic DNA adducts in the livers of infant male B6C3F1 mice. Biochem. Biophys. Res. Commun. 1990; 172: 85–91
   PubMed Web of Science ®Google Scholar
• Surh Y. -J., Liem A., Miller E. C., Miller J. A. 7-Sulfooxymethyl-12-methylbenz[a]anthracene is an electrophilic mutagen, but does not appear to play a role in carcinogenesis by 7,12-dimethylbenz[a]anthracene or 7-hydroxymethyl-12-methylbenz[a]anthracene. Carcinogenesis 1991; 12: 299–347
   PubMedGoogle Scholar
• Biological Reactive Species, Molecular and Cellular Effects and Their Impact on Human Health, R. R. Snyder, C. M. Widmer, D. J. Jollow, G. M. Kalf, J. J. Kocsis, et al. Plenum Press, New York 1977, Advances in Experimental Medicine and Biology Vols. I, IIA, IIB, III, and IV, 1982, 1985, 1991
   Google Scholar
• Loeb L. A., Zakour R. A. Metals and genetic miscoding. Nucleic Acid-Metal Ion Interactions, T. G. Spiro. Wiley, New York 1980; 115–144
   Google Scholar
• Ross W. C. J. Biological Alkylating Agents. Butterworth, London 1962
   Google Scholar
• Price C. C., Gaucher G. M., Koneru P., Shibakawa R., Sows J. R., Yamaguchi M. Mechanisms of action of alkylating agents. Ann. N.Y. Acad. Sci. 1969; 163: 593–598
   Web of Science ®Google Scholar
• Maher V. M., Miller E. C., Miller J. A., Szybalski W. Mutations and decreases in density of transforming DNA produced by derivatives of the carcinogens 2-acetylaminofluorene and N-methyl-4-aminoazobenzene. Molec. Pharmacol. 1968; 4: 411–426
   PubMed Web of Science ®Google Scholar
• Chemical Mutagens: Principles and Methods for their Detection, A. Hollaender, F. J. deSerres. Plenum, New York 1971–1982; Vols. 1–7
   Google Scholar
• Ames B. N., Durston W. E., Yamasaki E., Lee F. D. Carcinogens are mutagens: A simple test system combining liver homogenates for activation and bacteria for detection. Proc. Natl. Acad. Sci. USA 1973; 70: 2281–2285
   PubMed Web of Science ®Google Scholar
• Ames B. N., Mc Cann J., Yamasaki E. Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test. Mutat. Res. 1975; 31: 347–364
   PubMed Web of Science ®Google Scholar
• Fetterman B. A., Kim B. S., Margolin B. H., Schildcrout J. S., Smith M. G., Wagner S. M., Zeiger E. Predicting rodent carcinogenicity from mutagenic potency measured in the Ames Salmonella assay. Environ. Molec. Mutagen. 1997; 29: 312–322
   PubMed Web of Science ®Google Scholar
• Pitot H. C. Fundamentals of Oncology, 3rd ed. Marcel Dekker, Inc., New York 1986
   Google Scholar
• Pitot H. C., Dragan Y. P., Teeguarden J., Hsia S., Campbell H. Quantitation of multistage carcinogenesis in rat liver. Toxicol. Pathol. 1996; 24: 119–128
   PubMed Web of Science ®Google Scholar