The molecular etiology and prevention of estrogen-initiated cancers: Ockham's Razor: Pluralitas non est ponenda sine necessitate. Plurality should not be posited without necessity

Molecular Aspects of Medicine

Volumn 36, Issue 1, 2014, Pages 1-55

  Cavalieri, Ercole ^a   Rogan, Eleanor ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

1,4 Michael addition mechanism; Apurinic sites in DNA; Cancer prevention by N acetylcysteine and resveratrol; Carcinogenicity of 4 hydroxyestrogens; Cytochrome P4501B1; Depurinating estrogen DNA adducts; Depurinating PAH DNA adducts; Estrogen 3,4 quinones; Genotoxicity of estrogens; Hormonal carcinogenesis; Imbalance of estrogen homeostasis; Mutations by error prone repair; Nonhormonal carcinogenesis; PAH diol epoxides; PAH radical cations; Preneoplastic mutations

Indexed keywords

3 METHYLCHOLANTHRENE; 7,12 DIMETHYLBENZ[A]ANTHRACENE; ACETYLCYSTEINE; BENZENE; BENZO[A]PYRENE; CATECHOL ESTROGEN; CATECHOL METHYLTRANSFERASE; CYTOCHROME P450 1B1; DIBENZO[A,L]PYRENE; DIETHYLSTILBESTROL; EPOXIDE; ESTRADIOL; ESTROGEN; ESTRONE; HEXESTROL; NAPHTHALENE; QUINONE DERIVATIVE; RESVERATROL;

ANTINEOPLASTIC ACTIVITY; BREAST CANCER; BREAST CARCINOGENESIS; BREAST EPITHELIUM; CANCER PREVENTION; CANCER RISK; CARCINOGENESIS; CARCINOGENIC ACTIVITY; DNA ADDUCT; DNA DETERMINATION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG STRUCTURE; DRUG URINE LEVEL; ENDOPLASMIC RETICULUM; ENZYME ACTIVITY; ENZYME LOCALIZATION; ESTROGEN METABOLISM; GENOTOXICITY; HIGH RISK PATIENT; HOMEOSTASIS; HUMAN; METABOLIC ACTIVATION; MICRONUCLEUS; MOLECULAR PATHOLOGY; MUTATIONAL ANALYSIS; NONHODGKIN LYMPHOMA; NONHUMAN; ONCOGENE RAS; OVARY CANCER; OXYGEN TRANSPORT; PROSTATE CANCER; REVIEW; RISK ASSESSMENT; RISK FACTOR; SINGLE NUCLEOTIDE POLYMORPHISM; SKIN PAPILLOMA; STRUCTURE ANALYSIS; THYROID CANCER;

1,4-MICHAEL ADDITION MECHANISM; APURINIC SITES IN DNA; CANCER PREVENTION BY N-ACETYLCYSTEINE AND RESVERATROL; CARCINOGENICITY OF 4-HYDROXYESTROGENS; CYTOCHROME P4501B1; DEPURINATING ESTROGEN-DNA ADDUCTS; DEPURINATING PAH-DNA ADDUCTS; ESTROGEN-3,4-QUINONES; GENOTOXICITY OF ESTROGENS; HORMONAL CARCINOGENESIS; IMBALANCE OF ESTROGEN HOMEOSTASIS; MUTATIONS BY ERROR-PRONE REPAIR; NONHORMONAL CARCINOGENESIS; PAH DIOL EPOXIDES; PAH RADICAL CATIONS; PRENEOPLASTIC MUTATIONS;

ANIMALS; CARCINOGENS; CYTOCHROME P-450 ENZYME SYSTEM; DNA ADDUCTS; ESTRADIOL; ESTROGENS, CATECHOL; ESTRONE; FEMALE; HUMANS; MALE; MUTAGENS; NEOPLASMS; POLYCYCLIC HYDROCARBONS, AROMATIC; TUMOR MARKERS, BIOLOGICAL;

EID: 84895175096     PISSN: 00982997     EISSN: 18729452     Source Type: Journal    
DOI: 10.1016/j.mam.2013.08.002     Document Type: Review

References (321)

1. A.J. Alpert, and E.L. Cavalieri Metabolism of 6-substituted benzo[a]pyrene derivatives: O-dealkylation and regiospecificity in aromatic hydroxylations J. Med. Chem. 23 1980 919 927
2. S. Amin, K. Huie, G. Balanikas, S.S. Hecht, J. Pataki, and R.G. Harvey High stereoselectivity in mouse skin metabolic activation of methylchrysenes to tumorigenic dihydrodiols Cancer Res. 47 1987 3613 3617
3. S. Amin, K. Huie, A.A. Melikian, J.M. Leszczynska, and S.S. Hecht Comparative metabolic activation in mouse skin of the weak carcinogen 6-methylchrysene and the strong carcinogen 5-methylchrysene Cancer Res. 45 1985 6406 6442
4. J.C. Arcos, and M.F. Argus Chemical induction of cancer vol. IIA 1974 Academic Press New York
5. J.K. Atkinson, P.F. Hollenberg, K.U. Ingold, C.C. Johnson, M.H. Le Tadic, M. Newcomb, and D.A. Putt Cytochrome P450-catalyzed hydroxylation of hydrocarbons: kinetic deuterium isotope effects for the hydroxylation of an ultrafast radical clock Biochemistry 33 1994 10630 10637
6. M.H. Aziz, R. Kumar, and N. Ahmad Cancer chemoprevention by resveratrol: in vitro and in vivo studies and the underlying mechanisms Int. J. Oncol. 23 2003 17 28 (review)
7. W.M. Baird, A. Dipple, P.L. Grover, P. Sims, and P. Brookes Studies on the formation of hydrocarbon-deoxyribonucleoside products by the binding of derivatives of 7-methylbenz(a)anthracene to DNA in aqueous solution and in mouse embryo cells in culture Cancer Res. 33 1973 2386 2392
8. C. Bernelot-Moens, B.W. Glickman, and A.J. Gordon Induction of specific frameshift and base substitution events by benzo[a]pyrene diol epoxide in excision repair-deficient Escherichia coli Carcinogenesis 11 1990 781 785
9. C.A. Bigger, J.E. Tomaszewski, and A. Dipple Differences between products of binding of 7,12-dimethylbenz[a]anthracene to DNA in mouse skin and in a rat liver microsomal system Biochem. Biophys. Res. Commun. 80 1978 229 235
10. G.M. Blackburn, P.E. Taussig, and J.P. Will Binding of benzo[a]pyrene to DNA investigated by tritium displacement J. Chem. Soc., Chem. Commun. 1974 907 908
11. G. Blaich, M. Göttlicher, P. Cikryt, and M. Metzler Effects of various inducers on diethylstilbestrol metabolism, drug-metabolizing enzyme activities and the aromatic hydrocarbon (Ah) receptor in male Syrian golden hamster liver J. Steroid Biochem. 35 1990 201 204
12. W.P. Bocchinfuso, W.P. Hively, J.F. Couse, H.E. Varmus, and K.S. Korach A mouse mammary tumorvirus-Wnt-1 transgene induces mammary gland hyperplasia and tumorigenesis in mice lacking estrogen receptor-α Cancer Res. 59 1999 1869 1876
13. W.P. Bocchinfuso, and K.S. Korach Mammary gland development and tumorigenesis in estrogen receptor knockout mice. J Mammary Gland Biol. Neoplasia 2 1997 323 334
14. J.L. Bolton, and L. Shen p-Quinone methides are the major decomposition products of catechol estrogen o-quinones Carcinogenesis 17 1998 925 929
15. D.J. Boocock, G.E. Faust, K.R. Patel, A.M. Schinas, V.A. Brown, M.P. Ducharme, T.D. Booth, J.A. Crowell, M. Perloff, A.J. Gescher, W.P. Steward, and D.E. Brenner Phase I dose escalation pharmacokinetic study in health volunteers of resveratrol, a potential cancer chemopreventive agent Cancer Epidemiol. Biomarkers Prev. 16 2007 1246 1252
16. A. Borgen, H. Darvey, N. Castagnoli, T.T. Crocker, R.E. Rasmussen, and I.Y. Wang Metabolic conversion of benzo(a)pyrene by Syrian hamster liver microsomes and binding of metabolites to deoxyribonucleic acid J. Med. Chem. 16 1973 502 506
17. M.C. Bosland, H. Ford, and L. Horton Induction at high incidence of ductal prostate adenocarcinomas in NBL/Cr and Sprague-Dawley Hsd:SD rats treated with a combination of testosterone and estradiol-17β or diethylstilbestrol Carcinogenesis 16 1995 1311 1317
18. E. Boyland, and L.F. Chasseaud The role of glutathione and glutathione S-transferases in mercapturic acid biosynthesis Adv. Enzymol. Relat. Areas Mol. Biol. 32 1969 173 219
19. K. Brown, A. Buchmann, and A. Balmain Carcinogen-induced mutations in the mouse c-Ha-ras gene provide evidence of multiple pathways for tumor progression Proc. Natl. Acad. Sci. USA 87 1990 538 542
20. D.R. Buhler, F. Unlü, D.R. Thakker, T.J. Slaga, A.H. Conney, A.W. Wood, R.L. Chang, W. Levin, and D.M. Jerina Effect of a 6-fluoro substituent on the metabolism and biological activity of benzo[a]pyrene Cancer Res. 43 1983 1541 1549
21. H. Cai, L.B. Bloom, R. Eritja, and M.F. Goodman Kinetics of deoxyribonucleotide insertion and extension at abasic template lesions in different sequence contexts using HIV-1 reverse transcriptase J. Biol. Chem. 268 1993 23567 23572
22. K. Cao, P.D. Devanesan, R. Ramanathan, M.L. Gross, E.G. Rogan, and E.L. Cavalieri Covalent binding of catechol estrogens to glutathione catalyzed by horseradish peroxidase, lactoperoxidase, or rat liver microsomes Chem. Res. Toxicol. 11 1998 917 924
23. K. Cao, D.E. Stack, R. Ramanathan, M.L. Gross, E.G. Rogan, and E.L. Cavalieri Synthesis and structure elucidation of estrogen quinones conjugated with cysteine, N-acetylcysteine, and glutathione Chem. Res. Toxicol. 11 1998 909 916
24. P.L. Carmichael, K.L. Platt, M.N. Shé, S. Lecoq, F. Oesch, D.H. Phillips, and P.L. Grover 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 1993 944 948
25. W. Caspary, B. Cohen, S. Lesko, and P.O. Ts'o Electron paramagnetic resonance study of iodine-induced radicals of benzo[a]pyrene and other polycyclic hydrocarbons Biochemistry 12 1973 2649 2656
26. E. Cavalieri Minisymposium on endogenous carcinogens: the catechol estrogen pathway. An introduction Polycyclic Aromat. Compd. 6 1994 223 228
27. E. Cavalieri, and R. Auerbach Reactions between activated benzo[a]pyrene and nucleophilic compounds, with possible implications on the mechanism of tumor initiation J. Natl Cancer Inst. 53 1974 393 397
28. E. Cavalieri, and M. Calvin Molecular characteristics of some carcinogenic hydrocarbons Proc. Natl. Acad. Sci. U.S.A. 68 1971 1251 1253
29. E. Cavalieri, and M. Calvin 220 MHz nuclear magnetic resonance analysis and the selective protonation of benzo[a]pyrene and 6-methylbenzo[a]pyrene J. Chem. Soc. Perkin Trans. I 1972 1253 1256
30. E. Cavalieri, D. Chakravarti, J. Guttenplan, E. Hart, J. Ingle, R. Jankowiak, P. Muti, E. Rogan, J. Russo, R. Santen, and T. Sutter Catechol estrogen quinones as initiators of breast and other human cancers. Implications for biomarkers of susceptibility and cancer prevention BBA-Reviews on Cancer 1766 2006 63 78
31. E. Cavalieri, P. Devanesan, and E. Rogan Radical cations in the horseradish peroxidase and prostaglandin H synthase mediated metabolism and binding of benzo[a]pyrene to deoxyribonucleic acid Biochem. Pharmacol. 37 1988 2183 2187
32. E. Cavalieri, K. Frenkel, J.G. Liehr, E. Rogan, and D. Roy Estrogens as endogenous genotoxic agents: DNA adducts and mutations E. Cavalieri, E. Rogan, JNCI Monograph: Estrogens as Endogenous Carcinogens in the Breast and Prostate, No. 27 2000 Oxford University Press Maryland 75 93
33. E. Cavalieri, S. Higginbotham, and E. Rogan Dibenzo[a, l]pyrene: the most potent carcinogenic aromatic hydrocarbon Polycyclic Aromat. Compd. 6 1994 177 183
34. E. Cavalieri, and E. Rogan Role of radical cations in aromatic hydrocarbon carcinogenesis Environ. Health Perspectives. 64 1985 69 84
35. E. Cavalieri, and E. Rogan Mechanisms of tumor initiation by polycyclic aromatic hydrocarbons in mammals A.H. Neilson, The Handbook of Environmental Chemistry PAHs and Related Compounds vol. 3J 1998 Springer-Verlag Heidelberg 81 117
36. E. Cavalieri, and E. Rogan Unbalanced metabolism of endogenous estrogens in the etiology and prevention of human cancer. J Steroid Biochem. Mol. Biol. 125 2011 169 180
37. E. Cavalieri, E. Rogan, P. Cremonesi, and P. Devanesan Radical cations as precursors in the metabolic formation of quinones from benzo[a]pyrene and 6-fluorobenzo[a]pyrene: fluoro substitution as a probe for one-electron oxidation in aromatic substrates Biochem. Pharmacol. 37 1988 2173 2182
38. E. Cavalieri, E. Rogan, S. Higginbotham, P. Cremonesi, and S. Salmasi Tumor-initiating activity in mouse skin and carcinogenicity in rat mammary gland of fluorinated derivatives of benzo[a]pyrene and 3-methylcholanthrene J. Cancer Res. Clin. Oncol. 114 1988 16 22
39. E. Cavalieri, E. Rogan, R.W. Roth, R.K. Saugier, and A. Hakam The relationship between ionization potential and horseradish peroxidase/hydrogen peroxide-catalyzed binding of aromatic hydrocarbons to DNA Chem. Biol. Interact. 47 1983 87 109
40. E. Cavalieri, E. Rogan, and D. Sinha Carcinogenicity of aromatic hydrocarbons directly applied to rat mammary gland J. Cancer Res. Clin. Oncol. 114 1988 3 9
41. E. Cavalieri, E. Rogan, C. Warner, and A. Bobst Synthesis and characterization of benzo[a]pyrene and 6-methylbenzo[a]pyrene radical cations W.M. Cooke, A.J. Dennis, Polynuclear Aromatic Hydrocarbons: Mechanisms 1985 Battelle Press, Columbus Methods and Metabolism 227 236
42. E. Cavalieri, and R. Roth Reaction of methylbenzanthracenes and pyridine by one-electron oxidation: a model for metabolic activation and binding of carcinogenic aromatic hydrocarbons J. Org. Chem. 41 1976 2679 2684
43. E. Cavalieri, R. Roth, J. Althoff, C. Grandjean, K. Patil, S. Marsh, and D. McLaughlin Carcinogenicity and metabolic profiles of 3-methylcholanthrene oxygenated derivatives at the 1 and 2 positions Chem. Biol. Interact. 22 1978 69 81
44. E. Cavalieri, R. Roth, and E.G. Rogan Metabolic activation of aromatic hydrocarbons by one-electron oxidation in relation to the mechanism of tumor initiation R.I. Freudenthal, P.W. Jones, Polynuclear Aromatic Hydrocarbons: Chemistry, Metabolism and Carcinogenesis vol. 1 1976 Raven Press New York 181 190
45. E. Cavalieri, D. Sinha, and E. Rogan Rat mammary gland vs mouse skin: different mechanisms of activation of aromatic hydrocarbons A. Bjorseth, A.J. Dennis, Polynuclear Aromatic Hydrocarbons: Chemistry and Biological Effects 1980 Battelle Press Columbus 215 231
46. E.L. Cavalieri, P. Devanesan, M.C. Bosland, A.F. Badawi, and E.G. Rogan Catechol estrogen metabolites and conjugates in different regions of the prostate of Noble rats treated with 4-hydroxyestradiol: implications for estrogen-induced initiation of prostate cancer Carcinogenesis 23 2002 329 333
47. E.L. Cavalieri, S. Higginbotham, N.V.S. RamaKrishna, P.D. Devanesan, R. Todorovic, E.G. Rogan, and S. Salmasi Comparative dose-response tumorigenicity studies of dibenzo[a, l]pyrene vs 7,12-dimethylbenz[a]anthracene, benzo[a]pyrene and two dibenzo[a, l]pyrene dihydrodiols in mouse skin and rat mammary gland Carcinogenesis 12 1991 1939 1944
48. E.L. Cavalieri, S. Kumar, R. Todorovic, S. Higginbotham, A.F. Badawi, and E.G. Rogan Imbalance of estrogen homeostasis in kidney and liver of hamsters treated with estradiol: implications for estrogen-induced initiation of renal tumors Chem. Res. Toxicol. 14 2001 1041 1050
49. E.L. Cavalieri, K.-M. Li, N. Balu, M. Saeed, P. Devanesan, S. Higginbotham, J. Zhao, M.L. Gross, and E. Rogan Catechol ortho-quinones: the electrophilic compounds that form depurinating DNA adducts and could initiate cancer and other diseases Carcinogenesis 23 2002 1071 1077
50. E.L. Cavalieri, and E.G. Rogan The approach to understanding aromatic hydrocarbon carcinogenesis. The central role of radical cations in metabolic activation Pharmac. Ther. 55 1992 183 199
51. E.L. Cavalieri, and E.G. Rogan Depurinating estrogen-DNA adducts in the etiology and prevention of breast and other human cancers Future Oncology 6 2010 75 91
52. E.L. Cavalieri, E.G. Rogan, P.D. Devanesan, P. Cremonesi, R.L. Cerny, M.L. Gross, and W.J. Bodell Binding of benzo[a]pyrene to DNA by cytochrome P450-catalyzed one-electron oxidation in rat liver microsomes and nuclei Biochemistry 29 1990 4820 4827
53. E.L. Cavalieri, E.G. Rogan, S. Higginbotham, P. Cremonesi, and S. Salmasi Tumor-initiating activity in mouse skin and carcinogenicity in rat mammary gland of dibenzo[a]pyrenes: the very potent activity of dibenzo[a,l]pyrene J. Cancer Res. Clin. Oncol. 115 1989 67 72
54. E.L. Cavalieri, E.G. Rogan, S. Higginbotham, P. Cremonesi, and S. Salmasi Tumorigenicity of 7,12-dimethylbenz[a]anthracene, some of its fluorinated derivatives and 1,2,3,4-tetrahydro-7,12-dimethylbenz[a]anthracene in mouse skin and rat mammary gland Polycyclic Aromat. Compd. 1 1990 59 70
55. E.L. Cavalieri, E.G. Rogan, K.-M. Li, R. Todorovic, F. Ariese, R. Jankowiak, N. Grubor, and G.J. Small Identification and quantification of the depurinating DNA adducts formed in mouse skin treated with dibenzo[a,l]pyrene (DB[a,l]P), or its metabolites and in rat mammary gland treated with DB[a,l]P Chem. Res. Toxicol. 18 2005 976 983
56. E.L. Cavalieri, E.G. Rogan, W.J. Murray, and N.V.S. RamaKrishna Mechanistic aspects of benzo[a]pyrene metabolism P. Garrigues, M. Lamotte, Polycyclic Aromatic Compounds 1993 Gordon and Breach Langhorne, PA 1047 1054
57. E.L. Cavalieri, D.E. Stack, P.D. Devanesan, R. Todorovic, I. Dwivedy, S. Higginbotham, S.L. Johansson, K.D. Patil, M.L. Gross, J.K. Gooden, R. Ramanathan, R.L. Cerny, and E.G. Rogan Molecular origin of cancer: catechol estrogen-3,4-quinones as endogenous tumor initiators Proc. Natl. Acad. Sci. U.S.A. 94 1997 10937 10942
58. D. Chakravarti, P. Mailander, E.L. Cavalieri, and E.G. Rogan Evidence that error-prone DNA repair converts dibenzo[a,l]pyrene-induced depurinating lesions into mutations: formation, clonal proliferation and regression of initiated cells carrying H-ras oncogene mutations in early preneoplasia Mutat. Res. 456 2000 17 32
59. D. Chakravarti, P. Mailander, K.-M. Li, S. Higginbotham, H. Zhang, M.L. Gross, E. Cavalieri, and E. Rogan Evidence that a burst of DNA depurination in SENCAR mouse skin induces error-prone repair and form mutations in the H-ras gene Oncogene 20 2001 7945 7953
60. D. Chakravarti, J.C. Pelling, E.L. Cavalieri, and E.G. Rogan Relating aromatic hydrocarbon-induced DNA adducts and c-Harvey-ras mutations in mouse skin papillomas: the role of apurinic sites Proc. Natl. Acad. Sci. USA 92 1995 10422 10426
61. D. Chakravarti, M. Zahid, M. Backora, E.M. Myers, N. Gaikwad, D.D. Weisenburger, E.L. Cavalieri, E.G. Rogan, and S.S. Joshi Ortho-quinones of benzene and estrogen induce hyperproliferation of human peripheral blood mononuclear cells Leuk Lymp. 47 2006 2635 2644
62. T.K. Chang, W.B. Lee, and H.H. Ko Trans-resveratrol modulates the catalytic activity and mRNA expression of the procarcinogen-activating human cytochrome P450 1B1 Can. J. Physiol. Pharmacol 78 2000 874 881
63. P. Chary, G.J. Latham, D.L. Robberson, S.J. Kim, S. Han, C.M. Harris, T.M. Harris, and R.S. Lloyd In vivo and in vitro replication consequences of stereoisomeric benzo[a]pyrene-7,8-dihydrodiol 9,10-epoxide adducts on adenine N6 at the second position of N-ras codon 61 J. Biol. Chem. 270 1995 4990 5000
64. L. Chen, P.D. Devanesan, S. Higginbotham, F. Ariese, R. Jankowiak, G.J. Small, E.G. Rogan, and E.L. Cavalieri Expanded analysis of benzo[a]pyrene-DNA adducts formed in vitro and in mouse skin: their significance in tumor initiation Chem. Res. Toxicol. 9 1996 897 903
65. Z.H. Chen, Y.J. Hurh, H.K. Na, J.H. Kim, Y.J. Chun, D.H. Kim, K.S. Kang, M.H. Cho, and Y.J. Surh Resveratrol inhibits TCDD-induced expression of CYP1A1 and CYP1B1 and catechol estrogen-mediated oxidative DNA damage in cultured human mammary epithelial cells Carcinogenesis 25 2004 2005 2013
66. S.C. Cheng, A.S. Prakash, M.A. Pigott, B.D. Hilton, H. Lee, R.G. Harvey, and A. Dipple A metabolite of the carcinogen 7,12-dimethylbenz[a]anthracene that reacts predominantly with adenine residues in DNA Carcinogenesis 9 1988 1721 1723
67. S.C. Cheng, A.S. Prakash, M.A. Pigott, B.D. Hilton, J.M. Roman, H.M. Lee, R.G. Harvey, and A. Dipple Characterization of the 7,12-dimethylbenz[a] anthracene-adenine nucleoside adducts Chem. Res. Toxicol. 1 1988 216 221
68. M.W. Chou, and P.P. Fu Sterioselective metabolism of 8- and 9-fluorobenzo[a]pyrene by rat liver microsomes: absolute configurations of trans-dihydrodiol metabolites J. Toxic. Environ. Health 14 1984 221 223
69. M.W. Chou, S.K. Yang, W. Sydor, and C.S. Yang Metabolism of 7,12-dimethylbenz(a)anthracene and 7-hydroxymethyl-12-methylbenz(a)anthracene by rat liver and microsomes Cancer Res. 41 1981 1559 1564
70. I. Chouroulinkov, A. Gentil, P.L. Grover, and P. Sims Tumor-initiating activities on mouse skin of dihydrodiols derived from benzo[a]pyrene Br. J. Cancer 34 1976 523 532
71. I. Chouroulinkov, A. Gentil, B. Tierney, P.L. Grover, and P. Sims The initiation of tumours on mouse skin by dihydrodiols derived from 7,12-dimethylbenz(a)anthracene and 3-methylcholanthrene Int. J. Cancer 24 1979 455 460
72. Y.J. Chun, M.Y. Kim, and F.P. Guengerich Resveratrol is a selective human cytochrome P45 1A1 inhibitor Biochem. Biophys. Res. Commun. 262 1999 20 24
73. A.M. Colapietro, A.L. Goodell, and R.C. Smart Characterization of benzo[a]pyrene-initiated mouse skin papillomas for Ha-ras mutations and protein kinase C levels Carcinogenesis 14 1993 2289 2295
74. A.H. Conney Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydrocarbons. G.H.A Clowes Memorial Lecture. Cancer Res. 42 1982 4875 4917
75. J.W. Cook, C.L. Hewett, and I. Hieger The isolation of a cancer-producing hydrocarbon from coal tar, I, II and III J. Chem. Soc. 1933 395 405
76. C.S. Cooper, O. Ribeiro, A. Hewer, C. Walsh, K. Pal, P.L. Grover, and P. Sims The involvement of a 'bay-region' and a non-'bay-region' diol-epoxide in the metabolic activation of benz[a]anthracene in mouse skin and hamster embryo cells Carcinogenesis 1 1980 233 243
77. P. Cremonesi, E. Cavalieri, and E. Rogan One-electron oxidation of 6-substituted benzo[a]pyrenes by manganic acetate J. Org. Chem. 54 1989 3561 3570
78. P. Cremonesi, B. Hietbrink, E.G. Rogan, and E.L. Cavalieri One-electron oxidation of dibenzo[a]pyrenes by manganic acetate J. Org. Chem. 57 1992 3309 3312
79. P. Cremonesi, E. Rogan, and E. Cavalieri Correlation studies of anodic peak potentials and ionization potentials for polycyclic aromatic hydrocarbons Chem. Res. Toxicol. 5 1992 346 355
80. P. Cremonesi, D.E. Stack, E.G. Rogan, and E.L. Cavalieri Radical cations of benzo[a]pyrene and 6- substituted derivatives: synthesis and reaction with nucleophiles J. Org. Chem. 59 1994 7683 7687
81. R.G. Croy, J.K. Selkirk, R.G. Harvey, J.F. Engel, and H.V. Gelboin Separation of ten benzo(a)pyrene phenols by recycle high pressure liquid chromatography and identification of four phenols as metabolites Biochem. Pharmacol. 25 1976 227 230
82. S. Das, and D.K. Das Anti-inflammatory responses of resveratrol Inflammation & Allergy - Drug Targets 6 2007 168 173
83. J.H. Dawson Probing structure-function relations in heme-containing oxygenases and peroxidases Science 240 1988 433 439
84. S. De Flora, C.F. Cesarone, R.M. Balansky, A. Albini, F. D'Agostini, C. Bennicelli, M. Bagnasco, A. Camoirano, L. Scatolini, A. Rovida, and A. Izzotti Chemopreventive properties and mechanisms of N-acetylcysteine. The experimental background J. Cell. Biochem. 22 Suppl. 1995 33 41
85. P. Devanesan, E. Rogan, and E. Cavalieri The relationship between ionization potential and prostaglandin H synthase-catalyzed binding of aromatic hydrocarbons to DNA Chem. Biol. Interact. 61 1987 89 95
86. P. Devanesan, R.J. Santen, W.P. Bocchinfuso, K.S. Korach, E.G. Rogan, and E.L. Cavalieri Catechol estrogen metabolites and conjugates in mammary tumors and hyperplastic tissue from estrogen receptor alpha knock out (ERKO)/Wnt 1 mice; implications for initiation of mammary tumors Carcinogenesis 22 2001 1573 1576
87. P.D. Devanesan, P. Cremonesi, J.E. Nunnally, E.G. Rogan, and E.L. Cavalieri Metabolism and mutagenicity of dibenzo[a,e]pyrene and the very potent environmental carcinogen dibenzo[a,l]pyrene Chem. Res. Toxicol. 3 1990 580 586
88. P.D. Devanesan, S. Higginbotham, F. Ariese, R. Jankowiak, M. Suh, G.J. Small, E.L. Cavalieri, and E.G. Rogan Depurinating and stable benzo[a]pyrene-DNA adducts formed in isolated rat liver nuclei Chem. Res. Toxicol. 8 1996 1113 1116
89. P.D. Devanesan, N.V.S. RamaKrishna, N.S. Padmavathi, S. Higginbotham, E.G. Rogan, E.L. Cavalieri, G.A. Marsch, R. Jankowiak, and G.J. Small Identification and quantitation of 7,12-dimethylbenz[a]anthracene-DNA adducts formed in mouse skin Chem. Res. Toxicol. 6 1993 364 371
90. P.D. Devanesan, N.V.S. RamaKrishna, R. Todorovic, E.G. Rogan, E.L. Cavalieri, H. Jeong, R. Jankowiak, and G.J. Small Identification and quantitation of benzo[a]pyrene-DNA adducts formed by rat liver microsomes in vitro Chem. Res. Toxicol. 5 1992 302 309
91. R.B. Dickson, and G.M. Stancel Estrogen receptor-mediated processes in normal and cancer cells J. Natl. Cancer Inst. Monogr. 27 2000 135 145
92. J. DiGiovanni, L. Diamond, J.M. Singer, F.B. Daniel, D.T. Witiak, and T.J. Slaga Tumor-initiating activity of 4-fluoro-7,12-dimethylbenz[a]anthracene and 1,2,3,4-tetrahydro-7,12-dimethylbenz[a]anthracene in female SENCAR mice Carcinogenesis 3 1982 651 655
93. A. Dipple Polynuclear aromatic carcinogens C.E. Searle, Chemical Carcinogens 1976 American Chemical Society Washington 245 314
94. A. Dipple, R.C. Moschel, and C.A.H. Bigger Polynuclear aromatic carcinogens C.E. Searle, Chemical Carcinogens second ed. vol. 1 1984 American Chemical Society Washington 41 163
95. T.A. Dix, and L.J. Marnett Metabolism of polycyclic aromatic hydrocarbon derivatives to ultimate carcinogens during lipid-peroxidation Science 221 1983 77 79
96. C. Drevon, C. Piccoli, and R. Montesano Mutagenicity assays of estrogenic hormones in mammalian cells Mutat. Res. 89 1981 83 90
97. E.J. Duell, R.C. Millikan, G.S. Pittman, S. Winkel, R.M. Lunn, C.K. Tse, A. Eaton, H.W. Mohrenweiser, B. Newman, and D.A. Bell Polymorphisms in the DNA repair gene XRCC1 and breast cancer. Cancer Epidemiol Biomarkers Prev. 10 2001 217 222
98. W.F. Dunning, and M.P. Curtis Relative carcinogenic activity of monomethyl derivatives of benzo[a]anthracene in Fisher line 344 rats J. Natl Cancer Inst. 25 1960 387 391
99. I. Dwivedy, P. Devanesan, P. Cremonesi, E. Rogan, and E. Cavalieri Synthesis and characterization of estrogen 2,3- and 3,4-quinones. Comparison of DNA adducts formed by the quinones versus horseradish peroxidase-activated catechol estrogens Chem. Res. Toxicol. 5 1992 828 833
100. E. Eisenstadt, A.J. Warren, J. Porter, D. Atkins, and J.H. Miller Carcinogenic epoxides of benzo[a]pyrene and cyclopental[cd]pyrene induce base substitutions via specific transversions Proc. Natl. Acad. Sci. USA 79 1982 1945 1949
101. H.S. Feigelson, and B.E. Henderson Estrogens and breast cancer Carcinogenesis 17 1996 2279 2284
102. M. Floreani, E. Napoli, L. Quintieri, and P. Palatini Oral administration of trans-resveratrol to guinea pigs increases cardiac DT-diaphorase and catalase activities, and protects isolated atria from menadione toxicity Life Sci. 72 2003 2741 2750
103. J. Fried One-electron oxidation of polycyclic aromatics as a model for the metabolic activation of carcinogenic hydrocarbons P.O.P. Ts'o, J. DiPaolo, Chemical Carcinogens, Part A 1974 Marcel Dekker New York 197 215
104. J. Fried, and D.E. Schumm One electron transfer oxidation of 7,12-dimethylbenz[a]anthracene, a model for the metabolic activation of carcinogenic hydrocarbons J. Am. Chem. Soc. 89 1967 5508 5509
105. J. Fuchs, J. Mlcoch, F. Oesch, and K.L. Platt Characterization of highly polar DNA adducts derived from dibenz[a,h]anthracene (DBA), 3,4-dihydroxy-3,4- dihydro-DBA, and 3,4,10,11-tetrahydroxy-3,4,10,11-tetrahydro-DBA Toxicol. Ind. Health 9 1993 503 509
106. J. Fuchs, J. Mlcoch, K.L. Platt, and F. Oesch Characterization of highly polar bis-dihydrodiol epoxide-DNA adducts formed after metabolic activation of dibenz[a,h]anthracene Carcinogenesis 14 1993 863 867
107. J. Furth Hormones as etiological agents in neoplasia F.F. Becker, Cancer. A Comprehensive Treatise, 1. Etiology: Chemical and Physical Carcinogenesis 1982 Cancer Plenum Press NY, USA 89 134 (Chapter 4)
108. N. Gaikwad, L. Yang, D.D. Weisenburger, J. Vose, C. Beseler, E. Rogan, and E. Cavalieri Urinary biomarkers suggest that estrogen-DNA adducts may play a role in the aetiology of non-Hodgkin lymphoma Biomarkers 14 2009 502 512
109. N.W. Gaikwad, E.G. Rogan, and E.L. Cavalieri Evidence from ESI-MS for NQO1-catalyzed reduction of estrogen ortho-quinones Free Radic. Biol. Med. 43 2007 1289 1298
110. N.W. Gaikwad, L. Yang, P. Muti, J.L. Meza, S. Pruthi, J.N. Ingle, E.G. Rogan, and E.L. Cavalieri The molecular etiology of breast cancer: evidence from biomarkers of risk Int. J. Cancer 122 2008 1949 1957
111. N.W. Gaikwad, L. Yang, S. Pruthi, J.N. Ingle, N. Sandhu, E. Rogan, and E. Cavalieri Urine biomarkers of risk in the molecular etiology of breast cancer Breast Cancer Basic Clin. Res. 3 2009 1 8
112. N.W. Gaikwad, L. Yang, E.G. Rogan, and E.L. Cavalieri Evidence from ESI-MS for NQO2-catalyzed reduction of estrogen ortho-quinones Free Radic. Biol. Med. 46 2009 253 262
113. M.H. Gail, L.A. Brinton, D.P. Byar, D.K. Corle, S.B. Green, C. Schairer, and J.J. Mulvhill Projecting individualized probabilities of developing breast cancer for white females who are being examined annually J. Natl Cancer Inst. 81 1989 1879 1886
114. H.V. Gelboin Benzo[a]pyrene metabolism, activation and carcinogenesis: role and regulation of mixed-function oxidases and related enzymes Physiol. Rev. 60 1980 1107 1166
115. H.S. Gill, P.L. Kole, J.C. Wiley, K.M. Li, S. Higginbotham, E.G. Rogan, and E.L. Cavalieri Synthesis and tumor-initiating activity in mouse skin of dibenzo[a, l]pyrene syn- and anti-fjord-region diol epoxides Carcinogenesis 15 1994 2455 2460
116. R.D. Gill, B.E. Butterworth, A.N. Nettikumara, and J. DiGiovanni Relationship between DNA adduct formation and unscheduled DNA synthesis (UDS) in cultured mouse epidermal keratinocytes Environ. Mol. Mutagen. 18 1991 200 206
117. W.F. Greenlee, E.A. Gross, and R.D. Irons Relationship between benzene toxicity and the disposition of 14C-labelled benzene metabolites in the rat Chem. Biol. Interact. 33 1981 285 299
118. J.T. Groves, R.C. Haushalter, M. Nakamura, T.E. Nemo, and B.J. Evans High-valent iron-porphyrin complexes related to peroxidase and cytochrome P-450 J. Am. Chem. Soc. 103 1981 2884 2886
119. J.T. Groves, and G.A. McClusky Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450: evidence for a carbon radical intermediate Biochem. Biophys. Res. Commun. 81 1978 154 160
120. F.P. Guengerich, Y.J. Chun, D. Kima, E.M.J. Gillam, and T. Shimada Cytochrome P450 1B1: a target for inhibition in anticarcinogenesis strategies Mutat. Res. 523-524 2003 173 182
121. H. Haaf, and M. Metzler In vitro metabolism of diethylstilbestrol by hepatic, renal and uterine microsomes of rats and hamsters. Effects of different inducers Biochem. Pharmacol. 34 1985 3107 3115
122. W.C. Hahn, and R.A. Weinberg Rules for making human tumor cells N. Engl. J. Med. 347 2002 1593 1603
123. A.A. Hanson, E.G. Rogan, and E.L. Cavalieri Synthesis of adducts formed by iodine oxidation of aromatic hydrocarbons in the presence of deoxyribonucleosides and nucleobases Chem. Res. Toxicol. 11 1998 1201 1208
124. R.G. Harvey, and F.B. Dunne Multiple regions of metabolic activation of carcinogenic hydrocarbons Nature (Lond) 274 1978 566 568
125. C.L. Hayes, D.C. Spink, B.C. Spink, J.Q. Cao, N.J. Walker, and T.R. Sutter 17β-Estradiol hydroxylation catalyzed by human cytochrome P450 1B1 Proc. Natl. Acad. Sci. USA 93 1996 9776 9781
126. S.S. Hecht, W.E. Bondinell, and D. Hoffmann Chrysene and methylchrysenes: presence in tobacco smoke and carcinogenicity J. Natl Cancer Inst. 53 1974 1121 1133
127. S.S. Hecht, N. Hirota, M. Loy, and D. Hoffmann Tumor-initiating activity of fluorinated 5-methylchrysenes Cancer Res. 38 1978 1694 1698
128. S.S. Hecht, E. LaVoie, R. Mazzarese, S. Amin, V. Bedenko, and D. Hoffmann 1,2-Dihydro-1,2-dihydroxy-5-methylchrysene, a major activated metabolite of the environmental carcinogen 5-methylchrysene Cancer Res. 38 1978 2191 2194
129. S.S. Hecht, E. LaVoie, R. Mazzarese, N. Hirota, T. Ohmori, and D. Hoffmann Comparative mutagenicity, tumor-initiating activity, carcinogenicity and in vitro metabolism of fluorinated 5-methylchrysenes J. Natl Cancer Inst. 63 1979 855 861
130. S.S. Hecht, R. Mazzarese, S. Amin, E. La Voie, and D. Hoffmann On the metabolic activation of 5-methylchrysene P.W. Jones, P. Leber, Polynuclear Aromatic Hydrocarbons 1979 Ann Arbor Science Ann Arbor 733 752
131. A.L. Herbst, H. Ulfelder, and D.C. Poskanzer Adenocarcinoma of the vagina. Association of maternal stilbestrol therapy with tumor appearance in young women N. Engl. J. Med. 284 1971 878 881
132. I. Hieger The spectra of cancer-producing tars and oils and of related substances Biochem. J. 24 1930 505 511
133. S. Higginbotham, N.V.S. RamaKrishna, S.L. Johansson, E.G. Rogan, and E.L. Cavalieri Tumor-initiating activity and carcinogenicity of dibenzo[a,l]pyrene versus 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene at low doses in mouse skin Carcinogenesis 14 1993 875 878
134. B. Hinrichs, M. Zahid, M. Saeed, M.F. Ali, E.L. Cavalieri, and E.G. Rogan Formation of diethylstilbestrol-DNA adducts in human breast epithelial cells and inhibition by resveratrol J. Steroid Biochem. Mol. Biol. 127 2011 276 281
135. D. Hoffman, W.E. Bondinell, and E.L. Wynder Carcinogenicity of methylchrysenes Science 183 1974 215 216
136. G. Holder, H. Yagi, P. Dansette, D.M. Jerina, W. Levin, A.Y. Lu, and A.H. Conney Effects of inducers and epoxide hydrase on the metabolism of benzo[a]pyrene by liver microsomes and a reconstituted system: analysis by high pressure liquid chromatography Proc. Natl. Acad. Sci. USA 71 1974 4356 4360
137. H. Ide, H. Murayama, A. Murakami, T. Morii, and K. Makino Effects of base damages on DNA replication-mechanism of preferential purine nucleotide insertion opposite abasic site in template DNA Nucl. Acids Res. Symp. Ser. 27 1992 167 168
138. International Agency for Research on Cancer IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Humans vol. 3 1973 IARC Lyon
139. International Agency for Research on Cancer IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans vol. 32 1983 IARC Lyon
140. S.-T. Jan, P. Devanesan, D. Stack, R. Ramanathan, J. Byun, M.L. Gross, E. Rogan, and E. Cavalieri Metabolic activation and formation of DNA adducts of hexestrol, a synthetic non-steroidal carcinogenic estrogen Chem. Res. Toxicol. 11 1998 412 419
141. M. Jang, L. Cai, G.O. Udeani, K.V. Slowing, C.F. Thomas, C.W. Beecher, H.H. Fong, N.R. Farnsworth, A.D. Kinghorn, R.G. Mehta, R.C. Moon, and J.M. Pezzuto Cancer chemopreventive activity of resveratrol, a natural product derived from grapes Science 275 1997 218 220
142. C.R. Jefcoate, J.G. Liehr, R.J. Santen, T.R. Sutter, J.D. Yager, W. Yue, S.J. Santner, R. Tekmal, L. Demers, R. Pauley, F. Naftolin, G. Mor, and L. Berstein Tissue-specific synthesis and oxidative metabolism of estrogens E. Cavalieri, E. Rogan, JNCI Monograph 27: Estrogens as Endogenous Carcinogens in the Breast and Prostate 2000 Oxford Press 95 112
143. L. Jeftic, and R.N. Adams Electrochemical oxidation pathways of benzo[a]pyrene J. Am. Chem. Soc. 92 1970 1332 1337
144. D.M. Jerina, and J.W. Daly Arene oxides: a new aspect of drug metabolism Science 185 1974 573 582
145. D.M. Jerina, and J.W. Daly Oxidation at carbon D.V. Parke, R.L. Smith, Drug Metabolism - From Microbe to Man 1977 Taylor and Francis London 13 32
146. M.D. Johnson, and M. Calvin Induced nucleophilic substitution in benzo[a]pyrene Nature (London) 241 1973 271 272
147. H. Kappus Lipid peroxidation: mechanisms, analysis, enzymology and biological relevance H. Sies, Oxidative Stress 1985 Academic Press New York 273 310
148. C.B. Kasper Biochemical distinctions between the nuclear and microsomal membranes from rat hepatocytes J. Biol. Chem. 246 1971 577 581
149. A.S. Khandwala, and C.B. Kasper Preferential induction of aryl hydroxylase activity in rat liver nuclear envelope by 3-methylcholanthrene Biochem. Biophys. Res. Commun. 54 1973 1241 1246
150. S.U. Kim, S.K. Park, K.Y. Yoo, K.S. Yoon, J.Y. Choi, J.S. Seo, W.Y. Park, J.H. Kim, D.Y. Noh, S.H. Ahn, K.J. Choe, P.T. Strickland, A. Hirvonen, and D. Kang XRCC1 genetic polymorphism and breast cancer risk Pharmacogenetics 12 2002 335 338
151. D.K. Klinedinst, and N.R. Drinkwater Mutagenesis by apurinic sites in normal and ataxia telangiectasia human lymphoblastoid cells Mol. Carcinogenesis 6 1992 32 42
152. M. Koreeda, P.D. Moore, P.G. Wislocki, W. Levin, H. Yagi, and D.M. Jerina Binding of benzo[a]pyrene 7,8-diol-9,10-epoxides to DNA, RNA and protein of mouse skin occurs with high stereoselectivity Science 199 1978 778 781
153. R. Lang, and U. Redmann Non-mutagenicity of some sex hormones in the Ames salmonella/microsome mutagenicity test Mutat. Res. 67 1979 361 365
154. R. Lang, and R. Reimann Studies for a genotoxic potential of some endogenous and exogenous sex steroids. I. Communication: examination for the induction of gene mutations using the Ames Salmonella/microsome test and the HGPRT test in V79 cells Environ. Mol. Mutagen. 21 1993 272 304
155. M.H. Lareef, J. Garber, P.A. Russo, I.H. Russo, R. Heulings, and J. Russo The estrogen antagonist ICI-182-780 does not inhibit the transformation phenotypes induced by 17-beta-estradiol and 4-OH estradiol in human breast epithelial cells Int. J. Oncol. 26 2005 423 429
156. S. Lecoq, W. Pfau, P.L. Grover, and D.H. Phillips HPLC separation of 32P-postlabelled DNA adducts formed from dibenz[a,h]anthracene in skin Chem. Biol. Interact. 85 1992 173 185
157. S. Lecoq, M.N. She, A. Hewer, P.L. Grover, K.L. Platt, F. Oesch, and D.H. Phillips The metabolic activation of dibenz[a,h]anthracene in mouse skin examined by 32P-postlabelling: Minor contribution of the 3,4-diol 1,2-oxides to DNA binding Carcinogenesis 12 1991 1079 1083
158. S.S. Leonard, C. Xia, B.H. Jiang, B. Stinefelt, H. Klandorf, G.K. Harris, and X. Shi Resveratrol scavenges reactive oxygen species and effects radical-induced cellular responses Biochem. Biophys. Res. Commun. 309 2003 1017 1026
159. S. Lesko, W. Caspary, R. Lorentzen, and P.O.P. Ts'o Enzymic formation of 6-oxobenzo[a]pyrene radical in rat liver homogenates for carcinogenic benzo[a]pyrene Biochemistry 14 1975 3978 3984
160. S.A. Lesko Jr., A. Smith, P.O. Ts'o, and R.S. Umans Interaction of nucleic acids IV. The physical binding of 3,4-benzpyrene to nucleosides, nucleotides, nucleic acids and nucleoprotein Biochemistry 7 1968 434 447
161. W. Levin, M.K. Buening, A.W. Wood, R.L. Chang, D.R. Thakker, D.M. Jerina, and A.H. Conney Tumorigenic activity of 3-methylcholanthrene metabolites on mouse skin and in newborn mice Cancer Res. 39 1979 3549 3553
162. W. Levin, D.R. Thakker, A.W. Wood, R.L. Chang, R.E. Lehr, D.M. Jerina, and A.H. Conney Evidence that benzo(a)anthracene 3,4-diol-1,2-epoxide is an ultimate carcinogen on mouse skin Cancer Res. 38 1978 1705 1710
163. W. Levin, A.W. Wood, R.L. Chang, T.J. Slaga, H. Yagi, D.M. Jerina, and A.H. Conney Marked differences in the tumor-initiating activity of optically pure (+)- and (-)-trans-7,8-dihydrodroxy-7,8-dihydrobenzo[a]pyrene on mouse skin Cancer Res. 37 1977 2721 2725
164. W. Levin, A.W. Wood, P.G. Wislocki, J. Kapitulnik, H. Yagi, D.M. Jerina, and A.H. Conney Carcinogenicity of benzo-ring derivatives of benzo[a]pyrene on mouse skin Cancer Res. 37 1977 3356 3361
165. W. Levin, A.W. Wood, H. Yagi, P.M. Dansette, D.M. Jerina, and A.H. Conney Carcinogenicity of benzo[a]pyrene 4,5-, 7,8- and 9,10-oxides on mouse skin Proc. Natl. Acad. Sci. USA 73 1976 243 247
166. W. Levin, A.W. Wood, H. Yagi, D.M. Jerina, and A.H. Conney (±) trans-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene: a potent skin carcinogen when applied topically to mice Proc. Natl. Acad. Sci. USA 73 1976 3867 3871
167. D.F. Lewis, C. Ioannides, and D.V. Parke Molecular orbital studies of oxygen activation and mechanism of cytochromes P-450-mediated oxidative metabolism of xenobiotics Chem. Biol. Interact. 70 1989 263 280
168. J.J. Li Estrogen carcinogenesis in hamster tissues: update Endocr. Rev. 14 1993 94 95
169. J.J. Li, and S.A. Li Estrogen carcinogenesis in Syrian hamster tissues: role of metabolism Fed. Proc. 46 1987 1858 1863
170. J.J. Li, and S.A. Li Estrogen carcinogenesis in hamster tissues: a critical review Endocr. Rev. 11 1990 524 531
171. J.J. Li, S.A. Li, J.K. Klicka, J.A. Parsons, and L.K. Lam Relative carcinogenic activity of various synthetic and natural estrogens in the Syrian hamster kidney Cancer Res. 43 1983 5200 5204
172. K.-M. Li, R. Todorovic, P. Devanesan, S. Higginbotham, H. Köfeler, R. Ramanathan, M.L. Gross, E.G. Rogan, and E.L. Cavalieri Metabolism and DNA binding studies of 4-hydroxyestradiol and estradiol-3,4-quinone in vitro and in female ACI rat mammary gland in vivo Carcinogenesis 25 2004 289 297
173. K.-M. Li, R. Todorovic, P. Devanesan, E.G. Rogan, and E.L. Cavalieri Detection of 3-methylcholanthrene-DNA adducts formed in vitro Proc. Am. Assoc. Cancer Res. 37 1996 119
174. K.-M. Li, R. Todorovic, E.G. Rogan, E.L. Cavalieri, F. Ariese, M. Suh, R. Jankowiak, and G.J. Small Identification and quantitation of dibenzo[a, l]pyrene-DNA adducts formed by rat liver microsomes in vitro: preponderance of depurinating adducts Biochemistry 34 1995 8043 8049
175. J.G. Liehr Is estradiol a genotoxic mutagenic carcinogen? Endocr. Rev. 21 2000 40 54
176. J.G. Liehr, A.M. Ballatore, B.B. Dague, and A.A. Ulubelen Carcinogenicity and metabolic activation of hexestrol Chem. Biol. Interact. 55 1985 157 176
177. J.G. Liehr, W.F. Fang, D.A. Sirbasku, and A. Ari-Ulubelen Carcinogenicity of catechol estrogens in Syrian hamsters J. Steroid Biochem. 24 1986 353 356
178. T. Lindahl, and B. Nyberg Rate of depurination of native deoxyribonucleic acid Biochemistry 11 1972 3610 3618
179. L.A. Loeb, and B.D. Preston Mutagenesis by apurinic/apyrimidinic Ann. Rev. Genet. 20 1986 201 230
180. G.H. Loew, J. Wong, J. Phillips, L. Hjelmeland, and G. Pack Quantum chemical studies of the metabolism of benzo(a)pyrene Cancer Biochem. Biophys. 2 1978 123 130
181. R.J. Lorentzen, W.J. Caspary, S.A. Lesko, and P.O.P. Ts'o The autoxidation of 6-hydroxybenzo[a]pyrene and 6-oxobenzo[a]pyrene radical, reactive metabolites of benzo[a]pyrene Biochemistry 14 1975 3970 3977
182. F. Lu, M. Zahid, M. Saeed, E.L. Cavalieri, and E.G. Rogan Estrogen metabolism and formation of estrogen-DNA adducts in estradiol-treated MCF-10F cells. The effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin induction and catechol-O-methyltransferase inhibition J. Steroid Biochem. Mol. Biol. 105 2007 150 158
183. F. Lu, M. Zahid, M. Saeed, E.L. Cavalieri, and E.G. Rogan Resveratrol prevents estrogen-DNA adduct formation and neoplastic transformation in MCF-10F cells Cancer Prev. Res. 1 2008 135 145
184. R.M. Lunn, R.G. Langlois, L.L. Hsieh, C.L. Thompson, and D.A. Bell XRCC1 polymorphisms: effects on aflatoxin B1-DNA adducts and glycophorin A variant frequency Cancer Res. 59 1999 2557 2561
185. A.D. MacNicoll, P.L. Grover, and P. Sims The metabolism of a series of polycyclichydrocarbons by mouse skin maintained in short-term organ culture Chem. Biol. Interact. 29 1980 169 188
186. P.C. Mailander, J.L. Meza, S. Higginbotham, and D. Chakravarti Induction of A.T to G.C mutations by erroneous repair of depurinated DNA following estrogen treatment of the mammary gland of ACI rats.J Steroid Biochem. Mol. Biol. 101 2006 204 215
187. P.T. Männistö, and S. Kaakkola Catechol-O-methyltransferase (COMT): biochemistry, molecular biology, pharmacology, and clinical efficacy of the new selective COMT inhibitors Pharmacol. Rev. 51 1999 593 628
188. Y. Markushin, N. Gaikwad, H. Zhang, P. Kapke, E.G. Rogan, E.L. Cavalieri, B.J. Trock, C. Pavlovich, and R. Jankowiak Potential biomarker for early risk assessment of prostate cancer Prostate 66 2006 1565 1571
189. Y. Markushin, P. Kapke, M. Saeed, H. Zhang, A. Dawoud, E.G. Rogan, E.L. Cavalieri, and R. Jankowiak Development of monoclonal antibodies to 4-hydroxyestrogen-2-N-acetylcysteine conjugates: immunoaffinity and spectroscopic studies Chem. Res. Toxicol. 18 2005 1520 1527
190. L.J. Marnett Prostaglandin synthase-mediated metabolism of carcinogens and a potential role of peroxyl radicals as reactive intermediates Environ. Health Perspect. 88 1990 5 12
191. L.J. Marnett, P. Weller, and J.R. Battista Comparison of the peroxidase activity of heme-proteins and cytochrome P-450 P.R. Ortiz de Montellano, Cytochrome P-450 1986 Plenum Press New York 29 74
192. M.A. Mehlman Causal relationship between non-Hodgkin's lymphoma and exposure to benzene and benzene-containing solvents Ann. N.Y. Acad. Sci. 1076 2006 120 128
193. A.A. Melikian, E.J. LaVoie, S.S. Hecht, and D. Hoffmann Influence of bay-region methyl group on formation of 5-methylchrysene dihydrodiol epoxide: DNA adducts in mouse skin Cancer Res. 42 1982 1239 1242
194. A.A. Melikian, E.J. LaVoie, S.S. Hecht, and D. Hoffmann 5-Methylchrysene metabolism in mouse epidermis in vivo, diol epoxide-DNA adduct persistence, and diol epoxide reactivity with DNA as potential factors influencing the predominance of 5-methylchrysene-1,2-diol-3,4-epoxide-DNA adducts in mouse epidermis Carcinogenesis 4 1983 843 849
195. E.M. Menger, R.B. Spokane, and P.D. Sullivan Free radicals derived from benzo[a]pyrene Biochem. Biophys. Res. Commun. 71 1976 610 616
196. M. Metzler, and J.A. McLachlan Oxidative metabolism of the synthetic estrogens hexestrol and dienestrol indicates reactive intermediates Adv. Exp. Med. Biol. 136 Pt. A 1981 829 837
197. L. Miligi, A.S. Costantini, A. Benvenuti, D. Kriebel, V. Bolejack, R. Tumino, V. Ramazzotti, S. Rodella, E. Stagnaro, P. Crosignani, D. Amadori, and D. Mirabelli et al. Occupational exposure to solvents and the risk of lymphomas Epidemiology 17 2006 552 561
198. E.C. Miller, and J.A. Miller Mechanisms of chemical carcinogenesis: Nature of proximate carcinogens and interactions with macromolecules Pharmacol. Rev. 18 1966 805 838
199. E.C. Miller, and J.A. Miller Mechanisms of chemical carcinogenesis Cancer 47 1981 1055 1064
200. E.C. Miller, and J.A. Miller Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules Cancer 47 1981 2327 2345
201. J.H. Miller Mutational specificity in bacteria Ann. Rev. Genet. 17 1983 215 238
202. W.R. Miller, and J. O'Neill The importance of local synthesis of estrogen within the breast Steroids 50 1987 537 548
203. K. Mitrunen, and A. Hirvonen Molecular epidemiology of sporadic breast cancer. The role of polymorphic genes involved in oestrogen biosynthesis and metabolism Mutat. Res. 544 2003 9 41
204. J.A. Mobley, A.S. Bhat, and R.W. Brueggemeier Measurement of oxidative DNA damage by catechol estrogens and analogues in vitro Chem. Res. Toxicol. 12 1999 270 277
205. M.M. Montano, L.J. Chaplin, H. Deng, S. Mesia-Vela, N. Gaikwad, M. Zahid, and E. Rogan Protective roles of quinone reductase and tamoxifen against estrogen-induced mammary tumorigenesis Oncogene 26 2007 3587 3590
206. P.P.J. Mulder, L. Chen, B.C. Sekhar, M. George, M.L. Gross, E.G. Rogan, and E.L. Cavalieri Synthesis and structure determination of the adducts formed by electrochemical oxidation of 1,2,3,4-tetrahydro-7,12-dimethylbenz[a] anthracene in the presence of deoxyribonucleosides or adenine Chem. Res. Toxicol. 9 1996 1264 1277
207. P.P.J. Mulder, P. Devanesan, K. van Alem, G. Lodder, E.G. Rogan, and E.L. Cavalieri Fluorobenzo[a]pyrenes as probes of the mechanism of cytochrome P450-catalyzed oxygen transfer in aromatic oxygenations Free Rad. Biol. Med. 34 2003 734 745
208. C. Nagata, Y. Tagashira, and M. Kodama Metabolic activations of benzo(a)pyrene: significance of the free radical P.O.P. Ts'o, J.A. DiPaolo, Chemical Carcinogenesis, Part A 1974 Marcel Dekker 87 111
209. S. Nandi Role of hormones in mammary neoplasia Cancer Res. 38 1978 4046 4049
210. S. Nandi, R.C. Guzman, and J. Yang Hormones and mammary carcinogenesis in mice, rats, and humans: a unifying hypothesis Proc. Natl. Acad. Sci. USA 92 1995 3650 3657
211. National Toxicology Program Toxicology and Carcinogenesis Studies of Naphthalene (CAS No. 91-20-3) in F344/N Rats (Inhalation Studies) (NTP Technical Report No. 500; NIH Publ. No. 01-4434) 2000 Research Triangle Park NC
212. R.R. Newbold, and J.G. Liehr Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens Cancer Res. 60 2000 235 237
213. M.J. Nivard, A. Pastink, and E.W. Vogel Molecular analysis of mutations induced in the vermilion gene of Drosophila melanogaster by methyl methanesulfonate Genetics 131 1992 673 682
214. P.R. Ortiz de Montellano, and R.A. Stearns Timing of the radical recombination step in cytochrome P-450 catalysis with ring-strained probes J. Am. Chem. Soc. 109 1987 3415 3420
215. J.R. Pasqualini, G. Chetrite, C. Blacker, M.C. Feinstein, L. Delalonde, M. Talbi, and C. Maloche Concentrations of estrone, estradiol, and estrone sulfate and evaluation of sulfatase and aromatase activities in pre- and postmenopausal breast cancer patients J. Clin. Endocrinol. Metab. 81 1996 1460 1464
216. J. Pataki, and R. Balic Relative carcinogenicity of some diethylbenz(a)anthracenes J. Med. Chem. 15 1972 905 909
217. M.B. Paxton Leukemia risk associated with benzene exposure in the Pliofilm cohort Environ. Health Perspect. 104 Suppl 6 1996 1431 1436
218. K. Peltonen, B.D. Hilton, J. Pataki, H. Lee, R.G. Harvey, and A. Dipple Spectroscopic characterization of syn-5-methylchrysene 1,2-dihydrodiol 3,4-epoxide-deoxyribonucleoside adducts Chem. Res. Toxicol. 4 1991 305 310
219. K.L. Platt, M. Schollmeier, H. Frank, and F. Oesch Stereoselective metabolism of dibenz(a,h)anthracene to trans-dihydrodiols and their activation to bacterial mutagens Environ. Health Perspect. 88 1990 37 41
220. S. Preston-Martin, M.C. Pike, R.K. Ross, P.A. Jones, and B.E. Henderson Increased cell division as a cause of human cancer Cancer Res. 50 1990 7415 7421
221. S. Pruthi, L. Yang, N.P. Sandhu, J.N. Ingle, C.L. Beseler, V.J. Suman, E.L. Cavalieri, and E.G. Rogan Evaluation of serum estrogen-DNA adducts as potential biomarkers for breast cancer risk J. Steroid Biochem. Mol. Biol. 132 2012 73 79
222. A. Pullman, and B. Pullman Cancérisation par les Substances Chimiques et Structure Moléculaire 1955 Maisson et Cie, Paris
223. A. Pullman, and B. Pullman Molecular electrostatic potential of the nucleic acids Q. Rev. Biophys. 14 1981 289 380
224. M. Quintanilla, K. Brown, M. Ramsden, and A. Balmain Carcinogen-specific mutation and amplification of Ha-ras during mouse skin carcinogenesis Nature 322 1986 78 80
225. N.V.S. RamaKrishna, E.L. Cavalieri, E.G. Rogan, G.G. Dolnikowski, R.L. Cerny, M.L. Gross, H. Jeong, R. Jankowiak, and G.J. Small Synthesis and structure determination of the adducts of the potent carcinogen 7,12-dimethylbenz[a]anthracene and deoxyribonucleosides formed by electrochemical oxidation: models for metabolic activation by one-electron oxidation J. Am. Chem. Soc. 114 1992 1863 1874
226. N.V.S. RamaKrishna, P.D. Devanesan, E.G. Rogan, E.L. Cavalieri, H. Jeong, R. Jankowiak, and G.J. Small Mechanism of metabolic activation of the potent carcinogen 7,12-dimethylbenz[a]anthracene Chem. Res. Toxicol. 5 1992 220 226
227. N.V.S. RamaKrishna, F. Gao, N.S. Padmavathi, E.L. Cavalieri, E.G. Rogan, R.L. Cerny, and M.L. Gross Model adducts of benzo[a]pyrene and nucleosides formed from its radical cation and diol epoxide Chem. Res. Toxicol. 5 1992 293 302
228. N.V.S. RamaKrishna, K.-M. Li, E.G. Rogan, E.L. Cavalieri, M. George, R.L. Cerny, and M.L. Gross Adducts of 6-methylbenzo[a]pyrene and 6-fluorobenzo[a]pyrene formed by electrochemical oxidation in the presence of deoxyribonucleosides Chem. Res. Toxicol. 6 1993 837 845
229. N.V.S. RamaKrishna, N.S. Padmavathi, E.L. Cavalieri, E.G. Rogan, R.L. Cerny, and M.L. Gross Synthesis and structure determination of the adducts formed by electrochemical oxidation of the potent carcinogen dibenzo[a,l]pyrene in the presence of nucleosides Chem. Res. Toxicol. 6 1993 554 560
230. D.B. Reardon, A.S. Prakash, B.D. Hilton, J.M. Roman, J. Pataki, R.G. Harvey, and A. Dipple Characterization of 5-methylchrysene-1,2-dihydrodiol-3,4- epoxide-DNA adducts Carcinogenesis 8 1987 1317 1322
231. 32P-postlabeling test for structurally diverse DNA adducts Carcinogenesis 7 1986 1543 1551
232. D.E. Rickert, T.S. Baker, J.S. Bus, C.S. Barrow, and R.D. Irons Benzene disposition in the rat after exposure by inhalation Toxicol. Appl. Pharmacol. 49 1979 417 423
233. R.A. Rinsky, A.B. Smith, R. Hornung, T.G. Filloon, R.J. Young, A.H. Okun, and P.J. Landrigan Benzene and leukemia. An epidemiologic risk assessment N. Engl. J. Med. 316 1987 1044 1050
234. J. Rochlitz Neue Reaktionen der carcinogenen Kohlenwasserstoffe-II Tetrahedron 23 1967 3043 3048
235. H. Rodriguez, and E.L. Loechler Mutagenesis by (+)-anti-diol epoxide a of benzo[a]pyrene: what controls mutagenic specificity? Biochemistry 32 1993 1759 1769
236. E. Rogan, E. Cavalieri, S. Tibbels, P. Cremonesi, C. Warner, D. Nagel, K. Tomer, R. Cerny, and M. Gross Synthesis and identification of benzo[a]pyrene-guanine nucleoside adducts formed by electrochemical oxidation and horseradish peroxidase-catalyzed reaction of benzo[a]pyrene with DNA J. Am. Chem. Soc. 110 1988 4023 4029
237. E. Rogan, R. Roth, and E. Cavalieri Manganic acetate and horseradish peroxidase/hydrogen peroxide. In vitro models of activation of aromatic hydrocarbons by one-electron oxidation A. Bjorseth, A.J. Dennis, Polynuclear Aromatic Hydrocarbons: Chemistry and Biological Effects 1980 Battelle Press Columbus, OH 259 266
238. E.G. Rogan, A.F. Badawi, P.D. Devanesan, J.L. Meza, J.A. Edney, W.W. West, S.M. Higginbotham, and E.L. Cavalieri Relative imbalances in estrogen metabolism and conjugation in breast tissue of women with carcinoma: potential biomarkers of susceptibility to cancer Carcinogenesis 24 2003 697 702
239. E.G. Rogan, and E.L. Cavalieri 3-Methylcholanthrene-inducible binding of aromatic hydrocarbons to DNA in purified rat liver nuclei Biochem. Biophys. Res. Commun. 58 1974 1119 1126
240. E.G. Rogan, P.D. Devanesan, N.V.S. RamaKrishna, S. Higginbotham, N.S. Padmavathi, K. Chapman, E.L. Cavalieri, H. Jeong, R. Jankowiak, and G.J. Small Identification and quantitation of benzo[a]pyrene-DNA adducts formed in mouse skin Chem. Res. Toxicol. 6 1993 356 363
241. E.G. Rogan, P. Mailander, and E. Cavalieri Metabolic activation of aromatic hydrocarbons in purified rat liver nuclei: induction of enzyme activities and binding to DNA with and without monooxygenase-catalyzed formation of active oxygen Proc. Natl. Acad. Sci. U.S.A. 73 1976 457 461
242. E.G. Rogan, N.V.S. RamaKrishna, S. Higginbotham, E.L. Cavalieri, R. Jankowiak, and G.J. Small Identification and quantitation of 7-(benzo[a]pyren-6-yl)guanine in the urine and feces of rats treated with benzo[a]pyrene Chem. Res. Toxicol. 3 1990 441 444
243. J. Russo, S.V. Fernandez, P.A. Russo, R. Fernbaugh, F.S. Sheriff, H.M. Lareef, J. Garber, and I.H. Russo 17β-Estradiol induces transformations and tumorigenesis in human breast epithelial cells FASEB J. 20 2006 1622 1634
244. J. Russo, M. Hasan Lareef, G. Balogh, S. Guo, and I.H. Russo Estrogen and its metabolites are carcinogenic agents in human breast epithelial cells J. Steroid Biochem. Mol. Biol. 87 2003 1 25
245. J. Russo, and I.H. Russo Genotoxicity of steroidal estrogens Trends Endocrinol. Metab. 15 2004 211 214
246. P.J. Sabourin, W.E. Bechtold, W.C. Griffith, L.S. Birnbaum, G. Lucier, and R.F. Henderson Effect of exposure concentration, exposure rate, and route of administration on metabolism of benzene by F344 rats and B6C3F1 mice Toxicol. Appl. Pharmacol. 99 1989 421 444
247. A. Sadler, V.V. Subrahmanyam, and D. Ross Oxidation of catechol by horseradish peroxidase and human leukocyte peroxidase: reactions of o-benzoquinone and o-benzosemiquinone Toxicol. Appl. Pharmacol. 93 1988 62 71
248. M. Saeed, S.J. Gunselman, S. Higginbotham, E. Rogan, and E. Cavalieri Formation of the depurinating N3adenine and N7guanine adducts by reaction of DNA with hexestrol-3′-4′-quinone or enzyme-activated 3′-hydroxyhexestrol. Implications for a unifying mechanism of tumor initiation by natural and synthetic estrogens Steroids 70 2005 37 45
249. M. Saeed, S. Higginbotham, N. Gaikwad, D. Chakravarti, E. Rogan, and E. Cavalieri Depurinating naphthalene-DNA adducts in mouse skin related to cancer initiation Free Radic. Biol. Med. 47 2009 1075 1081
250. M. Saeed, S. Higginbotham, E. Rogan, and E. Cavalieri Formation of depurinating N3adenine and N7guanine adducts after reaction of 1,2-naphthoquinone or enzyme-activated 1,2-dihydroxynaphthalene with DNA. Implications for the mechanism of tumor initiation by naphthalene Chem. Biol. Interact. 165 2007 175 188
251. M. Saeed, E. Rogan, and E. Cavalieri Mechanism of metabolic activation and DNA adduct formation by the human carcinogen diethylstilbestrol: the defining link to natural estrogens Int. J. Cancer 124 2009 1276 1284
252. M. Saeed, E. Rogan, S.V. Fernandez, F. Sheriff, J. Russo, and E. Cavalieri Formation of depurinating N3Adenine and N7Guanine adducts by MCF-10F cells cultured in the presence of 4-hydroxyestradiol Int. J. Cancer 120 2007 1821 1824
253. M. Saeed, M. Zahid, S.J. Gunselman, E. Rogan, and E. Cavalieri Slow loss of deoxyribose from the N7deoxyguanosine adducts of estradiol-3,4-quinone and hexestrol-3′,4′-quinone. Implications for mutagenic activity Steroids 70 2005 29 35
254. D. Sagher, and B. Strauss Insertion of nucleotides opposite apurinic/apyrimidinic sites in deoxyribonucleic acid during in vitro synthesis: uniqueness of adenine nucleotides Biochemistry 22 1983 4518 4526
255. P. Saiko, A. Szakmary, W. Jaeger, and T. Szekeres Resveratrol and its analogs: defense against cancer, coronary disease and neurodegenerative maladies or just a fad? Mutat. Res. 658 2008 68 94
256. A.M. Samuni, E.Y. Chuang, M.C. Krishna, W. Stein, W. DeGraff, A. Russo, and J.B. Mitchell Semiquinone radical intermediate in catecholic estrogen-mediated cytotoxicity and mutagenesis: chemoprevention strategies with antioxidants Proc. Natl. Acad. Sci. U.S.A. 100 2003 5390 5395
257. R. Santen, E. Cavalieri, E. Rogan, J. Russo, J. Guttenplan, J. Ingle, and W. Yue Estrogen mediation of breast tumor formation involves estrogen receptor-dependent, as well as independent, genotoxic effects Ann. N.Y. Acad. Sci. 1155 2009 132 140
258. R.J. Santen, W. Yue, W. Bocchinfuso, K. Korach, J.P. Wang, E.G. Rogan, L. Yang, E. Cavalieri, J. Russo, P. Devanesan, and M. Verderame Estradiol-induced carcinogenesis via formation of genotoxic metabolites J.N. Ingle, M. Dowsett, Advances in Endocrine Therapy of Breast Cancer 2003 Marcel Dekker NY, USA 163 177
259. S.J. Santner, P.D. Feil, and R.J. Santen In situ estrogen production via the estrone sulfatase pathway in breast tumors: relative importance versus the aromatase pathway J. Clin. Endocrinol. Metab. 59 1984 29 33
260. T.W. Sawyer, R.D. Gill, T. Smith-Oliver, B.E. Butterworth, and J. DiGiovanni Measurement of unscheduled DNA synthesis in primary cultures of adult mouse epidermal keratinocytes Carcinogenesis 9 1988 1197 1202
261. R.M. Schaaper, T.A. Kunkel, and L.A. Loeb Infidelity of DNA synthesis associated with bypass of apurinic sites Proc. Natl. Acad. Sci. USA 80 1983 487 491
262. J.K. Selkirk, R.G. Croy, P.P. Roller, and H.V. Gelboin High-pressure liquid chromatographic analysis of benzo(a)pyrene metabolism and covalent binding and the mechanism of activation of 7,8-benzoflavone and 1,2-epoxy-3,3,3-trichloropropane Cancer Res. 34 1974 3474 3480
263. S. Shibutani, L.A. Margulis, N.E. Geacintov, and A.P. Grollman Translesional synthesis on a DNA template containing a single stereoisomer of dG(+) or dG(-) anti-BPDE (7,8-dihydroxy anti-9,10-epoxy 7,8,9,10- tetrahydrobenzo[a]pyrene) Biochemistry 32 1993 7531 7541
264. L.L. Shipman Ab initio quantum mechanical characterization of the ground electronic state of benzo[a]pyrene. Implications for the mechanism of polynuclear aromatic hydrocarbon oxidation to epoxides by cytochrome P-450 P.W. Jones, R.I. Freudenthal, Carcinogenesis Vol. 3 1978 Raven Press New York 139 144
265. M.G. Shou, and S.K. Yang Metabolism of 2S-hydroxy-3-methylcholanthrene by rat liver microsomes Carcinogenesis 11 1990 2037 2045
266. E.R. Simpson, M.S. Mahendroo, G.D. Means, M.W. Kilgore, M.M. Hinshelwood, S. Graham-Lorence, B. Amarneh, Y. Ito, C.R. Fisher, M.D. Michael, C.R. Mendelson, and S.E. Bulun Aromatase cytochrome P450, the enzyme responsible for estrogen biosynthesis Endocr. Rev. 15 1994 342 355
267. P. Sims The carcinogenic activities in mice of compounds related to 3-methylcholanthrene Int. J. Cancer 2 1967 505 508
268. P. Sims, and P.L. Grover Involvement of dihydrodiols and diol epoxides in the metabolic activation of polycyclic hydrocarbons other than benzo[a]pyrene H.V. Gelboin, P.O.P. Ts'o, Polycyclic Hydrocarbons and Cancer Vol. 3 1981 Academic Press New York 117 181
269. P. Sims, P.L. Grover, A. Swaisland, K. Pal, and A. Hewer Metabolic activation of benzo[a]pyrene proceeds by a diol epoxide Nature 252 1974 326 328
270. S. Singh, D. Chakravarti, J.A. Edney, R.R. Hollins, P.J. Johnson, W.W. West, S.M. Higginbotham, E.L. Cavalieri, and E.G. Rogan Relative imbalances in the expression of estrogen-metabolizing enzymes in the breast tissue of women with breast carcinoma Oncol. Rep. 14 2005 1091 1096
271. S. Singh, M. Zahid, M. Saeed, N.W. Gaikwad, J.L. Meza, E.L. Cavalieri, E.G. Rogan, and D. Chakravarti NAD(P)H:quinone oxidoreductase 1 Arg139Trp and Pro187Ser polymorphisms imbalance estrogen metabolism towards DNA adduct formation in human mammary epithelial cells J. Steroid Biochem. Mol. Biol. 117 2009 56 66
272. T.J. Slaga, W.M. Bracken, A. Viaje, W. Levin, H. Yagi, D.M. Jerina, and A.H. Conney Comparison of the tumor-initiating activities of benzo[a]pyrene arene oxides and diol-epoxides Cancer Res. 37 1977 4130 4133
273. T.J. Slaga, G.L. Gleason, J. DiGiovanni, K.B. Sukumaran, and R.G. Harvey Potent tumor-initiating activity of the 3,4-dihydrodiol of 7,12-dimethylbenz(a) anthracene in mouse skin Cancer Res. 39 1979 1934 1936
274. T.J. Slaga, A. Viaje, D.L. Betty, W. Brachen, S.G. Buty, and J.D. Scribner Skin tumor initiating ability of benzo[a]pyrene 4,5-, 7,8- and 7,8-diol-9,10-epoxides and 7,8-diol Cancer Lett. 2 1976 115 122
275. R. Snyder, and G.F. Kalf A perspective on benzene leukemogenesis Crit. Rev. Toxicol. 24 1994 177 209
276. D.C. Spink, C.L. Hayes, N.R. Young, M. Christou, T.R. Sutter, C.R. Jefcoate, and J.F. Gierthy The effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin on estrogen metabolism in MCF-7 breast cancer cells: evidence for induction of a novel 17 beta-estradiol 4-hydroxylase J. Steroid Biochem. Mol. Biol. 51 1994 251 258
277. D.C. Spink, B.C. Spink, J.Q. Cao, J.A. DePasquale, B.T. Pentecost, M.J. Fasco, Y. Li, and T.R. Sutter Differential expression of CYP1A1 and CYP1B1 in human breast epithelial cells and breast tumor cells Carcinogenesis 19 1998 291 298
278. D. Stack, J. Byun, M.L. Gross, E.G. Rogan, and E. Cavalieri Molecular characteristics of catechol estrogen quinones in reactions with deoxyribonucleosides Chem. Res. Toxicol. 9 1996 851 859
279. D.E. Stack, P. Cremonesi, A. Hanson, E.G. Rogan, and E.L. Cavalieri Radical cations of benzo[a]pyrene and 6-substituted derivatives: reaction with nucleophiles and DNA Xenobiotica 25 1995 755 760
280. D.E. Stack, G. Li, A. Hill, and N. Hoffman Mechanistic insights into the Michael addition of deoxyguanosine to catechol estrogen-3,4-quinones Chem. Res. Toxicol. 21 2008 1415 1425
281. A.A. Stark, L. Malca-Mor, Y. Herman, and D.F. Liberman DNA strand scission and apurinic sites induced by photoactivated aflatoxins Cancer Res. 48 1988 3070 3076
282. C. Steinmaus, A.H. Smith, R.M. Jones, and M.T. Smith Meta-analysis of benzene exposure and non-Hodgkin lymphoma: biases could mask an important association Occup. Environ. Med. 65 2008 371 378
283. J.L. Stevenson, and E. Von Haam Carcinogenicity of benz[a]anthracene and benzo[c]phenanthrene derivatives Am. Inst. Hyg. Ass. J. 26 1965 475 478
284. L.A. Stivala, M. Savio, F. Carafoli, P. Perucca, L. Bianchi, G. Maga, L. Forti, U.M. Pagnoni, A. Albini, E. Prosperi, and V. Vannini Specific structural determinants are responsible for theantioxidant activity and the cell cycle effects of resveratrol J. Biol. Chem. 276 2001 22586 22594
285. B.S. Strauss Cellular aspects of DNA repair Adv. Cancer Res. 45 1985 45 105
286. K. Subbaramaiah, W.J. Chung, P. Michaluart, N. Telang, T. Tanabe, H. Inoue, M. Jang, J.M. Pezzuto, and A.J. Dannenberg Resveratrol inhibits cyclooxygenase-2 transcription and activity in phorbol ester-treated human mammary epithelial cells J. Biol. Chem. 273 1998 21875 21882
287. P.D. Sullivan, F. Bannoura, and G.H. Daub 13C and 1H EPR analysis of the benzo[a]pyrene cation radical J. Am. Chem. Soc. 107 1985 32 35
288. P. Talalay, A.T. Dinkova-Kostova, and W.D. Holtzclaw Importance of phase 2 gene regulation in protection against electrophile and reactive oxygen toxicity and carcinogenesis Adv. Enzyme Regul. 43 2003 121 134
289. D.R. Thakker, W. Levin, T.A. Stoming, A.H. Conney, and D.M. Jerina Metabolism of 3-methylcholanthrene by rat liver microsomes and a highly purified monooxygenase system with and without epoxide hydrase Carcinog. Compr. Surv. 3 1978 253 264
290. D.R. Thakker, W. Levin, A.W. Wood, A.H. Conney, T.A. Stoming, and D.M. Jerina Metabolic formation of 1,9,10-trihydroxy-9,12-dihydro-3- methylcholanthrene J. Am. Chem. Soc. 100 1978 645 647
291. D.R. Thakker, W. Levin, H. Yagi, D. Ryan, P.E. Thomas, J.M. Karle, R.E. Lehr, D.M. Jerina, and A.H. Conney Metabolism of benzo[a]anthracene to its tumorigenic 3,4-dihydrodiol Mol. Pharmacol. 15 1979 138 153
292. D.R. Thakker, W. Levin, H. Yagi, S. Turujman, D. Kapadia, A.H. Conney, and D.M. Jerina Absolute stereochemistry of the trans-dihydrodiols formed from benzo[a]anthracene by liver microsomes Chem. Biol. Interact. 27 1979 145 161
293. R. Todorovic, P. Devanesan, E. Rogan, and E. Cavalieri Identification and quantification of stable DNA adducts of dibenzo[a,l]pyrene or its metabolites in vitro, and in mouse skin and rat mammary gland Chem. Res. Toxicol. 18 2005 984 990
294. L.M. Tolbert, R.K. Khanna, A.E. Popp, L. Gelbaum, and L.A. Bottomley Sterioelectronic effects in the deprotonation of arylalkylradical cations: meso-ethylanthracenes J. Am. Chem. Soc. 112 1990 2373 2378
295. D.M. Townsend, K.D. Tew, and H. Tapiero The importance of glutathione in human disease Biomed. Pharmacother. 57 2003 145 155
296. R. Vassilopoulou-Sellin, L. Palmer, S. Taylor, and C.S. Cooksley Incidence of breast carcinoma in women with thyroid carcinoma Cancer 85 1999 696 705
297. J. Vaught, and E. Bresnick Binding of polycyclic hydrocarbons to nuclear components in vitro Biochem. Biophys. Res. Commun. 69 1976 587 591
298. D. Venugopal, M. Zahid, P.C. Mailander, J.L. Meza, E.G. Rogan, E.L. Cavalieri, and D. Chakravarti Reduction of estrogen-induced transformation of mouse mammary epithelial cells by N-acetylcysteine J. Steroid Biochem. Mol. Biol. 109 2008 22 30
299. J.A. Vericat, S.C. Cheng, and A. Dipple Absolute configuration of 7,12-dimethylbenz[a]anthracene-DNA adducts in mouse skin epidermis Cancer Lett. 57 1991 237 242
300. A.E. Vidal, S. Boiteux, I.D. Hickson, and J.P. Radicella XRCC1 coordinates the initial and late stages of DNA abasic site repair through protein-protein interactions EMBO J. 20 2001 6530 6539
301. T. Walle, F. Hsieh, M.H. DeLegge, J.E. Oatis Jr., and U.K. Walle High absorption but very low bioavailability of oral resveratrol in humans Drug Metab. Dispo. 32 2004 1377 1382
302. M. Wilk, W. Bez, and J. Rochlitz Neue Reaktionen der carcinogenen Kohlenwasserstoffe 3,4-Benzpyren, 9,10-Dimethyl-1,2-Benzanthracen und 20-Methylcholanthren Tetrahedron 22 1966 2599 2608
303. M. Wilk, and W. Girke Reactions between benzo[a]pyrene and nucleobases by one-electron oxidation J. Natl Cancer Inst. 49 1972 1585 1597
304. P.G. Wislocki, M.K. Buening, W. Levin, R.E. Lehr, D.R. Thakker, D.M. Jerina, and A.H. Conney Tumorigenicity of the diastereomeric benz[a]anthracene 3,4-diol-1,2-epoxides and the (+)- and (-)-enantiomers of benz[a]anthracene 3,4-dihydrodiol in newborn mice J. Natl Cancer Inst. 63 1979 201 204
305. P.G. Wislocki, K.M. Fiorentini, P.P. Fu, S.K. Yang, and A.Y. Lu Tumor-initiating ability of the twelve monomethylbenz[a]anthracenes Carcinogenesis 3 1982 215 217
306. J. Yager Catechol-O-methyltransferase: characteristics, polymorphisms and role in breast cancer Drug Discov. Today Dis. Mech. 9 2013 e41 e46
307. L. Yang, N. Gaikwad, J. Meza, E. Cavalieri, P. Muti, B. Trock, and E. Rogan Novel biomarkers for risk of prostate cancer. Results from a case-control study Prostate 69 2009 41 48
308. S.K. Yang, P.P. Roller, and H.V. Gelboin 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 1977 3680 3687
309. G.P. Yu, J.C. Li, D. Branovan, S. McCormick, and S.P. Schantz Thyroid cancer incidence and survival in the national cancer institute surveillance, epidemiology, and end results race/ethnicity groups Thyroid 20 2010 465 473
310. W. Yue, R.J. Santen, J.P. Wang, Y. Li, M.F. Verderame, W.P. Bocchinfuso, K.S. Korach, P. Devanesan, R. Todorovic, E.G. Rogan, and E.L. Cavalieri Genotoxic metabolites of estradiol in breast: potential mechanism of estradiol induced carcinogenesis J. Steroid Biochem. Mol. Biol. 86 2003 477 486
311. Zahid, M., Beseler, C.L., Hall, J.B., LeVan, T., Cavalieri, E.L., Rogan, E.G., 2013a. Unbalanced estrogen metabolism in ovarian cancer. Int. J. Cancer, in press.
312. M. Zahid, N. Gaikwad, E.G. Rogan, and E.L. Cavalieri Inhibition of depurinating estrogen-DNA adductformation by natural compounds Chem. Res. Toxicol. 20 2007 1947 1953
313. M. Zahid, N.W. Gaikwad, M.F. Ali, F. Lu, M. Saeed, L. Yang, E.G. Rogan, and E.L. Cavalieri Prevention of estrogen-DNA adduct formation in MCF-10F cells by resveratrol Free Radic. Biol. Med. 45 2008 136 145
314. Zahid, M., Goldner, W., Beseler, C., Rogan, E., Cavalieri, E., 2013b. Unbalanced estrogen metabolism in thyroid cancer., doi:10.1002/ijc.28275.
315. M. Zahid, E. Kohli, M. Saeed, E. Rogan, and E. Cavalieri The greater reactivity of estradiol-3,4-quinone versus estradiol-2,3-quinone with DNA in the formation of depurinating adducts. Implications for tumor-initiating activity Chem. Res. Toxicol. 19 2006 164 172
316. M. Zahid, M. Saeed, M.F. Ali, E.G. Rogan, and E.L. Cavalieri N-acetylcysteine blocks formation of cancer-initiating estrogen-DNA adducts in cells Free Radic. Biol. Med. 49 2010 392 400
317. M. Zahid, M. Saeed, C. Beseler, E.G. Rogan, and E.L. Cavalieri Resveratrol and N-acetylcysteine block the cancer-initiating step in MCF-10F cells Free Radic. Biol. Med. 50 2011 78 85
318. M. Zahid, M. Saeed, E.G. Rogan, and E.L. Cavalieri Benzene and dopamine catechol quinones could initiate cancer or neurogenic disease Free Radic. Biol. Med. 48 2010 318 324
319. M. Zahid, M. Saeed, L. Yang, C. Beseler, E. Rogan, and E. Cavalieri Formation of dopamine quinone-DNA adducts and their potential role in the etiology of Parkinson's disease IUBMB Life 63 2011 1087 1093
320. Z. Zhao, W. Kosinska, M. Khmelnitsky, E.L. Cavalieri, E.G. Rogan, D. Chakravarti, P.G. Sacks, and J.B. Guttenplan Mutagenic activity of 4-hydroxyestradiol, but not 2-hydroxyestradiol, in BB rat2 embryonic cells, and the mutational spectrum of 4-hydroxyestradiol Chem. Res. Toxicol. 19 2006 475 479
321. B.T. Zhu, and A.H. Conney Functional role of estrogen metabolism in target cells: review and perspectives Carcinogenesis 9 1998 1 27