Bioalkylation of benz(a)anthracene: Implications for carcinogenesis

Polycyclic Aromatic Compounds

Volumn 27, Issue 4, 2007, Pages 311-337

  Myers, Steven R ^a  

^a University of Louisville School of Medicine   (United States)

Author keywords

Benz(a)anthracene; Carcinogen; Metabolism; Methylation

Indexed keywords

ALKYLATION; AMINO ACIDS; ANTHRACENE; AROMATIZATION; CELL CULTURE; METABOLITES; SUBSTITUTION REACTIONS;

ANIMAL CELLS; ANIMAL MODEL; BENZ[A]ANTHRACENE; CARCINOGENESES; HYDROXYALKYLS; METABOLIC ACTIVATION; METABOLIC PRODUCTS; MICROSOMAL ENZYMES; OXIDATION PRODUCTS; PRODUCTS OF REACTION;

METABOLISM;

EID: 34548304550     PISSN: 10406638     EISSN: 15635333     Source Type: Journal    
DOI: 10.1080/10406630701509070     Document Type: Article

References (115)

1. P. L. Graver, Pathways Involved in the Metabolism and Activation of Polycyclic Hydrocarbons, Xenobiotica 16 (1986):915-931.
2. D.M. Jerina, The 1982 Bernard B. Brodie Award Lecture. Metabolism of Aromatic Hydrocarbons by the Cytochrome P-450 System and Epoxide Hydrolase, Drug Metab. Dispos. 11 (1983): 1-4.
3. J. K. Selkirk, Chemical Carcinogenesis: Az Brief Overview of the Mechanism of Action of Polycyclic Hydrocarbons, Aromatic Amines, Nitrosamines, and Anatoxins, Carcinog. Compr. Surv. 5 (1980:1-31.
4. P. Brookes, Mutagenicity of Polycyclic Aromatic Hydrocarbons, Mutat Res. 39 (1977):257-283.
5. E. Boyland, P. Sims, and C. Huggins, Induction of Adrenal Damage and Cancer with Metabolites of 7,12-Dimethylbenz(a)Anthracene, Nature 207 (1965):816-817.
6. E. Boyland and P. Sims, Metabolism of Polycyclic Compounds. The Metabolism of 7,12-D:imethylbenz(Alpha)Anthracene by Rat-Liver Homogenates, Biochem. J. 95 (1965):780-787.
7. E. Boyland and P. Sims, Metabolism of Polycyclic Compounds. 24. The Metabolism of Benz[alpha]Anthracene, Biochem. J. 91 (1964):493-506.
8. E. J. Hall, From Chimney Sweeps to Astronauts: Cancer Risks in the Work Place: The 1998 Lauriston Taylor Lecture, Health Phys. 75 (1998):357-366.
9. E. Repath, Percival Pott, Nurs. Times 64 (1968): 1665.
10. J. Huff, Long-term Chemical Carcinogenesis Bioassays Predict Human Cancer Hazards. Issues, Controversies, and Uncertainties, Ann. N. Y. Acad. Sci. 895 (1999):56-79.
11. E. Kennaway, The Identification of a Carcinogenic Compound in Coal-tar, Br. Med. J. 2 (1955):749-752.
12. A. Haddow, Sir Ernest Laurence Kennaway FRS, 1881-1958: Chemical Causation of Cancer Then and Today, Perspect. Biol. Med. 17 (1974):543-588.
13. R. Bachmann, [In Memoriam Prof. Max Clara], Tip Fak Mecm. 29 (1966):190-194.
14. Percival Pott, Jama 186 (1963):795-796.
15. A. Haddow, Sir Ernest Kennaway, Cancer Res. 18 (1958):365.
16. E. L. Kennaway, Further Experiments on Cancer-producing Substances, Biochem J. 24 (1930):497-504.
17. A. Lacassagne, Kennaway and the Carcinogens, Nature 191 (1961):743-747.
18. E. Boyland and A. A. Levi, Metabolism of Polycyclic Compounds: Production of Dihydroxydihydroanthraceneglycuronic Acid from Anthracene, Biochem. J. 30 (1936):728-731.
19. E. Boyland and A. A. Levi, Metabolism of Polycyclic Compounds: Production of Dihydroxydihydroanthracene from Anthracene, Biochem. J. 29 (1935):2679-2683.
20. H.Marquardt, S. S. Sternberg, and F. S. Philips,7,12-Dimethylbenz(a) Anthracene and Hepatic Neoplasia in Regenerating Rat Liver, Chem. Biol. Interact. 2 (1970): 401-403.
21. D. N. Wheatley and M. S. Inglis, Mammary Tumours Induced in Sprague-Dawley Female Rats by 7,12-Dimethylbenz(a)Anthracene and its Hydroxymethyl Derivatives, Br. J. Cancer. 22 (1968):122-127.
22. E. B. Gammal, K. K. Carroll, B. H. Muhlstock, and E. R. Plunkett, Quantitative Estimation of 7,12-Dimethylbenz(a)Anthracene in Rat Mammary Tissue by Gas Liquid Chromatography, Proc. Soc. Exp. Biol. Med. 119 (1965): 1086-1089.
23. C. Huggins and S. Morii, Selective Adrenal Necrosis and Apoplexy Induced by 7, 12-Dimethylbenz(a)Anthracene, J. Exp. Med. 114 (1961):741-760.
24. C. Huggins, L. Grand, and R. Fukunishi, Aromatic Influences on the Yields of Mammary Cancers Following Administration of 7,12-Dimethylbenz(a)Anthracene, Proc. Natl. Acad. Sci. USA. 51 (1964):737-742.
25. L. Granberg, B. Brunstrom, and I. Brandt, Formation of Benzo[a]Pyrene and 7,12-Dimethylbenz[a] Anthracene Adducts in Vascular Endothelia of Cytochrome P4501 A-Induced Chicken Embryos, Environ. Toxicol. Chem. 22 (2003):2393-2399.
26. T. L. Weimer, A. P. Reddy, U. Harttig, D. Alexander, S. C. Stamm, M. R. Miller, W. Baird, J. Hendricks, and G. Bailey, Influence of Beta-Naphthoflavone on 7,12Dimethylbenz(a)Anthracene Metabolism., DNA Adduction, and Tumorigenicity in Rainbow Trout, Toxicol. Sci. 57 (2000):217-228.
27. N. M. Johnsen, G. Brunborg, K. Haug, T. Scholz, and J. A. Holme, Metabolism and Activation of Cyclopenta Polycyclic Aromatic Hydrocarbons in Isolated Human Lymphocytes, HL-60 Cells and Exposed Rats, Chem. Biol. Interact. 114 (1998):77-95.
28. T. W. Sawyer, E. P. Fisher, and J. DiGiovanni, Skin Tumor Initiating Activities of the 9- and 10-Fluoro Derivatives of 7- or 12-Methylbenz[a] Anthracene and the 9- and 10-Trifluoromethyl Derivatives of 7,.12-D. imethylbenz[a]Anthracene in SENCAR Mice, Carcinogenesis 8 (1987): 1465-1468.
29. T. W. Sawyer, K. Chang, R. G. Harvey, and J. DiGiovanni, Further Investigations into the Effect of Non-benzo Ring Bay-Region Methyl Substituents on TumorInitiating Activity of Polycyclic Hydrocarbons, Cancer Lett 36 (1987):317-324.
30. W. Lijinsky, W. B. Manning, and A. W. Andrews, Skin Carcinogenesis Tests in Mice of Derivatives of 7,12-D.imethylbenz[a]Anthracene Substituted in the 'A' Ring, Carcinogenesis 4 (1983); 1221-1224.
31. J. Pataki and C. Huggins, Molecular Site of Substituents of Benz(a)Anthracene Related to Carcinogenicity, Cancer Res. 29 (1969):506-509.
32. T. Vu-Duc, C. K. Huynh, and S, Binet, Laboratory Generated Bitumen Fumes Under Standardized Conditions. Clean-up Scheme and Ion Trap GC-MS Analysis of VOC, Semi-Volatile and Particulate PAH and PASH, J. Occup. Environ. Hyg. 4 Suppl 1 (2007):245-248.
33. H. Marquardt, S. Baker, B. Tierney, P. L. Grover, and P. Sims, The Metabolic Activation of 7-Methylbenz(a)Anthracene: The Induction of Malignant Transformation and Mutation in Mammalian Cells by Non-K-Region Dihydrodiols, Int. J. Cancer 19 (1977):828-833.
34. C. C. Bird and K. Mainzer, Leukaemia Evoked with 7,8,12-Trimethylbenz(a) Anthracene in Rat. 3. Changes in Lymphoid Tissues, Br. J. Cancer 26 (1972):373-379.
35. C.C. Bird, Dehydrogenase Activity in Rat Leukemia Induced by 7,8,12-Trimethylbenz(a)A.nthracene, J. Pathol. 107 (1972):xi.
36. M. S. Newman and R. F. Cunico, The Synthesis of 5-Hydroxymethyl-, 5-Acetoxym- ethyl-, and 5-Methylmercapto-7,12-Dimethylbenz(a)Anthracenes, and of 5,7,12-Trimethylbenz (a)Anthracene, J. Med. Chem. 15 (1972):323-325.
37. D. N. Wheatley, A. G. Hamilton, A. R. Currie, E. Boyland, and P. Sims, Adrenal Necrosis Induced by 7-Hydroxymethyl-12-Methylbenz(a)Anthracene and Its Prevention, Nature 211 (1966):1311-1312.
38. E. Boyland and P. Sims, Metabolism of Polycyclic Compounds the Metabolism of 9,10-Epoxy-9,10-Dihydrophenanthrene in Rats, Biochem. J. 95 (1965):788-792.
39. P. G. Wislocki, K. M. Fiorentini, P. P. Fu, M. W. Chou, S. K. Yang, and A. Y. Lu, Tumor-Initiating Activity of the Dihydrodiols of 8-Methylbenz[a] Anthracene and 8-Hydroxymethylbenz[a]Anthracene, Carcinogenesis 2 (1981):507-509.
40. S. K. Yang, M. W. Chou, H. B. Weems, and P. P. Fu, Enzymatic Formation of an 8,9-Diol from 8-Methylbenz[a]Anthracene, Biochem. Biophys. Res. Commun. 90 (1979): 1136-1141.
41. H. S. Lamparczyk, S. McKay, P. B. Farmer, P. D. Cary, P. L. Grover, and P. Sims, The Metabolism of 9-Methylanthracene by Rat-Liver Microsomal Preparations, Xenobiotica 16 (1986):325-333.
42. H. Glatt, R. G. Harvey, D. H. Phillips, A. Hewer, and P. L. Grover, Influence of the Alkyl Substituent on Mutagenicity and Covalent DNA Binding of Bay Region Diol-Epoxides of 7-Methyl- and 7-Ethylbenz(a)Anthracene in. Salmonella and V79 Chinese Hamster Cells, Cancer Res. 49 (1989): 1778-1782.
43. B. Tierney, A. Hewer, C. Walsh, P. L. Grover, and P. Sims, The Metabolic Activation of 7-Methylbenz(a)Anthracene in Mouse Skin, Chem. Biol. Interact. 18 (1977): 179-193.
44. W. M. Baird, P. L. Grover, P. Sims, and P. Brookes, Comparison of the Products of the Reaction of 7-Methylbenz(a)Anthracene 5,6-Oxide and RNA, with Those Formed in 7-Methylbenz(a)Anthracene-Treated Cells, Cancer Res. 36 (1976): 2306-2311.
45. H. Marquardt, J. E. Sodergren, P. Sims, and P. L. Grover, Malignant Transformation In Vitro of Mouse Fibroblasts by 7,12-Dimethylbenz(A)Anthracene and 7-Hydroxymethylbenz(A)Anthracene and by Their K-Region Derivatives, Int. J. Cancer. 13 (1974):304-310.
46. F. J. Roe, R. L. Carter, and W. H. Percival, Carcinogenesis in Rabbits Injected at Birth with 7,12-Dimethylbenz(a)Anthracene, Br. J. Cancer 21 (1967):815-820.
47. H. Marquardt, P. L. Grover, and P. Sims, In. Vitro MalignantTtransformation of Mouse Fibroblasts by Non-K-Region Dihydrodiols Derived from 7-Methylbenz(a) Anthracene, 7,12-D.imethylbenz(a)Anthracene, and Benzo(a)Pyrene, Cancer Res. 36 (1976):2059-2064.
48. M. S. Newman, J. H. Cecil, and W. M. Hung, Synthesis of 5-Fluoro-6,8-Dimethylbenz (a)Anthracene, J. Med. Chem. 15 (1972):569-570.
49. S. McKay, D. H. Phillips, A. J. Hewer, and P. L. Grover, Metabolic Activation of 7-Ethyl- and 7-Methylbenz[a]Anthracene in Mouse Skin, Carcinogenesis. 9 (1988): 141-145.
50. V. Heisig, R. G. Harvey, and A. M. Jeffrey, Covalent Binding of Ethylated Analogs of 7,12-Dimethylbenz[a]Anthracene to the DNA of Mouse Embryo Fibroblast 10T.1/2 Cells, Cancer Lett. 33 (1986):19-24.
51. J. DiGiovanni, P. C. Decina, and L. Diamond, Tumor Initiating Activity of 9- and 10-Fluoro-7,12-Dimethylbenz[a]-Anthracene (DMBA) and the Effect, of 2,3,7,8-Tetrachlorodibenzo-p-Dioxin on. Tumor Initiation, by Monofluoro Derivatives of DMBA in SENCAR Mice, Carcinogenesis 4 (1983): 1045-1049.
52. A. W. Wood, W. Levin, R. L. Chang, A. H. Conney, T. J. Slaga, R. F. O'Malley, M. S. Newman, D. R. Buhler, and D. M. Jerina, Mouse Skin Tumor-Initiating Activity of 5-, 7-, and 12-Methyl- and Fluorine-Substituted Benz[a]Anthracenes, J. Natl. Cancer Inst. 69 (1982):725-728.
53. F.B. Daniel andN.J. Joyce, DNAAdduct Formation by 7,12-Dimethylbenz[a] Anthracene and its Noncarcinogenic 2-Fluoro Analogue in Female Sprague-Dawley Rats, J. Natl. Cancer Inst. 70 (1983):111-118.
54. J. DiGiovanni, L. Diamond, J. M. Singer, F. B. Daniel, D. T. Witiak, and T. J. Slaga, Tumor-Initiating Activity of 4-F.luoro-7,12-Dimethylbenz[a] Anthracene and l,2,3,4-Tetrahydro-7,12-Dimethylbenz[a]Anthracene in Female SENCAR Mice, Carcinogenesis 3 (1982):651-655.
55. M. S.Newman, L. E. Fikes, M. M. Hashem,R. Kannan, and V. Sankaran, Synthesis and Carcinogenic Activity of 5-Fluoro-7-(Oxygenated Methyl)- 12-Methylvenz[a] Anthracenes, J. Med. Chem. 21 (1978):1076-1078.
56. A. K. Karamalidis and E. A. Voudrias, Cement-Based Stabilization/ Solidification of Oil Refinery Sludge: Leaching Behavior of Alkanes and PAHs, J. Hazard Mater. (2007).
57. M. T. Chien and J. W. Flesher, Binding of the Carcinogens 5-Fluoro-7-Hydroxy-methyl-12-Methylbenz(a)Anthracene and Its Acetate Ester to DNA In Vitro, Life Sci. 28(1981):1175-1181.
58. S. R. Myers and J. W. Flesher, Metabolism of Chrysene, 5-Methylchrysene, 6-Methylchrysene and 5,6-Dimethylchrysene in Rat Liver Cytosol, In Vitro, and in Rat Subcutaneous Tissue, In Vivo, Chem. Biol. Interact. 77 (1991):203-221.
59. S. R. Myers and J. W. Flesher, Biooxidation of 7,12-Dimethylbenz[a] Anthracene in Rat Subcutaneous Tissue, Biochem Pharmacol. 38 (1989):3199-3206.
60. J. W. Flesher, S. R. Myers, and J. W. Blake, Biosynthesis of the Potent Carcinogen 7,12-Dimethylbenz[a]Anthracene, Cancer Lett. 24 (1984):335-343.
61. Y.J. Surh, J. C. Blomquist, A. Liem, and J. A. Miller, Metabolic Activation of 9-Hydroxymethyl-10-Methylanthracene and 1-Hydroxymethylpyrene to Electrophilic, Mutagenic and Tumorigenic Sulfuric Acid Esters by Rat Hepatic Sulfotransferase Activity, Carcinogenesis 11 (1990): 1451-1460.
62. Y. J. Surh, A. Liem, E. C. Miller, and J. A. Miller, Metabolic Activation of the Carcinogen 6-Hydroxymethylbenzo[a]Pyrene: Formation of an Electrophilic Sulfuric Acid Ester and Benzylic DNAAdducts in Rat Liver In Vivo and in Reactions In Vitro, Carcinogenesis 10 (1989):1519-1528.
63. T. Watabe, Y. Hakamata, A. Hiratsuka, and K. Ogura, A 7-Hydroxymethyl Sulphate Ester as an Active Metabolite of the Carcinogen, 7-Hydroxymethylbenz[a] Anthracene, Carcinogenesis 7 (1986):207-214.
64. T. Watabe, T. Fujieda, A. Hiratsuka, T. Ishizuka, Y. Hakamata, and K. Ogura, The Carcinogen, 7-Hydroxymethyl-12-Methylbenz[a]Anthracene, is Activated, and Covalently Binds to DNA via a Sulphate Ester, Biochem. Pharmacol. 34 (1985):3002-3005.
65. T. Watabe, T. Ishizuka, T. Fujieda, A. Hiratsuka, and K. Ogura, Sulfate Esters of Hydroxymethyl-Methyl-Benz[a]Anthracenes as Active Metabolites of 7,12Dimet-hylbenz[a]Anthracene, Jpn. J. Cancer Res. 76 (1985):684-698.
66. T. Watabe, T. Ishizuka, N. Ozawa, and M. Isobe, Conjugation of 7-Hydroxymethyl-12-Methylbenz[a]Anthracene (7-HMBA) with Glutathione via a Sulphate Ester in Hepatic Cytosol, Biochem. Pharmacol. 31 (1982):2542-2544.
67. T. Watabe, T. Ishizuka, M. Isobe, and N. Ozawa, A 7-Hydroxymethyl Sulfate Ester as an Active Metabolite of 7,12-Dimethylbenz[alpha]Anthracene, Science 215 (1982):403-405.
68. P. Sims, The Preparation of 7-Hydroxymethylbenz(a)Anthracene 5,6-Oxide and its Metabolism by Rat-Liver Preparations, Xenohiotica 2 (1972):469-477.
69. A. R. Currie, C. C. Bird, A. M. Crawford, and P. Sims, Embryopathie Effects of 7,12-Dimethylbenz(a)Anthracene and its Hydroxymethyl Derivatives in the Sprague-Dawley Rat, Nature 226 (1970):911-914.
70. C. C. Bird, A. M. Crawford, and A. R. Currie, Foetal Adrenal Necrosis Induced by 7-Hydroxymethyl- 12-Methylbenz(a)-Anthracene and its Prevention, Nature 228 (1970):72-73.
71. P. H. Jellinck and G. Smith, Metabolism of 7-Hydroxymethyl-12- Methylbenz(a) Anthracene-,12-,14C In Vitro, Biochem. Pharmacol. 18 (1969):680-682.
72. N. Hempel, N. Gamage, J. L. Martin, and M. E. McManus, Human Cytosolic Sulfotransferase SULTlAl, Int. J. Biochem. Cell Biol. 39 (2007):685-689.
73. C. N. Falany, J. Wheeler, L. Coward, D. Keehan, J.L. Falany, andS. Barnes. Bioactivat:ionof7-Hydroxym.ethyl-12-Methylbenz[a] AnthracenebyRatLiverBileAcid Sulfotransferase I, J. Biochem. Toxicol. 1 (1992):241-248.
74. S. T. Vater, L. Hollingsworth, D. M. Baldwin, and D. Warshawsky, Comparative Metabolism of 7,12-Dimethylbenz[a]Anthracene by the Perfused Liver and Liver Microsomal Preparations from Sprague-Dawley Rats, Carcinogenesis 12 (1991):2379-2382.
75. E. Hallberg and J. Rydstrom, Effect of 7-Hydroxymethyl- 12-Methylbenz[a] Anthracene and l,3-Bis-(2-Chloroethyl)-l-Nitrosourea on Enzyme Activities andOxidation of Glutathione in Cultured. Rat Adrenal Cells, Xenobiotica 19 (1989): 315-327.
76. Y. J. Surh, Bioactivation of Benzylic and Allylic Alcohols via Sulfo-Conjugation, Chem. Biol. Interact. 109 (1998):221-235.
77. H. Glatt, R. Henschier, H. Frank, A. Seidel, C. Yang, E. Abu-Shqara, and R.G. Harvey, Sulfotransferase-Mediated Mutagenicity of 1-Hydroxymethylpyrene and 4H-Cyclopenta[def]Chrysen-4-O1 and its Enhancement by Chloride Anions, Carcinogenesis 14 (1993):599-602.
78. J. A. Miller, Y. J. Surh, A. Liem, and E. C. Miller, Electrophilic Sulfuric Acid Ester Metabolites of Hydroxy-Methyl Aromatic Hydrocarbons as Precursors of Hepatic Benzylic DNA Adducts In Vivo, Adv. Exp. Med. Biol. 283 (1991):555-567.
79. S. R. Myers, J. W. Blake, and J. W. Flesher, Bioalkylation and Biooxidation of Anthracene, In Vitro and In Vivo, Biochem. Biophys. Res. Commun. 151 (1988): 1441-1445.
80. A. Dipple, P. Brookes, D. S. Mackintosh, and M. P. Rayman, Reaction of 7-Bromom-ethylbenz(a)Anthracene with Nucleic Acids, Polynucleotides, and Nucleosides, Biochemistry 10 (1971):4323-4330.
81. A. W. Wood, W. Levin, P. E. Thomas, D. Ryan, J. M. Karle, H. Yagi, D. M. Jerina, and A. H. Conney, Metabolic Activation of Dibenzo(a,h)Anthracene and its Dihydrodiols to Bacterial Mutagens, Cancer Res. 38 (1978):1967-1973.
82. T. J. Slaga, E. Huberman, J. K. Selkirk, R. G. Harvey, and W. M. Bracken, Carcinogenicity and Mutagenicity of Benz(a)Anthracene Diols and Diol-Epoxides, Cancer Res. 38 (1978): 1699-1704.
83. P. Sims, Epoxy Derivatives of Aromatic Polycyclic Hydrocarbons. The Preparation, and Metabolism of Epoxides Related to 7,12-Dimethylbenz(a) Anthracene, Biochem. J. 131 (1973):405-413.
84. P. Sims, Epoxy Derivatives of Aromatic Polycyclic Hydrocarbons. The Synthesis of Dibenz[a,c] Anthracene 10,11 -Oxide and its Metabolism by Rat Liver Preparations, Biochem. J. 130 (1972):27-35.
85. R. E. Lehr and D. M. Jerina, Metabolic Activations of Polycyclic Hydrocarbons. Structure-Activity Relationships, Arch. Toxicol. 39 (1977): 1-6.
86. D. M. Jerina, H. Selander, H. Yagi, M. C. Wells, J. F. Davey, V. Mahadevan, and D. T. Gibson, Dihydrodiols from Anthracene and Phenanthrene, J. Am. Chem. Soc. 98 (1976):5988-5996.
87. N.M.Wilson, M.Christou, C.R.Turner, S. A.Wrighton, and C. R.Jefcoate, Binding and Metabolism, of Benzo[a]Pyrene and 7,12-Dimethylbenz[a]Anthracene by Seven Purified Forms of Cytochrome P-450, Carcinogenesis 5 (1984):1475-1483.
88. T. A. Dix and L. J. Marnett, Metabolism of Polycyclic Aromatic Hydrocarbon Derivatives to Ultimate Carcinogens during Lipid Peroxidation, Science 221 (1983):77-79.
89. G. Loew, M. Poulsen, J. Ferrell, and D. Chaet, Quantum Chemical Studies of Methylbenz[a]Anthracenes: Metabolism and Correlations with Carcinogenicity, Chem. Biol. Interact. 31 (1980):319-340.
90. L. K. Wong, C. L. Wang, and F. B. Daniel, Mass Spectral Characterization of the K-Region and Non K-Region Dihydrodiols of 7,12-Dimethylbenz (a) Anthracene, Biomed. Mass. Spectrom. 6 (1979):305-308.
91. W. Levin, A. W.Wood, R. L.Chang, M. S.Newman, D.R.Thakker, A. H.Conney, and D. M. Jerina, The Effect of Steric Strain in the Bay-Region of Polycyclic Aromatic Hydrocarbons: Tumorigenicity of Alkyl-Substituted Benz[a]Anthracenes, Cancer Lett. 20 (1983): 139-146.
92. K. el-Bayoumy, Y. H. Chae, P. Upadhyaya, C. Meschter, L. A. Cohen, and B. S. Reddy, Inhibition of 7,12-Dimethylbenz(a)Anthracene-Induced Tumors and DNA Adduct Formation in the Mammary Glands of Female Sprague-Dawley Rats by the Synthetic Organoselenium Compound, l,4-Phenylenebis(methylene)Selenocyanate, Cancer Res. 52 (1992):2402-2407.
93. A. Dipple, J. E. Tomaszewski, R. C. Moschel, C. A. Bigger, J. A. Nebzydoski, and M. Egan, Comparison of Metabolism-Mediated Binding to DNA of 7-Hydroxymethyl-12-Methylbenz(a)Anthracene and 7,12-Dimethylbenz(a)Anthracene, Cancer Res. 39 (1979):1154-1158.
94. J. W. Flesher and S. R. Myers, Rules of Molecular Geometry for Predicting Carcinogenic Activity of UnsubstitutedPolynuclear Aromatic Hydrocarbons, Teratog. Carcinog. Mutagen. 11 (1991):41-54.
95. S. R. Myers and J. W. Flesher, Bioalkylation of Benz[a]Anthracene, 7-Methylbenz [ajAnthracene, and 12-Methylbenz[a]Anthracene in Rat Lung Cytosol Preparations, Biochem. Pharmacol. 41 (1991):1683-1689.
96. J. W. Flesher and S. R. Myers, Bioalkylation of Benz[a]Anthracene as a Biochemical Probe for Carcinogenic Activity. Lack of Bioalkylation in a Series of Six Noncarcinogenic Polynuclear Aromatic Hydrocarbons, Drug Metab. Dispos. 18 (1990): 163-167.
97. J. W. Flesher, S. R. Myers, and K. H. Stansbury, The Site of Substitution of the Methyl Group in the Bioalkylation of Benzo[a]Pyrene, Carcinogenesis 11 (1990):493-496.
98. J. W. Flesher, S. R. Myers, C. H. Bergo, and J. W. Blake, Bioalkylation of Dibenz[a,b] Anthracene in Rat Liver Cytosol, Chem. Biol. Interact. 57 (1986):223-233.
99. A. Dipple and J. A. Nebzydoski, Evidence for the Involvement of a Diol-Epoxide in the Binding of 7,12-Dimethylbenz(a)Anthracene to DNA in Cells in Culture, Chem. Biol. Interact. 20 (1978): 17-26.
100. M. Buratti, L. Campo, S. Fustinoni, C. Valla, I. Martinotti, P. E. Cirla, D. Cavallo, and V. Foa, Application of Ultraviolet Spectrophotometry to Estimate Occupational Exposure to Airborne Polyaromatic Compounds in Asphalt Pavers, J. Occup. Environ. Hyg. 4 (2007):412-419.
101. I. Al-S aleh and I. Al-Doush, Gas Chromatography-Mass Spectrometric Determination of Polycyclic Aromatic Hydrocarbons in Five Species of Fish from. Three Sites in the Arabian Gulf, Int. J. Environ. Health Res. 12 (2002):193-200.
102. A. Bettencourt, G. Lhoest, M. Roberfroid, and M. Mercier, Gas Chromatographic and Mass Fragmentographic Assays of Carcinogenic Polycyclic Hydrocarbon Epoxide Hydratase Activity, J Chromatogr. 134 (1977):323-330.
103. V. Librando and A. Alparone, Electronic Polarizability as a Predictor of Biodegradation Rates of Dimethylnaphthalenes. an Ab Initio and Density Functional Theory Study, Environ. Sci. Technol. 41 (2007):1646-1652.
104. G. L. Borosky and K. K. Laali, Carbocations from Oxidized Metabolites of Benzo[a] Anthracene: A Computational Study of Their Methylated and Fluorinated Derivatives and Guanine Adducts, Chem. Res. Toxicol. 19 (2006):899-907.
105. C. L. Klein, E. D. Stevens, D. E. Zacharias, and J. P. Glusker, 7,12-D.imethylbenz[a] Anthracene: Refined Structure, Electron Density Distribution, and Endo-Peroxide Structure, Carcinogenesis 8 (1987):5-18.
106. K. Ogura, T. Sohtome, A. Sugiyama, H. Okuda, A. Hiratsuka, and T. Watabe, Rat Liver Cytosolic Hydroxysteroid Sulfotransferase (Sulfotransferase a) Catalyzing the Formation of Reactive Sulfate Esters from Carcinogenic Polycyclic Hydroxymethylarenes, Mol. Pharmacol. 37 (1990):848-854.
107. F. Hobbiger, The Action of Carbamic Esters and Tetraethylpyrophosphate on Normal and Curarized Frog Rectus Muscle, Br. J. Pharmacol. Chemother. 5 (1950):37-48.
108. B. D. Silverman and J. P. Lowe, Carcinogenicity of Methylated Hydrocarbons: Effector Methylation on the Calculated Diol-Epoxide Reactivity, Cancer Biochem. Biophys. 6 (1982):89-94.
109. S. J. Stowers and M. W. Anderson, Formation and Persistence of Benzo(a)Pyrene Metabolite-DNA Adducts, Environ. Health Perspect. 62 (1985):31-39.
110. J. DiGiovanni, A. P. Nebzydoski, and P.C. Decina, Formation of 7-Hydroxymethyl-12-Methylbenz(a)Anthracene-DNA Adducts from 7,12-Dimethylbenz(a) Anthracene in Mouse Epidermis, Cancer Res. 43 (1983):4221-4226.
111. N. J. Joyce and F. B. Daniel, 7, 12-Dimethylbenz [a] Anthracene- Deoxyribonucleoside Adduct Formation In Vivo: Evidence for the Formation and Binding of a Mono-Hydroxymethyl-DMBA Metabolite to Rat Liver DNA, Carcinogenesis 3 (1982):297-301.
112. K. Frenkel, D. Grunberger, H. Kasai, H. Komura, and K. Nakanishi, Identification of Novel 7,12-D.imethylbenz[a] Anthracene Adducts in Cellular Ribonucleic Acid, Biochemistry 20 (1981):4377-4381.
113. C. A. Bigger, J. E. Tomaszewski, A. W. Andrews, and A. Dipple, Evaluation of Metabolic Activation of 7,12-Dimethylbenz(a)Anthracene In Vitro by Aroclor 1254-Induced Rat Liver S-9 Fraction, Cancer Res. 40 (1980):655-661.
114. A. D. MacNicoll, C. S. Cooper, O. Ribeiro, P. G. Gervasi, A. Hewer, C. Walsh, P. L. Graver, and P. Sims, The Involvement of a Non-'Bay-Region' Diol-Epoxide in the Formation of Benz(a)Anthracene-DNA Adducts in a Rat-liver Microsomal System, Biochem. Biophys. Res. Commun. 91 (1979):490-497.
115. K. H. Stansbury, J. W. Flesher, and R. C. Gupta, Mechanism of Aralkyl-DNA Adduct Formation from Benzo[a]Pyrene In Vivo, Chem. Res. Toxicol. 7 (1994): 254-259.