Formation of benzylic alcohols and meso-aldehydes by one-electron oxidation of dmba, a model for the first metabolic step in methylated carcinogenic hydrocarbon activation

Polycyclic Aromatic Compounds

Volumn 24, Issue 4-5, 2004, Pages 501-511

  Flesher, James W ^a   Horn, Jamie ^a   Lehner, Andreas F ^b  

^a UNIVERSITY OF KENTUCKY   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

Benzylic alcohols; DMBA; Meso aldehydes; One electron oxidation

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; BENZYL DERIVATIVE; CARCINOGEN; DIMETHYLBENZ[A]ANTHRACENE; HYDROCARBON;

AEROBIC METABOLISM; CONFERENCE PAPER; HYDROXYLATION; METABOLIC ACTIVATION; METABOLITE; METHYLATION; OXIDATION;

EID: 4444222507     PISSN: 10406638     EISSN: None     Source Type: Journal    
DOI: 10.1080/10406630490471546     Document Type: Conference Paper

References (31)

1. J. W. Flesher and K. L. Sydnor, Carcinogenicity of Derivatives of 7,12-Dimethylbe-nz[a]anthracene, Cancer Research 31 (1971):1951-1954.
2. J. W. Flesher and K. L. Sydnor, Possible Role of 6-Hydroxymethylbenzo[a] pyrene as a Proximate Carcinogen of Benzo[a]pyrene and 6-Methylbenzo[a]pyrene, Int. J. Cancer 11 (1973):433-437.
3. J. W. Flesher, J. Horn, and A. F. Lehner, The Meso-Region Theory of Aromatic Hydrocarbon Carcinogenesis, Polycyclic Aromatic Compounds 22 (2002):379-393.
4. E. Cavalieri and E. Rogan, One-Electron Oxidation of Aromatic Hydrocarbons in Chemical and Biological Systems, in Polycyclic Aromatic Hydrocarbons 7th International Symposium (Columbus, Ohio: Battelle Press, 1983), 1-26.
5. 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.
6. 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. Amer. Chem. Society 89 (1967):5508-5509.
7. J. Fried, One Electron Oxidation of Polycyclic Aromatics as a Model for the Metabolic Activation of Carcinogenic Hydrocarbons, in Chemical Carcinogenesis (New York: Marcel Dekker, 1974), 197-215.
8. E. Boyland, P. Sims, and C. Huggins, Induction of Adrenal Damage and Cancer with Metabolites of 7,12-Dimethylbenz[o]anthracene, Nature 207 (1965):816-817.
9. A. F. Lehner, J. Horn, and J. W. Flesher, Benzylic Carbonium Ions as Ultimate Carcinogens of Polynuclear Aromatic Hydrocarbons, J. Mol. Structure Theochem. 336 (1996):203-217.
10. E. Boyland and P. Sims, The Metabolism of 7,12-Dimethylbenz[a]anthracene by Rat Liver Homogenates, Biochem. Journal 95 (1965):780-787.
11. E. Boyland and P. Sims, The Carcinogenic Activities in Mice of Compounds Related to Benz[o]anthracene, Int. J. Cancer 2 (1967):500-504.
12. T. Watabe, Metabolic Activation of 7,12-Dimethylbenz[a]anthracene (DMBA) and 7-Methylbenz[a]anthracene (7-MBA) by Rat Liver P-450 and Sulfotransferase, J. Toxicol. Science 8 (1983):119-131.
13. J. W. Flesher, J. Horn, and A. F. Lehner, 7-Sulfooxymethyl-12- methylbenz[a]anthracene is an Exceptionally Reactive Electrophilic Mutagen and Ultimate Carcinogen, Biochem. Biophys. Res. Communications 231 (1997):144-148.
14. J. W. Flesher, J. Horn, and A. F. Lehner, 7-Sulfooxymethy]benz[a] anthracene is an Ultimate Electrophilic and Carcinogenic form of 7-Hydroxymethylbenz[a]anthracene, Biochem. Biophys. Res. Communications 231 (1997):712-716.
15. J. W. Flesher, J. Horn, and A. F. Lehner, 6-Sulfooxymethylbenzo[a]pyrene Is an Ultimate Electrophilic and Carcinogenic form of the Intermediary Metabolite 6-Hydroxymethylbenzo[a]pyrene, Biochem. Biophys. Res. Communications 234 (1997):554-558.
16. J. W. Flesher, J. Horn, and A. F. Lehner, Carcinogenicity of 1-Hydroxy-3-Methylcholanthrene and its Electrophilic Sulfate Ester 1-Sulfooxy-3-methylcholanthrene in Sprague-Dawley Rats, Biochem. Biophys. Res. Communications 243 (1998): 30-35.
17. J. W. Flesher, J. Horn, and A. F. Lehner, 9-Sulfooxymethylanthracene Is an Ultimate Electrophilic and Carcinogenic Form of 9-Hydroxymethylanthracene, Biochem. Biophys. Res. Communications 251 (1998):239-243.
18. J. W. Flesher, S. Soedigdo, and D. R. Kelley, Syntheses of Metabolites of 7,12-Dimethylbenz[a]anthracene, 4-Hydroxy-7,12-dimethylbenz[a]anthracene, 7-Hydroxymethyl-12-methylbenz[a]anthracene, Their Methyl Ethers and Acetoxy Derivatives, J. Med. Chemistry 10 (1967):932-936.
19. J. Pataki, R. Wlos, and Y.-J. Cho, Adrenocorticolytic Derivatives of Benz[a]anthracene, J. Med. Chemistry 11 (1968):1083-1085.
20. G. M. Badger and J. W. Cook, The Synthesis of Growth-Inhibitory Polycyclic Compounds: I, J. Chem. Society (1939):802-806.
21. J. Horn, J. W. Flesher, and A. F. Lehner, The Metabolism of Formyl-Substituted Benz[a]anthracenes to Hydroxymethyl Metabolites in Rat Liver In Vitro and In Vivo, Chem. Biol. Interactions 145 (2003):17-32.
22. M. W. Chou and S. K. Yang, Combined Reversed-Phase and Normal-Phase High-Performarice Liquid Chromatography in the Purification and Identification of 7,12-Dimethylbenz[a]anthracene Metabolites, J. Chromatography 185 (1979):635-654.
23. P. Sims, The Metabolism of 3-Methylcholanthrene and Some Related Compounds by Rat-Liver Homogenates, Biochem. Journal 98 (1966):215-228.
24. P. Sims, Qualitiative and Quantitative Studies on the Metabolism of a Series of Aromatic Hydrocarbons by Rat-Liver Preparations, Biochem. Pharmacology 19 (1970):795-818.
25. J. W. Cook and E. L. Kennaway, Chemical Compounds as Carcinogenic Agents, Am. J. Cancer 39 (1940):381-582.
26. C. Grandjean and E. Cavalieri, The Mechanism of Microsomal Hydroxylation of 7-Methylbenz[a]anthracene and 7,12-Dimethylbenz[a]anthracene by Oxygen-18 Studies, Biochem. Biophys. Res. Communications 61 (1974):912-919.
27. N. V. S. RamaKrishna, E. L. Cavalieri, E. G. Rogan, G. Dolnikowski, R. L. Cerny, M. L. Gross, H. Jeong, R. Jankowiar, 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. Society 114 (1992): 1863-1874.
28. P. Anzenbacher, T. Niwa, L. M. Tolbert, S. R. Sirimanne, and F. P. Guengerich, Oxidation of 9-Alkylanthracenes by Cytochrome P450 2B1, Horseradish Peroxidase, and Iron Tetraphenylporphine/Iodosylbenzene Systems: Anaerobic and Aerobic Mechanisms, Biochemistry 35 (1996):2512-1520.
29. H. Glatt, K. Pauly, H. Frank, A. Seidel, F. Oesch, R. G. Harvey, and G. Werle-Schneider, Substance-Dependent Sex Differences in the Activation of Benzylic Alcohols to Mutagens by Hepatic Sulfotransferases of the Rat, Carcinogenesis 15 (1994):2605-2611.
30. H. C. Chou, S. Ozawa, P. P. Fu, N. P. Lang, and F. F. Kadlubar, Metabolic Activation of Methyl-Hydroxylated Derivatives of 7,12-Dimethylbenz[a]anthracene by Human Liver Dehydroepiandrosteron-Steroid Sulfotransferase, Carcinogenesis 19 (1998):1071-1076.
31. E. Banoglu, Current Status of the Cytosolic Sulfotransferases in the Metabolic Activation of Promutagens and Procarcinogens, Curr. Drug Metabolism 1 (2000): 1-30.