Synthesis of adducts formed by iodine oxidation of aromatic hydrocarbons in the presence of deoxyribonucleosides and nucleobases

Chemical Research in Toxicology

Volumn 11, Issue 10, 1998, Pages 1201-1208

  Hanson, Aaron A ^a   Rogan, Eleanor G ^a   Cavalieri, Ercole L ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7,12 DIMETHYLBENZ[A]ANTHRACENE; ADENINE; BENZO[A]PYRENE; CATION; DEOXYADENOSINE; DEOXYGUANOSINE; DEOXYRIBONUCLEOSIDE; EPOXIDE; GUANINE; IODINE; MESYLIC ACID; N,N DIMETHYLFORMAMIDE; NUCLEIC ACID BASE; POLYCYCLIC AROMATIC HYDROCARBON; RADICAL; UNSPECIFIC MONOOXYGENASE;

ARTICLE; CHEMICAL REACTION; DNA ADDUCT; ELECTROCHEMICAL ANALYSIS; OXIDATION; SYNTHESIS;

DEOXYRIBONUCLEOSIDES; DNA ADDUCTS; IODINE; OXIDATION-REDUCTION; POLYCYCLIC HYDROCARBONS, AROMATIC;

EID: 0031772349     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx980127q     Document Type: Article

References (24)

1. Cavalieri, E. L., and Rogan, E. G. (1992) The approach to understanding aromatic hydrocarbon carcinogenesis. The central role of radical cations in metabolic activation. Pharmacol. Ther. 55, 183-199.
2. Cavalieri, E. L., and Rogan, E. G. (1998) Mechanisms of tumor initiation by polycyclic aromatic hydrocarbons in mammals. In The Handbook of Environmental Chemistry: PAHs and Related Compounds (Neilson, A. H., Ed.) Vol. 3J, pp 81-117, Springer, Heidelberg, Germany.
3. RamaKrishna, N. V. S., Gao, F., Padmavathi, N. S., Cavalieri, E. L., Rogan, E. G., Cerny, R. L., and Gross, M. L. (1992) Model adducts of benzo[α]pyrene and nucleosides formed from its radical cation and diol epoxide. Chem. Res. Toxicol. 5, 293-302.
4. RamaKrishna, N. V. S., Padmavathi, N. S., Cavalieri, E. L., Rogan, E. G., Cerny, R. L., and Gross, M. L. (1993) Synthesis and structure determination of the adducts formed by electrochemical oxidation of the potent carcinogen dibenzo[α,l]pyrene in the presence of nucleosides. Chem. Res. Toxicol. 6, 554-560.
5. RamaKrishna, N. V. S., Cavalieri, E. L., Rogan, E. G., Dolnikowski, G. G., Cerny, R. L., Gross, M. L., Jeong, H., Jankowiak, R., and Small, G. J. (1992) Synthesis and structure determination of the adducts of the potent carcinogen 7,12-dimethylbenz[α]-anthracene and deoxyribonucleosides formed by electrochemical oxidation: Models for metabolic activation by one-electron oxidation. J. Am. Chem. Soc. 114, 1863-1874.
6. RamaKrishna, N. V. S., Li, K.-M., Rogan, E. G., Cavalieri, E. L., George, M., Cerny, R. L., and Gross, M. L. (1993) Adducts of 6-methylbenzo[α]pyrene and 6-fluorobenzo[α]pyrene formed by electrochemical oxidation in the presence of deoxyribonucleosides. Chem. Res. Toxicol. 6, 837-845.
7. Mulder, P. P. J., Chen, L., Sekhar, B. C., George, M., Gross, M. L., Rogan, E. G., and Cavalieri, E. L. (1996) Synthesis and structure determination of the adducts formed by electrochemical oxidation of 1,2,3,4-tetrahydro-7,12-dimethylbenz[α]anthracene in the presence of deoxyribonucleosides or adenine. Chem. Res. Toxicol. 9, 1264-1277.
8. Rogan, E. G., Devanesan, P. D., RamaKrishna, N. V. S., Higginbotham, S., Padmavathi, N. S., Chapman, K., Cavalieri, E. L., Jeong, H., Jankowiak, R., and Small, G. J. (1993) Identification and quantitation of benzo[α]pyrene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 6, 356-363.
9. Chen, L., Devanesan, P. D., Higginbotham, S., Ariese, F., Jankowiak, R., Small, G. J., Rogan, E. G., and Cavalieri, E. L. (1996) Expanded analysis of benzo[α]pyrene-DNA adducts formed in vitro and in mouse skin: Their significance in tumor initiation. Chem. Res. Toxicol. 9, 897-903.
10. Li, K.-M., Todorovic, R., Rogan, E. G., Cavalieri, E. L., Ariese, F., Suh, M., Jankowiak, R., and Small, G. J. (1995) Identification and quantitation of dibenzo[α,l]pyrene-DNA adducts formed by rat liver microsomes in vitro: Preponderance of depurinating adducts. Biochemistry 34, 8043-8049.
11. Devanesan, P. D., RamaKrishna, N. V. S., Padmavathi, N. S., Higginbotham, S., Rogan, E. G., Cavalieri, E. L., Marsch, G. A., Jankowiak, R., and Small, G. J. (1993) Identification and quantitation of 7,12-dimethylbenz[α]anthracene-DNA adducts formed in mouse skin. Chem. Res. Toxicol. 6, 364-371.
12. Todorovic, R., Ariese, F., Devanesan, P., Jankowiak, R., Small, G. J., Rogan, E., and Cavalieri, E. (1997) Determination of benzo[α]pyrene- and 7,12-dimethylbenz[α]anthracene-DNA adducts formed in rat mammary glands. Chem. Res. Toxicol. 10, 941-947.
13. Rochlitz, J. (1967) Neue Reaktionen der carcinogenen Kohlenwasserstoffe. II. Tetrahedron 23, 3043-3048.
14. Wilk, M., and Girke, W. (1972) Reactions between benzo[α]pyrene and nucleobases by one-electron oxidation. J. Natl Cancer Inst. 49, 1585-1597.
15. Cavalieri, E., and Roth, R. (1976) Reaction of methylbenzan-thracenes and pyridine by one-electron oxidation: A model for metabolic activation and binding of carcinogenic aromatic hydrocarbons. J. Org. Chem. 41, 2679-2684.
16. Johnson, M. D., and Calvin, M. (1973) Induced nucleophilic substitution in benzo[α]pyrene. Nature 241, 271-272.
17. Cremonesi, P., Stack, D. E., Rogan, E. G., and Cavalieri, E. L. (1994) Radical cations of benzo[α]pyrene and 6-substituted derivatives: Synthesis and reaction with nucleophiles. J. Org. Chem. 59, 7683-7687.
18. Stack, D. E., Cremonesi, P., Hanson, A., Rogan, E. G., and Cavalieri, E. L. (1995) Radical cations of benzo[α]pyrene and 6-substituted derivatives: Reaction with nucleophiles and DNA. Xenobiotica 25, 755-760.
19. National Institutes of Health (1981) NIH Guidelines for the Laboratory Use of Chemical Carcinogens, NIH Publication 81-2385, U.S. Government Printing Office, Washington, DC.
20. Masuda, Y., and Kagawa, R. (1972) A novel synthesis and carcinogenicity of dibenzo[α,l]pyrene. Chem. Pharm. Bull. 20, 2736-2737.
21. Chen, L., Devanesan, P. D., Byun, J., Gooden, J. K., Gross, M. L., Rogan, E. G., and Cavalieri, E. L. (1997) Synthesis of depurinating DNA adducts formed by one-electron oxidation of 7H-dibenzo[c,g]carbazole and identification of these adducts after activation with rat liver microsomes. Chem. Res. Toxicol. 10, 225-233.
22. Dolnikowski, G. G., Cavalieri, E. L., and Gross, M. L. (1991) Isomer differentiation in 7,12-dimethylbenz[α]anthracene-pyridine adducts by fast atom bombardment tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 2, 256-258.
23. Pullman, A., and Pullman, B. (1981) Molecular electrostatic potential of nucleic acids. Q. Rev. Biophys. 14, 289-380.
24. Kim, H. S., Yu, M., Jiang, Q., and LeBreton, P. (1993) UV photoelectron and ab initio quantum mechanical characterization of 2′-deoxyguanosine 5′-phosphate: Electronic influences on DNA alkylation patterns. J. Am. Chem. Soc. 115, 6169-6183.