Crystal and molecular structure of a benzo[a]pyrene 7,8-diol 9,10-epoxide N2-deoxyguanosine adduct: Absolute configuration and conformation

Proceedings of the National Academy of Sciences of the United States of America

Volumn 101, Issue 6, 2004, Pages 1433-1438

  Karle, Isabella L ^a   Yagi, Haruhiko ^b   Sayer, Jane M ^b   Jerina, Donald M ^b  

^a NAVAL RESEARCH LABORATORY   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[A]PYRENE 7,8 DIOL 9,10 EPOXIDE N 2 DEOXYGUANOSINE; CARBON; DEOXYGUANOSINE DERIVATIVE; DEOXYRIBOSE; DNA POLYMERASE; GUANINE; HYDROCARBON; PYRENE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; CONFORMATION; CRYSTAL STRUCTURE; DNA ADDUCT; DNA CONFORMATION; ENANTIOMER; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

7,8-DIHYDRO-7,8-DIHYDROXYBENZO(A)PYRENE 9,10-OXIDE; CIRCULAR DICHROISM; DEOXYGUANOSINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION;

EID: 1242342262     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0307305101     Document Type: Article

References (34)

1. Cook, J. W., Hewett, C. L. & Hieger, I. (1933) J. Chem. Soc. 396-398.
2. Committee on the Biologic Effects of Atmospheric Pollutants (1972) Particulate Polycyclic Organic Matter (Natl. Acad. Sci., Washington, DC).
3. Thakker, D. R., Yagi, H., Akagi, H., Koreeda, M., Lu, A. Y. H., Levin, W., Wood, A. W., Conney, A. H. & Jerina, D. M. (1977) Chem. Biol. Interact. 16, 281-300.
4. Buening, M. K., Wislocki, P. G., Levin, W., Yagi, H., Thakker, D. R., Akagi, H., Koreeda, M., Jerina, D. M. & Conney, A. H. (1978) Proc. Natl. Acad. Sci. USA 75, 5358-5361.
5. Moore, P. D., Koreeda, M., Wislocki, P. G., Levin, W., Conney, A. H., Yagi, H. & Jerina, D. M. (1977) in Drug Metabolism Concepts, ACS Symposium Series no. 44, ed. Jerina, D. M. (Am. Chem. Soc., Washington, DC), pp. 127-154.
6. Sayer, J. M., Chadha, A., Agarwal, S. K., Yeh, H. J. C., Yagi, H. & Jerina, D. M. (1991) J. Org. Chem. 56, 20-29.
7. Cheng, S. C., Hilton, B. D., Roman, J. M. & Dipple, A. (1989) Chem. Res. Toxicol. 2, 334-340.
8. Koreeda, M., Moore, P. D., Wislocki, P. G., Levin, W., Conney, A. H., Yagi, H. & Jerina, D. M. (1978) Science 199, 778-781.
9. Neidle, S. & Culbush, S. D. (1983) Carcinogenesis 4, 415-418.
10. Neidle, S., Subbiah, A., Cooper, C. S. & Riberio, O. (1980) Carcinogenesis 1, 249-254.
11. Yagi, H., Hernandez, O. & Jerina, D. M. (1975) J. Am. Chem. Soc. 97, 6881-6883.
12. Yagi, H., Thakker, D. R., Hernandez, O., Koreeda, M. & Jerina, D. M. (1977) J. Am. Chem. Soc. 99, 1604-1611.
13. Yagi, H., Akagi, H., Thakker, D. R., Mah, H. D., Koreeda, M. & Jerina, D. M. (1977) J. Am. Chem. Soc. 99, 2358-2359.
14. Boyd, D. R., Gadaginamath, G. S., Kher, A., Malone, J. F., Yagi, H. & Jerina, D. M. (1980) J. Chem. Soc. Perkin Trans. I, 2112-2116.
15. Kroth, H., Yagi, H., Seidel, A. & Jerina, D. M. (2000) J. Org. Chem. 65, 5558-5564.
16. Kroth, H., Yagi, H., Sayer, J. M., Kumar, S. & Jerina, D. M. (2001) Chem. Res. Toxicol. 14, 708-719.
17. Yagi, H., Ramesha, A. R., Kalena, G., Sayer, J. M., Kumar, S. & Jerina, D. M. (2002) J. Org. Chem. 67, 6678-6689.
18. Jeffrey, A. M., Grzeskowiak, K., Weinstein, I. B., Nakanishi, K., Roller, P. & Harvey, R. G. (1979) Science 206, 1309-1311.
19. Harada, N. & Nakanishi, K. (1983) Circular Dichroic Spectroscopy: Exciton Coupling in Organic Stereochemistry (University Science Books, New York).
20. Matsuoka, Y. & Nordén, B. (1982) J. Phys. Chem. 86, 1378-1386.
21. Clark, L. B. (1994) J. Am. Chem. Soc. 116, 5265-5270.
22. Thulstrup, E. W., Michl, J. & Eggers, J. H. (1970) J. Phys. Chem. 74, 3868-3878.
23. Xie, X.-M., Geacintov, N. E. & Broyde, S. (1999) Biochemistry 38, 2956-2968.
24. de los Santos, C., Cosman, M., Hingerty, B. E., Ibanez, V., Margulis, L. A., Geacintov, N. E., Broyde, S. & Patel, D. J. (1992) Biochemistry 31, 5245-5252.
25. Cosman, M., de los Santos, C., Fiala, R., Hingerty, B. E., Singh, S. B., Ibanez, V., Margulis, L. A., Live, D., Geacintov, N. E., Broyde, S. & Patel, D. J. (1992) Proc. Natl. Acad. Sci. USA 89, 1914-1918.
26. Arnott, S. (1998) in Oxford Handbook of Nucleic Acid Structure, ed. Neidle, S. (Oxford Univ. Press, Oxford), pp. 1-36.
27. Larson, S. B., Cottam, H. B. & Robins, R. K. (1989) Acta Crystallogr. C 45, 1979-1983.
28. Krishnan, R. & Seshadri, T. P. (1994) Biopolymers 34, 1637-1646.
29. Carrell, H. L., Glusker, J. P., Moschel, R. C., Hudgins, W. R. & Dipple, A. (1981) Cancer Res. 41, 2230-2234.
30. Cosman, M., Hingerty, B. E., Geacintov, N. E., Broyde, S. & Patel, D. J. (1995) Biochemistry 34, 15334-15350.
31. Altona, C. & Sundaralingam, M. (1972) J. Am. Chem. Soc. 94, 8205-8212.
32. Bothner-By, A. A. (1965) Adv. Magn. Res. 1, 195-316.
33. Chiapperino, D., Kroth, H., Kramarczuk, I. H., Sayer, J. M., Masutani, C., Hanaoka, F., Jerina, D. M. & Cheh, A. M. (2002) J. Biol. Chem. 277, 11765-11771.
34. Perlow, R. A. & Broyde, S. (2003) J. Mol. Biol. 327, 797-818.