Solution conformation of the (-)-trans-anti-[BP]dG adduct opposite a deletion site in a DNA duplex: Intercalation of the covalently attached benzo[a]pyrene into the helix with base displacement of the modified deoxyguanosine into the minor groove

Biochemistry

Volumn 36, Issue 45, 1997, Pages 13780-13790

  Feng, Binbin ^a   Gorin, Andrey ^a   Kolbanovskiy, Alexander ^b   Hingerty, Brian E ^c,d   Geacintov, Nicholas E ^b   Broyde, Suse ^b   Patel, Dinshaw J ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b NEW YORK UNIVERSITY   (United States)

^c OAK RIDGE NATIONAL LABORATORY   (United States)

^d Knox Computer Consultants   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[A]PYRENE; DEOXYGUANOSINE; DOUBLE STRANDED DNA;

ANALYTIC METHOD; ARTICLE; BASE PAIRING; CHIRALITY; COVALENT BOND; DNA CONFORMATION; DNA FLANKING REGION; DNA HELIX; ENANTIOMER; GENE DELETION; INTERCALATION COMPLEX; MOLECULAR INTERACTION; NONHUMAN; PRIORITY JOURNAL;

7,8-DIHYDRO-7,8-DIHYDROXYBENZO(A)PYRENE 9,10-OXIDE; BASE COMPOSITION; BENZO(A)PYRENE; CRYSTALLOGRAPHY, X-RAY; DEOXYGUANOSINE; DNA ADDUCTS; MAGNETIC RESONANCE SPECTROSCOPY; NUCLEIC ACID CONFORMATION; POLYDEOXYRIBONUCLEOTIDES; PROTONS; SEQUENCE DELETION; SOLUTIONS;

EID: 0030665486     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi970070r     Document Type: Article

References (49)

1. Altona, C., & Sundaralingam, M. (1972) J. Am. Chem. Soc. 94, 8205-8212.
2. Belguise-Valladier, P., & Fuchs, R. P. P. (1991) Biochemistry 30, 10091-10100.
3. Berman, H. M., Olson, W. K., Beveridge, D. L., Westbrook, J., Gelbin, A., Demeny, T., Hsieh, S. H., Srinivasan, A. R., & Schneider, B. (1992) Biophys. J. 63, 751-759.
4. Brookes, P., & Osborne, M. R. (1982) Carcinogenesis 3, 1223-1226.
5. 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. U.S.A. 75, 5358-5361.
6. Cheng, S. C., Hilton, B. D., Roman, J. M., & Dipple, A. (1989) Chem. Res. Toxicol. 2, 334-340.
7. Conney, A. H. (1982) Cancer Res. 42, 4875-4917.
8. Cosman, M., Ibanez, V., Geacintov, N. E., & Harvey, R. G. (1990) Carcinogenesis 11, 1667-1672.
9. Cosman, M., de los Santos, C., Fiala, R., Hingerty, B. E., Ibanez, V., Margulis, L. A., Live, D., Geacintov, N. E., Broyde, S., & Patel, D. J. (1992) Proc. Natl. Acad. Sci. U.S.A. 89, 1914-1918.
10. Cosman, M., de los Santos, C., Fiala, R., Hingerty, B. E., Ibanez, V., Luna, E., Harvey, R. G., Geacintov, N. E., Broyde, S., & Patel, D. (1993a) Biochemistry 32, 4145-4155.
11. Cosman, M., Fiala, R., Hingerty, B. E., Laryea, A., Lee, H., Harvey, R. G., Amin, S., Geacintov, N. E, Broyde, S., & Patel, D. J. (1993b) Biochemistry 32, 12488-12497.
12. Cosman, M., Fiala, R., Hingerty, B. E., Amin, S., Geacintov, N. E., Broyde, S., & Patel, D. J. (1994a) Biochemistry 33, 11507-11517.
13. Cosman, M., Fiala, R., Hingerty, B. E., Amin, S., Geacintov, N. E., Broyde, S., & Patel, D. J. (1994b) Biochemistry 33, 11518-11527.
14. Cosman, M., Laryea, A., Fiala, R., Hingerty, B. E., Amin, S., Geacintov, N. E., Broyde, S., & Patel, D. J. (1995) Biochemistry 34, 1295-1307.
15. Cosman, M., Hingerty, B. E., Luneva, N., Amin, S., Geacintov, N. E., Broyde, S., & Patel, D. J. (1996) Biochemistry 35, 9850-9863.
16. de los Santos, Cosman, M., Hingerty, B. E., Ibanez, V., Margulis, L. A., Geacintov, N. E., Broyde, S., & Patel, D. J. (1992) Biochemistry 31, 5245-5252.
17. Feng, B., Zhou, L., Passarelli, Harris, C. M., Harris, T. M., & Stone, M. P. (1995) Biochemistry 34, 14021-14036.
18. Feng, B., Gorin, A., Voehler, M., Zhou, L., Passarelli, Harris, C. M., Harris, T. M., & Stone, M. P. (1996) Biochemistry 35, 7316-7329.
19. Feng, B., Kolbanovskiy, A., Hingerty, B. E., Geacintov, N. E., Broyde, S., & Patel, D. J. (1997) Biochemistry 36, xxx-xxx (accompanying paper in this issue).
20. Fountain, M. A., & Krugh, T. R. (1995) Biochemistry 34, 3152-3161.
21. Garcia, A., Lambert, I. B., & Fuchs, R. P. P. (1993) Proc. Natl. Acad. Sci. U.S.A. 90, 5989-5993.
22. Geacintov, N. E., Cosman, M., Hingerty, B. E., Amin, S., Broyde, S., & Patel, D. J. (1997) Chem. Res. Toxicol. 10, 111-146.
23. Harvey, R. G., Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity, Cambridge University Press, Cambridge, U.K., 1991.
24. Hingerty, B. E., Figueroa, S., Hayden, T., & Broyde, S. (1989) Biopolymers 28, 1195-1222.
25. Kumar, A, Ernst, R. R., & Wuthrich, K. (1980) Biochem. Biophys. Res. Commun. 95, 1-6.
26. Kunkel, T. A. (1990) Biochemistry 29, 8003-8011.
27. Lambert, I. B., Napolitano, R. L., & Fuchs, R. P. (1992) Proc. Natl. Acad. Sci. U.S.A. 89, 1310-1314.
28. Majumdar A., & Hosur, R. V. (1992) Prog. NMR Spectrosc. 24, 109-158.
29. Mao, B., Cosman, M., Hingerty, B. E., Broyde, S., & Patel, D. J. (1995a) Biochemistry 34, 6226-6238.
30. Mao, B., Hingerty, B. E., Broyde, S., & Patel, D. J. (1995b) Biochemistry 34, 16641-16653.
31. Meehan, T., & Straub, K. (1979) Nature 277, 410-412.
32. Milhe, C., Fuchs, R. P. P., & Lefevre, J.-F. (1996) Eur. J. Biochem. 235, 120-127.
33. Moriya, M., Spiegel, S., Fernandes, A., Amin, S., Liu, T.-M., Geacintov, N. E., & Grollman, A. P. (1996) Biochemistry 35, 16646-16651.
34. Napolitano, R. L., Lambert, I. B., & Fuchs, R. P. (1994) Biochemistry 33, 1311-1315.
35. Neidle, S., Subiah, A., Kuroda, R., & Cooper, C. S. (1982) Cancer Res. 42, 3716-3768.
36. Patel, D. J., Shapiro, L., & Hare, D. (1987) Annu. Rev. Biophys. Biophys. Chem. 16, 423-454.
37. Schurter, E. J., Yeh, H. J. C., Sayer, J. M., Lakshman, M. K., Yagi, H., Jerina, D. M., & Gorenstein, D. G. (1995a) Biochemistry 34, 1364-1375.
38. Schurter, E. J., Sayer, J. M., Oh-hara, T., Yeh, H. C. J., Yagi, H., Luxon, B. A., Jerina, D. M., & Gorenstein, D. G. (1995b) Biochemistry 34, 9009-9020.
39. Shibutani, S., & Grollman, A. P. (1993) J. Biol. Chem. 268, 11703-11710.
40. Singer, B., & Grunberger, D. (1983) Molecular Biology of Mutagens and Carcinogens, Plenum Press, New York.
41. Slaga, T. J., Bracken, W. J., Gleason, G., Levin, W., Yagi, H., Jerina, D. M., & Conney, A. H. (1979) Cancer Res. 39, 67-71.
42. Streisinger, G., Okada, Y., Emrich, J., Newton, J., Tsugita, A., Terzaghi, F., & Inouye, M. (1966) Cold Spring Harbor Symp. Quant. Biol. 31, 77-84.
43. van der Ven, F. J., & Hilbers, C. W. (1988) Eur. J. Biochem. 178, 1-38.
44. Wei, S.-J. C., Chang, R. L., Hennig, E., Cui, X. X., Merkler, K. A., Wong, C.-Q., Yagi, H., & Conney, A. H. (1994) Carcinogenesis 15, 1729-1735.
45. Wood, A. W., Chang, R. L., Levin, W., Yagi, H., Thakker, D. R., Jerina, D. M., & Conney, A. H. (1977) Biochem. Biophys. Res. Commun. 77, 1389-1396.
46. Ya, N.-Q., Smirnov, S., Cosman, M., Bhanot, S., Ibanez, V., & Geacintov, N. E. (1994) In: Structural Biology: The State of the Art, Proceedings of the 8th Conversation Sarma, R. H., & Sarma, M. H., Eds.) Vol. 2, pp 349-366, Adenine Press, Schenectady, NY.
47. Yeh, H. J. C., Sayer, J. M., Liu, X., Altieri, A. S., Byrd, R. A., Lakshman, M. K., Yagi, H., Schurter, E. J., Gorenstein, D. G., & Jerina, D. M. (1995) Biochemistry 34, 13570-13581.
48. Zegar, I. S., Setayesh, F. R., DeCorte, B. L., Harris, C. M., Harris, T. M., & Stone, M. P. (1996a) Biochemistry 35, 4334-4348.
49. Zegar, I. S., Kim, S. J., Johansen, T. N., Harris, C. M., Harris, T. M., & Stone, M. P. (1996b) Biochemistry 35, 6212-6224.