Major groove (S)-α-(N6-adenyl)styrene oxide adducts in an oligodeoxynucleotide containing the human N-ras codon 61 sequence: Conformations of the S(61,2) and S(61,3) sequence isomers from 1H NMR

Biochemistry

Volumn 35, Issue 23, 1996, Pages 7316-7329

  Feng, Binbin ^a,b   Voehler, Markus ^a   Zhou, Liang ^a,c   Passarelli, Mariella ^a,d   Harris, Constance M ^a   Harris, Thomas M ^a   Stone, Michael P ^a  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^c GEORGETOWN UNIVERSITY   (United States)

^d UNIVERSITY OF MAINE AT FARMINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA (N6 ADENYL)STYRENE OXIDE; OLIGODEOXYNUCLEOTIDE; PROTEIN P21; STYRENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CODON; DIASTEREOISOMER; DNA ADDUCT; DNA CONFORMATION; DNA SEQUENCE; PRIORITY JOURNAL; PROTO ONCOGENE; PROTON NUCLEAR MAGNETIC RESONANCE;

ADENINE; BASE SEQUENCE; CODON; COMPUTER GRAPHICS; DNA ADDUCTS; GENES, RAS; HUMANS; HYDROGEN; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; NUCLEIC ACID CONFORMATION; OLIGODEOXYRIBONUCLEOTIDES; THERMODYNAMICS;

EID: 0029952630     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi952526f     Document Type: Article

References (71)

1. Balmain, A., & Brown, K. (1988) Adv. Cancer Res. 51, 147-182.
2. Barbacid, M. (1987) Annu. Rev. Biochem. 56, 779-827.
3. Bax, A., Sklenar, V., & Clore, G. M. (1987) J. Am. Chem. Soc. 109, 6511-6513.
4. Bizub, D., Wood, A. W., & Skalka, A. M. (1986) Proc. Natl. Acad. Sci. U.S.A. 83, 6048-6052.
5. Bodenhausen, G., Kogler, H., & Ernst, R. R. (1984) J. Magn. Reson. 58, 370-388.
6. Boelens, R., Scheck, R. M., Dijkstra, K., & Kaptein, R. (1985) J. Magn. Reson. 62, 378-386.
7. Bonatti, S., Abbondandolo, A., Corti, G., Fiorio, R., & Mazzaccaro, A. (1978) Mutat. Res. 52, 295-300.
8. Bond, J. A. (1989) CRC Crit. Rev. Toxicol. 19, 227-249.
9. Borer, P. N. (1975) in Handbook of Biochemistry and Molecular Biology, CRC Press, Cleveland, OH.
10. Borgias, B. A., & James, T. L. (1990) J. Magn. Reson. 87, 475-487.
11. Brooks, B. R., Bruccoleri, R. E., Olafson, B. D., States, D. J., Swaminathan, S., & Karplus, M. (1983) J. Comput. Chem. 4, 187-217.
12. Brunger, A. T. (1992) In X-PLOR. Version 3.1. A System for X-ray Crystallography and NMR, Yale University Press, New Haven, CT.
13. Calladine, C. R. (1982) J. Mol. Biol. 161, 343-352.
14. Cha, R. S., Thilly, W. G., & Zarbl, H. (1994) Proc. Natl. Acad. Sci. U.S.A. 91, 3749-3753.
15. Cho, B. P., Beland, F. A., & Marques, M. M. (1992) Biochemists 31, 9587-9602.
16. Cho, B. P., Beland, F. A., & Marques, M. M. (1994) Biochemists 33, 1373-1384.
17. Cosman, M., Fiala, R., Hingerty, B. E., Laryea, A., Lee, H., Harvey, R. G., Amin, S., Geacintov, N. E., Broyde, S., & Patel, D. (1993) Biochemistry 32, 2488-2497.
18. Cosman, M., Laryea, A., Fiala, R., Hingerty, B. E., Amin, S., Geacintov, N. E., Broyde, S., & Patel, D. J. (1995) Biochemistry 34, 1295-1307.
19. de Meester, C., Poncelet, F., Roberfroid, M., Rondelet, J., & Mercier, M. (1977) Mutat. Res. 56, 147-152.
20. Eckel, L. M., & Krugh, T. R. (1994a) Nat. Struct. Biol. 1, 89-94.
21. Eckel, L. M., & Krugh, T. R. (1994b) Biochemistry 33, 13611-13624.
22. Elovaara, E., Engstrom, K., Nakajima, T., Park, S. S., Gelboin, H. V., & Vainio, H. (1991) Xenobiotica 21, 651-661.
23. Feng, B., & Stone, M. P. (1995) Chem. Res. Toxicol. 8, 821-832.
24. Feng, B., Zhou, L., Passarelli, M., Harris, C. M., Harris, T. M., & Stone, M. P. (1995) Biochemistry 34, 14021-14036.
25. Foureman, G. L., Harris, C., Guengerich, F. P., & Bend, J. R. (1989) J. Pharmacol. Exp. Ther. 248, 492-497.
26. Guengerich, F. P. (1992) FASEB J. 6, 745-748.
27. Guengerich, F. P., Kim, D.-H., & Iwasaki, M. (1991) Chem. Res. Toxicol. 4, 168-179.
28. Harris, C., Philpot, R. M., Hernandez, O., & Bend, J. R. (1986) J. Pharmacol. Exp. Ther. 236, 144-149.
29. Harris, C. M., Zhou, L., Strand, E. A., & Harris, T. M. (1991) J. Am. Chem. Soc. 113, 4328-4329.
30. Havel, T. F., & Wuthrich, K. (1985) J. Mol. Biol. 182, 281-294.
31. Hodgson, J. T., & Jones, P. D. (1985) J. Work Environ. 11, 347-352.
32. Keepers, J. W., & James, T. L. (1984) J. Magn. Reson. 57, 404-426.
33. Latham, G. J., & Lloyd, R. S. (1994) J. Biol. Chem. 269, 28527-28530.
34. Latham, G. J., Zhou, L., Harris, C. M., Harris, T. M., & Lloyd, R. S. (1993) J. Biol. Chem. 268, 23427-23434.
35. Latham, G. J., Harris, C. M., Harris, T. M., & Lloyd, R. S. (1995) Chem. Res. Toxicol. 8, 422-430.
36. Madrid, M., Llinas, E., & Llinas, M. (1991) J. Magn. Reson. 93, 329-346.
37. Marion, D., Ikura, M., & Bax, A. (1989) J. Magn. Reson. 84, 425-430.
38. Matanoski, G. M., & Schwarts, L. (1987) J. Occup. Med. 29, 675-680.
39. Miller, E. C. (1978) Cancer Res. 38, 1479-1496.
40. Miller, J. A. (1970) Cancer Res. 30, 559-576.
41. Mujeeb, A., Kerwin, S. M., Kenyon, G. L., & James, T. L. (1993) Biochemistry 32, 13419-13431.
42. Nakajima, T., Elovaara, E., Gonzalez, F. J., Gelboin, H. V., Raunio, H., Pelkonen, O., Vainio, H., & Aoyama, T. (1994a) Chem. Res. Toxicol. 7, 891-896.
43. Nakajima, T., Wang, R.-S., Elovaara, E., Gonzalez, F. J., Gelboin, H. V., Vainio, H., & Aoyama, T. (1994b) Biochem. Pharmacol. 48, 637-642.
44. Nelson, D. R., Kamataki, T., Waxman, D. J., Guengerich, F. P., Estabrook, R. W., Feyereisen, R., Gonzalez, F. J., Coon, M. J., Gunsalus, I. C., Goto, O., Okuda, K., & Nebert, D. W. (1993) DNA Cell Biol. 10, 1-51.
45. Nilsson, L., & Karplus, M. (1986) J. Comput. Chem. 7, 591-616.
46. Nilsson, L., Clore, G. M., Gronenborn, A. M., Brunger, A. T., & Karplus, M. (1986) J. Mol. Biol. 188, 455-475.
47. Norppa, H., Sorsa, M., Pfaffli, P., & Vainio, H. (1980) Carcinogenesis 1, 357-361.
48. Norppa, H., Hemminki, K., Sorsa, M., & Vainio, H. (1981) Mutat. Res. 91, 243-250.
49. Ott, M. G., Kolesar, R. C., Schamweber, H. C., Schneider, E. J., & Venable, J. R. (1980) J. Occup. Med. 22, 445-460.
50. Plateau, P., & Gueron, M. (1982) J. Am. Chem. Soc. 104, 7310-7311.
51. Quintanilla, M., Brown, K., Ramsden, M., & Balmain, A. (1986) Nature 322, 78-80.
52. Randall, S. K., Eritja, R., Kaplan, B. E., Petruska, J., & Goodman, M. F. (1987) J. Biol. Chem. 262, 6864-6870.
53. Ravishankar, G., Swaminathan, S., Beveridge, D. L., Lavery, R., & Sklenar, H. (1989) J. Biomol. Struct. Dyn. 6, 669-699.
54. Rodriguez, H., & Loechler, E. L. (1993a) Cartinogenesis 14, 373-383.
55. Rodriguez, H., & Loechler, E. L. (1993b) Biochemistry 32, 1759-1769.
56. Ryckaert, J.-P., Ciccotti, G., & Berendsen, H. J. C. (1977) J. Comput. Phys. 23, 327-341.
57. Savela, K., & Hemminki, K. (1986) Arch. Toxicol., Suppl. 9, 281-285.
58. Schurter, E. J., Sayer, J. M., Oh-hara, T., Yeh, H. J. C., Yagi, H., Luxon, B. A., Jerina, D. M., & Gorenstein, D. G. (1995a) Biochemistry 34, 9009-9020.
59. Schurter, E. J., Yeh, H. J. C., Sayer, J. M., Lakshman, M. K., Yagi, H., Jerina, D. M., & Gorenstein, D. G. (1995b) Biochemistry 34, 1364-1375.
60. Singer, B., Chavez, F., Goodman, M. F., Essigmann, J. M., & Dosanjh, M. K. (1989) Proc. Natl. Acad. Sci. U.S.A. 86, 8271-8274.
61. Singh, U. S., Moe, J. G., Reddy, G. R., Weisenseel, J. P., Marnett, L. J., & Stone, M. P. (1993) Chem. Res. Toxicol. 6, 825-836.
62. Sklenar, V., Brooks, B. R., Zon, G., & Bax, A. (1987) FEBS Lett. 216, 249-252.
63. Voigt, J. M., & Topal, M. D. (1990) Biochemistry 29, 5012-5018.
64. Wade, D. R., Airy, S. C., & Sinsheimer, J. E. (1978) Mutat. Res. 58, 217-223.
65. Weisz, K., Shafer, R. H., Egan, W., & James, T. L. (1994) Biochemistry 33, 354-366.
66. Wiseman, R., Stowers, S., Miller, E., Anderson, M., & Miller, J. (1986) Proc. Natl. Acad. Sci. USA. 83, 5285-5289.
67. Wong, O. (1990) J. Ind. Med. 47, 753-762.
68. Wuthrich, K. (1986) in NMR of Proteins and Nucleic Acids, John Wiley & Sons, New York.
69. Wuthrich, K., & Wagner, G. (1978) Trends Biochem. 3, 227-230.
70. Zarbl, H., Sukumar, S., Arthuyr, A. V., Martin-Zanca, D., & Barbacid, M. (1985) Nature 315, 382-385.
71. Zegar, I. S., Kim, S. J., Johansen, T. N., Horton, P. J., Harris, C. M., Harris, T. M., & Stone, M. P. (1996) Biochemistry 35, 6212-6224.