Differential hydration thermodynamics of stereoisomeric DNA-benzo[a]pyrene adducts derived from diol epoxide enantiomers with different tumorigenic potentials

Journal of the American Chemical Society

Volumn 118, Issue 16, 1996, Pages 3804-3810

  Marky, Luis A ^a   Rentzeperis, Dionisios ^a,c   Luneva, Nataly P ^a,d   Cosman, Monique ^a,e   Geacintov, Nicholas E ^a   Kupke, Donald W ^b  

^a NEW YORK UNIVERSITY   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

^c MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^d RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

^e LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[A]PYRENE; BENZO[A]PYRENE DERIVATIVE;

ARTICLE; CARCINOGENICITY; DNA BINDING; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

EID: 0030009945     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9538703     Document Type: Article

References (51)

1. Ashurst, S. W.; Cohen, G. M.; Nesnow, S.; DiGiovanni, J.; Slaga, T. J. Cancer Res. 1983, 43, 1024.
2. Weinstein, I. B. Cancer Res. 1988, 48, 4135.
3. Singer, B ; Grunberger, D. In Molecular Biology of Mutagens and Carcinogens; Plenum Press; New York, 1983.
4. Singer, B.; Essigman, J. M. Carcinogenesis 1991, 12, 949.
5. Conney, A. H. Cancer Res. 1982, 42, 4875
6. Wood, A. W.; Chang, R. L.; Levin, W.; Yagi, H.; Thakker, D. R.; Jerina, D. M.; Conney, A. H. Biochem. Biophys. Res. Commun. 1977, 77, 1389.
7. Brookes, P.; Osborne, M R. Carcinogenesis 1982, 3, 1223.
8. Burgess, J A.; Stevens, C. W.; Fahl, W. E. Cancer Res. 1985, 45, 4257.
9. Stevens, C. W.; Bouck, N.; Burgess, J A., Fahl, W. E. Mutation Res. 1985, 152, 5.
10. Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1987, 21, 66.
11. Geacintov, N. E. In Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure Activity Relationships; Yang, S. K., Silverman, B. D., Eds.; CRC Press: Boca Raton, FL, 1988; Vol. II. pp 181-206.
12. Grädslund, A.; Jernström, B. Q. Rev Biophys. 1989, 22, 1.
13. Cosman, M.; Ibanez, V.; Geacintov, N E.; Harvey, R. G. Carcinogenesis 1990, 11, 1667
14. Geacintov, N. E.; Cosman, M.; Mao, B.; Alfano, A.; Ibanez, V.; Harvey, R. G. Carcinogenesis 1991, 12, 2099.
15. (a) Cosman, M.; Geacintov, N. E.; Amin, S. In Polycyclic Aromatic Compounds: Synthesis, Properties, Analytical Measuremenid, Occurrence and Biological Effects; Garrigues P., Lamotte M., Eds.: Gordon and Breach Science Publishers: France, 1991; Vol. 3. pp 1151-1158.
16. (b) Ya, N.-Q.; Smirnov. S.; Cosman, M.; Bhanot, S.; Ibanez, V ; Geacintov, N. E. In Structural Biology: The State of the Art. Proceedings of the 8th Conversation; Sarma, R. H., Sarma, M. H. Adenine Press: Schenectady, NY, 1994: Vol. 2, pp 349-366.
17. 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. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 1914.
18. De los Santos, C.; Cosman, M.; Hingerty, B. E.; Ibanez, V.; Margulis, L. A., Geacintov, N. E.; Broyde, S.; Patel, D. J. Biochemistry 1992, 31, 5245.
19. Weinstein, I. B.; Jeffrey, A. M.; Jennette, K. W.; Blobstein, S. H.; Harvey, R. G.; Harris, C.; Autrup, H.; Kasai, H.; Nakanishi, K. Science 1976, 193, 592.
20. Koreeda, M.; Moore, P. D.; Wislocki, P. G.; Levin, W.; Conney, A. H., Yagi, H.; Jerina, D. M. Science 1978, 199, 778.
21. Meehan, T.; Straub, K. Nature 1979, 277, 410.
22. Cheng, S. C.; Hilton, B. D.; Roman, J. M.; Dipple, A. Chem. Res. Toxicol. 1989, 2, 334.
23. Mao, B. Ph.D. Dissertation, New York University, 1994.
24. (a) Xu, R.; Mao, B.; Xu, J.; Li, B.; Birke, S.; Swenberg, C. E.; Geacintov, N. E. Nucleic Acids Res. 1995, 23, 2314-2319
25. (b) Xu, R.; Mao, B.; Amin, S.; Geacintov, N. E. In preparation.
26. Breslauer, K. J.; Frank, R.; Blöcker, H.; Marky, L. A. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 3746.
27. Freier, S. M.; Kierzek, R.; Jaeger, J. A.; Sugimoto, N.; Caruthers, M. H.; Neilson, T.; Turner, D. H. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 9373.
28. Caruthers, M. H. In Chemical and Enzymatic Synthesis of Gene Fragments; Gassen, H. G., Lang. A., Eds.; Verlag Chemie: Weinheim, FRG, 1982; pp 71-79.
29. Cantor, C. R.; Warshow, M. M.; Shapiro, H. Biopolymers 1970, 9, 1059.
30. Marky, L. A.; Blumenfeld, K. S.; Kozlowski, S.; Breslauer, K J. Biopolymers 1983, 22, 1247.
31. Gillies, G. T.; Kupke, D. W. Rev. Sci. Instrum. 1988, 59, 307.
32. Wiseman, T.; Williston, S., Brandts, J. F.; Lin, L. N. Anal. Biochem. 1989, 179, 131.
33. Marky, L. A.; Breslauer, K. J. Biopolymers 1987, 26, 1601.
34. Rentzeperis, D.; Kupke, D. W ; Marky, L. A. Biopolymers 1993, 33, 117.
35. Rentzepens, D.; Rippe, K.; Jovin, T. M.; Marky, L. A. J. Am. Chem. Soc. 1992, 114, 5926.
36. Record, T. M., Jr.; Anderson, C. F.; Lohman, T. M. Q. Rev. Biophys. 1978, 11, 103.
37. Zieba, K., Chu, T. M.; Kupke, D. W.; Marky, L. A. Biochemistry 1991, 30, 8018.
38. Rentzeperis, D.; Kupke, D. W.; Marky, L. A. Biochemistry 1994, 33, 9588.
39. Singh, S. S.; Hingerty, B. E ; Singh, U C.; Greenberg, J. P.; Geacintov, N. E.; Broyde, S. Cancer Res. 1991, 51, 3482.
40. Fountain, M. A.; Krugh, T. R. Biochemistry 1995, 34, 3152.
41. Enksson, M.; Nordin, B.; Jernstrvm, B.; Gradslund, A. Biochemistry 1988, 27, 1213
42. Roche, C. J ; Geacintov, N E ; Ibanez, V ; Harvey, R. G. Biophys. Chem. 1989, 33, 277
43. Norden, B ; Kubista, M.; Kurucsev, T. Q. Rev. Biophys. 1992, 25, 51.
44. Gasan, A. J.; Maleev, V. Ya.; Semenov, M. A. Stud. Biophys. 1990, 136, 171.
45. Marky, L. A.; Kupke, D. W. Biochemistry 1989, 28, 9982.
46. Cosman, M. Ph.D Dissertation. New York University, 1991.
47. Stezowski, J. J.; Loos-Guba, G.; Schvnwdlder, K. H.; Straub, A.; Glusker, J. P. J. Biomol. Struct., Dynamics 1987, 5, 615.
48. Casale, R.; McLaughlin, L. W J. Am. Chem. Soc. 1990, 112, 5264.
49. Telser, J.; Cruickshank, K. A.; Morrison, L. E.; Netzel, T. L. J. Am. Chem. Soc. 1989, 111, 6966
50. Telser, J.; Cruickshank, K. A.; Morrison, L. E.; Netzel, T. L.; Chan, C.-K. J. Am. Chem. Soc. 1989, 111, 7226.
51. Le Blanc, D. A.; Morden, K. M. Biochemistry 1991, 31, 4042.