Origins of conformational differences between cis and trans DNA adducts derived from enantiomeric anti-benzo[a]pyrene diol epoxides

Chemical Research in Toxicology

Volumn 12, Issue 7, 1999, Pages 597-609

  Xie, Xiao Ming ^a   Geacintov, Nicholas E ^a   Broyde, Suse ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CIS TRANS ISOMERASE; DOUBLE STRANDED DNA; EPOXIDE; PYRENE DERIVATIVE;

ARTICLE; CIS TRANS ISOMERISM; CONFORMATION; DNA ADDUCT; DNA REPAIR; DNA REPLICATION; DNA TRANSCRIPTION; ENANTIOMER; MATHEMATICAL ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM;

7,8-DIHYDRO-7,8-DIHYDROXYBENZO(A)PYRENE 9,10-OXIDE; CARCINOGENS; DNA ADDUCTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM; THERMODYNAMICS;

EID: 0032817450     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990021a     Document Type: Article

References (50)

1. Meehan, T., and Straub, K. (1979) Double stranded DNA stereo-selectively binds benzo[a]pyrene diol epoxides. Nature 277, 410-412.
2. Cheng, S. C., Hilton, B. D., Roman, J. M., and Dipple, A. (1989) DNA adducts from carcinogenic and noncarcinogenic enantiomers of benzo[a]pyrene dihydrodiol epoxide. Chem. Res. Toxicol. 2, 334-340.
3. Geacintov, N. E., Cosman, M., Hingerty, B. E., Amin, S., Broyde, S., and Patel, D. J. (1997) NMR solution structures of stereoisomeric polycyclic aromatic carcinogen-DNA adducts: principles, patterns and diversity. Chem. Res. Toxicol. 10, 111-146.
4. Cosman, M., de los Santos, C., Fiala, R., Hingerty, B. E., Ibanez, V., Margulis, L. A., Live, D., Geacintov, N. E., Broyde, S., and Patel, D. J. (1992) Solution conformation of the major adduct between the carcinogen (+)-anti-benzo[a]pyrene diol epoxide and DNA. Proc. Natl. Acad. Sci. U.S.A. 89, 1914-1918.
5. de los Santos, C., Cosman, M., Hingerty, B. E., Ibanez, V., Margulis, L. A., Geacintov, N. E., Broyde, S., and Patel, D. J. (1992) Influence of benzo[a]pyrene diol epoxide chirality on solution conformations of DNA covalent adducts: the (-)-trans-anti-[BP]G-C adduct structure and comparison with the (+)-trans-anti-enantiomer. Biochemistry 31, 5245-5252.
6. Fountain, M. A., and Krugh, T. R. (1995) Structural characterization of a (+)-trans-anti-benzo[a]pyrene-DNA adduct using NMR, restrained energy minimization and molecular dynamics. Biochemistry 34, 3152-3161.
7. Cosman, M., Fiala, R., Hingerty, B. E., Amin, S., Geacintov, N. E., Broyde, S., and Patel, D. J. (1994) 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 major groove. Biochemistry 33, 11507-11517.
8. Feng, B., Gorin, A., Kobanovskiy, A., Hingerty, B. E., Geacintov, N. E., Broyde, S., and Patel, D. J. (1997) 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 36, 13780-13790.
9. Cosman, M., de los Santos, C., Fiala, R., Hingerty, B. E., Ibanez, V., Luna, E., Harvey, R. G., Geacintov, N. E., Broyde, S., and Patel, D. (1993) Solution conformation of the (+)-cis-anti-[BP]dG adduct in a DNA duplex: intercalation of the covalently attached benzo[a]pyrenyl ring into the helix and displacement of the modified deoxyguanosine. Biochemistry 32, 4145-4155.
10. Cosman, M., Hingerty, B. E., Luneva, N., Amin, S., Geacintov, N. E., Broyde, S., and Patel, D. J. (1996) Solution conformation of the (-)-cis-anti-benzo[a]pyrenyl-dG adduct opposite dC in a duplex: intercalation of the covalently attached BP ring into the helix with base displacement of the modified deoxyguanosine into the major groove. Biochemistry 35, 9850-9863.
11. Cosman, M., Fiala, R., Hingerty, B. E., Amin, S., Geacintov, N. E., Broyde, S., and Patel, D. J. (1994) Solution conformation of the (+)-cis-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 33, 11518-11527.
12. 2 in a duplex dodecamer. Cancer Res. 51, 3482-3492.
13. Jerina, D. M., Sayer, J. M., Yeh, H. J. C., Liu, X., Yagi, H., Schurter, E., and Gorenstein, D. (1997) NMR conformational analysis of DNA duplexes containing diol epoxide adducts of polycyclic aromatic hydrocarbons. Polycyclic Aromatic Hydrocarbons 10, 145-152.
14. Cosman, M., Fiala, R., Hingerty, B., Laryea, A., Lee, H., Harvey, R. G., Amin, S., Geacintov, N. E., Broyde, S., and Patel, D. (1993) Solution conformation of the (+)-trans-anti-[BPh]dA adduct opposite dT in a DNA duplex: intercalation of the covalently attached benzo[c]phenanthrene to the 5′-side of the adduct site without disruption of the modified base pair. Biochemistry 32, 12488-12497.
15. Cosman, M., Laryea, A., Fiala, R., Hingerty, B. E., Amin, S., Geacintov, N. E., Broyde, S., and Patel, D. J. (1995) Solution conformation of the (-)-trans-anti-[BPh]dA opposite dT adduct in a DNA duplex: intercalation of the covalently attached benzo-[c]phenanthrenyl residue to the 3′-side of the adduct site and comparison with the (+)-trans-anti-[BPh]dA opposite dT. Biochemistry 34, 1295-1307.
16. 6-amino group to (-)-(7S,8R,9R,10S)-7,8-dihydroxy9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. Biochemistry 34, 1364-1375.
17. 6-amino group to (+)-(7R,8S,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene: an unusual syn glycosidic torsion angle at the modified dA. Biochemistry 34, 13570-13581.
18. 1H NMR. Biochemistry 35, 4334-4348.
19. 1H NMR. Biochemistry 35, 6212-6224.
20. 1H NMR. Biochemistry 34, 14021-14036.
21. 1H NMR. Biochemistry 34, 14037-14050.
22. Schwartz, J. L., Rice, J. S., Luxon, B. A., Sayer, J. M., Xie, G., Yeh, H. J., Liu, X., Jerina, D. M., and Gorenstein, D. G. (1997) Solution structure of the minor conformer of a DNA duplex containing a dG mismatch opposite a benzo[a]pyrene diol epoxide/ dA adduct: glycosidic rotation from syn to anti at the modified deoxyadenosine. Biochemistry 36, 11069-11076.
23. Xie, X., Geacintov, N. E., and Broyde, S. (1999) Stereochemical origin of opposite orientations in DNA adducts derived from enantiomeric anti-benzo[a]pyrene diol epoxides with different tumorigenic potentials. Biochemistry 38, 2956-2968.
24. Altona, C., and Sundaralingam, M. (1972) Conformational analysis of the sugar ring in nucleosides and nucleotides. A new dexription using the concept of pseudorotation. J. Am. Chem. Soc. 94, 8205-8212.
25. Pearlman, D., Case, D., Caldwell, J., Seibel, G., Singh, U. C., Weiner, P., and Kollman, P. A. (1986) AMBER 4.0 Documentation, University of California, Berkeley, CA.
26. Hingerty, B. E., Ritchie, R. H., Ferrell, T. L., and Turner, J. E. (1985) Dielectric effects in biopolymers: the theory of ionic saturation revisited. Biopolymers 24, 427-439.
27. Friedman, R. A., and Honig, B. (1992) The electrostatic contribution to DNA base stacking interactions. Biopolymers 32, 145-159.
28. Atkins, P. W. (1990) Physical Chemistry, 4th ed., pp 661-662, W. H. Freeman, New York.
29. Berman, H. M. (1997) Crystal studies of B-DNA: the answers and the questions. Biopolymers 44, 23-44.
30. Olson, W. K. (1973) Syn-anti effects on the spatial configuration of polynucleotides. Biopolymers 12, 1787-1814.
31. Sundaralingam, M. (1973) The concept of a conformationally "rigid" nucleotide and its significance in polynucleotide conformational analysis in conformations of biological molecules and polymers. in Jerusalem Symposia on Quantum Chemistry and Biochemistry (Bergmann, E. D., and Pullman, B., Eds.) pp 417-456, Academic Press, New York.
32. Xie, X. (1999) Origin of opposite orientations in stereoisomeric DNA guanine adducts derived from benzo[a]pyrene diol epoxides with different tumorigenic potentials: a computational study of modified nucleosides. Ph.D. Thesis, New York University, New York.
33. Mao, B., Hingerty, B. E., Broyde, S., and Patel, D. J. (1998) Solution structure of the aminofluorene [AP]-intercalated conformer of the syn [AF]-C8-dG adduct opposite dC in a DNA duplex. Biochemistry 37, 81-94.
34. Mao, B., Hingerty, B. E., Broyde, S., and Patel, D. J. (1998) Solution structure of the aminofluorene [AF]-external conformer of the anti [AF]-C8-dG adduct opposite dC in a DNA duplex. Biochemistry 37, 95-106.
35. Patel, D., Mao, B., Gu, Z., Hingerty, B. E., Gorin, A., Basu, A., and Broyde, S. (1998) NMR solution structures of covalent aromatic amine-DNA adducts and their mutational relevance. Chem. Res. Toxicol. 11, 391-407.
36. Kozack, R., and Loechler, E. L. (1999) Molecular modeling of the major adduct of (+)-anti-B[a]PDE (N2-dG) in the eight conformations and five DNA sequences most relevant to base substitution mutagenesis. Carcinogenesis 20, 85-94.
37. 2-dG) causes G→T vs G→A mutations based upon a correlation between mutagenesis and molecular modeling results. Carcinogenesis 20, 95-102.
38. 2-2′-deoxyguanosine adducts in Escherichia coli and simian kidney cells. Biochemistry 37, 10164-10172.
39. Moriya, M., Spiegel, S., Fernandes, A., Amin, S., Liu, T., Geacintov, N., and Grollman, A. P. (1996) Fidelity of translesional synthesis past benzo[a]pyrene diol epoxide-2′-deoxyguanosine DNA adducts: marked effects of host cell, sequence context, and chirality. Biochemistry 35, 16646-16651.
40. 2-dG adduct of (+)-anti-B[a]PDE shows a dramatically different mutagenic specificity (predominantly, G → A) in a 5′-CGT-3′ sequence context. Biochemistry 36, 10256-10261.
41. 2-deoxyguanosine adducts of 7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene: configuration of the adduct bond is more important than those of the hydroxyl groups. Biochemistry 36, 13263-13269.
42. Page, J. E., Zajc, B., Oh-hara, T., Lakshman, M. K., Sayer, J. M., Jerina, D. M., and Dipple, A. (1998) Sequence context profoundly influences the mutagenic potency of trans-opened benzo[o]pyrene 7,8-diol-epoxide-purine nucleoside adducts in site-specific mutation studies. Biochemistry 37, 9127-9137.
43. Rodriguez, H., and Loechler, E. L. (1993) Mutational specificity of the (+)-anti-diol epoxide of benzo[a]pyrene in a supF gene of an Escherichia coli plasmid: DNA sequence context influences hotspots, mutagenic specificity and the extent of SOS enhancement of mutagenesis. Carcinogenesis 14, 373-383.
44. Rodriguez, H., and Loechler, E. L. (1993) Mutagenesis by the (+)-anti-diol epoxide of benzo[a]pyrene: what controls mutagenic specificity? Biochemistry 32, 1759-1769.
45. Kozack, R., and Loechler, E. L. (1997) Molecular modeling of the conformational complexity of (4-)-anti-B[a]PDE-adducted DNA using simulated annealing. Carcinogenesis 18, 1585-1593.
46. Choi, D.-J., Liu, T., Geacintov, N. E., and Scicchitano, D. A. (1996) Site-specific benzo[a]pyrene diol epoxide-DNA adducts inhibit transcription elongation by bacteriophage T7 RNA polymerase. Biochemistry 33, 780-787.
47. Choi, D.-J., Liu, T., Geacintov, N. E., and Scicchitano, D. A. (1996) Incorrect base insertion and prematurely terminated transcripts during T7 RNA polymerase transcription elongation past benzo-[a]pyrene modified DNA. J. Mol. Biol. 264, 213-219.
48. Mao, B., Li, B., Amin, S., Cosman, M., and Geacintov, N. E. (1993) Opposite stereoselective resistance to digestion by phosphodiesterases I and II of benzo[a]pyrene diol epoxide-modified oligonucleotide adducts. Biochemistry 32, 11785-11793.
49. Zou, Y., Liu, T., Geacintov, N. E., and Van Houten, B. (1995) Interaction of the UvrABC nuclease system with a DNA duplex containing a single stereoisomer of dG-(+)-or dG-(-)-anti-BPDE. Biochemistry 34, 13582-13593.
50. Hess, T. M., Gunz, D., Luneva, N., Geacintov, N. E., and Naegeli, H. (1997) Base pair conformation-dependent excision of benzo-[a]pyrene diol epoxide-guanine adducts by human nucleotide excision repair. Mol. Cell. Biol. 17, 7069-7076.