Site-specific synthesis of aflatoxin B1 adducts within an oligodeoxyribonucleotide containing the human p53 codon 249 sequence

Chemical Research in Toxicology

Volumn 12, Issue 8, 1999, Pages 707-714

  Jones, Wendelyn R ^a,b   Johnston, David S ^a   Stone, Michael P ^a  

^a VANDERBILT UNIVERSITY   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AFLATOXIN B1; DNA; GUANINE; OLIGODEOXYNUCLEOTIDE; OLIGODEOXYRIBONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE; PIPERIDINE; PROTEIN P53;

ALKYLATION; AMINO ACID SEQUENCE; ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE; POLYACRYLAMIDE GEL ELECTROPHORESIS; STRUCTURE ANALYSIS; SYNTHESIS;

AFLATOXIN B1; AUTORADIOGRAPHY; CARCINOGENS; CHEMISTRY, PHYSICAL; CODON; DNA ADDUCTS; ELECTROPHORESIS, POLYACRYLAMIDE GEL; EPOXY COMPOUNDS; GENES, P53; HUMANS; MUTAGENESIS, SITE-DIRECTED; OLIGODEOXYRIBONUCLEOTIDES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0032765557     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990048u     Document Type: Article

References (61)

1. McCann, J., Spingarn, N. E., Koburi, J., and Ames, B. N. (1975) Detection of carcinogens as mutagens - bacterial tester strains with R-factor plasmids. Proc. Natl. Acad. Sci. U.S.A. 72, 979-983.
2. Busby, W. F., Jr., and Wogan, G. N. (1984) Aflatoxins. In Chemical Carcinogens (Searle, C. E., Ed.) pp 945-1136, American Chemical Society, Washington, DC.
3. 1-induced rat liver tumors. Proc. Natl. Acad. Sci. U.S.A. 87, 1104-1108.
4. Wogan, G. N. (1992) Aflatoxin carcinogenesis: Interspecies potency differences and relevance for human risk assessment. Prog. Clin. Biol. Res. 374, 123-137.
5. Hsu, I. C., Metcalf, R. A., Sun, T., Welsh, J. A., Wang, N. J., and Harris, C. C. (1991) Mutational hotspot in the p53 gene in human hepatocellular carcinomas. Nature 350, 427-428.
6. Bressac, B., Kew, M., Wands, J., and Ozturk, M. (1991) Selective G to T mutations of p53 in hepatocellular carcinoma from southern Africa. Nature 350, 429-431.
7. 1-induced hepatocellular carcinoma and adenoma in the rat: Detection by denaturing gradient gell electrophoresis. Proc. Natl. Acad. Sci. U.S.A. 90, 2045-2049.
8. Shimada, T., and Guengerich, F. P. (1989) Evidence for cytochrome P-450NF, the nifedipine oxidase, being the principal enzyme involved in the bioactivation of aflatoxins in human liver. Proc. Natl. Acad. Sci. U.S.A. 86, 462-465.
9. 1. Proc. Natl. Acad. Sci. U.S.A. 87, 4790-4793.
10. 1: The ultimate carcinogenic species. J. Am. Chem. Soc. 110, 7929-7931.
11. 1 8,9-epoxide using m-chloroperbenzoic acid. Chem. Res. Toxicol. 6, 313-316.
12. 1 in vitro. Proc. Natl. Acad. Sci. U.S.A. 74, 1870-1874.
13. 1 epoxide. J. Am. Chem. Soc. 116, 8863-8869.
14. 1-DNA adduct formed in vivo in rat liver. Proc. Natl. Acad. Sci. U.S.A. 75, 1745-1749.
15. 1 creates alkali-labile lesions in DNA at positions of guanine and adenine. Proc. Natl. Acad. Sci. U.S.A. 75, 4120-4124.
16. 1 adduct with the oligodeoxynucleotide d(ATCGAT). J. Am. Chem. Soc. 111, 7232-7239.
17. 1H NMR. Biochemistry 37, 4374-4387.
18. 1 adduct. Chem. Res. Toxicol. 11, 873-881.
19. 2. Biochemistry 29, 10438-10448.
20. 1H NMR. Biochemistry 34, 14037-14050.
21. 1-N7-guanine DNA adduct situated at a unique site. Nucleic Acids Res. 24, 2821-2828.
22. 1-DNA adduct. Proc. Natl. Acad. Sci. U.S.A. 93, 1535-1539.
23. Gopalakrishnan, S., Liu, X., and Patel, D. J. (1992) Solution structure of the covalent sterigmatocystin-DNA adduct. Biochemistry 31, 10790-10801.
24. Gopalakrishnan, S., and Patel, D. J. (1993) Formation and structural features of a sterigmatocystin-formamidopyrimidine adduct at the DNA duplex level. J. Am. Chem. Soc. 115, 9321-9322.
25. Greenblatt, M. S., Bennett, W. P., Hollstein, M., and Harris, C. C. (1994) Mutations in the p53 tumor suppressor gene: Clues to cancer etiology and molecular pathogenesis. Cancer Res 54, 4855-4878.
26. Shen, H. M., and Ong, C. N. (1996) Mutations of the p53 tumor suppressor gene and ras oncogenes in aflatoxin hepatocarcinogenesis. Mutat. Res. 366, 23-44.
27. Soini, Y., Chia, S. C., Bennett, W. P., Groopman, J. D., Wang, J. S., DeBenedetti, V. M., Cawley, H., Welsh, J. A., Hansen, C., Bergasa, N. V., Jones, E. A., DiBisceglie, A. M., Trivers, G. E., Sandoval, C. A., Calderon, I. E., Munoz Espinosa, L. E., and Harris, C. C. (1996) An aflatoxin-associated mutational hotspot at codon 249 in the p53 tumor suppressor gene occurs in hepatocellular carcinomas from Mexico. Carcinogenesis 17, 1007-1012.
28. Lunn, R. M., Zhang, Y. J., Wang, L. Y., Chen, C. J., Lee, P. H., Lee, C. S., Tsai, W. Y., and Santella, R. M. (1997) P53 mutations, chronic hepatitis B virus infection, and aflatoxin exposure in hepatocellular carcinoma in Taiwan. Cancer Res. 57, 3471-3477.
29. 1-induced DNA adduct formation and p53 mutations in cyp450-expressing human liver cell lines. Carcinogenesis 18, 1291-1297.
30. 1-DNA adducts and hepatitis B virus antigens in hepatocellular carcinoma and nontumorous liver tissue. Environ. Health Perspect. 99, 199-202.
31. Chen, C. J., Yu, M. W., Liaw, Y. F., Wang, L. W., Chiamprasert, S., Matin, F., Hirvonen, A., Bell, D. A., and Santella, R. M. (1996) Chronic hepatitis B carriers with null genotypes of glutathione S-transferase m1 and t1 polymorphisms who are exposed to aflatoxin are at increased risk of hepatocellular carcinoma. Am. J. Hum. Genet. 59, 128-134.
32. Yu, M. W., Lien, J. P., Chiu, Y. H., Santella, R. M., Liaw, Y. F., and Chen, C. J. (1997) Effect of aflatoxin metabolism and DNA adduct formation on hepatocellular carcinoma among chronic hepatitis B carriers in Taiwan. J. Hepatol. 27, 320-330.
33. Kobertz, W. R., and Essigmann, J. M. (1996) Total synthesis of a cis-syn 2-carbomethoxypsoralen furan-side thymidine monadduct. J. Am. Chem. Soc. 118, 7101-7107.
34. Kobertz, W. R., and Essigmann, J. M. (1997) Solid-phase synthesis of oligonucleotides containing a site-specific psoralen derivative. J. Am. Chem. Soc. 119, 5960-5961.
35. 1 adducts in a p53 mutational hotspot. Proc. Natl. Acad. Sci. U.S.A. 94, 9579-9584.
36. 2. J. Biomol. Struct. Dyn. 5, 1025-1041.
37. 2 and with plasmid pBR322 support intercalative association with the B-DNA helix. Biochemistry 28, 726-734.
38. Raney, K. D., Gopalakrishnan, S., Byrd, S., Stone, M. P., and Harris, T. M. (1990) Alteration of the aflatoxin cyclopentenone ring to a δ-lactone reduces intercalation with DNA and decreases formation of guanine N7 adducts by aflatoxin epoxides. Chem. Res. Toxicol. 3, 254-261.
39. 1-8,9-exo-epoxide. Chem. Res. Toxicol. 6, 64-68.
40. 1: Mechanistic studies. J. Am. Chem. Soc. 118, 1603-1609.
41. Strobel, S. A., Moser, H. E., and Dervan, P. B. (1988) Double-strand cleavage of genomic DNA at a single site by triple-helix formation. J. Am. Chem. Soc. 110, 7927-7929.
42. Moser, H. E., and Dervan, P. B. (1987) Sequence-specific cleavage of double helical DNA by triple helix formation. Science 238, 645-650.
43. Strobel, S. A., and Dervan, P. B. (1991) Single-site enzymatic cleavage of yeast genomic DNA mediated by triple helix formation. Nature 360, 172-174.
44. Strobel, S. A., Doucette-Stamm, L. A., Riba, L., Housman, D. E., and Dervan, P. B. (1997) Site-specific cleavage of human chromosome 4 mediated by triple helix formation. Science 254, 1639-1642.
45. Jones, W. R., and Stone, M. P. (1998) Site-specific targeting of aflatoxin adduction directed by triple helix formation in the major groove of oligodeoxyribonucleotides. Nucleic Acids Res. 26, 1070-1075.
46. 3 incorporated in an intramolecular DNA triplex binds sequence-specifically by intercalation. J. Am. Chem. Soc. 115, 7908-7909.
47. Radhakrishnan, I., Patel, D. J., Priestly, E. S., Nash, H. M., and Dervan, P. B. (1993) NMR structural studies on a nonatural deoxyribonucleoside which mediates recognition of GC base pairs in pyrimidine-purine-pyrimidine DNA triplexes. Biochemistry 32, 11228-11234.
48. 3. J. Mol. Biol. 257, 1052-1069.
49. Maxam, A. M., and Gilbert, W. (1980) Sequencing end-labeled DNA with base-specific chemical cleavage. Methods Enzymol. 65, 499-560.
50. Muro, A. F., Peace, C. G., and Kornblihtt, A. R. (1993) DNA sequencing by the chemical method. Trends Genet. 9, 337-338.
51. 1H NMR spectroscopy. In Molecular Basis of Specificity in Nucleic Acid-Drug Interactions (Pullman, B., and Jortner, J., Eds.) pp 451-480, Kluwer Academic Publisher. Dordrecht, The Netherlands.
52. 1: A new metabolite. Chem. Res. Toxicol. 5, 333-335.
53. 1 exo-8,9-epoxide and rearrangement of the dihydrodiol. J. Am. Chem. Soc. 118, 8213-8220.
54. 1-DNA interactions Proc. Natl. Acad. Sci. U.S.A. 80, 6-10.
55. 1 with guanines in different DNA sequences. Biochemistry 27, 472-481.
56. Mancini, D., Singh, S., Ainsworth, P., and Rodenhiser, D. (1997) Constitutively methylated CpG dinucleotides as mutation hot spots in the retinoblastoma gene (rb1). Am. J. Hum. Genet. 61, 80-87.
57. Denissenko, M. F., Pao, A., Tang, M., and Pfeifer, G. P. (1996) Preferential formation of benzo[α]pyrene adducts at lung cancer mutational hotspots in p53. Science 274, 430-432.
58. Jones, P. A., Rideout, W. M., Shen, J. C., Spruck, C. H., and Tsai, Y. C. (1992) Methylation, mutation and cancer. BioEssays 14, 33-36.
59. Calladine, C. R. (1982) Mechanics of sequence-dependent stacking of bases in B-DNA. J. Mol. Biol. 161, 343-352.
60. Dickerson, R. E. (1983) Base sequence and helix structure variation in B and A DNA. J. Mol. Biol. 166, 419-441.
61. Basu, A. K., and Essigmann, J. M. (1988) Site-specifically modified oligodeoxynucleotides as probes for the structural and biological effects of DNA-damaging agents. Chem. Res. Toxicol. 1, 1-18.