Reactions of formaldehyde plus acetaldehyde with deoxyguanosine and DNA: Formation of cyclic deoxyguanosine adducts and formaldehyde cross-links

Chemical Research in Toxicology

Volumn 16, Issue 2, 2003, Pages 145-152

  Cheng, Guang ^a   Shi, Yongli ^a   Sturla, Shana J ^a   Jalas, John R ^a   McIntee, Edward J ^a   Villalta, Peter W ^a   Wang, Mingyao ^a   Hecht, Stephen S ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(N6 DEOXYADENOSYL N2 DEOXYGUANOSYL)METHANE; 3 (2' DEOXYRIBOSYL) 5,6,7,8 TETRAHYDRO 6 HYDROXYPYRIMIDO[1,2 A]PURIN (3H) ONE; 3 (2' DEOXYRIBOSYL) 5,6,7,8 TETRAHYDRO 8 HYDROXYPYRIMIDO[1,2 A]PURIN (3H) ONE; 3 (2' DEOXYRIBOSYL) 6 METHYL 1,3,5 DIAZINAN[4,5 A]PURIN 10(3H) ONE; 3 (2' DEOXYRIBOSYL) 6,8 DIMETHYL 1,3,5 DIAZINAN[4,5 A]PURIN 10(3H) ONE; ACETALDEHYDE; ACROLEIN; DEOXYGUANOSINE; DEOXYRIBONUCLEOSIDE; DI (N2 DEOXYGUANOSYL)METHANE; DI (N6 DEOXYADENOSYL)METHANE; DNA; FORMALDEHYDE; N6 HYDROXYMETHYLDEOXYADENOSINE; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DIASTEREOISOMER; DNA ADDUCT; DNA CROSS LINKING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIPID PEROXIDATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ULTRAVIOLET SPECTROSCOPY;

ACETALDEHYDE; ANIMALS; CATTLE; CROSS-LINKING REAGENTS; CYCLIZATION; DEOXYGUANOSINE; DNA; DNA ADDUCTS; DOSE-RESPONSE RELATIONSHIP, DRUG; FORMALDEHYDE; HUMANS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

ANIMALIA; STAPHYLOCOCCUS PHAGE 3A;

EID: 0037330015     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx025614r     Document Type: Article

References (20)

1. 2-propanodeoxyguanosine adducts. Mutat. Res. 424, 71-81.
2. 2-propanodeoxyguanosine adduct formation in aortic DNA following inhalation of acrolein. Environ. Health Perspect. 109, 219-224.
3. 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 44, 990-995.
4. Chung, F. L., Chen, H. J. C., and Nath, R. G. (1996) Lipid peroxidation as a potential source for the formation of exocyclic DNA adducts. Carcinogenesis 17, 2105-2111.
5. Pan, J., and Chung, F. L. (2002) Formation of cyclic deoxyguanosine adducts from omega-3 and omega-6 polyunsaturated fatty acids under oxidative conditions. Chem. Res. Toxicol. 15, 367-372.
6. Wang, M., McIntee, E. J., Cheng, G., Shi, Y., Villalta, P. W., and Hecht, S. S. (2000) Identification of DNA adducts of acetaldehyde. Chem. Res. Toxicol. 13, 1149-1157.
7. Esterbauer, H., Zollner, H., and Schaur, R. J. (1990) Aldehydes formed by lipid peroxidation: mechanisms of formation, occurrence, and determination. In Membrane Lipid Oxidation (Vigo-Pelfrey, C., Ed.), Vol. I, pp 239-268, CRC Press, Boca Raton, FL.
8. International Agency for Research on Cancer (1995) Wood Dust and Formaldehyde. IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 62, pp 217-362, IARC, Lyon, FR.
9. International Agency for Research on Cancer (1999) Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide (Part Two). IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 71, pp 319-335, IARC, Lyon, FR.
10. Chaw, Y. F., Crane, L. E., Lange, P., and Shapiro, R. (1980) Isolation and identification of cross-links from formaldehydetreated nucleic acids. Biochemistry 19, 5525-5531.
11. Beland, F. A., Fullerton, N. F., and Heflich, R. H. (1984) Rapid isolation, hydrolysis and chromatography of formaldehyde-modified DNA. J. Chromatogr. 308, 121-131.
12. 2,7,8 bis-cyclic adducts. Chem. Res. Toxicol. 5, 802-808.
13. Wang, M., McIntee, E. J., Cheng, G., Shi, Y., Villalta, P. W., and Hecht, S. S. (2001) Reactions of 2,6-dimethyl-1,3-dioxane-4-ol (aldoxane) with deoxyguanosine and DNA. Chem. Res. Toxicol. 14, 1025-1032.
14. Nielsen, A. T., and Houlihan, W. J. (1968) The aldol condensation. In Organic Reactions (Cope, A. C., Ed.) Vol. 16, pp 1-87, John Wiley & Sons.
15. Huang, H., Solomon, M. S., and Hopkins, P. B. (1992) Formaldehyde preferentially interstrand cross-links duplex DNA through deoxyguanosine residues at the sequence 5′-d(AT). J. Am. Chem. Soc. 114, 9240-9241.
16. Huang, H., and Hopkins, P. B. (1993) DNA interstrand crosslinking by formaldehyde: nucleotide sequence preference and covalent structure of the predominant cross-link formed in synthetic oligonucleotides. J. Am. Chem. Soc. 115, 9402-9408.
17. International Agency for Research on Cancer (2002) Tobacco Smoke and Involuntary Smoking. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 83, IARC, Lyon, FR (in press).
18. Fang, J. L., and Vaca, C. E. (1997) Detection of DNA adducts of acetaldehyde in peripheral white blood cells of alcohol abusers. Carcinogenesis 18, 627-632.
19. Vaca, C. E., Nilsson, J. A., Fang, J. L., and Grafstrom, R. C. (1998) Formation of DNA adducts in human buccal epithelial cells exposed to acetaldehyde and methylglyoxal in vitro. Chem.-Biol. 108, 197-208.
20. 2-ethyl-2′deoxyguanosine triphosphate during DNA synthesis catalyzed by mammalian replicative DNA polymerases. Biochemistry 38, 929-935.