DNA alkylation by 4,5-dioxovaleric acid, the final oxidation product of 5-aminolevulinic acid

Chemical Research in Toxicology

Volumn 11, Issue 2, 1998, Pages 150-157

  Douki, Thierry ^a   Onuki, Janice ^b   Medeiros, Marisa H G ^b   Bechara, Etelvino J H ^b   Cadet, Jean ^a   Mascio, Paolo Di ^b  

^a CEA GRENOBLE   (France)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; AMINOLEVULINIC ACID; DEOXYGUANOSINE; DNA; GUANINE; NUCLEOSIDE; REACTIVE OXYGEN METABOLITE; SCHIFF BASE; VALERIC ACID DERIVATIVE;

ACUTE INTERMITTENT PORPHYRIA; ARTICLE; CANCER INCIDENCE; DISEASE ASSOCIATION; DNA ADDUCT; DNA ALKYLATION; DNA STRAND BREAKAGE; GENOTOXICITY; LIVER CANCER; LIVER CARCINOGENESIS; LIVER CELL CARCINOMA; OXIDATION; TYROSINEMIA;

ALKYLATION; AMINOLEVULINIC ACID; DNA ADDUCTS; DNA DAMAGE; GUANINE; HUMANS; LIVER NEOPLASMS; MUTAGENESIS; OXIDATION-REDUCTION; PORPHYRIA, ACUTE INTERMITTENT; VALERATES;

EID: 0031932699     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970157d     Document Type: Article

References (33)

1. Kappas, A., Sassa, S., and Andersen, K. E. (1983) In The Metabolic Basis of Inherited Diseases (Stanbury, J. B., Wyngaarden, J. B., Fredrickson, D. S., Goldstein, J. L., and Brown, M. S., Eds.) pp 1301-1384, McGraw-Hill, New York.
2. Hindmarsh, J. T. (1986) The porphyrias: Recent advances. Clin, Chem. 32, 1255-1263.
3. Chisolm, J. J., Jr. (1971) Lead poisoning. Sci. Am. 224, 15-23.
4. Lithner, F., and Wetterberg, L. (1984) Hepatocellular carcinoma in patients with acute intermittent porphyria. Acta Med. Scand. 215, 271-274.
5. Gubler, J. G., Bergetzi, M. J., and Meyer, U. A. (1990) Primary liver carcinoma in two sisters with acute intermittent porphyria. Am. J. Med. 89, 540-541.
6. Thunnissen, P. L., Meyer, J., and de Koning, R. W. (1991) Acute intermittent porphyria and primary liver cancer. Neth. J. Med. 38, 171-174.
7. Fiedler, D. M., Eckl, P. M., and Krammer, B. (1996) Does δ-aminolaevulinic acid induce genotoxic effects? J. Photochem. Photobiol. B: Photobiol. 33, 39-44.
8. Kennedy, J. C., and Pottier, R. H. (1992) Endogenous protoporphyrin IX, a clinically useful photosensitizer for photodynamic therapy. J. Photochem. Photobiol. B: Biol. 14, 275-292.
9. Ortel, B., Tanew, A., and Hönigsmann, H. (1993) Lethal photosensitization by endogenous porphyrins of PAM cells modification by desferrioxamine. J. Photochem. Photobiol. B: Photobiol. 17, 273-278.
10. Peng, Q., Berg, K., Moan, J., Kongshaug, M., Giercksky, K. E., and Nesland, J. M. (1997) 5-Aminolevulinic acid-based photodynamic therapy: Principles and experimental research. Photochem. Photobiol. 65, 235-251.
11. Bechara, E. J. H., Medeiros, M. H. G., Monteiro, H. P., Hermes-Lima, M., Pereira, B., Demasi, M., Costa, C. A., Abdalla, D. S. P., Onuki, J., Wendel, C. M. A., and Di Mascio, P. (1993) A free radical hypothesis of lead poisoning and inborn porphyrias associated with 5-aminolevulinic acid overload. Quim. Nova 16, 385-392.
12. Fraga, C. G., Onuki, J., Lucesoli, F., Bechara, E. J. H., and Di Mascio, P. (1994) 5-Aminolevulinic acid mediates the in vivo and in vitro formation of 8-hydroxy-2'-deoxyguanosine in DNA. Carcinogenesis 15, 2241-2244.
13. Hiraku, Y., and Kawanishi, S. (1996) Mechanism of oxidative DNA damage induced by δ-aminolevulinic acid in the presence of copper ion. Cancer Res. 56, 1786-1793.
14. Demasi, M., Penatti, C. A. A., DeLucia, R., and Bechara, E. J. H. (1996) The prooxidant effect of 5-aminolevulinic in the brain tissue of rats: Implications in neuropsychiatric manifestations in porphyrias. Free Radical Biol. Med. 20, 291-299.
15. Oteiza, P. I., Kleinman, C. G., Demasi, M., and Bechara, E. J. H. (1995) 5-Aminolevulinic acid induces iron release from ferritin. Arch. Biochem. Biophys. 316, 607-611.
16. 2+ ions. Biochim. Biophys. Acta 1225, 259-263.
17. Basu, A. K., O'Hara, S. M., Valladir, P., Stone, K., Mols, O., and Marnett, L. J. (1988) Identification of adducts formed by reaction of guanine nucleosides with malondialdehyde and structurally related aldehydes. Chem. Res. Toxicol. 1, 53-59.
18. Chaudhary, A. K., Nokubo, N., Ramachandra Reddy, G., Yeola, S. N., Morrow, J. D., Blair, I. A., and Marnett, L. J. (1994) Detection of endogenous malondialdehyde-deoxyguanosine adducts in human liver. Science 265, 1580-1582.
19. 32P-postlabeling. Carcinogenesis 13, 593-599.
20. Vaca, C. E., Fang, J.-L., and Schweda, E. K. H. (1995) Studies of the reaction of acetaldehyde with deoxynucleosides. Chem.-Biol. Interact. 98, 51-67.
21. Fang, F. L., and Vaca, C. E. (1997) Detection of adducts of acetaldehyde in peritethial white blood cells of alcohol abusers. Carcinogenesis 18, 627-632.
22. Shapiro, R., and Hachmann, J. (1966) The reaction of guanine derivatives with 1,2-dicarbonyl compounds. Biochemistry 5, 2799- 2807.
23. 2alkylguanines. Biochemistry 8, 238-245.
24. 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 44, 990-995.
25. Winter, C. K., Segall, H. J., and Haddon, W. F. (1986) Formation of cyclic adducts of deoxygunosine with the aldehydes trans-4hydroxy-2-hexenal and trans-4-hydroxy-2-nonenal in vitro. Cancer Res. 46, 5682-5686.
26. Eder, E., Scheckenbach, S., Deininger, C., and Huffman, C. (1993) The possible role of α,β-unsaturated carbonyl compounds in mutagenesis and carcinogenesis. Toxicol. Lett. 67, 87-103.
27. 2propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc. Natl. Acad. Sci. U.S.A. 91, 7491-7495.
28. 2propano adducts of 2'-deoxyguanosine with 4-hydroxynonenal and other α,β-unsaturated aldehydes. Chem. Res. Toxicol. 7, 511-518.
29. Marnett, L. J., Hurd, H. K., Hollstein, M. C., Levin, D. E., Esterbauer, H., and Ames, B. N. (1985) Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA104. Mutat. Res. 148, 25-34.
30. Dellarco, V. L. (1993) A mutagenicity assessment of acetaldehyde. Mutat. Res. 195, 1-20.
31. Bjeldanes, L. F., and Chew, H. (1979) Mutagenicity of 1,2-dicarbonyl compounds: maltol, kojic acid, diacetyl and related substances. Mutat. Res. 67, 367-371.
32. Monteiro, H. P., Abdalla, D. S. P., Augusto, O., and Bechara, E. J. H. (1989) Free radical generation during δ-aminolevulinic acid autoxidation: Induction by hemoglobin and connections with porphyrinpathies. Arch. Biophys. Biochem. 271, 206-216.
33. Biempica, L., Kosower, N., Ma, M. H., and Goldfisher, S. (1974) Cytochemical and ultra structural studies of liver in acute intermitent porphyria and porphyria cutanea tarda. Arch. Pathol. 98, 336-343.