Temperature-dependent formation of a conjugate between Tris(hydroxymethyl)aminomethane buffer and the malondialdehyde-DNA adduct pyrimidopurinone

Chemical Research in Toxicology

Volumn 10, Issue 5, 1997, Pages 556-561

  Niedernhofer, Laura J ^a   Riley, Michael ^a   Schnetz Boutaud, Nathalie ^a   Sanduwaran, Geeganage ^a   Chaudhary, Ajai K ^a   Reddy, G Ramachandra ^b   Marnett, Lawrence J ^a  

^a VANDERBILT INGRAM CANCER CENTER   (United States)

^b Lumigen   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUFFER; DEOXYGUANOSINE; MALONALDEHYDE; PURINE DERIVATIVE; PYRIMIDINONE DERIVATIVE; TROMETAMOL;

ARTICLE; CARCINOGENESIS; DNA ADDUCT; DNA CROSS LINKING; HYDROLYSIS; MUTAGENICITY; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE DEPENDENCE;

CROSS-LINKING REAGENTS; DEOXYGUANOSINE; DNA; DNA ADDUCTS; DRUG STABILITY; HYDROGEN-ION CONCENTRATION; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPERATURE; TROMETHAMINE;

EID: 0030978416     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960191c     Document Type: Article

References (32)

1. Diczfalusy, U., Falardeau, P., and Hammarstrom, S. (1977) Conversion of prostaglandin endoperoxides to C17-hydroxyacids by human platelet thromboxane synthase. FEBS Lett. 84, 271-274.
2. Hamberg, M., and Samuelsson, B. (1967) Oxygenation of unsaturated fatty acids by the vesicular gland of sheep. J. Biol. Chem. 242, 5344-5354.
3. Pryor, W. A., and Stanley, J. P. (1975) A suggested mechanism for the production of malondialdehyde during the autoxidation of polyunsaturated fatty acids. Non-enzymatic production of prostaglandin endoperoxides during autoxidation. J. Org. Chem. 40, 3615-3617.
4. Mukai, F. H., and Goldstein, B. D. (1976) Mutagenicity of malondialdehyde, a decomposition product of peroxidized polyunsaturated fatty acids. Science 191, 868-869.
5. Benamira, M., Johnson, K., Chaudhary, A., Bruner, K., Tibbetts, C., and Marnett, L. J. (1995) Induction of mutations by replication of malondialdehyde-modified M13 DNA in Escherichia coli: Determination of the extent of DNA modification, genetic requirements for mutagenesis, and types of mutations induced. Carcinogenesis 16, 93-99.
6. Yau, T. M. (1979) Mutagenicity and cytotoxicity of malondialdehyde in mammalian cells. Mech. Ageing Dev. 11, 137-144.
7. Spalding, J. W. (1988) Toxicology and carcinogenesis studies of malondialdehyde sodium salt (3-hydroxy-2-propenal, sodium salt) in F344/N rats and B6C3F1 mice. NTP Tech. Rep. 331, 5-13.
8. Seto, H., Okuda, T., Takesue, T., and Ikemura, T. (1983) Reaction of malondialdehyde with nucleic acid. I. Formation of fluorescent pyrimido[1,2-a]purin-10(3H)-one nucleosides. Bull. Chem. Soc. Jpn. 56, 1799-1802.
9. Basu, A. K., O'Hara, S. M., Valladier, 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.
10. Nair, V., Turner, G. A., and Offerman, R. J. (1984) Novel adducts from the modification of nucleic acid bases by malondialdehyde. J. Am. Chem. Soc. 106, 3370-3371.
11. Stone, K., Ksebati, M., and Marnett, L. J. (1990) Investigation of the adducts formed by reaction of malondialdehyde with adenosine. Chem. Res. Toxicol. 3, 33-38.
12. Stone, K., Uzieblo, A., and Marnett, L. J. (1990) Studies of the reaction of malondialdehyde with cytosine nucleosides. Chem. Res. Toxicol. 3, 467-472.
13. 6-oxopropenyl-2′-deoxyadenosine adduct in malondialdehyde-modified DNA using liquid chromatography electrospray ionization tandem mass spectrometry. Carcinogenesis 17, 1167-1170.
14. Chaudhary, A. K., Nokubo, M., Reddy, G. R., 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.
15. 32P-Postlabeling determination of DNA adducts of malonaldehyde in humans: Total white blood cells and breast tissue. Carcinogenesis 16, 1847-1851.
16. Fang, J. L., Vaca, C. E., Valsta, L. M., and Mutanen, M. (1996) Determination of DNA adducts of malonaldehyde in humans: Effects of dietary fatty acid composition. Carcinogenesis 17, 1035-1040.
17. Rouzer, C. A., Chaudhary, A. K., Nokubo, M., Ferguson, D. M., Reddy, G. R., Blair, I. A., and Marnett, L. J. (1997) Analysis of the malondialdehyde-2′-deoxyguanosine adduct, pyrimidopurinone, in human leukocyte DNA by gas chromatography/electron capture negative chemical ionization/mass spectrometry. Chem. Res. Toxicol. 10, 181-188.
18. Chaudhary, A. K., Nokubo, M., Oglesby, T. D., Marnett, L. J., and Blair, I. A. (1995) Characterization of endogenous DNA adducts by liquid chromatography/electrospray ionization/tandem mass spectrometry. J. Mass Spectrom. 30, 1157-1166.
19. Reddy, G. R., and Marnett, L. J. (1995) Synthesis of an oligodeoxynucleotide containing the alkaline labile malondialdehydedeoxyguanosine adduct pyrimido[1,2-a]purin-10(3H)-one. J. Am. Chem. Soc. 117, 5007-5008.
20. Sambrook, J., Fritsch, E. F., and Maniatis, T. (1989) Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory, Cold Spring Harbor, NY.
21. Perrin, D. D., and Dempsey, B. (1974) Buffers for pH and Metal Ion Control, Chapman and Hall, London, U.K.
22. Chapeau, M. C., and Marnett, L. J. (1991) Enzymatic synthesis of purine deoxynucleoside adducts. Chem. Res. Toxicol. 4, 636-638.
23. Bull, A. W., and Marnett, L. J. (1985) Determination of malondialdehyde by ion-pairing high-performance liquid chromatography. Anal. Biochem. 149, 284-290.
24. Largilliere, C., and Melancon, S. B. (1988) Free malondialdehyde determination in human plasma by high-performance liquid chromatography. Anal. Biochem. 170, 123-126.
25. Siu, G. M., and Draper, H. H. (1982) Metabolism of malonaldehyde in vivo and in vitro. Lipids 17, 349-355.
26. Chin, D. H., Kappen, L. S., and Goldberg, I. H. (1987) 3′-Formyl phosphate-ended DNA: High energy intermediate in antiobiotic-induced DNA sugar damage. Proc. Natl. Acad. Sci. U.S.A. 84, 7070-7074.
27. Nair, V., Cooper, C. S., Vietti, D. E., and Turner, G. A. (1986) The chemistry of lipid peroxidation metabolites: crosslinking reactions of malondialdehyde. Lipids 21, 6-10.
28. Buttkus, H., and Bose, R. J. (1972) Amine-malonaldehyde condensation products and their relative color contribution in the thiobarbituric acid test. J. Am. Oil Chem. Soc. 49, 440-443.
29. Basu, A. K., Marnett, L. J., and Romano, L. J. (1984) Dissociation of malondialdehyde mutagenicity in Salmonella typhimurium from its ability to induce interstrand DNA cross-links. Mutat. Res. 129, 39-46.
30. Montine, T. J., Huang, D. Y., Valentine, W. M., Amaranth, V., Saunders, A., Weisgraber, K. H., Graham, D. G., and Strittmatter, W. J. (1996) Crosslinking of apolipoprotein E by products of lipid peroxidation. J. Neuropathol. Exp. Neurol. 55, 202-210.
31. Montine, T. J., Martin, M. E., Strittmatter, W. U., and Graham, D. G. (1996) E-4-hydroxy-2-nonenal is cytotoxic and cross-links cytoskeletal proteins in P19 neuroglial cultures. Am. J. Pathol. 148, 89-93.
32. Brooks, B. R., and Klamerth, O. L. (1968) Interaction of DNA with bifunctional aldehydes. Eur. J. Biochem. 5, 178-182.