(E)-2-hexenal-induced DNA damage and formation of cyclic 1,N2-(1,3- propano)-2'-deoxyguanosine adducts in mammalian cells

Chemical Research in Toxicology

Volumn 9, Issue 7, 1996, Pages 1207-1213

  Gölzer, Petra ^a   Janzowski, Christine ^a   Pool Zobel, Beatrice L ^b   Eisenbrand, Gerhard ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

^b FEDERAL RESEARCH INSTITUTE OF NUTRITION AND FOOD   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 HEXENAL; CROTONALDEHYDE; DEOXYGUANOSINE DERIVATIVE;

ANIMAL CELL; ARTICLE; COLON MUCOSA; CONTROLLED STUDY; DNA ADDUCT; DNA DAMAGE; ESOPHAGUS MUCOSA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; LIQUID SCINTILLATION COUNTING; LYMPHOBLASTOID CELL; NONHUMAN; RAT; STOMACH MUCOSA; THIN LAYER CHROMATOGRAPHY;

ALDEHYDES; ANIMALS; BURKITT LYMPHOMA; CELL LINE; DEOXYGUANOSINE; DNA ADDUCTS; DNA DAMAGE; FLAVORING AGENTS; GASTRIC MUCOSA; HUMANS; INTESTINAL MUCOSA; RATS;

ANIMALIA; MAMMALIA;

EID: 0029958580     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9600107     Document Type: Article

References (53)

1. Götz-Schmidt, E.-M., and Schreier, P. (1986) Neutral volatiles from blended endive (Cichorium endivia, L.). J. Agric. Food Chem. 34, 212-215.
2. De Vincenzi, M., Badellino, E., Di Folco, S., Dracos, A., Magliola, M., Stacchini, A., Stacchini, P., and Silano, V. (1989) A basis for estimation of consumption: literature values for selected food volatiles, Part III. Food Addit. Contam. 6, 235-267.
3. Feron, V. J., Til, H. P., de Vrijer, F., Woutersen, R. A., Cassee, F. R., and van Bladeren, P. J. (1991) Aldehydes: occurrence, carcinogenic potential, mechanism of action and risk assessment. Mutat. Res. 259, 363-385.
4. Luning, P. A., de Rijk, T., Wichers, H. J., and Roozen, J. P. (1994) Gas chromatography, mass spectrometry, and sniffing port analyses of volatile compounds of fresh bell peppers (Capsicum annuum) at different ripening stages. J. Agric. Food Chem. 42, 977-983.
5. van Ruth, S. M., Roozen, J. P., and Cozijnsen, J. L. (1995) Volatile compounds of rehydrated French beans, bell peppers and leeks. Part 1. Flavor release in the mouth and in three mouth model systems. Food Chem. 53, 15-22.
6. Hatanaka, A., Kajiwara, T., and Sekiya, J. (1986) Fatty acid hydroperoxide lyase in plant tissues: volatile aldehyde formation from linoleic and linolenic acid. In Biogeneration of aromas (Parliment, T. H., and Croteau, R., Eds) pp 167-175, American Chemical Society, Washington, DC.
7. Schreier, P., and Lorenz, G. (1981) Formation of "green-grassy"-notes in disrupted plant tissues: characterization of the tomato enzyme systems. In Flavour 81, Weurman Symp., 3rd (Schreier, P., Ed.) pp 495-507, de Gruyter, Berlin, FRG.
8. Wu, C.-M., and Liou, S.-E. (1986) Effect of tissue disruption on volatile constituents of bell peppers. J. Agric. Food Chem. 34, 770-772.
9. Andersen, R. A., McCracken, C. T., Jr., Hamilton-Kemp, T. R., and Hildebrand, D. F. (1995) Nitrosation of tobacco alkaloids during storage reduced by antimicrobial (E)-2-hexenal vapor. ACS Symposium Series 584 (Synthesis and Chemistry of Agrochemicals IV), 463-472.
10. Hamilton-Kemp, T. R., McCracken, C. T., Andersen, R. A., and Hildebrand, D. F. (1995) Antimicrobial properties of natural volatile compounds. ACS Symposium Series 584 (Synthesis and Chemistry of Agrochemicals IV), 449-462.
11. Esterbauer, H., Eckl, P., and Ortner, A. (1990) Possible mutagens derived from lipids and lipid precursors. Mutat. Res. 238, 223-233.
12. Boelens, M. H., and van Gemert, L. J. (1987) Organoleptic properties of aliphatic aldehydes. Perfum. Flavor. 12, 31-43.
13. Ziegler, E. (1982) Die natürlichen und künstlichen Aromen, Dr. Alfred Hüthig Verlag GmbH, Heidelberg.
14. Opdyke, D. L. J. (1975) Monographs on fragrance raw materials. Hexen-2-al. Food Cosmet. Toxicol. 13, 453-454.
15. Council of Europe (1981) Flavouring substances and natural sources of flavourings, 3rd ed., Strasbourg, Maisonneuve, France.
16. Wynder, E. L., Goodman, D. A., and Hoffmann, D. (1965) Ciliatoxic compounds in cigarette smoke. II. Carboxylic acids and aldehydes. Cancer 18, 505-509.
17. Sakuma, H., Murakata, S., and Sugawara, S. (1981) Volatile products of cellulose pyrolysis. Agric. Biol. Chem. 45, 443-451.
18. Simmon, V. F., Kauhanen, K., and Tardiff, R. G. (1977) Mutagenic activity of chemicals identified in drinking water. In Progress in genetic toxicology (Scott, D., Bridges, B. A., and Sobels, F. H., Eds.) pp 249-258, Elsevier, Amsterdam.
19. Lutz, D., Eder, E., Neudecker, T., and Henschler, D. (1982) Structure mutagenicity relationship in α,β-unsaturated carbonylic compounds and their corresponding allylic alcohols. Mutat. Res. 93, 305-315.
20. Marnett, L. J., Hurd, H. K., Hollstein, M. C., Levin, D. E., Esterbauer, H., and Ames, B. N. (1985) Natural occurring carbonyl compounds are mutagens in Salmonella tester strain TA 104. Mutat. Res. 148, 25-34.
21. Eder, E., Deininger, C., Neudecker, T., and Deininger, D. (1992) Mutagenicity of β-alkylsubstituted acrolein congeners in the Salmonella typhimurium strain TA 100 and genotoxicity testing in the SOS-chromotest. Environ. Mol. Mutagen. 19, 338-345.
22. Canonero, R., Martelli, A., Marinari, U. M., and Brambilla, G. (1990) Mutation induction in Chinese hamster lung V79 cells by five alk-2-enals produced by lipid peroxidation. Mutat. Res. 244, 153-156.
23. Dittberner, U., Eisenbrand, G., and Zankl, H. (1995) Genotoxic effects of the α,β-unsaturated aldehydes 2-trans-butenal, 2-transhexenal and 2-trans,6-cis-nonadienal. Mutat. Res. 335, 259-265.
24. Eisenbrand, G., Schuhmacher, J., and Gölzer, P. (1995) The influence of glutathione and detoxifying enzymes on DNA damage induced by 2-alkenals in primary rat hepatocytes and human lymphoblastoid cells. Chem. Res. Toxicol. 8, 40-46.
25. Chung, F.-L., Tanaka, T., and Hecht, S. S. (1986) Induction of liver tumors in F344 rats by crotonaldehyde. Cancer Res. 46, 1285-1289.
26. Gaunt, I. F., Colley, J., Wright, M., Creasy, M., Grasso, P., and Gangolli, S. D. (1971) Acute and short-term toxicity studies of trans-2-hexenal. Food Cosmet. Toxicol. 9, 775-786.
27. Kautiainen, A. (1992) Determination of hemoglobin adducts from aldehydes formed during lipid peroxidation in vitro. Chem.-Biol. Interact. 83, 55-63.
28. Eder, E., and Hoffman, C. (1993) Identification and characterization of deoxyguanosine adducts of mutagenic β-alkyl-substituted acrolein congeners. Chem. Res. Toxicol. 6, 486-494.
29. Schuhmacher, J. (1990) Untersuchungen zur Gentoxizität und zum Metabolismus aromawirksamer α,β-ungesättigter Aldehyde, Diss. D 386, Kaiserslautern, FRG.
30. 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 44, 990-995.
31. 32P-postlabeling method for simultaneous detection and quantification of exocyclic etheno and propano adducts in DNA. Carcinogenesis 15, 979-984.
32. Foiles, P. G., Akerkar, S. A., Miglietta, L. M., and Chung, F.-L. (1990) Formation of cyclic deoxyguanosine adducts in Chinese hamster ovary cells by acrolein and crotonaldehyde. Carcinogenesis 11, 2059-2061.
33. 2-propanodeoxyguanosine adducts in DNA of rats treated with N-nitrosopyrrolidine and mice treated with crotonaldehyde. Carcinogenesis 10, 1291-1297.
34. 32P-postlabelling. J. Cancer Res. Clin. Oncol. 119 (Suppl. 2), 56.
35. Pool-Zobel, B. L., Guigas, C., Klein, R., Neudecker, Ch., Renner, H. W., and Schmezer P. (1993) Assessment of genotoxic effects of lindane. Food Chem. Toxicol. 31, 271-283.
36. 2,7,8 bis-cyclic adducts. Chem. Res. Toxicol. 5, 802-808.
37. 2-adducts by reaction of deoxyguanosine with α-acetoxy-N-nitrosopyrrolidine, 4-(carbethoxynitrosamino)butanal, and crotonaldehyde. Cancer Res. 43, 1230-1235.
38. Müllenbach, R., Lagoda, P. J. L., and Welter, C. (1989) An efficient salt-chloroform extraction of DNA from blood and tissue. Trends Genet. 5, 391.
39. Davis, L. G., Dibner, M. D., and Battey J. F. (1986) Basic methods in molecular biology, Elsevier, New York.
40. 32P-postlabeling and nucleotide chromatography. Carcinogenesis 12, 1483-1490.
41. Wurm, F., Polastri, G., Hilfenhaus, J., Harth, H., and Zankl, H. (1985) Long term cultivation of Namalva cells for Interferon production: stable cytogenetic markers for identification of cells in spite of drastic chromosomal variation. Dev. Biol. Stand. 60, 393-403.
42. Burlinson, B. (1989) An in vivo unscheduled DNA synthesis (UDS) assay in the rat gastric mucosa: preliminary development. Carcinogenesis 10, 1425-1428.
43. Pool-Zobel, B. L., Lotzmann, N., Knoll, M., Kuchenmeister, F., Lambertz, R., Leucht, U., Schroder, H. G., and Schmezer, P. (1994) Detection of genotoxic effects in human gastric and nasal mucosa cells isolated from biopsy samples. Environ. Mol. Mutagen. 24, 23-45.
44. Singh, N. P., McCoy, M. T., Tice, R. R., and Schneider, E. L. (1988) A simple technique for quantitation of low levels of DNA damage in individual cells. Exp. Cell Res. 175, 184-191.
45. Betti, C., Barale, R., and Pool-Zobel, B. L. (1993) Comparative studies on cytotoxic and genotoxic effects of two organic mercury compounds in lymphocytes and gastric mucosa cells of Sprague-Dawley rats. Environ. Mol. Mutagen. 22, 172-180.
46. Grollman, A. P. (1989) Molecular mechanisms of chemical mutagenesis. Proc. Am. Assoc. Cancer Res. 30, 682.
47. 2-propanodeoxyguanosine. Proc. Am. Assoc. Cancer Res. 30, A 555.
48. Moriya, M., Zhang, W., Johnson, F., and Grollman, A. P. (1994) Mutagenic potency of exocyclic DNA adducts marked differences between Escherichia coli and simian kidney cells. Proc. Natl. Acad. Sci. U.SA. 91, 11899-11903.
49. 4 hot-spot of Salmonella typhimurium his D3052 carried on an M13 vector. J. Biol. Chem. 267, 22392-22400.
50. Janzowski, C., Jacob, D., Henn, I., Zankl, H., Pool-Zobel, B. L., Wiessler, M., and Eisenbrand, G. (1989) Investigation on organspecific metabolism and genotoxic effects of the urinary bladder carcinogen N-nitrosobutyl-3-carboxypropylamine (BCPN) and its analogs N-nitrosodibutylamine (NDBA) and N-nitrosobutyl-4-hydroxybutylamine (4-OH-NDBA). Toxicology 59, 195-209.
51. Pfeifer, E., and Metzler, M. (1992) Inhibitors of microtubule assembly: covalently and non-covalently binding substances have different no-effect-level characteristics in vitro. Mutagenesis 7, 165-166.
52. 32P-postlabeling. Proc. Am. Assoc. Cancer Res. 34, 137.
53. Benedetti, A., Pompella, A., Fulceri, R., Romani, A., and Comporti M. (1986) Detection of 4-hydroxynonenal and other lipid peroxidation products in the liver of bromobenzene-poisoned mice. Biochim. Biophys. Acta 876, 658-666.