Abstract
Crotonaldehyde and acetaldehyde are mutagenic in S. typhimurium and other systems used for detection of genetic damage (IARC, 1985; 1995; 1999). Crotonaldehyde induces altered liver cell foci, neoplastic nodules, and hepatocellular carcinoma upon oral administration to F344 rats (Chung et al, 1986; IARC, 1995). Acetaldehyde causes tumors of the respiratory tract in rats and hamsters upon exposure by inhalation (IARC, 1985; 1999). Crotonaldehyde and acetaldehyde are commonly detected in cigarette smoke, mobile source emissions and other products of thermal degradation (IARC, 1985; 1995; 1999). Their concentrations in cigarette smoke are far higher, while their carcinogenic activities are considerably lower, than those of polycyclic hydrocarbons, aromatic amines and N-nitrosamines, which are considered to be important carcinogens in cigarette smoke (IARC, 1985; 1986; 1995; 1999). Crotonaldehyde and acetaldehyde are also important endogenous compounds. Crotonaldehyde is a product of lipid peroxidation while acetaldehyde is the principal metabolite of ethanol.
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References
Baigrie, L. M., Cox, R. A., Slebocka-Tilk, H., Tencer, M., and Tidwell, T. T., 1985, Acid-catalyzed enolization and aldol condensation of acetaldehyde.J. Chem. Soc 107:3640–3645.
Chung, F.-L. and Hecht, S. S., 1983, Formation of cyclic 1,N2-adducts by reaction of deoxyguanosine with α-acetoxy-N-nitrosopyrrolidine, 4-(carbethoxynitrosamino)butanal, or crotonaldehyde.Cancer Res 43:1230–1235.
Chung, F.-L., Tanaka, T., and Hecht, S. S., 1986, Induction of liver tumors in F344 rats by crotonaldehyde.Cancer Res 46:1285–1289.
Chung, F.-L., Zhang, L., Ocando, J. E., and Nath, R. G., 1999, Role of 1,N 2-propanodeoxyguanosine adducts as endogenous DNA lesions in rodents and humans. in:Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis(Singer, B. and Bartsch, H., Eds.), IARC Scientific Publ. 150, International Agency for Research on Cancer, Lyon, France, pp. 45–54.
Eder, E., Schuler, D., and Budiawan, 1999, Cancer risk assessment for crotonaldehyde and 2-hexenal: an approach. in:Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis(Singer, B. and Bartsch, H., Eds.), IARC Scientific Publ. 150, International Agency for Research on Cancer, Lyon, France, pp. 219–232.
Fang, J.-L. and Vaca, C. E., 1995, Development of a32P-postlabelling method for the analysis of adducts arising through the reaction of acetaldehyde with 2’-deoxyguanosine-3’- mono-phosphate and DNA.Carcinogenesis 16:2177–2185.
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.
International Agency for Research on Cancer, 1985, Allyl compounds, aldehydes, epoxides and peroxides. in:Monographs on the Evolution of the Carcinogenic Risk of Chemicals to HumansVol. 36, IARC, Lyon, France, pp. 101–132.
International Agency for Research on Cancer, 1986, Tobacco smoking. in:Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to HumansVol. 38, IARC, Lyon, France, pp. 312–314.
International Agency for Research on Cancer, 1995, Dry cleaning, some chlorinated solvents and other industrial chemicals. in:Monographs on the Evaluation of Carcinogenic Risks to HumansVol. 63, IARC, Lyon, France, pp. 373–391.
International Agency for Research on Cancer, 1999, Re-evaluation of some organic chemicals, hydrazine and hydrogen peroxide (part two). in:Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to HumansVol.71, IARC, Lyon, France, pp. 319–335.
Kawanishi, M., Matsuda, T., Sasaki, G., Yagi, T., Matsui, S., and Takebe, H., 1998, A spectrum of mutations induced by crotonaldehyde in shuttle vector plasmids propagated in human cells.Carcinogenesis 19: 69–72.
Matsuda, T., Kawanishi, M., Yagi, T., Matsui, S., and Takebe, H., 1998, Specific tandem GG to TT base substitutions induced by acetaldehyde are due to intra-strand crosslinks between adjacent guanine bases.Nucleic Acids Res 26: 1769–1774.
Moriya, M., Pandya, G. A., Johnson, F., and Grollman, A. P., 1999, Cellular response to exocyclic DNA adducts, in:Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis (Singer, B. and Bartsch, H., Eds.), IARC Scientific Publ. 150, International Agency for Research on Cancer, Lyon, France, pp. 263–270.
Tuma, D. J., Thiele, G. M., Xu, D., Klassen, L. W., and Sorrell, M.F, 1996, Acetaldehyde and malondialdehyde react together to generate distinct protein adducts in the liver during long-term ethanol administration.Hepatol 23: 872–880.
Vaca, C. E., Fang, J.-L., and Schweda, E. K. H., 1995, Studies of the reaction of acetaldehyde with deoxynucleosides.Chem.-Biot. Interact 98: 51–67.
Vaca, C. E., Nilsson, J. A., Fang, J. L., and Grafstrom, R. C., 1998, Formation of DNA adducts in human buccal epithetial cells exposed to acetaldehyde and methylglyoxal in vitro.Chem-Biol Interact 108: 197–208.
Wang, M., Upadhyaya, P., Dinh, T. T., Bonilla, L. E., and Hecht, S. S., 1998, Lactols in hydrolysates of DNA reacted with α-acetoxy-N-nitrosopyrrolidine and crotonaldehyde.Chem. Res. Toxicol 11:1567–1573.
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Hecht, S.S., McIntee, E.J., Cheng, G., Shi, Y., Villalta, P.W., Wang, M. (2001). New Aspects of DNA Adduct Formation by the Carcinogens Crotonaldehyde and Acetaldehyde. In: Dansette, P.M., et al. Biological Reactive Intermediates VI. Advances in Experimental Medicine and Biology, vol 500. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-0667-6_7
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DOI: https://doi.org/10.1007/978-1-4615-0667-6_7
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