Electrophilic intermediates produced by bioactivation of furan

Drug Metabolism Reviews

Volumn 38, Issue 4, 2006, Pages 615-626

  Peterson, Lisa A ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

, Unsaturated aldehyde; Carcinogenesis; Furan; Glutathione conjugates; Metabolism; Stable isotope methods; Toxicity

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; ALPHA,BETA UNSATURATED DIALDEHYDE; CARCINOGEN; CIS 2 BUTENE 1,4 DIAL; CYTOCHROME P450; DNA; FURAN;

BACTERIAL STRAIN; CARCINOGENESIS; CATALYSIS; CONFERENCE PAPER; DRUG METABOLISM; HUMAN; LIVER TOXICITY; NONHUMAN; OXIDATION; PROTEIN BINDING; PROTEIN DNA INTERACTION;

ANIMALS; BIOTRANSFORMATION; CARCINOGENS; ENVIRONMENTAL POLLUTANTS; FURANS; HEPATITIS, TOXIC; HUMANS;

EID: 33845432139     PISSN: 03602532     EISSN: 10979883     Source Type: Journal    
DOI: 10.1080/03602530600959417     Document Type: Conference Paper

References (37)

1. Adger, B. J., Barrett, C., Brennan, J., McGuigan, P., McKervey, M. A., Tarbit, B. (1993). Oxidations of furans with dimethyldioxirane. Interception of malealdehyde and related aldehydes via Wittig reactions. J Chem. Soc., Chem. Comm. 1220-1222.
2. Breusch, F. L., Ulusoy, E. (1952). cis- and trans-b-formylacrylic acid in tissue respiration. Hoppe-Seylers Zeitschr. Physiol. Chem. 291:60-63.
3. 14C]furan in the male F344 rat. J. Toxicol. Environ. Health 34:245-257.
4. Byrns, M. C., Predecki, D. P., Peterson, L. A. (2002). Characterization of nucleoside adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem. Res. Toxicol. 15:373-379.
5. Byrns, M. C., Vu, C. C., Neidigh, J. W., Abad, J. L., Jones, R .A., Peterson, L. A. (2006). Detection of DNA adducts derived from the reactive metabolite of furan, cis-2-butene-1,4-dial. Chem. Res. Toxicol. 19:414-420.
6. 2-etheno-2′-deoxyguanosine adducts by cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem. Res. Toxicol. 17:1607-1613.
7. 4 and its distribution in air. Clin. Toxicol. 6:109-124.
8. Carfagna, M. A., Held, S. D., Kedderis, G. L. (1993). Furan-induced cytolethality in isolated rat hepatocytes: Correspondence with in vivo dosimetry. Toxicol. Appl. Pharmacol. 123:265-273.
9. Chen, L .J., Hecht, S. S., Peterson, L. A. (1995). Identification of cis-2-butene-1,4-dial as a microsomal metabolite of furan. Chem. Res. Toxicol. 8:903-906.
10. Chen, L. J., Hecht, S. S., Peterson, L. A. (1997). Characterization of amino acid and glutathione adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem. Res. Toxicol. 10:866-874.
11. DeMarini, D. M., Landi, S., Ohe, T., Shaughnessy, D. T., Franzen, R., Richard, A. M. (2000). Mutation spectra in Salmonella of analogues of MX: implications of chemical structure for mutational mechanisms. Mutat. Res. 453:51-65.
12. Franzen, R., Goto, S., Tanabe, K., Morita, M. (1998). Genotoxic activity of chlorinated butenoic acids in Salmonella typhimurium strains TA98, TA100 and TA104. Mutat. Res. 417:31-37.
13. Gingipalli, L., Dedon, P. C. (2001). Reaction of cis-and trans-2-butene-1,4-dial with 2′-deoxycytidine to form stable oxadiazabicyclooctaimine adducts. J. Am. Chem. Soc. 123:2664-2665.
14. Higashi, Y., Ida, N., Tokushige, M. (1988). Fumaraldehydic acid-induced inactivation of aspartase. Biochem. Int. 17:103-109.
15. International Agency for Research on Cancer (1995). Furan, in Dry Cleaning, Some Chlorinated Solvents and Other Industrial Chemicals, vol. 53p 393, IARC, Lyon.
16. Johansson, E., Reynolds, S., Anderson, M., Maronpot, R. (1997). Frequency of Ha-ras-1 gene mutations inversely correlated with furan dose in mouse liver tumors. Mol. Carcinogenesis 18:199-205.
17. Kedderis, G. L., Carfagna, M. A., Held, S. D., Batra, R., Murphy, J. E., Gargas, M. L. (1993). Kinetic analysis of furan biotransformation by F-344 rats in vivo and in vitro. Toxicol. Appl. Pharmacol. 123:274-282.
18. Koc, H., Swenberg, J.A. (2002). Applications of mass spectrometry for quantitation of DNA adducts. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 778:323-343.
19. Maga, J. (1979). Furans in foods. Crit. Rev. Food Sci. Nutr. 11:355-366.
20. Marinari, U. M., Ferro, M., Sciaba, L., Finollo, R., Bassi, A. M., Brambilla, G. (1984). DNA-damaging activity of biotic and xenobiotic aldehydes in Chinese hamster ovary cells. Cell Biochem. Funct. 2:243-248.
21. Mohuczy-Dominiak, D., Pacanis, A., Rogulski, J., Angielski, S. (1983). Significance of CoA-transferase in the reaction of maleate with amino acids and proteins. Acta Biochim. Pol. 30:39-49.
22. Mortelmans, K., Haworth, S., Lawlor, T., Speck, W., Tainer, B., Zeiger, E. (1986). Salmonella mutagenicity tests. II. Results from the testing of 270 chemicals. Environ. Mutagen. 7 (suppl):1-119.
23. Mugford, C. A., Carfagna, M. A., Kedderis, G. L. (1997). Furan-mediated uncoupling of hepatic oxidative phosphorylation in Fischer-344 rats: an early event in cell death. Toxicol. Appl. Pharmacol. 144:1-11.
24. National Toxicology Program. (1993). Toxicology and carcinogenesis studies of furan in F344/N rats and B6C3F1 mice. [NTP Technical Report No. 402]. Research Triangle Park, NC, US Department of Health and Human Services, Public Health Service, National Institutes of Health.
25. National Toxicology Program. (2005). 11th Report on Carcinogens. Washington DC, US Department of Health and Human Services.
26. Pacanis, A., Strzelecki, T., Rogulski, J. (1981). Effects of maleate on the content of CoA and its derivatives in rat kidney mitochondria. J. Biol. Chem 256:13035-13038.
27. Parmar, D., Burka, L. T. (1993). Studies on the interaction of furan with hepatic cytochrome P-450. J. Biochem. Toxicol. 8:1-9.
28. Peterson, L. A., Cummings, M. E., Chan, J. Y., Matter, B., Vu, C. C. (2006). Identification of a cis-2-butene-1,4-dial-derived glutathione conjugate in the urine of furan-treated rats. Chem. Res. Toxicol. in press.
29. Peterson, L. A., Cummings, M. E., Vu, C. C., Matter, B. A. (2005). Glutathione trapping to measure microsomal oxidation of furan to cis-2-butene-1,4-dial. Drug Metab Dispos. 33:1453-1458.
30. Peterson, L. A., Naruko, K. C., Predecki, D. (2000). A reactive metabolite of furan, cis-2-butene-1, 4-dial, is mutagenic in the Ames assay. Chem. Res. Toxicol. 13:531-534.
31. Quoc-Bruguera, I. D., Gaudemer, Y. (1973). Evidence for maleate penetration into rat liver mitochondria. Biochimie 55:1511-1513.
32. 1 mouse liver tumors: implications for risk assessment. Science 237:1309-1316.
33. Rogulski, J., Pacanis, A., Adamowicz, W., Angielski, S. (1974). On the mechanism of maleate action on rat kidney mitochondria. Effect on oxidative metabolism. Acta Biochim. Pol. 21:403-413.
34. Stich, H. F., Rosin, M. P., Wu, C. H., Powrie, W. D. (1981). Clastogenicity of furans found in food. Cancer Let. 13:89-95.
35. 6-[4-oxo-4-(3- pyridyl)butyl]-2′-deoxyguanosine. Chem. Res. Toxicol. 17:1600-1606.
36. Wiley, R. A., Traiger, G. J., Baraban, S., Gammal, L. M. (1984). Toxicity-distribution relationships among 3-alkylfurans in mouse liver and kidney. Toxicol. Appl. Pharmacol. 74:1-9.
37. Wilson, D. M., Goldsworthy, T. L., Popp, J. A., Butterworth, B. E. (1992). Evaluation of genotoxicity, pathological lesions, and cell proliferation in livers of rats and mice treated with furan. Environ. Mol. Mutagen. 19:209-222