Quantification of urinary aflatoxin B1 dialdehyde metabolites formed by aflatoxin aldehyde reductase using isotope dilution tandem mass spectrometry

Chemical Research in Toxicology

Volumn 21, Issue 3, 2008, Pages 752-760

  Johnson, Denise N ^a   Egner, Patricia A ^a   OBrian, Greg ^b   Glassbrook, Norman ^b   Roebuck, Bill D ^c   Sutter, Thomas R ^d   Payne, Gary A ^b   Kensler, Thomas W ^a   Groopman, John D ^a  

^a The Johns Hopkins University   (United States)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

^c DARTMOUTH MEDICAL SCHOOL   (United States)

^d UNIVERSITY OF MEMPHIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AFLATOXIN B1; AFLATOXIN B1 ALDEHYDE REDUCTASE; AKR7A1 ENZYME; ALCOHOL DERIVATIVE; ALDEHYDE REDUCTASE; BETA GLUCURONIDASE; CREATININE; SULFATASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIBODY AFFINITY; ARTICLE; ASPERGILLUS FLAVUS; CONTROLLED STUDY; CREATININE URINE LEVEL; ISOTOPE DILUTION ASSAY; MALE; NONHUMAN; PROTEIN EXPRESSION; RAT; SENSITIVITY AND SPECIFICITY; TANDEM MASS SPECTROMETRY; URINALYSIS;

AFLATOXIN B1; ALDEHYDE REDUCTASE; ALDEHYDES; ANIMALS; CARCINOGENS; CHROMATOGRAPHY, AFFINITY; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIET; ESCHERICHIA COLI; GLUCURONIDASE; MALE; RADIOISOTOPE DILUTION TECHNIQUE; RATS; RATS, SPRAGUE-DAWLEY; REFERENCE STANDARDS; SOLID PHASE EXTRACTION; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFATASES;

ASPERGILLUS FLAVUS; RATTUS;

EID: 41849140005     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700397n     Document Type: Article

References (32)

1. Groopman, J. D., and Cain, L. G. (1990) Interactions of fungal and plant toxins with DNA: Aflatoxins, sterigmatocystin, safrole, cycasin, and pyrrolizidine alkaloids. In Handbook of Experimental Pharmacology, Chapter 10, Vol. 94/1, Springer-Verlag, Berlin Heidelberg, Germany.
2. Busby, W. F. J., and Wogan, G. N. (1984) Aflatoxins. In Chemical Carcinogens, 2nd ed. (Searle, C. B., Ed.) pp 945-1136, American Chemical Society, Washington, D.C.
3. Council for Agricultural Science and Technology. (2003) Mycotoxins: Risks in plant, animal, and human systems. In Task Force Report, number 139.
4. Guengerich, F. P. (2003) Cytochrome P450 oxidations in the generation of reactive electrophiles: Epoxidation and related reactions. Arch. Biochem. Biophys. 409, 59-71.
5. Johnson, W. W., and Guengerich, F. P. (1997) Reaction of aflatoxin B1 exo-epoxide with DNA: Kinetic analysis of covalent binding and DNA-induced hydrolysis. Proc. Natl. Acad. Sci. U.S.A. 94, 6121-6125.
6. Sabbioni, G., Skipper, P. L., Buchi, G., and Tannenbaum, S. R. (1987) Isolation and characterization of the major serum albumin adduct formed by aflatoxin B1 in vivo in rats. Carcinogenesis 8, 819-824.
7. Scholl, P. F., Musser, S. M., and Groopman, J. D. (1997) Synthesis and characterization of aflatoxin B1 mercapturic acids and their identification in rat urine. Chem. Res. Toxicol. 10, 1144-1151.
8. Guengerich, F. P., Cai, H., McMahon, M., Hayes, J. D., Sutter, T. R., Groopman, J. D., Deng, Z., and Harris, T. M. (2001) Reduction of aflatoxin B1 dialdehyde by rat and human aldo-keto reductases. Chem. Res. Toxicol. 14, 727-737.
9. Walton, M., Egner, P., Scholl, P. F., Walker, J., Kensler, T. W., and Groopman, J. D. (2001) Liquid chromatography electrospray-mass spectrometry of urinary aflatoxin biomarkers: Characterization and application to dosimetry and chemoprevention in rats. Chem. Res. Toxicol. 14, 919-926.
10. Egner, P. A., Groopman, J. D., Wang, J., Kensler, T. W., and Friesen, M. D. (2006) Quantification of aflatoxin-B1-N7-guanine in human urine by high-performance liquid chromatography and isotope dilution tandem mass spectrometry. Chem. Res. Toxicol. 19, 1191-1195.
11. Scholl, P. F., Turner, P. C., Sutcliffe, A. E., Sylla, A., Diallo, M. S., Friesen, M. D., Groopman, J. D., and Wild, C. P. (2006) Quantitative comparison of aflatoxin B1 serum albumin adducts in humans by isotope dilution mass spectrometry and ELISA. Cancer Epidemiol., Biomarkers Prev. 15 (4), 823-826.
12. Egner, P. A., Yu, X., Johnson, J. K., Nathasingh, C. K., Groopman, J. D., Kensler, T. W., and Roebuck, B. D. (2003) Identification of aflatoxin M1-N7-guanine in liver and urine of tree shrews and rats following administration of aflatoxin B1. Chem. Res. Toxicol. 16, 1174-1180.
13. Jez, J. M., Flynn, T. G., and Pennings, T. M. (1997) A new nomenclature for the aldo-keto reductase superfamily. Biochem. Pharmacol. 54, 639-647.
14. Hayes, J. D., Judah, D. J., and Neal, G. E. (1993) Resistance to aflatoxin B1 is associated with the expression of a novel aldo-keto reductase which has catalytic activity towards a cytotoxic aldehyde-containing metabolite of the toxin. Cancer Res. 53, 3887-3894.
15. Knight, L. P., Primiano, T., Groopman, J. D., Kensler, T. W., and Sutter, T. R. (1999) cDNA cloning, expression and activity of a second human aflatoxin B1-metabolizing member of the aldo-keto reductase superfamily, AKR7A3. Carcinogenesis 20 (7), 1215-1223.
16. Ellis, E. M., Judah, D. J., Neal, G. E., and Hayes, J. D. (1993) An ethoxyquin-inducible aldehyde reductase from rat liver that metabolizes aflatoxin B1 defines a subfamily of aldo-keto reductases. Proc. Natl. Acad. Sci. U.S.A. 90, 10350-10354.
17. Kwak, M. K., Egner, P. E., Dolan, P. M., Ramos-Gomez, M., Groopman, J. D., Itoh, K., Yamamoto, M., and Kensler, T. W. (2001) Role of phase 2 enzyme induction in chemoprotection by dithiolethiones. Mutat. Res. 480-481, 305-315.
18. Primiano, T., Gastel, J. A., Kensler, T. W., and Sutter, T. R. (1996) Isolation of cDNAs representing dithiolethione-responsive genes. Carcinogenesis 17, 2297-2303.
19. Ellis, E. M., and Hayes, J. D. (1995) Substrate specificity of an aflatoxin-metabolizing aldehyde reductase. Biochem. J. 312, 535-541.
20. Baertschi, S. W., Raney, K. D., Stone, M. P., and Harris, T. M. (1988) Preparation of the 8,9-epoxide of the mycotoxin aflatoxin B1: The ultimate carcinogenic species. J. Am. Chem. Soc. 110, 7929-7931.
21. Adye, J., and Mateles, R. I. (1964) Incorporation of labeled compounds into aflatoxins. Biochim. Biophys. Acta 88, 418-420.
22. Buchanan, R. L., Hoover, D. G., and Jones, S. B. (1983) Caffeine inhibition of aflatoxin production: Mode of action. Appl. Environ. Microbiol. 46, 1193-2000.
23. Groopmam, J. D., Trudel, L. J., Donahue, P. R., Marshak-Rothstein, A., and Wogan, G. N. (1984) High affinity monoclonal antibodies for aflatoxins and their application to solid-phase immunoassays. Proc. Natl. Acad. Sci. U.S.A. 81, 7728-7731.
24. Groopman, J. D., Donahue, P. R., Zhu, J., Chen, J., and Wogan, G. N. (1985) Aflatoxin metabolism in humans: Detection of metabolites and nucleic acid adducts in urine by affinity chromatography. Proc. Natl. Acad. Sci. U.S.A. 82, 6492-6496.
25. Guengerich, F. P., Shimada, T., Raney, K. D., Yun, C., Meyer, D. J., Ketterer, B., Harris, T. M., Groopman, J. D., and Kadlubar, F. F. (1992) Elucidation of catalytic specificities of human cytochrome P450 and glutathione S-transferases enzymes and relevance to molecular epidemiology. Environ. Health Perspect. 98, 75-80.
26. Scholl, P. F., Turner, P. C., Sutcliffe, A. E., Sylla, A., Diallo, M. S., Friesen, M. D., Groopman, J. D., and Wild, C. P. (2006) Quantitative comparison of aflatoxin B1 serum albumin adducts in humans by isotope dilution mass spectrometry and ELISA. Cancer Epidemiol., Biomarkers Prev. 15 (4), 823-826.
27. Chapot, B., and Wild, C. P. (1991) ELISA for quantification of aflatoxin-albumin adducts and their application to human exposure assessment. In Techniques in Diagonostic Pathology (Van Warhol, M., Velzen, D., and Bullock, G. R., Eds.) Vol. 2, pp 139-155, Academic Press, Inc., New York.
28. Gan, L.-S., Skipper, P. L., Peng, X., Groopman, J. D., Chen, J.-S., Wogan, G. N., and Tannenbaum, S. R. (1988) Serum albumin adducts in the molecular epidemiology of aflatoxin carcinogenesis: correlation with aflatoxin B1 intake and urinary excretion of aflatoxin M1. Carcinogenesis 9, 1323-1325.
29. Sabbioni, G., Ambs, S., Wogan, G. N., and Groopman, J. D. (1990) The aflatoxin-lysine adduct quantified by high-performance liquid chromatography from human serum albumin samples. Carcinogenesis 11, 2063-2066.
30. Wild, C. P., Jiang, Y.-Z., Sabbioni, G., Chapot, B., and Montesano, R. (1990) Evaluation of methods for quantitation of aflatoxin-albumin adducts and their application to human to human exposure assessment. Cancer Res. 50, 245-251.
31. Hsieh, D. P. H., and Wong, J. J. (1994) Pharmacokinetics and excretion of aflatoxins. In The Toxicology of Aflatoxins: Human Health, Veterinary, and Agricultural Significance (Eaton, D. L., and Groopman, J. D., Eds.) pp 73-88, Academic Press, San Diego, CA.
32. Groopman, J. D., DeMatos, P., Egner, P. A., Love-Hunt, A., and Kensler, T. W. (1992) Molecular dosimetry of urinary aflatoxin N7-guanine and serum aflatoxin albumin adducts predict chemoprotection by 1,2-dithiole-3-thione in rats. Carcinogenesis 13, 101-106.