Chromatographic characterization of hemoglobin benzo[a]pyrene-7,8-diol-9,10-epoxide adducts

Fundamental and Applied Toxicology

Volumn 29, Issue 1, 1996, Pages 94-101

  Myers, Steven R ^a   Spinnato, Joseph A ^a   Pinorini, Maria T ^a  

^a University of Louisville School of Medicine   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7,8 DIHYDROXYBENZO[A]PYRENE 9,10 OXIDE; CARCINOGEN; HEMOGLOBIN; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; HUMAN; ION EXCHANGE CHROMATOGRAPHY; METABOLITE; PROTEIN BINDING;

ANIMALIA;

EID: 85033050435     PISSN: 02720590     EISSN: None     Source Type: Journal    
DOI: 10.1006/faat.1996.0010     Document Type: Article

References (37)

1. Bryant, M. S., Skipper, P. L., Tannenbaum, S. R., and Maclure, M. (1987). Hemoglobin adducts of 4-aminobiphenyl in smokers and nonsmokers. Cancer Res. 47(2), 602-608.
2. Carmella, S. G., and Hecht, S. S. (1987). Formation of hemoglobin adducts upon treatment of F344 rats with the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N′-nitrosonornicotine. Cancer Res. 47(10), 2626-2630.
3. Day, B. W., Naylor, S., Gan, L. S., Sahali, Y., Nguyen, T. T., Skipper, P. L., Wishnok, J. S., and Tannenbaum, S. R. (1990). Molecular dosimetry of polycyclic aromatic hydrocarbon epoxides and diol epoxides via hemoglobin adducts. Cancer Res. 50(15), 4611-4618.
4. Day, B. W., Skipper, P. L., Rich, R. H., Naylor, S., and Tannenbaum, S. R. (1991). Conversion of a hemoglobin alpha chain aspartate(47) ester to N-(2,3-dihydroxypropyl)asparagine as a method for identification of the principal binding site for benzo[a]pyrene anti-diol epoxide. Chem. Res. Toxicol. 4(3), 359-363.
5. Dipple, A., Moschel, R. C., and Bigger, C. A. H. (1984) Polynuclear aromatic hydrocarbons. In Chemical Carcinogens (C. E. Searle, Ed.), Vol. 1, pp. 41-163. ACS, Washington, DC.
6. Dock, L., Martinez, M., and Jernstrom, B. (1987). Increased stability of (+/-)-7 beta, 8 alpha-dihydroxy 9 alpha, 10 alpha epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene through interaction with subcellular fractions of rat liver. Chem. Biol. Interact. 61, 31-44.
7. Ehrenberg, L., Hiesche, K. D., Osterman-Golkar, S., and Wennberg, I. (1974). Evaluation of genetic risks of alkylating agents: Tissue doses in the mouse from air contaminated with ethylene oxide. Mutat. Res. 24, 83-103.
8. Farmer, P. B., Shuker, E. G., and Bird, I. (1986). DNA and protein adducts as indicators of in vivo methylation by nitrosatable drugs. Carcinogenesis 7(1), 49-52.
9. Garel, M. C., Beuzard, Y., Thillet, J., Domenget, C., Martin, J., Galacteros, F., and Rosa, J. (1982). Binding of 21 thiol reagents to human hemoglobin in solution and in intact cells. Eur. J. Biochem. 123, 513-519.
10. Grassetti, D. R., and Murray, J. F. (1967). Determination of sulfhydryl groups with 2,2′- or 4,4′-dithiodipyridine. Arch. Biochem. Biophys. 119, 41-49.
11. Green, L. C., Skipper, P. L., Turesky, R. J., Bryant, M. S., and Tannenbaum, S. R. (1984). In vivo dosimetry of 4-aminobiphenyl in rats via a cysteine adduct in hemoglobin. Cancer Res. 44(10), 4254-4259.
12. Guidotti, G., Konigsberg, W., and Craig, L. C. (1963). On the dissociation of normal adult human hemoglobin. Proc. Natl. Acad. Sci. USA 50, 774.
13. Hallaway, B. E., Hedlund, B., and Bensen, E. S. (1980). Studies on the effect of reagent and protein charges on reactivity of the beta 93 sulfhydryl group of human hemoglobin using selected mutations. Arch. Biochem. Biophys. 203, 332-342.
14. Hutchins, D. A., Skipper, P. L., Naylor, S., and Tannenbaum, S. R. (1988). Isolation and characterization of the major fluoranthene-hemoglobin adducts formed in vivo in the rat. Cancer Res. 48(17), 4756-4761.
15. Jerstrom, B., Martinez, M., Svensson, S. A., and Dock, L. (1984). Metabolism of benzo[a]pyrene-7,8-dihydrodiol and benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide to protein-binding products and glutathione conjugates in isolated rat hepatocytes. Carcinogenesis 5, 1079-1085.
16. Kim, S., Paik, W. K., Choi, J., Lotlikar, P. D., and Magee, P. N. (1981). Microsome-dependent methylation of erythrocyte proteins by dimethylnitrosamine. Carcinogenesis 2, 179-182.
17. MacLeod, M. C., Adair, G., Dickson-Black, D., Pevny, T., and Humphrey, R. M. (1987). Stabilization of a reactive, electrophilic carcinogen, benzo-[a]pyrene diol epoxide, by mammalian cells. Chem. Biol. Interact. 63, 279-289.
18. Michaud, D. P., Gupta, S. C., Whalen, D. L., Sayer, J. M., and Jerina, D. M. (1983). Effects of pH and salt concentration on the hydrolysis of a benz[alpha]pyrene 7,8-diol-9,10-epoxide catalyzed by DNA and polyadenylic acid. Chem. Biol. Interact. 44, 41-52.
19. Pereira, M. A., and Chang, L. W. (1981). Binding of chemical carcinogens and mutagens to rat hemoglobin. Chem. Biol. Interact. 33(2-3), 301-305.
20. Pereira, M. A., Chang, J. L., Ferguson, J., and Couri, D. (1984). Binding of chloroform to the cysteine of hemoglobin. Chem. Biol. Interact. 51, 115-124.
21. Perera, F. P., Poirier, M. C., Yupsa, S. H., Nakayama, J., Jaretzki, A., Curnen, M. M., Knowles, D. M., and Weinstein, I. B., (1982). A pilot project in molecular carncer epidemiology: Determination of benzo[a]-pyrene-DNA adducts in animal and human tissues by immunoassays. Carcinogenesis 3, 1405.
22. Perutz, M. F. (1970). Stereochemistry of cooperative effects in haemoglobin. Nature 228, 726.
23. Roche, C. J., Zinger, D., Geacintov, N. E., and Harvey, R. G. (1985). Enhancement of stability of anti-BaPDE by complex formation with serum albumin. Cancer Biochem. Biophys. 8, 35.
24. Rosen, N. L., Bishop, L., Burnett, J. B., Bishop, M., and Colman, R. F. (1973). Methionyl residue critical for activity and regulation of bovine liver glutamate dehydrogenase. J. Biol. Chem. 248, 7359-7369.
25. Schroeder, W. A., and Huisman, T. (1980). The Chromatography of Hemoglobin, pp. 74-81. Marcel Dekker, New York.
26. Segerback, D. (1983). Alkylation of DNA and hemoglobin in the mouse following exposure to ethene and ethene oxide. Chem. Biol. Interact. 45, 139-151.
27. Shamsuddin, A., Sinopoli, N. T., Hemminki, K., Boesch, R. R., and Harris, C. C. (1985). Detection of benzo[a]pyrene:DNA adducts in human white blood cells. Cancer Res. 45, 66.
28. Shapiro, R., McManus, M. J., Zalut, C., and Bunn, H. F. (1980). Sites of nonenzymatic glycosylation of human hemoglobin. J. Biol. Chem. 255, 3120.
29. Shugart, L. (1985). Quantitating exposure to chemical carcinogens: In vivo alkylation of hemoglobin by benzo[a]pyrene. Toxicology 34, 211.
30. Skipper, P. L., Bryant, M. S., and Tannenbaum, S. R. (1988). Determination of human exposure to carcinogenic aromatic amines from hemoglobin adducts in selected population groups. In Carcinogenic and Mutagenic Responses to Aromatic Amines and Nitroarenes (C. M. King, L. J. Romano, and D. Schuetzle, Eds.), pp. 65-71. Elsevier, New York.
31. Tentori, L., and Salvati, A. M. (1981). Hemoglobinometry in human blood. Methods Enzymol. 76, 707.
32. Törnqvist, M., Mowrer, J., Jensen, S., and Ehrenberg, L. (1986). Monitoring of environmental cancer initiators through hemoglobin adducts by a modified Edman degradation method. Anal. Biochem. 154, 255.
33. Wallin, H., Jeffrey, A. M., and Santella, R. M. (1987). Investigation of benzo[a]pyrene-globin adducts. Cancer Lett. 35, 139.
34. Weston, A., Rowe, M. L., Manchester, D. K., Farmer, P. B., Mann, D. L., and Harris, C. C. (1989). Fluorescence and mass spectral evidence for the formation of benzo[a]pyrene anti-diol-epoxide-DNA and hemoglobin adducts in humans. Carcinogenesis 10(2), 251-257.
35. Whalen, D. L., Montemarano, J. A., Thakker, D. R., Yagi, H., and Jerina, D. M. (1977). Changes of mechanisms and product distributions in the hydrolysis of benzo[a]pyrene-7,8-diol-9,10-epoxide metabolites induced by changes in pH. J. Am. Chem. Soc. 99, 5522.
36. Whalen, D. L., Ross, A. M., Montemarano, J. A., Thakker, D. R., Yagi, H., and Jerina, D. M. (1979). General acid catalysis in the hydrolysis of benzo[a]pyrene 7,8-diol-9,10-epoxides. J. Am. Chem. Soc. 101, 5086.
37. Yagi, H., Thakker, D. R., Hernandez, O., Koreeda, M., and Jerina, D. M., (1977). Synthesis and reactions of the hightly mutagenic 7,8-diol-9,10-epoxides of the carcinogen benzo[a]pyrene. J. Am. Chem. Soc. 99, 1604.