A new assay for albumin and hemoglobin adducts of 1,2- and 1,4-benzoquinones

Chemico-Biological Interactions

Volumn 115, Issue 2, 1998, Pages 117-139

  Waidyanatha, Suramya ^a   Yeowell O'Connell, Karen ^a   Rappaport, Stephen M ^a  

^a IL   (United States)

Author keywords

Albumin adducts; Benzoquinones; Hemoglobin adducts

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; ALBUMIN; BENZENE; BENZOQUINONE DERIVATIVE; HEMOGLOBIN;

ANIMAL EXPERIMENT; ARTICLE; BIOASSAY; CONTROLLED STUDY; GAS CHROMATOGRAPHY; HUMAN; HUMAN CELL; MALE; MASS SPECTROMETRY; NONHUMAN; RAT;

ANIMALS; BENZENE; BENZOQUINONES; CARCINOGENS; CYCLOHEXANES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HEMOGLOBINS; HUMANS; MALE; MESYLATES; RATS; RATS, INBRED F344; SERUM ALBUMIN; TRIFLUOROACETIC ACID;

EID: 0031669747     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(98)00067-2     Document Type: Article

References (31)

1. J.E. Huff, J.K. Haseman, D.M. Demarini, S. Eustis, R.R. Maronpot, A.C. Peters, R.L. Persing, C.E. Chrisp, A.C. Jacobs, Multiple site carcinogenicity of benzene in Fischer 344 rats and B6C3F1 mice, Environ. Health Perspect. 82 (1989) 125-163.
2. K.R. Cooper, R. Snyder, Benzene metabolism (toxicokinetics and the molecular aspects of benzene toxicity), in: M. Aksoy (Ed.), Benzene carcinogenicity, CRC Press, Boca Raton, FL, 1988, pp. 35-58.
3. IPCS, Benzene-Environmental Health Criteria 150. World Health Organization, Geneva, 1993.
4. International Agency for Research on Cancer IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans: Some industrial chemicals and dyestuffs. 29, 1982, IARC, Lyon.
5. R. Snyder, C.C. Heidli, An overview of benzene metabolism, Environ. Health Perspect. 104 (6) (1996) 1165-1171.
6. M.T. Smith, The mechanism of benzene-induced leukemia: a hypothesis and speculations on the causes of leukemia, Environ. Health Perspect. 104 (6) (1996) 1219-1225.
7. S.G. Carmella, E.J. LaVoie, S.S. Hecht, Quantitative analysis of catechol and 4-methyl catechol in human urine, Food Chem. Toxicol. 20 (1982) 587-590.
8. J.A. Marga, Simple phenol and phenolic compounds in food flavor, CRC Crit. Rev. Food Sci. Nutr. 4 (1978) 323-372.
9. P.J. Deisinger, T.S. Hill, C. English, Human exposure to naturally occuring hydroquinone, J. Toxicol. Environ. Health 47 (1996) 31-46.
10. E. Bone, A. Tamm, M. Hill, The production of urinary phenols by gut bacteria and their possible role in the causation of large bowl cancer, Am. J. Clin. Nutr. 29 (1976) 1448-1454.
11. E.A. Smith, G.T. Macfarlane, Enumeration of human colonic bacteria producing phenolic and indolic compounds: effects of pH, carbohydrate availability and retention time on dissimilatory aromatic amino acid metabolism, J. Appl. Bacteriol. 81 (1996) 288-302.
12. T.A. McDonald, S. Waidyanatha, S.M. Rappaport, Measurement of adducts of benzoquinone with hemoglobin and albumin, Carcinogenesis 14 (1993) 1927-1932.
13. 6]benzene to rats, Carcinogenesis 14 (1993) 1921-1925.
14. 6]benzene, Cancer Res. 54 (1994) 4907-4914.
15. S.S. Lau, B.A. Hill, R.J. Higher, T.J. Monks, Sequential oxidation and glutathione addition to 1,4-benzoquinone: correlation of toxicity with increased glutathione substitution, Mol. Pharmacol. 34 (1988) 829-836.
16. K.-G. Eckert, P. Eyer, J. Sonnenbichler, I. Zetl, Activation and detoxication of aminophenols. III. Synthesis and structural elucidation of various glutathione addition products to 1,4-benzoquinone, Xenobiotica 20 (1990) 351-361.
17. K. Yeowell-O'Connell, T.A. McDonald, S.M. Rappaport, Analysis of hemoglobin adducts of benzene oxide by gas chromatography-mass spectrometry, Anal. Biochem. 237 (1996) 49-55.
18. A.A. Melikian, A.K. Prahalad, S. Coleman, Isolation and characterization of two benzene-derived hemoglobin adducts in vivo in rats, Cancer Epidemiol. Biomark. Prevent. 1 (1992) 307-313.
19. G.A. Pascoe, C.J. Calleman, T.A. Baille, Identification of S-(2,5-dihydroxyphenyl)-cysteine and S-(2,5-dihydroxyphenyl)-N-acetyl cysteine as urinary metaboltes of acetaminophen in the mouse. Evidence for p-benzoquinone as a reactive intermediate in acetaminophen metabolism, Chem.-Biol. Interact. 68 (1988) 85-98.
20. R. Willstätter, A. Pfannenstiel, Ueber o-Chinon, Chem. Ber. 37 (1904) 4744-4746.
21. S. Waidyanatha, P-H Lin, S.M. Rappaport, Characterization of chlorinated adducts of hemoglobin and albumin following administration of pentachlorophenol to rats, Chem. Res. Toxicol. 9 (1996) 647-653.
22. A.B. Lindstrom, K. Yeowell-O'Connell, S. Waidyanatha, T.A. McDonald, B.T. Golding, S.M. Rappaport, Formation of hemoglobin and albumin adducts of benzene oxide in mouse, rat and human blood, Chem. Res. Toxicol. 21 (1998) 302-310.
23. J.D. Sun, M.A. Medinsky, L.S. Birnbaum, G. Lucier, R.F. Henderson, Benzene hemoglobin adducts in mice and rats: characterization of formation and physiological modeling, Fund. Appl. Toxicol. 15 (1990) 468-475.
24. 32P-analysis of DNA adducts in tissues of benzene-treated rats, Environ. Health Perspect. 82 (1989) 253-257.
25. L. Hogarth, M. English, L. Price, R. Wyllie, A.D.J. Pearson, A.G. Hall, The effect of treatment with high dose melphalan, cisplatin or carboplatin on levels of glutathione in plasma, erythrocytes, mononuclear cells and urine, Cancer Chemother. Pharmacol. 37 (1996) 479-485.
26. M.F. Perutz, Structure and mechanism of haemoglobin, Br. Med. Bull. 32 (1976) 195-208.
27. H. Hamboek, R.W. Fischer, E.E. Di Iorio, K.H. Winterhalter, The binding of s-triazine metabolites to rodent hemoglobin appears irrelevant to other species, Mol. Pharmacol. 20 (1981) 579-584.
28. M.A. Rothschild, M. Oratz, S.S. Schreiber, Serum albumin, Hepatology 8 (1988) 385-401.
29. T.D. Sargent, M. Yang, J. Bonner, Nucleotide sequence of cloned rat serum albumin messenger RNA, Proc. Natl. Acad. Sci. USA 78 (1981) 243-246.
30. G. Schreiber, J. Urban, J. Zahringer, W. Reutter, U. Frosch, The secretion of serum protein and the synthesis of albumin and total protein in regenerating rat liver, J. Biol. Chem. 25 (1970) 4531-4538.
31. F. Granath, L. Ehrenberg, M. Törnqvist, Degree of alkylation of macromolecules in vivo from variable exposure, Mutat. Res. 284 (1992) 297-306.