Metabolic basis of benzene toxicity

European Journal of Haematology, Supplement

Volumn 57, Issue 60, 1996, Pages 111-118

  Ross, David ^a,b  

^a UNIVERSITY OF COLORADO   (United States)

^b UNIVERSITY OF COLORADO   (United States)

Author keywords

Benzene; Blood dyscrasias; Bone marrow stroma; Haemopoietic progenitor cells; Hydroquinone; Myeloperoxidase; NAD(P)H: quinoline oxidoreductase

Indexed keywords

BENZENE; HYDROQUINONE; MYELOPEROXIDASE; PEROXIDASE;

BLOOD DYSCRASIA; BLOOD TOXICITY; CONFERENCE PAPER; HEMATOPOIETIC STEM CELL; METABOLISM; PRIORITY JOURNAL; ANIMAL; BONE MARROW; CELL LINE; DRUG EFFECT; ENZYMOLOGY; HEMATOPOIESIS; HUMAN; REVIEW;

ANIMALS; BENZENE; BONE MARROW; CELL LINE; HEMATOPOIESIS; HUMANS; PEROXIDASE;

EID: 0029804643     PISSN: 09024506     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (82)

1. SANTESSON CG. Uber chronische vergigtung mit steinkohlentheerbenzin vir todesfalle. Arch Hyg Berlin 1897: 31: 336-376.
2. LE NOIRE MM, CLAUDE H. Sur un cas de purpura attribue a l'intoxication par le benzene. Bull Mem Soc Med Hosp Paris 1897: 3: 1251.
3. DELORE P AND BORGOMANO J. Leucemie aique au cours de intoxication benzenique. Sur origine toxique de certaines leucemies aigues et leurs relations avec le anemies graves. J Med Lyon 1928: 9: 227.
4. AKSOY M. Benzene hematotoxicity. In: AKSOY M, ed. Benzene Carcinogenicity. Boca Raton: CRC Press, 1988: 59-112.
5. GOLDSTEIN BD. Hematotoxicity in humans. J Toxicol Environ Health 1977: 2 (suppl): 69-105.
6. AKSOY M. Benzene carcinogenicity. In: AKSOY M, ed. Benzene Carcinogenicity. Boca Raton: CRC Press, 1988: 113-151.
7. DEGOWIN RL. Benzene exposure and aplastic anemia followed by leukemia 15 years later. JAMA 1963: 185: 748-751.
8. COOPER KR, SNYDER R. Benzene metabolism. In: AKSOY M, ed. Benzene Carcinogenicity. Boca Raton: CRC Press, 1988: 33-58.
9. PARKE DV, WILLIAMS RT. Studies in detoxication 54. The metabolism of benzene. A) The formation of phenylglucuronide and phenyl sulphuric acid from 14C-benzene. B) The metabolism of 14C-phenol. Biochem J 1953: 55: 337-340.
10. SEATON MJ, SCHLOSSER PM, MEDINSKY MA. In vitro conjugation of benzene metabolites by human liver: potential influence of interindividual variability on benzene toxicity. Carcinogenesis 1995: 16: 1519-1528.
11. JOHANSSON I, INGELMAN-SUNDBERG M. Benzene metabolism by ethanol-, acetone-, and benzene-inducible cytochrome P450IIE1 in rat and rabbit liver microsomes. Cancer Res 1988: 48: 5387-5390.
12. SCHNIER GG, LAETHEM CL, KOOP DR. Identification and induction of cytochromes P450, P450IIE1 and P450IA1 in rabbit bone marrow. J Pharmacol Exp Ther 1989: 251: 790-796.
13. CENTER MB, RECIO L. Absence of detectable P450 2E1 in bone marrow of B6C3F1 mice: relevance to butadiene-induced bone marrow toxicity. Fund Appl Toxicol 1994: 22: 469-473.
14. O'DowD JJ. The metabolism in-vitro of 7,12-dimethyl-benz[a]anthracene by human bone marrow. Cancer Lett 1987: 36: 83-92.
15. SELKIRK JK, CROY RG, WHITLOCK JP, GELBION HV. In vitro metabolism of benzo(a)pyrene by human liver microsomes and lymphocytes. Cancer Res 1975: 35: 3651-3655.
16. SMITH MT, YAGER JW, STEINMETZ KL, EASTMOND DA. Peroxidase-dependent metabolism of benzene's phenolic metabolites and its potential role in benzene toxicity and carcinogenicity. Environ Health Perspect 1989: 82: 23-29.
17. RICKERT DE, BAKER TS, Bus JS, BARROW CS, IRONS RD. Benzene disposition in the rat after exposure by inhalation. Toxicol Appl Pharmacol 1979: 49: 417-423.
18. BAINTON DF, ULLYOT JL, FARQUHAR MG. The development of neutrophilic polymorphonuclear leukocytes in human bone marrow. J Exp Med 1971: 134: 907-934.
19. SADLER A, SUBRAHMANYAM VV, ROSS D. Oxidation of catechol by horseradish peroxidase and human leukocyte peroxidase: reactions of o-benzoquinone and o-benzosemiquinone. Toxicol Appl Pharmacol 1988: 93: 62-71.
20. SUBRAHMANYAM VV, ROSS D, EASTMOND DA, SMITH MT. Potential role of free radicals in benzene-induced myelotoxicity and leukemia. Free Rad Biol Med 1991: 11: 495-515.
21. SAWAHATA T, NEAL RA. Horseradish peroxidase-mediated oxidation of phenol. Biochem Biophys Res Commun 1982: 109: 988-994.
22. GANOUSIS LG, GOON D, ZYGLEWSKA T, WU KK, ROSS D. Cell-specific metabolism in mouse bone marrow stroma: studies of activation and detoxification of benzene metabolites. Mol Pharmacol 1992: 42: 1118-1125.
23. SUBRAHMANYAM VV, SADLER A, SUBA E, ROSS D. Stimulation of the in-vitro bioactivation of hydroquinone by phenol in bone marrow cells. Drug Metab Dispos 1989: 17: 348-350.
24. LÉVAY G, ROSS D, BODELL WJ. Peroxidase activation of hydroquinone results in the formation of DNA adducts in HL-60 cells, mouse bone marrow macrophages and human bone marrow. Carcinogenesis 1993: 14: 2329-2334.
25. GAIDO K, WIERDA D. Suppression of bone marrow stromal cell function by benzene and hydroquinone is ameliorated by indomethacin. Toxicol Appl Pharmacol 1987: 89: 378-390.
26. WEVER R, PLAT H, HAMERS MN. Human eosinophil peroxidase: a novel isolation procedure, spectral properties and chlorinating activity. FEBS Lett 1981: 123: 327-331.
27. BHAT RV, SUBRAHMANYAM VV, SADLER A, ROSS D. Bioactivation of catechol in rat and human bone marrow cells. Toxicol Appl Pharmacol 1988: 94: 297-304.
28. TUNEK A, OLOFSSON T, BERLIN M. Toxic effects of benzene and benzene metabolites on granulopoietic stem cells and bone marrow cellularity in mice. Toxicol Appl Pharmacol 1981: 59: 149-156.
29. GAD-EL-KARIM MM, RAMANUJAM VM, AHMED AE, LEGATOR MS. Benzene myeloclastogenicity: a function of its metabolism. Am J Ind Med 1985: 7: 475-484.
30. KENYON EM, MEDINSKY MA. Incorporation of heterogeneous enzyme distribution into a physiological model for benzene, phenol and hydroquinone. Toxicologist 1995: 15: 49.
31. EASTMOND DA, SMITH MT, IRONS RD. An interaction of benzene metabolites reproduces the myelotoxicity observed with benzene exposure. Toxicol Appl Pharmacol 1987: 91: 85-95.
32. SUBRAHMANYAM VV, DOANE-SETZER P, STEINMETZ KL, ROSS D, SMITH MT. Phenol-induced stimulation of hydroquinone bioactivation in mouse bone marrow in-vivo:possible implications in benzene myelotoxicity. Toxicology 1990: 62: 107-116.
33. ROBERTSON ML, EASTMOND DA, SMITH MT. Two benzene metabolites, catechol and hydroquinone, produce a synergistic induction of micronuclei and toxicity in cultured human lymphocytes. Mutat Res Fundam Mol Mech Mutagen 1991: 249: 201-209.
34. LATRIANO L, GOLDSTEIN BD, WITZ G. Formation of muconaldehyde, an open ring metabolite of benzene, in mouse liver microsomes: an additional pathway of toxic metabolites. Proc Natl Acad Sci USA 1986: 83: 8356-8360.
35. GOON D, CHENG X, RUTH JA, PETERSEN DR, ROSS D. Metabolism of trans,trans-muconaldehyde by aldehyde and alcohol dehydrogenases: identification of a novel metabolite. Toxicol Appl Pharmacol 1992: 114: 147-155.
36. KLINE SA, XIANG Q, GOLDSTEIN BD, WITZ G. Reaction of (E,E)-muconaldehyde and its aldehydic metabolites, (E,E)-6-oxohexadienoic acid and (E,E)-6-hydroxyhexa-2,4-dienal, with glutathione. Chem Res Toxicol 1993: 6: 578-583.
37. ZHANG Z, KLINE SA, KIRLEY TA, GOLDSTEIN BD, WITZ G. Pathways of trans,trans-muconaldehyde metabolism in mouse liver cytosol: reversibility of monoreductive metabolism and formation of end products. Arch Toxicol 1993: 67: 461-467.
38. ZHANG Z, XIANG Q, GLATT H, PLATT KL, GOLDSTEIN BD, WITZ G. Studies on pathways of ring opening of benzene in a Fenton system. Free Rad Biol Med 1995: 18: 411-419.
39. HUFF JE, HASEMAN JK, DEMARINI DM, et al. Multiple site carcinogenicity of benzene in Fischer 344 rats and B6C3F1 mice. Environ Health Perspect 1989: 82: 125-163.
40. OSBORNE JC, METZLER M, NEUMANN HG. Peroxidase activity in the rat zymbal gland and its possible role in the metabolic activation of aminostilbenes in the target tissue. Cancer Lett 1980: 8: 221-226.
41. DE PK, BANNERJEE RK. Purification and characterization of a soluble peroxidase of rat preputial gland: comparison with lactoperoxidase. Biochim Biophys Acta 1992: 1120: 167-172.
42. STRUM JM, SHEAR CR. Harderian glands in mice: fluorescence, peroxidase activity and fine structure. Tissue Cell 1982: 14: 135-148.
43. SMART RC, ZANNONI VG. DT- Diaphorase and peroxidase influence the covalent binding of the metabolites of phenol, the major metabolite of benzene. Mol Pharmacol 1984: 26: 105-111.
44. 2-forming NADPH oxidase of the phagocytes; nature, mechanisms of activation and function. Biochim Biophys Acta 1986: 853: 65-89.
45. ZAKHIREH B, ROOT RK. Development of oxidase activity by human bone marrow granulocytes. Blood 1979: 54: 429-439.
46. MEAGHER RC, SALVADO AJ, WRIGHT DG. An analysis of the multilineage production of human hematopoietic progenitors in long term bone marrow culture: evidence that reactive oxygen intermediates derived from mature phagocytic cells have a role in limiting progenitor cell self renewal. Blood 1988: 72: 273-281.
47. IRONS RD, GREENLEE WF, WIERDA D, BUS JS. Relationship between benzene metabolism and toxicity: a proposed mechanism for the formation of reactive intermediates from polyphenol metabolites. Adv Exp Med Biol 1981: 136: 229-243.
48. EVER P. Effects of superoxide dismutase on the autoxidation of 1,4-hydroquinone. Chem Biol Interact 1991: 80: 159-176.
49. GAIDO K, WIERDA D. In vitro effects of benzene metabolites in mouse bone marrow stromal cells. Toxicol Appl Pharmacol 1984: 76: 45-55.
50. SUTHERLAND HJ, LANSDORP PM, HENKELMAN DH, EAVES AC, EAVES CJ. Functional characterization of individual human hematopoietic stem cells cultured at limiting dilution on supportive marrow stromal layers. Proc Natl Acad Sci USA 1990: 87: 3584-3588.
51. GREAVES MF. Stem cell origins of leukemia and curability. Br J Cancer 1993: 67: 413-423.
52. KING AF, LANDRETH KS, WIERDA D. Bone marrow stromal cell regulation of B-lymphopoiesis II. Mechanisms of hydroquinone inhibition of pre B cell maturation. J Pharmacol Exp Ther 1989: 250: 582-590.
53. CHERTKOV JL, LUTTON JD, JIANG S, DA SILVA J-L, ABRAHAM NG. Hematopoietic effects of benzene inhalation assessed by murine long-term bone marrow culture. J Lab Clin Med 1992: 119: 412-419.
54. THOMAS DJ, REASOR MJ, WIERDA D. Macrophage regulation of myelopoiesis is altered by exposure to the benzene metabolite hydroquinone. Toxicol Appl Pharmacol 1989: 97: 440-453.
55. THOMAS DJ, SADLER A, SUBRAHMANYAM VV, et al. Bone marrow stromal cell bioactivation and detoxification of the benzene metabolite hydroquinone: comparison of macrophages and fibroblastoid cells. Mol Pharmacol 1990: 37: 255-262.
56. TWERDOK LE, REMBISH SJ, TRUSH MA. Induction of quinone reductase and glutathione in bone marrow cells by 1,2-dithiole-3-thione. Effect on hydroquinone-induced cytotoxicity. Toxicol Appl Pharmacol 1992: 112: 273-281.
57. TWERDOK LE, REMBISH SJ, TRUSH MA. Studies with 1,2-dithiole-3-thione as a chemoprotector of hydroquinone-induced toxicity to DBA/2-derived bone marrow stromal cells. Environ Health Perspect 1993: 101: 172-177.
58. RENZ JF, KALF GF. Role for Interleukin-1 (IL1) in benzene-induced hematotoxicity: inhibition of conversion of pre-IL1α to mature cytokine in murine macrophages by hydroquinone and prevention of benzene induced hematotoxicity in mice by IL1-α. Blood 1991: 78: 938-944.
59. MILLER ACK, SCHATTENBERG DG, MALKINSON AM, ROSS D. Decreased content of the IL1α processing enzyme calpain in murine bone marrow-derived macrophages after treatment with the benzene metabolite hydroquinone. Toxicol Lett 1994: 74: 177-184.
60. KOBAYASHI Y, YAMAMOTO K, SAIDO T, KAWASAKI H, OPPENHEIM JJ, MATSUSHIMA K. Identification of calcium-activated neutral protease as a processing enzyme of human interleukin 1α. Proc Natl Acad Sci USA 1990: 87: 5548-5552.
61. ROSS D, SIEGEL D, SCHATTENBERG DG, MORAN JL. Cell-specific metabolism in benzene toxicity. A metabolic basis for benzene induced toxicity at the level of the progenitor cell in human bone marrow. Fund Appl Toxicol 1996: 30: 339.
62. TOBLER A, KOEFFLER HP. Myeloperoxidase: localization, structure and function. In: HARRIS JR, ed. Blood Cell Biochemistry. Vol 3. New York: Plenum, 1991: 255-288.
63. Hu Z-B, MA W, UPHOFF CC, METGE K, GIGNAC SM, DREXLER HG. Myeloperoxidase: expression and modulation in a large panel of human leukemia-lymphoma cell lines. Blood 1993: 82: 1599-1607.
64. SCHATTENBERG DG, STILLMAN WS, GRUNTMEIR JJ, HELM KM, IRONS RD, ROSS D. Peroxidase activity in murine and human hematopoietic progenitor cells: potential relevance to benzene-induced toxicity. Mol Pharmacol 1994: 46: 346-351.
65. BUROW S, VALET G. Flow cytometric characterization of stimulation, free radical formation, peroxidase activity and phagocytosis of human granulocytes with 2,7-dichlorofluorescein. Eur J Cell Biol 1987: 43: 128-133.
66. + normal human hematopoietic cells. Blood 1993: 82: 2069-2078.
67. FAIRBAIRN LJ, COWLING GJ, REIPERT BM, DEXTER TM. Suppression of apoptosis allows differentiation and development of a multipotent hemopoietic cell line in the absence of added growth factors. Cell 1993: 74: 823-832.
68. KOURY MJ. Programmed cell death (apoptosis) in hematopoiesis. Exp Hematol 1992: 20: 391-394.
69. FAIRBAIRN LJ, COWLING GJ, DEXTER TM, RAFFERTY JA, MARGISON GP, REIPERT B. bcl-2 delay of alkylating agent-induced apoptotic death in a murine hemopoietic stem cell line. Mol Carcinog 1994: 11: 49-55.
70. + human bone marrow progenitor cells. Fund Appl Toxicol 1996: 30: 167.
71. TRAVER RD, HORIKOSHI T, DANENBERG KD, et al. NAD(P)H:quinone oxidoreductase gene expression in human colon carcinoma cells: characterization of a mutation which modulates DT-diaphorase activity and mitomycin sensitivity. Cancer Res 1992: 52: 797-802.
72. SIEGEL D, TRAVER RD, BEALL HD, ROSS D. Cloning and purification of a mutant DT-diaphorase protein from human colon and lung cancer cell lines. Proc Am Assoc Cancer Res 1995: 36: 291.
73. ROSVOLD EA, MCGLYNN KA, LUSTBADER ED, BUETOW KH. Identification of an NAD(P)H:quinone oxidoreductase polymorphism and its association with lung cancer and smoking. Pharmacogenetics 1995: 5: 199-206.
74. EDWARDS YH, POTTER J, HOPKINSON DA. Human FAD-dependent NAD(P)H diaphorase. Biochem J 1980: 187: 429-436.
75. EICKELMANN P, EBERT T, WARSKULAT U, SCHULZ WA, SIES H. Expression of NAD(P)H:quinone oxidoreductase and glutathione S-transferases α and π in human renal cell carcinoma and in kidney cancer-derived cell lines. Carcinogenesis 1994: 15: 219-225.
76. EICKELMANN P, SCHULZ WA, ROHDE D, SCHMITZ-DRÄGER B, SIES H. Loss of heterozygosity at the NAD(P)H:quinone oxidoreductase locus associated with increased resistance against mitomycin C in a human bladder carcinoma cell line. Biol Chem Hoppe Seyler 1994: 375: 439-445.
77. BENSON AM, HUNKLER MJ, TALALAY P. Increase of NAD(P)H:quihone reductase by dietary antioxidants: possible role in protection against carcinogenesis and toxicity. Proc Natl Acad Sci USA 1980: 77: 5216-5220.
78. TALALAY P, BENSON AM. Elevation of quinone reductase activity by anticarcinogenic antioxidants. Adv Enz Reg 1981: 20: 287-300.
79. MARSHALL RS, PATERSON MC, RAUTH AM. DT-diaphorase activity and mitomycin C sensitivity in non-transformed cell strains derived from members of a cancer-prone family. Carcinogenesis 1991: 12: 1175-1180.
80. MARSHALL RS, PATERSON MC, RAUTH AM. Studies on the mechanism of resistance to mitomycin C and porfiromycin in a human cell strain derived from a cancer-prone individual. Biochem Pharmacol 1991: 41: 1351-1360.
81. FURST SM, UETRECHT JP. Carbamazepine metabolism to a reactive intermediate by the myeloperoxidase system of activated neutrophils. Biochem Pharmacol 1993: 45: 1267-1275.
82. JAUNKALNS R, SHEAR NH, SOKOLUK B, GARDNER D, CLAAS F, UETRECHT JP. Antimyeloperoxidase antibodies and adverse reactions to clozapine. Lancet 1992: 339: 1611-1612.