Phenol and catechol induce prehemolytic and hemolytic changes in human erythrocytes

Toxicology Letters

Volumn 152, Issue 1, 2004, Pages 73-84

  Bukowska, Bozena ^a   Kowalska, Sylwia ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

Catechol; Erythrocyte; Free radical; Glutathione; Haemoglobin; Phenol

Indexed keywords

CATALASE; CATECHOL; GLUCOSE 6 PHOSPHATE DEHYDROGENASE; GLUTATHIONE REDUCTASE; GLUTATHIONE TRANSFERASE; HEMOGLOBIN; HEMOPROTEIN; HYDROGEN PEROXIDE; HYDROXYL RADICAL; METHEMOGLOBIN; OXYGEN RADICAL; PHENOL; SEMIQUINONE; SUPEROXIDE; SUPEROXIDE DISMUTASE; TOXIN;

ARTICLE; BLOOD CELL; CELL FUNCTION; CHEMICAL BINDING; CONTROLLED STUDY; CYTOTOXICITY; ENZYME ACTIVITY; ENZYME DENATURATION; ERYTHROCYTE; HEMOLYSIS; HUMAN; HUMAN CELL; MACROMOLECULE; OXIDATION; PRIORITY JOURNAL; STATISTICAL SIGNIFICANCE; TOXICITY TESTING;

BENZOQUINONES; CATALASE; CATECHOLS; CELL CULTURE TECHNIQUES; DISINFECTANTS; ERYTHROCYTES; FREE RADICALS; GLUTATHIONE; HEMOGLOBINS; HEMOLYSIS; HUMANS; PHENOL; SUPEROXIDE DISMUTASE;

FELIS CATUS;

EID: 3543050047     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxlet.2004.03.025     Document Type: Article

References (55)

1. Aebi, H., 1984, Catalase in vitro. In: Packer L. (Ed.), Methods in Enzymology, Vol. 105. Academic Press, Orlando, pp. 121-126.
2. Akerboom T.P.M., Sies H. Assay of glutathione, glutathione disulfide and glutathione mixed disulfides in biological samples. Met. Enzymol. 77:1981;373-382
3. Bachowski S., Kolaja K.L., Xu Y., Ketcham C.A., Stevenson D.E., Walburg E.F., Klauning J. Role of oxidative stress in the mechanism of dieldrin's hepatotoxicity. Ann. Clin. Lab. Sci. 27:1997;196-209
4. Bartosz, G., 1995. The Other Face of Oxygen (in Polish), PWN Warszawa.
5. Boge G., Roche H. Cytotoxicity of phenolic compounds on Dicentrachus labrax erythrocytes. Bull. Environ. Contam. Toxicol. 57:1996;171-178
6. Bruce R.M., Santodonato J., Neal M.W. Summary review of the health effects associated with phenol. Toxicol. Indust. Health. 3:1987;535-568
7. Bukowska B. Effects of 2,4-D and its metabolite 2,4-dichlorophenol on antioxidant enzymes and level of glutathione in human erythrocytes. Comp. Biochem. Physiol. C. 135/4:2003;435-441
8. Bukowska B., Chajdys A., Duda W., Duchnowicz P. Effect of phenoxyherbicides and their metabolites on the activity of catalase in the human erythrocyte. Cell Biol. Int. 24:2000;705-711
9. Bukowska B., Goszczynska K., Duda W. Effect of 4-chloro-2- methylphenoxyacetic acid (MCPA) and 2, 4-dimethylphenol (2, 4-DMP) on human erythrocytes. Pest. Biochem. Physiol. 77:2003;92-98
10. Carlberg I., Mannervik B. Purification and characterrization of the flavoenzyme glutathione reductase from rat liver. J. Biol. Chem. 250:1972;5475-5480
11. Cavalieri E.L., Li K.M. Catechol ortho-quinones: the electrophilic compounds that form depurinating DNA adducts and could initiate cancer and other diseases. Carcinogenesis. 23:2003;1071-1077
12. Dalin N.M., Kristofferson R. Physiological effects of a sublethal concentration of inhaled phenol on the rat. Ann Zool. Fenn. 11:1974;193-199
13. Drabkin D.L. Spectrophotometric studies. XIV the crystalographic and optical properties of the hemoglobin of man in comparision with these of other species. J. Biol. Chem. 164:1946;703-723
14. Ellman G.K. Tissue sulfhydryl groups. Arch. Biochem, Biophys. 82:1959;70-77
15. Emdadul Haque M., Asanuma M. Apoptosis- inducing neurotoxicity iof dopamine and its metabolites via reactive quinine generation in neuroblasmtoma cells. Biochim. Biophys. Acta. 1619:2003;39-52
16. Everse J., Hsia N. The toxicities of native and modified hemoglobins. Free Radic. Biol. Med. 22:1997;1075-1099
17. Eyer P., Hertle H., Kiese M., Klein G. Kinetics of ferrihaemoglobin formation by some reducing agents and the role of hydrogen peroxide. Mol. Pharmacol. 11:1975;326-334
18. Geinoz S., Rey S., Boss G., Bunge A.L., Guy R.H., Carrupt P.A., Reist M., Testa B. Quantitative structuru-permeation relationships for solute transport across silicone membranes. Pharma. Res. 19:2002;1622-1629
19. Grootveld M., Halliwell B. Aromatic hydroxylation as a potential measure of hydroxy-radical formation in vivo. Biochem. J. 237:1986;499-504
20. Grootveld M., Halliwell B. 2,3-dihyroxybenzoic acid is a product of human aspirin metabolism. Biochem. Pharmacol. 37:1988;271-280
21. Gut I., Nedelcheva V., Soucek P., Stopka P., Tichavska B. Cytochromes P450 in benzene metabolism and involvement of their metabolites and reactive oxygen species in toxicity. Environ. Health Perspect. 104:1996;1211-1218
22. Habig W.H., Pabst M.J., Jakoby W.B. Glutathione-S-transferases: the first enzymatic step in mercapturic acid formation. J. Biol. Chem. 249:1974;7130-7139
23. Hiraku Y., Kawanishi S. Oxidative DNA damages and apoptosis induced by benzene metabolites. Cancer Res. 56:1996;5172-5178
24. Hooiveld M., Heederick D.J.J., Kogevinas M., Boffetta P., Needham L.L., Patterson D.G., Bas Bueno-de-Mesquita H. Jr. Second follow-up of a duch cohort occupationally exposed to phenoxy herbicydes, chlorophenols, and contaminants. Am. J. Epidemiol. 147:1998;891-901
25. Irons R.D. Quinones as toxic metabolites of benzene. J. Toxicol. Environ. Health. 16:1985;673-678
26. Jones D.P., Meyer D.B., Andersson B., Orrenius S. Conversion of catalase to the secondary-catalase-peroxide complex (compound 11) by a-methyldopa. Mol. Pharmacol. 20:1981;159-164
27. Kappus H., Kieczka H., Scheulen M., Remmer H. Molecular aspects of catechol and pyrogallol inhibition of liver microsomal lipid peroxidation stimulated by ferrous ion-ADP-complexes or by carbon tetrachloride. Arch Pharmacol. 300:1977;179-188
28. Kettle A.J., Winterbourn C.C. Superoxide-dependent hydroxylation by myeloperoxidase. J. Biol. Chem. 269:1994;17146-17151
29. Krol E.S., Bolton J.L. Oxidation of 4-alkylohenols and catechols by tyrosinase: orthosubstituents alter the mechanism of quinoid formation. Chem. Biol. Interact. 104:1997;11-27
30. Lee S.F., Lin J.K. Generation of hydrogen peroxide, superoxide anion and the hydroxyl free radical from polyphenols and active benzene metabolites: their possible role in mutagenesis. J. Biomed. Sci. 1:1994;125-130
31. Lown J.W. Molecular mechanisms of action of anticancer agents involving free radical intermediates. Adv. Free Radic. Biol. Med. 1:1985;225-264
32. May J.M. Plant catechols prevent lipid peroxidation in human plasma and erythrocytes. Mol. Cell Biochem. 226:2001;89-95
33. Misra H., Fridovich I. The role of superoxide anion in the autooxidation of epinephryne and a simple assay for superoxide dismutase. J. Biol. Chem. 247:1972a;3170-3175
34. Misra H.P., Fridovich K. The generation of superoxide radical during the autooxidation of hemoglobin. J Biol. Chem. 247:1972b;6960-6962
35. Molina Portela M.P., Fernandez Villamil S.H., Perissinotti L.J., Stoppani A.O. Redox cycling of o-naphthoquinones in trypanosomati. Superoxide and hydrogen peroxide production. Biochem. Parmacol. 52:1996;1875-1882
36. Nagel R. Species differences, influence of dose and application on biotransformation of phenol in fish. Xenobiotica. 13:1983;101-106
37. Nelson S.K., Bose S.K., McCord J.M. The toxicity of high-dose superoxide dismutase suggests that superoxide can both initiate and terminate lipid peroxidation in the reperfused heart. Free Radic. Biol. Med. 16:1994;195-200
38. Nelson S.D., Mitchell J.R., Dybing E., Sasame H.A. Cytochrome P-450 mediated oxidation of 2-hydroxyestrogens to reactive intermediates. Biochem. Biophys. Res. Commun. 70:1976;1157-1165
39. Nimmagudda R., Snyder R. Oxidative modifications produced in HL-60 cells on exposure to benzene metabolities. J. Appl. Toxicol. 15:1995;403-409
40. Nohl H., Stolze K. The effects of Xenobiotics on Erythrocytes. Gen. Pharmacol. 31:1998;343-347
41. Ohtsuji H., Ikeda M. Quantitative relationship between atmospheric phenol vapour and phenol in the urine of employees in Bakelite factories. Br. J. Ind. Med. 29:1972;70-73
42. Oikawa S., Hirosawa I., Hirakawa K., Kawanishi S. Site specificity and mechanism of oxidative DNA damage induced by carcinogenic catechol. Carcinogenesis. 22:2001;1239-1245
43. Ovasaka M., Yliniemela A. A semiempirical study on inhibition of catechol O-methyl-transpherase by substituted catechols. J. Comput. Aided Mol. Des. 12:1998;301-307
44. Penning T.M., Ohnishist S.T., Ohnishi T., Harvey R.G. Generation of reactive oxygen species during the enzymatic oxidation of polycyclic aromatic hydrocarbon trans-dihydrodiols catalyzed by dihydrodiol dehydrogenase. Chem. Res. Toxicol. 9(1):1996;84-92
45. Piotrowski J.K. Evaluation of exposure to phenol, absorption of phenol vapour in the lungs and through the skin and excretion of phenol in urine. Br. J. Ind. Med. 28:1971;172-178
46. Riley P.A., 1984. Hydroxyanisole: the current status. In: Hydroxyanisole: Recent Advances in Anti-Melanoma Therapy, IRL Press, Oxford, pp. 25-34.
47. Schweigert N., Alexander J., Zehnder J., Eggen R. Chemical properties of catechols and their molecular modes of toxic action in cells from microoorganisms to mammals. Environ. Microbiol. 3:2001;81-91
48. Segura-Aguilar J., Baez S., Widersten M., Welch C.J., Mannervik B. Human class Mu glutathione transferases, in particular isoenzyme M2-2, catalyze detoxication of the dopamine metabolite aminochromel. J. Biol. Chem. 272:1997;5727-5731
49. Smith M.T., Zhang L., Jeng M., Wang Y., Guo W., Duramad P., Hubbard A.E., Hofstadler G., Holland N.T. Hydroquinone, a benzene metabolite, increases the level of aneusomy of chromosomes 7 and 8 in human CD34-positive blood progenitor cells. Carcinogenesis. 21:2000;1485-1490
50. Stenius U., Warholm M., Rannug A., Walles S., Lundberg I., Hogberg J. The role of GSH depletion and toxicity in hydroquinone-induced development of enzyme-altered foci. Carcinogenesis. 10:1989;593-599
51. Stock J., Dormandy T.L. The oxidation of human red cell lipids induced hydrogen peroxide. Br. J. Haemat. 20:1971;95-111
52. Stolze K., Dadak A., Liu Y., Nohl H. Hydroxylamine and phenol induced formation of methemoglobin and free radical intermediates in erythrocytes. Biochem. Pharmacol. 52:1996;1821-1829
53. Takahashi N., Schreiber J., Fischer V., Mason R.P. Formation of glutathione-conjugated semiquinones by the reaction of quinones with glutathine: an ESR study. Arch. Biochem. Biophys. 252:1987;41-48
54. Tsuruta Y., Watanabe S., Inoue H. Fluorometric determination of phenol and p-cresol in urine by precolumn high-performance liquid chromatography using 4-(N-phthalimidinyl) benzenesulfonyl chloride. Anal. Biochem. 243:1996;86-91
55. WHO, 1994. IPCS Environmental Health Criteria for Phenol (161). First draft prepared by MS G.K. Montizan, Published by WHO, Printed in Finland.