PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
2007 | 16 | 3 |

Tytuł artykułu

Phenols - sources and toxicity

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
Phenols and their derivatives commonly exist in the environment. These compounds are used as the components of dyes, polymers, drugs and other organic substances. The presence of phenols in the ecosystems is also related with production and degradation of numerous pesticides and the generation of industrial and municipal sewages. Some phenols are also formed during natural processes. These compounds may be substituted with chlorine atoms, may be nitrated, methylated or alkylated. Both phenols and catechols are harmful ecotoxins. Toxic action of these compounds stems from unspecified toxicity related to hydrophobocity and also to the generation of organic radicals and reactive oxygen species. Phenols and catechols reveal peroxidative capacity, they are hematotoxic and hepatotoxic, provoke mutagenesis and carcinogenesis toward humans and other living organisms.

Wydawca

-

Rocznik

Tom

16

Numer

3

Opis fizyczny

p.347-362,fig.,ref.

Twórcy

  • University of Lodz, Banacha 12/16 str., 90-237 Lodz, Poland
autor

Bibliografia

  • 1. JAROMIR M., OŻADOWICZ R., DUDA W. Analysis of chlorophenols, chlorocatechols, chlorinated methoxyphenols and monoterpenes in communal sewage of Łódź and in the Ner river in 1999-2000. 16, 205, 2005.
  • 2. RÓŻAŃSKI L. The transformations of pesticides in living organisms and the environment, Agra-Enviro Lab. Poznań. 1998. [In Polish]
  • 3. LAINE M., JORGENSEN K. Straw compost and bioremediated soil as inocula for the bioremedation of chlorophenol - contaminated soil. Appl. Environ. Microbiol. 54, 1507, 1996.
  • 4. SCHMIDT S. Biodegradation of diaryl ether pesticides, from: Biodegradation of dioxins and furans, chapter 8, 229-281. 1998.
  • 5. SWARTS M., VERHAGEN F., FIELD J., WIJNBERG J. Trichlorinated phenols from Hypholoma elongatum. Phytochem. 49, 203, 1998.
  • 6. HANSCH C., McCARNS S., SMITH C., DODITTLE D. Comparative QSAR evidence for a free-radical mechanism of phenol-induced toxicity. Chem. Biol. Interact. 127, 61, 2000.
  • 7. BOYD E., KILLHAM K., MEHARG A. Toxicity of mono-, di- and tri-chlorophenols to lux marked terrestrial bacteria Burkholderia species Rasc C2 and Pseudomonas fluorescens. Microbiol. Let. 43, 157, 2001.
  • 8. BOBRAŃSKI B. Organic chemistry, PWN. Warszawa. 1973.
  • 9. BRUCE R., SANTODONATO J., NEAL M. Summary review of the health effects associated with phenol. Toxicol. Indust. Health. 3, 535, 1987.
  • 10. BUDAVARI S., The Merck Index, 13th ed. Whitehouse station,NJ: Merck Co; Inc, pp. 1299-1367, 2001.
  • 11. US. EPA. Ambient Water Quality Criteria DOC : Phenol, US EPA-440/5-80-066 (PB 81-117772), pp. 1100-1156, 1980.
  • 12. DAVIDSON R. The photodegradation of some naturally occurring polymers. J. Photochem. Photobiol. B: Biol. 33, 3, 1996.
  • 13. TSURUTA Y., WATANABE S., INOUE H. Fluorometric determination of phenol and p-cresol in urine by precolumn high-performance liquid chromatography using 4-(N-phtha limidinyl)benzenesulfonyl chloride, Analyt. Biochem. 243, 86, 1996.
  • 14. MICHAŁOWICZ J., DUDA W. Chlorophenols and their derivatives in waters of the drainage of the Dzierżązna river. State and anthropogenic changes of the quality of waters in Poland, tom III, ed. Burchard J. Hydrological committee of Polish Geographical Society, University of Łódź, Łódź, 2004. [In Polish]
  • 15. RIVM [Criteria Document: Phenol]. Bilthoven, The Netherlands, National Institute of Public Health and Environmental Protection (Document No. 738513002). 1986.
  • 16. ALLEN S., ALLEN C. Phenol concentrations in air and water samples collected near a wood preserving facility. Bull. Environ. Contam. Toxicol. 59, 702, 1997.
  • 17. GYROIK M., HERPAI Z., SZECSENYI I., VARGA U., SZIGETI J. Rapid and sensitive determination of phenol in honey by high performance liquid chromatography with fluorescence detection. J. Agric. Food Chem. 51, 5222, 2003.
  • 18. DORFNER R., FERGE T., KETTRUP A., ZIMMERMANN R., YERETZIAN C. Real time monitoring of 4-vinylguaiacol, guaiacol and phenol during coffee roasting by resonant laser ionization time-of-flight mass spectrometry. J. Agric. Food Chem. 51, 5768, 2003.
  • 19. US EPA. Treatability Manual, 1:I.8.6-1 to I.8.6-5, US EPA 600/8-80-042, 1980.
  • 20. DELFINO F., DUBE D. Persistent contamination of ground water by phenol. J. Environ. Sci. Health. 43, 345, 1976.
  • 21. NIEDAN V., PAVASARS J. OBERG G. Chloroperoxidasemediated chlorination of aromatic groups in fulvic acid. Chemosphere. 41, 779, 2000.
  • 22. VERHAGEN F., SWARTS M., WIJNBERG J., FIEL D J. Biotransformation of the major fungal metabolite 3.5-dichloro- p-anisyl alcohol under anaerobic conditions and its role in formation of bis (3.5-dichloro-4-hydroxyphenyl) methane. Appl. Environ. Microbiol. 64, 3225, 1998.
  • 23. MICHAŁOWICZ J. The occurrence of chlorophenols, chlorocatechols and chlorinated methoxyphenols in drinking water of the largest cities of Poland, Polish J. Environ. Sci. 14, 143, 2005.
  • 24. CZAPLICKA M. Sources and transformation of chlorophenols in the naturalenvironment. Sci. Total Environ. 322, 21, 2004.
  • 25. DELFINO F., DUBE D. Persistent contamination of ground water by phenol. J. Environ. Sci. Health. 43, 345, 1976.
  • 26. JONES , P. Chlorophenols and their impurities in the Canadian environment: Supplement, Ottawa Environmental Protection Service, Environmental Canada, pp. 99, 1981 (Report No. EPS-3-EP-84-3).
  • 27. HEUDORF U., ANGERER J., DREXLER H. Current internal exposure to pesticides in children and adolescens in Germany: Blood plasma levels of pentachlorophenol (PCP), lindane (Gamma-HCH ) and dichloro(Diphenyl)ethene (DDE), a biostable metabolite of dichloro(Diphenyl)trichlo roethane (DDT), Internat. J. Hygiene Environ. Health. 206, 485. 2003.
  • 28. SANDANGER T., DUMAS P., BERGER U. BURKOW I. Qanalysis of HO -PCB s and PCP in blood plasma frm individuals with PCB exposure living on the Chukotka Penisula in the Russian Arctic. J. Environ. Monit. 6, 758. 2004.
  • 29. NRCC . Chlorinated phenols: Criteria for environmental quality, Ottawa, Associate Committee on Scientific Criteria for Environmental Quality, National Research Council of Canada, pp. 191, 1982 (NRCC Publication, No. 18578).
  • 30. OBERG T. Halogenated aromatics from steel production: results of pilot-scale investigation. Chemosphere. 56, 441, 2004.
  • 31. McBRAIN A., SENIOR E., PATERSON A., Du PLESSIS CH ., WATSON-CRAIK IRENE A. Bioremedation of soil contaminated with 4-chloro-2-methylphenoxyacetic acid(MC PA): essential laboratory studies. S. Afric. J. Sci. 92, 426, 1996.
  • 32. CERNAKOWA M., ZEMANOVICOWA A. Microbial activity of soil contaminated with chlorinated phenol derivatives. Folia Microbiol. 43, 411, 1998.
  • 33. GUNSCHER A J., FUHRMANN F., SALTHAMMER T., SCHULTZE A., UHDE E. Formation and emission of chloroanisoles as indoor pollutants. Environ. Sci. Pollut. Res. 11, 147, 2004.
  • 34. KRAB-HUSKE N. Production of catechols: microbiology and technology. Wageningen University, disertation, no. 3291, 2002.
  • 35. SCHWEIGERT N., ALEXANDER J., ZEHNDER J., EGGEN R. Chemical properties of catechols and their molecular modes of toxic action in cells from microoorganisms tomammals. Environ. Microbiol. 3, 81, 2001.
  • 36. DAUNERT S. A cellular biosensor to detect chlorocatechols. Res. Brief. 79, 123, 2001.
  • 37. IARC, IARC Monographs on the evaluation of carcinogenic risks to humans: catechol. 71, 433, 1999.
  • 38. CHAEH., YOO Y. Mathematical modelling and simulation of catechol production from benzoate using resting cells of Pseudomonas putida. Proc. Biochem. 32, 423, 1997.
  • 39. LIN P., SANGAIAH R., RANASINGHE A., BALL L., SWENBERG J., GOLD A. Synthesis of chlorinated and nono-chlorinated biphenyl-2.3-and 3.4-catechols and their [H-2(3)]-isotopomers. Organ. Biomol. Chem. 2, 2624, 2004.
  • 40. MOISEVA O., SOLYAMIKOWA J., KASCHABEK S. GRONING J., THIEL M., GOLOVLEVA L., SCHOMANN M. A New Modified ortho Cleavage Pathway of 3-Chlorocatechol Degradation by Rhodococcus opacus 1CP: Gen. Biochem. Evid. J. Biotechnol. 184, 5282, 2002.
  • 41. SAURET-IGNAZI G., GAGNON J., BEGUIN C., BARELLE M., MARKOWICZ Y., PELMONT J., TOUSSAINT T. Characterization of a chromosomally encoded catechol 1.2-dioksygenase [E.C. 1.13.11.1.] from Alicagenes eutrophus CH34. Arch. Microbiol. 166, 42, 1996.
  • 42. PATNAIK P., KHOURY J. Reaction of phenol with nitrite ion: pathways of formation of nitrophenols in environmental waters. Water. Res. 38, 206, 2004.
  • 43. VIONE D., MAURINO V., PELIZZETI Z., MINERO C. Phenol photonitration and photonitrosation upon nitrite photolysis in basic solution. Internat. J. Environ. Analyt. Chem. 84, 493, 2004.
  • 44. HARRISON M., BARA S., BORGHESI D., VIONE D., ARSENE C., OLARIU R. Nitrated phenols in the atmosphere: a review. Atmospher. Environ. 39, 231, 2005.
  • 45. BUDDECH ., BEYERA., MUMIR I., DORICK ., KHMELINSKY Y. Enzymatic nitration of phenols. J. Mol. Catal. B: Enzym. 15, 123, 2001.
  • 46. FLOX C., GARRIDO J., RODRIQUEZ R., CENTELLAS F., CABOT P-L., ARIAS C., BRILLAS E. Degradation of 4.6-dinitroo-cresol from water by anodic oxidation with a boro-doped diamond electrode. Electrochim. Acta. 50, 3685, 2005.
  • 47. POCURULL E., MARCE R., BORRULL B. Determination of phenolic compounds in natural waters by liquid chromatography with ultraviolet and electrochemical detection after on-line trace enrichment. J. Chromat. A. 738, 1, 1996.
  • 48. FURUTA C., SUZUKI AK., TANAEDA S., KAMATA K., HAYASHI H., MORI Y., Li CM ., WATANABE G., TAYA K. Estrogenic activities of nitrophenols in diesel exhaust particles. Biol. Reproduct. 70, 1527, 2004.
  • 49. BRAVO R., DRISKE W., PATTERSON D., HILL R., NEEDHAM L., PIRKLE J., SAMPSON E. Measurement of p-nitrophenol in the urine of residents whose homes were contaminated with methyl parathion. Environ. Health Perspect. 110, 1085, 2002.
  • 50. PRUPPACHER , H., KLETT, J. Microphysis of clouds and precipitation. Dordrecht/Boston/London. D. Reidel Publishing Co. 1978.
  • 51. MASSELTER S., ZEMANN A. & BOBLETER O. Separation of cresols using coelectroosmotic capillary electrophoresis. Electrophoresis. 14, 36, 1993.
  • 52. RE-POPPI N., SANTIAGO-SILVA M. Identification of Polycyclic Aromatic Hydrocarbons and Methoxylated Phenols in Wood Smoke Emitted During Production of charcoal. Chromat. 55, 475, 2002.
  • 53. IPPOLO-ARMANIOS M., ALEXANDER R., KAGI R. Geosynthesis of organic compounds: I. Alkylphenols. Geochim. Cosmochem. Acta. 59, 3017, 1995.
  • 54. KAHL M., MAKYNEN E., KOSIAN P., ANKLEY G. Toxicity of 4-nonylophenol in a life – cycle test with the midge Chironomus tentaus. Ecotoxicol. Environ. Saf. 38, 155, 1997.
  • 55. LATORE A., LACORTE S., BARCELO D. Presence of nonylphenol, octylphenol and bisphenol in two aquifiers close to agricultural, industrial and urban areas. Chromatographia 57, 116, 2003.
  • 56. BERRYMAN D., HOUDE F., DeBLOIS C., OSHE A M. Nonylphenolic compounds in drinking and surface waters downstream of treated textile and pulp paper effluents: a survey and preliminary assessment of their potential effects on public health and quatic life. Chemosphere. 56, 247, 2004.
  • 57. FRIES E., PUTTMAN W. Occurence and behaviour of 4-nonylphenol in river water of Germany. J. Environ. Monit. 5, 598, 2003.
  • 58. FRIES E., PUTTMAN W. Occurrence of 4-nonylphenol in rain and snow. Atmospheric Environ. 38, 2013, 2004.
  • 59. KANNAN K., KEITH T., NAYLOR C., STAPLES C., SNYDER S., GIESY J. Nonylphenol and nonylphenol ethoxylates in fish, sediment and water of the Kalamazoo River, Michigan. Arch. Environ. Contam. Toxicol. 44, 77, 2003.
  • 60. WENZEL A., BOHMER W., MULLER J., RUDEL H., SCHORTERKERMANI C. Retrospective monitoring of alkylphenols and alkylphenol monoethoxylates in aquaticbiota from 1985 to 2001: Results from the German Environmental Speciment Bank. Environ. Sci. Technol. 38, 1654, 2004.
  • 61. OZAKI A., BABA T. Alkylphenol and bisphenol A levels in rubber products. Food Additiv. Contam. 20, 92, 2003.
  • 62. GUENTHER K., HEINKE V., THIELE B., KLEIST E., PRAST H., RAECKER T. . Endocrine disrupting nonylphenols are ubiquitous in food. Environ. Sci. Technol. 36, 1676, 2002.
  • 63. PETERS R. Hazardous Chemicals in Consumer Products. TNO reports. 2003.
  • 64. MEIJER L., PETERS R., SAUER P. Man-made chemicals in human blood levels of forty-six chemicals in a Dutch cohort. Groningen, pp. 18, 2004.
  • 65. FURHACKER M., SCHARF S., WEBER H. Bisphenol A emissions from point sources. Chemosphere 41, 751, 2000.
  • 66. SINNKONEN S., LAHTIPER A M., VATTULAINEN A., TAKHISTOV V.V., VIKTOROVSKII I.V., UTSA V.A. PAASIVIRTA J. Analyses of known and new types of polyhalogenated aromatic substances in oven ash from recycled aluminium production. Chemosphere. 52, 761, 2003.
  • 67. STACHEL B., EHRHORN U., HEEMKEN O.P., LEPOM P., REINCKLE H., SAWAL G., THEOBALD N. Xenoestrogens in the River Elbe and its tributaries. Environ. Pollut. 124, 497, 2003.
  • 68. VAN RY D.A., DACHS J., GIGLIOTTI C.L., BRUNCIAK P.A., NELSON E. D., EISENREICH S. J. Atmospheric sesonal trends and environmental fate of alkylphenols in the Lower Hudson River Estuary. Environ. Sci. Technol. 34, 2410, 2000.
  • 69. BERKNER S., STRECK G., HERRMANN R. Development and validation of a method for determination of trace levels of alkylphenols and bisphenol A in atmospheric samples. Chemosphere, 54, 575, 2004.
  • 70. LAMBERT C., LARROQUE M. Chromatographic analysis of water and wine sample for phenolic compounds relased from food-contact epoxy resins. J. Chromat. Sci. 35, 57, 1997.
  • 71. INOUNE K., MURAYAMA S., TAKEBA K., YOSHIMURA Y., NAKAZAWA H. Contamination of xenoestrogens bisphenol A and F in honey: safety assessment and analytical method of these compounds in honey, J. Food Composit. Anal. 16, 497, 2003.
  • 72. BREDE C., FJELDAL P., SKJEVRAK I., HERIKSTADT. Increased migration levels of bisphenol A from polycarbonate baby bottles after dishwashing, boilling and brushing. Food Additiv. Contam. 20, 684, 2003.
  • 73. HOULIHAN J., WILES R., THAYER K., GRAYS S. Body burden. The pollution in people. Washington. DC, USA: Environmental Working Grooup. 2003.
  • 74. INOUNE K., KATO K., YOSHIMURA Y., MAKINO T., NAKANAWA H. Determination of bisphenol A in human serum by high performance liquid chromatography with multi-electrode electrochemical detection. J. Chromat. B. Biomed. Sci. Appl. 749, 17, 2000.
  • 75. KYM P., HUMMERT K., NILSSON A., LUBIN M., KATZENELLE NBOGE N J. Bisphenolic compounds that enhance cell cation transport are found in commercial phenol. Med. Chem. 39, 4897, 1996.
  • 76. RITU K., KUNJAN R., SURENDA S. Paracetamol hepatotoxicity and microsomal function. Environ. Toxicol. Pharmacol. 7, 67, 1999.
  • 77. NAGARAJA P., YATHIRAJAN H., RAJU C., VASANTHA R., NAGENDRA P., KUMAR M. 3-aminophenol as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives. Il Farmaco, 58, 1295, 2003.
  • 78. La VECCHI A C., TAVANI A. Epidemiologic evidence on hair dyes and the risk of cancer in humans. Eur. J. Cancer Prev. 4, 31, 1995.
  • 79. CHEN J., JIANG J., ZHANG F., Yu H., ZHANG J. Cytotoxic environmentally relevant chlorophenols on L929 cells and their mechanisms. Cell Biol Toxicol. 20, 183, 2004.
  • 80. NIKONOROW M. Pesticides in the light of environmental toxicology., Agricultural and Forest National Publishing. Warszawa, 1979. [In Polish]
  • 81. BAYER A.G. Calculation of environmental distribution of BH T according to Mackay fugacity model level I. Method published in Mackay, D., Multimedia Environmental Models: The Fugacity Approach. Lewis Publ. Inc. Michigan, 2001.
  • 82. KOT-WASIK A., DĘBSKA J., NAMIEŚNIK J. Monitoring of organic pollutants in coastal waters of the Gulf of Gdańsk, Southern Baltic. Mar. Pollut. Bull. 49, 264, 2004.
  • 83. LEBRECH T G., CZERCZAK S., SZYMCZAK W. Benzene-documentation. Bases and Methods of Occupational Environment Evaluation, 1, 35, 2003. [In Polish]
  • 84. GALWAS-ZAKRZEWSKA, M. Biocydes in occupational environment. Work safety, 11, 26, 2004. [In Polish]
  • 85. XIAODONG W., CHUNSHEUNG Y., WANG L. Structure-activity relationships and response-surface analysis of nitroaromatics toxicity to the yeasts (Saccharomyces cerevisae). Chemosphere. 46, 1045, 2002.
  • 86. MORIDANI M.Y., SIRAKI A., CHEVALDINA T., SCOBIE H., OBRIEN P.J. Quantitative structure toxicity relationship for catechols in isolated rat hepatocytes, Chem. Biol. Interact. 147, 297, 2004.
  • 87. TSUTSUI T., MAYASHI N., MAIZUMI H., HUFF J., BARRETT J. Benzene-, catechol-, hydroquinone- and phenol- induced cell transformation, gene mutation, chromosome aberrations, aneuploidy, sister chromatid exchanges and unscheduled DNA synthesis in Syrian hamster embryo cells, Mut. Res. 373, 113, 1997.
  • 88. SELASSIE C., DeSOYA T., ROSARIO M., GAO H., HANSCH C. Phenol toxicity in leukemia cells: a radical process? Chem-Biol. Interact. 113, 175, 1998.
  • 89. HAYASHI M., NAKAMURA Y., HIGASHI K., KATO H., KISHIDA F., KANEKO H. A quantitative structure-activity relationship study of the skin irritation potential of phenols. Toxicol. in vitro. 13, 915, 1999.
  • 90. SCHWEIGERT N., ALEXANDER J., ZEHNDER J., EGGE N R. Chemical properties of catechols and their molecular modes of toxic action in cells from microoorganisms to mammals. Environ. Microbiol. 3, 81, 2001.
  • 91. SCHWEIGERT N., MUNZIKER R., ESCHER B., EGGEN R. Acute Toxicity of (chloro) Catechols and (chloro-) Catechol – Copper Combinations in Eschericha coli Corresponds to Their Membrane Toxicity in Vitro. Environ. Toxicol. Chem. 20, 247, 2000.
  • 92. KAHRU A., POLLUMAA L., REIMAN R., RATSEP A., LIIDERS M. HALOVERYAN A. The Toxicity and Biodegradability of Eight Main Phenolic Compounds Characteristic to the Oil-Shale Industry Wastewaters: A Test Battery, Inc. Environ. Toxicol. 15, 431, 2000.
  • 93. CLAYTON G.D., CLAYTON F.E. Patty’s Industrial Hygiene and Toxicology. 4th ed.; John Wiley & Sons Inc: New York, Vol. 2A, pp.132, 1994.
  • 94. FORD M.D., DELANY K.A., LING L.J., ERICKSON. Clinical Toxicology. W. B. Saunders Company: Philadelphia, pp.753, 2001.
  • 95. IARC , Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. World Health Organization, International Agency for Research on Cancer: Geneva. 1972.
  • 96. GOSSELIN R.E., SMITH R.P., HODGE H.C. Clinical Toxicology of Commercial Products, 5th ed.; Williams and Wilkings: Baltimore, pp. III -192-346, 1984.
  • 97. DUDAVARIS The Merck Index – Encyclopedia of Chemicals, Drugs and Biologicals, Merc and Co., Inc: Rahway, pp. 518-1126, 1989.
  • 98. JUHL G.A., KIM E.H., BENITEZ J.G., MANGIONES. A community exposure to 2-chloro-6-floorophenol, Vet. Hum. Toxicol. 45, 41, 2003.
  • 99. Mc FEE R.B., CARACCIO T.R., McGUIGAN M.A., REYNOLDS S.A., BELLANGER P. Dying to be thin: A dinitrophenol related fatality, Vet. Human Toxicol. 46, 251, 2004.
  • 100. NATIONAL RESEARCH COUNCIL . Drinking Water & Health, Vol. 1. Washington, DC: National Acxademy Press, p. 730, 1981.
  • 101. GRANT W.M. Toxicology of the Eye. 3rd ed. Springfield IL : Charles C. Thbomas Publisher, p.359, 1986.
  • 102. SITTING M., Handbook of Toxic and Hazardous Chemicals Park Ridge, NJ: Noyes Data Corporation, p. 185, 1981.
  • 103. KAMIJO Y., SOM A., KOKUTO M., OHBU M., FUKE C., OHWADA T. Hepatocellular injury with hyperaminotransferasemia after cresol ingestion, Arch. Pathol. Lab. Med. 127, 364, 2003.
  • 104. ELLENHORN M., SCHONWALD S., ORDOG G., WASSENBERG J. Ellenhorn’s Medical Toxicology: Diagnosis and Treatment of Human Poisoning, 2nd.; MD Williams and Wilkins: Baltimore, pp. 1211, 1997.
  • 105. LEWIS R. Hawley,s Condensed Chemical Dictionary, 12th ed.; Van Nostrans Rheinhold Co: New York, pp. 837, 1996.
  • 106. KAUBAK G., INAL M., BAYCU C. The role of free radicals in p-aminophenol – induced nephrotoxicity: doses reduced glutathione have a protective effect. Clinic. Chim. Acta, 252, 61, 1996.
  • 107. LAMPI P., VOHLONEN J., TUOMISTO I. & HEINONEN P. Increase of specific symptons after long-term use of chlorophenol polluted drinking water in a community, Eur. J. Epidemiol. 16, 245, 2000.
  • 108. PAINTNER R. & HOWARD R. The HeLa DNA-synthesis inhibition test as a rapid screen for mutagenic carcinogens. Mutat. Res. 92, 427, 1982.
  • 109. ZH ANG L., WANG Y., SHANG N., SMITH M. Benzene metabolites induce the loss and long arm deletion of chromosomes 5 and 7 in human lymphocytes. Leuk. Res. 22, 105, 1998.
  • 110. Mc CUE J., LAZIS S., COHEN J., MODIANO J., FREED B. Hydroquinone and catecholinterfere with T cell entry and progression through the G(1) phase. Mol. Immunol. 39, 995, 2003.
  • 111. SILVA M.D., GASPAR J., SILVA I.D., LEAO D., RUEFF J. Induction of chromosomal aberrations by phenolic compounds: possible role of reactive oxygen species. Mut. Res. – Gen. Toxicol. Environ. Mutagen. 540, 29, 2003.
  • 112. ATEEQ B., FARAH H., ALI M. & AHMAD W. Clastogenity of pentachlorophenol, 2.4-D and butachlor evaluated by Alium root, tip test, Mut. Res. Gen. Toxicol. 514, 105, 2002.
  • 113. PURSCHKE M., JACOBI H., WITE J. Differences in genotoxicity of H2O2 and tetrachlorohydroquinone in human fibroblasts. Mut. Res. 513, 159, 2002.
  • 114. SUEIRO R., SUAREZ S., ARAUJO S., GARRIDO M. Mutagenic and genotoxic evaluation of bisphenyl F diglycidyl ether (BFDGE ) in procaryotic and eucaryotic systems. Mut. Res. – Gen. Toxicol. Environ. Mutagen. 536, 39, 2003.
  • 115. YOSHIDA R., OIKAWA S., OGAWA Y., MIYAKOSHI Y., OOIDA M., ASANUMA K., SHIMIZU H. Mutagenicity of paminophenol in E. coli WP2uvrA/pKM 101 and its revelance to oxidative DNA damage. Mutat. Res. 415, 139, 1998.
  • 116. OKUBO T., NAGON F., USHIYAMA K., ITSU K. Contribution of oxygen radicals to DNA cleavage by quinone compounds derived from phenolic antioxidants, tert-butylhydroquinone and 2.5-di-tert-butylhydroquinone,. Toxicol. Let. 90, 11, 1997.
  • 117. OIKAWA S., NISHINO K., OIKAWA S., INOUNE S., MIZUTANI T. KAWANISHI S. Oxidative DNA damage and apoptosis induced by metabolities of buthylated hydroksytoluene. Biochem. Pharmacol. 56, 361, 1998.
  • 118. SCHWETZ B., QUAST J., KEELER P., HUMISTON C., KOUBA R. Results of 2-year toxicity and reproduction studies of pentachlorophenol in rats, Chemistry, Pharmacology and Environmental Toxicology. Ed. Plenum Press: New York, pp. 301, 1978.
  • 119. U.S ENVIRONMENTAL PROTECTION AGENCY . Integrated Risk Information System(IRIS ) on Methylphenol (106-44-5), Available from http://www.epa.gov/ngispgm3/iris on the Substance File List as March 15, 2000.
  • 120. SITTING M. Handbook of Toxic and Hazardous Chemicals and Carcinogens, 2nd ed.; Noyes Data Corporation: Park Ridge, pp 368, 1985.
  • 121. MORIDANI M.Y., SIRAKI A., CHEVALDINA T., SCOBIE H., OBRIEN P. Quantitative structure toxicity relationship for catechols in isolated rat hepatocytes, Chem. Biol. Interact. 147, 297, 2004.
  • 122. HOOVIELD M., HEEDERICK D., KOGEVINAS M., BOFETTA., NEDHAM L., PATTERSON D., BAS BAUENO-DE-MESQUITA J., BAS BAUENO-DE-MESQUITA. Second follow-up of a duch cohort occupationally exposed to phenoxy hrbicides, chlorophenols, and contaminants. Amer. J. Epidemiol. 147, 891, 1998.
  • 123. BUCKLEY J., MEADOWA., KADIN M., LeBEAU M., SIEGEL S., ROBINSO N L. Pesticide exposures in children with non-Hodking lymphoma. Cancer. 89, 2315, 2000.
  • 124. MUNOULT K., DELL L., AUSTIN R., LUIPPOLD R., NOESS R., BIGELOW C. Historical cohort study of 10109 men in the North American vinyl chloride industry, 1942-72: update of cancer mortality to 31 December 1995. Occup. Environ. Med. 57, 774, 2000.
  • 125. JORENS P., SCHEME P. Human pentachlorophenol poisoning. Hum. Exp. Toxicol. 12, 479, 1993.
  • 126. HIROSE M., TAKESADA Y., TANAKA H., TAMANO S., KATO T., SHIRAI T. Carcinogenicity of antioxidants BH A, caffeic acid, sezamol, 4-metoxyphenol and catechol at low doses, either alone or in combination and modulation of their effects in a rat medium-term multi-organ carcinogenesis model, Carcinogen. 19, 207, 1997.
  • 127. SEIKE N., WANIBUCHI H., MORIMUR A K., WEI M., NISHIKAWA T., HIRATA K., YOSHIKAWA J. & FUKUSHIM A S. Enhancement of lung carcinogenesis by nonylphenol and genistein in a F344 rat multiorgan carcinogenesis model. Cancer Lett. 192, 25, 2003.
  • 128. TSAICH -H., LIN P-H., WAIDYANATHA S., RAPPAPOR T M. Characterization of metabolic activation of pentachlorophenol to quinones and semiquinones in rodent liver. Chem.-Biol. Interact. 134, 55, 2001.
  • 129. IWATA M., ESHIMA Y., KAGECHIKA H., MIYAURA H. The endocrine disruptors nonylphenol and octylphenol exert dirrect effects on T cells to suppres TH1 development and enhance Th2 development. Immunol. Lett. 94, 135, 2004.
  • 130. YAO G., HOU Y. Nonylphenol induces thymocyte apoptosis through Fas/FasL pathway by mimicking estrogen in vivo. Environ. Toxicol. Pharmacol. 17, 19, 2004.
  • 131. AOYAMA H., ARAKI M., HOJO H., TAKAHASHI K., SCHIMIZU N., TANAKA N., AKASADA M., SHIRASAKA N., NAKASHIMA N., YAMAMOTO E. A twogeneration reproductive toxicity study in rats with 2.4-dichlorophenol. Cogenit. Anom. Kyoto. 42, 270, 2002.
  • 132. JUNG J., ISHIDA K., NISHIHARA T. Anti-estrogenic activity of fifty chemicals evaluated by in vitro assays. Life Sci. 74, 3065, 2004.
  • 133. NIWA-KURUTO R., NOZAWA R., MIYAKOSHI T., TATSUI S., TERAO Y. Estrogenic activity of alkylphenols, bisphenols and their chlorinated derivatives using a GFP expression system. Environ. Toxicol. Pharmacol. 19, 121, 2005.
  • 134. ROY G., BERNATCHEZ G., SAUVE R. Halide and alkyl phenols block volume-sensitive chloride channels in human glial cells (U-138MG ). J. Memb. Biol. 162, 191, 1998.
  • 135. GAIKWARD N., BODWELL W. Formation of DNA adducts in HL -60 cells treated with the toluene metabolite pcresol: a potential biomarker for toluene exposure, Chem- Biol. Interact. 145, 149, 2003.
  • 136. PEDERSEN G., BRYNSKOV J., SAERMARK T. Phenol toxicity and conjugation in human colonic epithelial cells. Scan. J. Gastroenterol. 37, 74, 2002.
  • 137. BUKOWSKA, B., KOWALSKA S. Phenol and catechol induce prehemolytic and hemolytic changes in human erythrocytes. Toxicol. Lett. 152, 73, 2004.
  • 138. DUCHNOWICZ P., KOTER M., DUDA W. Damage of erythrocyte by phenoxyacetic herbicides and their metabolites. Pest. Bioch. Physiol. 74, 1, 2002.
  • 139. DUCHNOWICZ P., KOTER M. Damage to the erythrocyte membrane caused bychlorophenoxyacetic herbicides. Cell. Mol. Biol. Lett. 8, 25, 2003.
  • 140. BUKOWSKA, B., DUDA W. 3-Dimethylaminophenol induced oxidative change in human red blood cells. Current. Topics Biophys. 22, 3, 2000.
  • 141. BUKOWSKA B., HUTNIK K. Phenoxyherbicides and their derivatives: Effect on the activity of erythrocytes acetylcholinesterase (in vitro). Pesticide Biochem. Physiol. 85, 174, 2006.
  • 142. DUCHNOWICZ P., SZCZEPANIAK P., KOTER M.. Erythrocyte membrane protein damage by phenoxyacetic herbicides. Pest. Bioch. Physiol. 82, 59, 2005.
  • 143. 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, 705, 2000.
  • 144. BUKOWSKA B. 2.4.5-T and 2.4.5-TCP induce oxidative damage in human erythrocytes: role of glutathione. Cell Biol. Int. 28, 557, 2004.
  • 145. BUKOWSKA B., GOSZCZYŃSKA K., DUDA W. Effect of 4-chloro-2-methylphenoxyacetic acid and 2,4-dimethylphenol on human erythrocytes. Pest. Biochem. Physiol. 77, 92, 2003.

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

bwmeta1.element.agro-article-e0b73606-9564-45f7-afd6-cac1de68b135
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.