Further arguments in favour of direct covalent binding of Ochratoxin A (OTA) after metabolic biotransformation

References

• Arlt , VM , Pfohl-Leszkowicz , A , Cosyns , J-P and Schmeiser , HH . 2001 . Analyses of DNA adducts formed by ochratoxin A and aristolochic acid in patients with Chinese herbs nephropathy . Mutation Research , 494 : 143 – 150 .
   PubMed Web of Science ®Google Scholar
• Arlt , VM , Ferluga , D , Stiborova , M , Pfohl-Leszkowicz , A , Vukelic , M , Ceovic , S , Schmeiser , HH and Cosyns , J-P . 2002 . Is aristolochic acid a risk factor for Balkan endemic nephropathy-associated urothelial cancer? . International Journal of Cancer , 101 : 500 – 502 .
   PubMed Web of Science ®Google Scholar
• Atanasova , SY , von Ahsen , N , Toncheva , D , Dimitrov , TG , Oellerich , M and Armstrong , VW . 2005 . Genetic polymorphisms of cytochrome P450 among patients with Balkan endemic nephropathy (BEN) . Clinical Biochemistry , 38 : 223 – 228 .
   PubMed Web of Science ®Google Scholar
• Brambilla , G and Martelli , A . 2004 . Failure of the standard battery of short-term tests in detecting some rodent and human genotoxic carcinogens . Toxicology , 196 : 1 – 19 .
   PubMed Web of Science ®Google Scholar
• Calcutt , MW , Gillman , IG , Noftle , RE and Manderville , RA . 2001 . Electrochemical oxidation of ochratoxin A: Correlation with 4-chlorophenol . Chemical Research in Toxicology , 14 : 1266 – 1272 .
   PubMed Web of Science ®Google Scholar
• Castegnaro , M , Mohr , U , Pfohl-Leszkowicz , A , Esteve , J , Steinmann , J , Tillmann , T , Michelon , J and Bartsch , H . 1998 . Strain- and sex-specific induction of renal tumours by ochratoxin A in rats correlates with DNA adduction . International Journal of Cancer , 77 : 70 – 75 .
   PubMed Web of Science ®Google Scholar
• Dai , J , Park , G , Wright , MW , Adams , M , Akman , SA and Manderville , RA . 2002 . Detection and characterization of a glutathione conjugate of ochratoxin A . Chemical Research in Toxicolology , 15 : 1581 – 1588 .
   PubMed Web of Science ®Google Scholar
• Dai , J , Wright , MW and Manderville , RA . 2003 . Ochratoxin A forms a carbon-bonded C8-deoxyguanosine nucleoside adduct: Implications for C8 reactivity by a phenolic radical . Journal American Chemistry Society , 125 : 3716 – 3717 .
   PubMed Web of Science ®Google Scholar
• Dai , J , Park , G , Perry , JL , Ill’ichev , YV , Bow , DAJ , Pritchard , JB , Faucet , V , Pfohl-Leszkowicz , A , Manderville , R and Simon , JD . 2004 . Molecular aspects of the transport and toxicity of ochratoxin A . Account of Chemical Research , 37 : 874 – 881 .
   PubMed Web of Science ®Google Scholar
• De Groene , EM , Hassing , IGAM , Blom , MJ , Seinen , W , Fink-Gremmels , J and Horbach , GJ . 1996 . Development of human cytochrome P450-expressing cell lines: Application in mutagenicity testing of ochratoxin A . Cancer Research , 56 : 299 – 304 .
   PubMed Web of Science ®Google Scholar
• El Adlouni , C , Pinelli , E , Azémar , B , Zaoui , D , Beaune , P and Pfohl-Leszkowicz , A . 2000 . Role of CYP 2C and microsomal glutathione-S-transferase in modulating susceptibility to ochratoxin A genotoxicity . Environmental Molecular Mutagenesis , 35 : 123 – 131 .
   PubMed Web of Science ®Google Scholar
• Eling , TE , Thompson , DC , Fouremen , GL , Curtis , JF and Hughes , MF . 1990 . Prostaglandin H synthase and xenobiotic oxidation . Annual Reviews of Pharmacology and Toxicology , 30 : 1 – 45 .
   PubMed Web of Science ®Google Scholar
• Esaka , Y , Inagaki , S and Goto , M . 2003 . Separation procedures capable of revealing DNA adducts . Journal of Chromatography B , 797 : 321 – 329 .
   PubMed Web of Science ®Google Scholar
• Faucet , V , Pfohl-Leszkowicz , A , Dai , J , Castegnaro , M and Manderville , R . 2004 . Evidence for covalent DNA adduction by ochratoxin A following chronic exposure to rat and subacute exposure to pig . Chemical Research in Toxicology , 17 : 1289 – 1296 .
   PubMed Web of Science ®Google Scholar
• Farmer , PB . 2004 . DNA and protein adducts as markers of genotoxicity . Toxicology , 149 : 3 – 9 .
   Google Scholar
• Gautier , J-C , Richoz , J , Welti , DH , Markovik , J , Gremaud , E , Guengerich , FP and Turesky , RJ . 2001 . Metabolism of ochratoxin A: Absence of formation of genotoxic derivatives by human and rat enzymes . Chemical Research in Toxicology , 14 : 34 – 45 .
   PubMed Web of Science ®Google Scholar
• Gillman , IG , Clark , TN and Manderville , RA . 1998 . Oxidation of ochratoxin A by an Fe-porphyrin system: Model for enzymatic activation and DNA cleavage . Chemical Research in Toxicology , 12 : 1066 – 1076 .
   Google Scholar
• Gustafsson , JA , Mode , A , Norstedt , G and Skett , P . 1983 . Sex steroid induced changes in hepatic enzymes . Annual Reviews of Physiology , 45 : 51 – 60 .
   PubMed Web of Science ®Google Scholar
• Gross-Steinmeyer , K , Weymann , J , Hege , H-G and Metzler , M . 2002 . Metabolism and lack of DNA reactivity of the mycotoxin ochratoxin A in cultured rat and human primary hepatocytes . Journal of Agricultural and Food Chemistry , 50 : 938 – 945 .
   PubMed Web of Science ®Google Scholar
• Grosse , Y , Baudrimont , I , Castegnaro , M , Creppy , EE , Dirheimer , G and Pfohl-Leszkowicz , A . 1995 . Ochratoxin A metabolites and DNA adducts formation in monkey . Kidney Cell , 95 : 175 – 187 .
   Google Scholar
• Grosse , Y , Chekir-Ghedira , L , Huc , Z , Obrecht-Pflumio , S , Dirheimer , G , Bacha , H and Pfohl-Leszkowicz , A . 1997a . Retinol, ascorbic acid and alpha tocopherol prevent DNA adduct formation in mice treated with the mycotoxins ochratoxin A and zearalenone . Cancer Letters , 114 : 225 – 229 .
   PubMed Web of Science ®Google Scholar
• Grosse , Y , Monje , MC , Macé , K , Pfeifer , A and Pfohl-Leszkowicz , A . 1997b . Use of bronchial epithelial cells expressing human cytochrome P450 for study on metabolism and genotoxicity of ochratoxin A.In vitro . Toxicology , 10 : 93 – 102 .
   Google Scholar
• IARC . 1993a . “ IARC monographs on the evaluation of carcinogenic risks to humans ” . In Some naturally occurring substances: Some food items and constituents, heterocyclic aromatic amines and mycotoxins , Vol. 56 , Lyon : IARC .
   Google Scholar
• IARC . 1993b . Postlabelling methods for detection of DNA adducts , IARC publication No. 124
   Google Scholar
• JECFA WHO . 2002 . Evaluation of certain mycotoxins , (56th report of the Joint FAO/Who Expert Committee on Food Additives) 906
   Google Scholar
• Kamataki , T , Maeda , K , Yamazoe , Y , Nagai , T and Kato , R . 1983 . Sex difference of cytochrome P-450 in the rat: Purification, characterization, and quantitation of constitutive forms of cytochrome-P450 from liver microsomes of male and female rats . Archive of Biochemistry Biophysics , 225 : 758 – 770 .
   PubMed Web of Science ®Google Scholar
• Kamataki , T , Shimada , M , Maeda , K and Kato , R . 1985 . Pituitary regulation of sex-specific forms of cytochromeP-450 in liver microsomes of rats . Biochemical Biophysical Research Communication , 130 : 1247 – 1253 .
   PubMed Web of Science ®Google Scholar
• Lash , LH and Anders , MW . 1986 . Cytotoxicity of S-(1,2-dichlorovinyl) glutathione and S-(1,2 dichlorovinyl)-L-cysteine in isolated rat kidney cells . Journal of Biological Chemistry , 261 : 13076 – 13081 .
   PubMed Web of Science ®Google Scholar
• Lutz , W and Gaylor , D . 1996 . Significance of DNA adducts at low dose: Shortening the time to spontaneous tumor occurrence . Regulatory Toxicology and Pharmacology , 23 : 29
   PubMed Web of Science ®Google Scholar
• Mally , A , Zepnik , H , Wanek , P , Eder , E , Dingley , K , Ihmels , H , Völkel , W and Dekant , W . 2004 . Ochratoxin A: Lack of formation of covalent DNA adducts . Chemical Research in Toxicology , 17 : 234 – 242 .
   PubMed Web of Science ®Google Scholar
• Manderville , RA and Pfohl-Leszkowicz , A . 2005 . Genotoxicity of chlorphenols and ochratoxin A . Advances in Molecular Toxicology , (in press)
   Google Scholar
• Miljkovic , A , Pfohl-Leszkowicz , A , Dobrota , M and Mantle , PG . 2002 . Comparative responses to mode of oral administration and dose of ochratoxin A or nephrotoxic extract of Penicillium polonicum in rats . Experimental Toxicology and Pathology , 54 : 305 – 312 .
   Google Scholar
• Miller , JA and Miller , EC . 1981 . Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules . Cancer , 47 : 2327 – 2345 .
   PubMed Web of Science ®Google Scholar
• Molinié , A , Faucet , V , Castegnaro , M and Pfohl-Leszkowicz , A . 2005 . Analysis of some breakfast cereals collected on the French market for their content in ochratoxin A, citrinin and fumonisin B1 . Development of a new method for simultaneous extraction of ochratoxin A and citrinin. Food Chemistry , 92 : 391 – 400 .
   Google Scholar
• Monaci , L and Palmisano , F . 2004 . Determination of ochratoxin A in foods: State-of-the art and analytical challenges . Analytical Bioanalytical Chemistry , 378 : 96 – 103 .
   PubMed Web of Science ®Google Scholar
• Moroi , K , Suzuki , S , Kuga , T , Yamazaki , M and Kanizawa , M . 1985 . Reduction of ochratoxin A toxicity in mice treated with phenylalanine and phenobarbital . Toxicology Letters , 25 : 1 – 5 .
   PubMed Web of Science ®Google Scholar
• Nikolov , IG , Chernozemsky , IN and Idle , JR . 1991 . Genetic predisposition to Balkan endemic nephropathy: Ability to hydroxylate debrisoquine as a host risk factor . IARC Scientific Publication , 115 : 289 – 296 .
   PubMedGoogle Scholar
• Obrecht-Pflumio , S , Grosse , Y , Pfohl-Leszkowicz , A and Dirheimer , G . 1996 . Protection by indomethacin and aspirin against genotoxicity of ochratoxin A, particulary in the urinary bladder and kidney . Archives of Toxicology , 70 : 244 – 248 .
   PubMed Web of Science ®Google Scholar
• Obrecht-Pflumio , S and Dirheimer , G . 2000 . In vitro DNA and dGMP adducts formation caused by ochratoxin A . Chemico-Biological Interaction , 127 : 29 – 44 .
   PubMed Web of Science ®Google Scholar
• Obrecht-Pflumio , S and Dirheimer , G . 2001 . Horseradish peroxidase mediates DNA and deoxyguanosine 3′-monophosphate adduct formation in the presence of ochratoxin A . Archive of Toxicology , 75 : 583 – 590 .
   PubMed Web of Science ®Google Scholar
• Omar , RF , Hasinoff , BB , Mejilla , F and Rahimtula , AD . 1990 . Mechanism of ochratoxin A stimulated lipid peroxidation . Biochemical Pharmacology , 40 : 1183 – 1191 .
   PubMed Web of Science ®Google Scholar
• Petkova-Bocharova , T , Castegnaro , M , Pfohl-Leszkowicz , A , Garren , L , Grosso , F , Nikolov , I , Vrabcheva , T , Dragacci , S and Chernozemsky , I . 2003a . Analysis of ochratoxin A in serum and urine of inhabitants from an area with Balkan Endemic Nephropathy: A one-month follow up study . Facta universitatis, series: Medicine & Biology , 10 ( 2 ) : 62 – 68 .
   Google Scholar
• Petkova-Bocharova , T , El Adlouni , C , Faucet , V , Pfohl-Leszkowicz , A and Mantle , P . 2003b . Analysis for DNA adducts, ochratoxin A content and enzymes expression in kidneys of pigs exposed to mild experimental chronic ochratoxicosis . Facta universitatis, series: Medicine & Biology , 10 ( 3 ) : 111 – 115 .
   Google Scholar
• Petkova-Bocharova , T , Stoichev , IT , Chernozemsky , IN and Pfohl-Leszkowicz , A . 1998 . Formation of DNA adducts in tissues of mice progeny through transplacental contamination after administration of a single dose of ochratoxin A to the pregnant mother . Environmental and Molecular Mutagenesis , 32 : 155 – 162 .
   PubMed Web of Science ®Google Scholar
• Pfohl-Leszkowicz , A , Chakor , K , Creppy , EE and Dirheimer , G . 1991 . DNA-adducts formation after treatment of mice with ochratoxine A . IARC Scientific Publication, Mycotoxins, Endemic Nephropathy and Urinary Tracts Tumours , 115 : 245 – 253 .
   Google Scholar
• Pfohl-Leszkowicz , A , Grosse , Y , Kane , A , Creppy , EE and Dirheimer , G . 1993a . Differential DNA adduct formation and disappearance in three mice tissues after treatment by the mycotoxin, ochratoxin A . Mutation Research , 289 : 265 – 273 .
   PubMed Web of Science ®Google Scholar
• Pfohl-Leszkowicz , A , Grosse , Y , Obrecht , S , Kane , A , Castegnaro , M , Creppy , EE and Dirheimer , G . 1993b . “ Preponderance of DNA adducts in kidney after ochratoxin A exposure ” . In Human ochratoxicosis and related pathologies , Edited by: Libbey , J . Vol. 231 , 199 – 207 . London : Colloque INSERM . editor
   Google Scholar
• Pfohl-Leszkowicz , A , Grosse , Y , Kane , A , Gharbi , A , Baudrimont , I , Obrecht , S , Creppy , EE and Dirheimer , G . 1993c . “ Is the oxydative pathway implicated in the genotoxicity of ochratoxin A? ” . In Human ochratoxicosis and related pathologies , Edited by: Libbey , J . Vol. 231 , 177 – 187 . London : Colloque INSERM . editor
   Google Scholar
• Pfohl-Leszkowicz , A , Grosse , Y , Castegnaro , M , Petkova-Bocharova , T , Nicolov , IG , Chernozemsky , IN , Bartsch , H , Betbeder , AM , Creppy , EE and Dirheimer , G . 1993d . Ochratoxin A related DNA adducts in urinary tract tumours of Bulgarian subjects . IARC Scientific Publication, Postlabelling methods for detection of DNA adducts , 124 : 141 – 148 .
   Google Scholar
• Pfohl-Leszkowicz , A , Pinelli , E , Bartsch , H , Mohr , U and Castegnaro , M . 1998 . Sex- and strain-specific expression of CYPs involved in ochratoxin A genotoxicity and carcinogenicity in rats . Molecular Carcinogenesis , 23 : 78 – 85 .
   Web of Science ®Google Scholar
• Pfohl-Leszkowicz , A , Petkova-Bocharova , T , Chernozemsky , IN and Castegnaro , M . 2002a . Balkan endemic nephropathy and the associated urinary tract tumours: Review on etiological causes, potential role of mycotoxins . Food Additives and Contaminants , 19 : 282 – 302 .
   PubMed Web of Science ®Google Scholar
• Pfohl-Leszkowicz , A , Bartsch , H , Azémar , B , Mohr , U , Estève , J and Castegnaro , M . 2002b . MESNA protects rats against nephrotoxicity but not carcinogenicity induced by ochratoxin A, implicating two separate pathways . Facta universitatis, series Medicine & Biology , 9 : 57 – 63 .
   Google Scholar
• Phillips , DH and Castegnaro , M . 1999 . Standardization and validation of DNA adduct postlabeling methods: Report of interlaboratory trials and production of recommended protocols . Mutagenesis , 14 : 301 – 315 .
   PubMed Web of Science ®Google Scholar
• Pinelli , E , El Adlouni , C , Pipy , B , Quartulli , F and Pfohl-Leszkowicz , A . 1999 . Respective implication of cyclooxygenase and lipoxygenase in ochratoxin A genotoxicity on human epithelial lung cells . Environmental Toxicology and Pharmacology , 7 : 95 – 107 .
   PubMed Web of Science ®Google Scholar
• Poirier , MC and Beland , FA . 1992 . DNA adduct measurements and tumor incidence during chronic carcinogen exposure in animal models: Implications for DNA adduct-based human cancer risk assessment . Chemical Research in Toxicology , 5 : 749 – 755 .
   PubMed Web of Science ®Google Scholar
• Rahimtula , AD , Bereziat , JC , Bussacchini-Griot , V and Bartsch , H . 1988 . Lipid peroxydation as a possible cause of ochratoxin toxicity . Biochemical Pharmacology , 37 : 4469 – 4477 .
   PubMed Web of Science ®Google Scholar
• Reddy , MV and Randerath , K . 1986 . Nuclease P1 mediated enhancement of sensitivity of 32P-postlabeling test for structurally diverse DNA-adducts . Carcinogenesis , 7 : 1543 – 1551 .
   PubMed Web of Science ®Google Scholar
• Rendic , S and Di Carlo , FJ . 1997 . Human cytochrome P450 enzymes: A status report summarizing their reactions, inducers and inhibitors . Drug Metabolism Reviews , 29 : 413 – 580 .
   PubMed Web of Science ®Google Scholar
• Simarro Doorten , AY , Bull , S , van der Doelen , MAM and Fink-Gremmels , J . 2004 . Metabolism-mediated cytotoxicity of ochratoxin A . Toxicology In Vitro , 18 : 271 – 277 .
   PubMed Web of Science ®Google Scholar
• Suzuki , S , Moroi , K , Kanizawa , M and Satoh , T . 1986 . Effects of drug metabolizing enzyme inducers on carcinogenesis and toxicity of ochratoxin A in mice . Toxicology Letters , 31 ( Suppl. ) : 206 (Abstract)
   Google Scholar
• Turesky , RJ and Vouros , P . 2004 . Formation and analysis of heterocyclic aromatic amine-DNA adducts in vitro and in vivo . Journal of Chromatography B , 802 : 155 – 166 .
   PubMed Web of Science ®Google Scholar
• Zepnik , H , Pahler , A , Schaver , V and Dekant , W . 2001 . Ochratoxin A-induced tumors formation: is there a role of reactive OTA metabolites? . Toxicology Sciences , 59 : 59 – 67 .
   PubMed Web of Science ®Google Scholar