Molecular aspects of the transport and toxicity of ochratoxin A

Accounts of Chemical Research

Volumn 37, Issue 11, 2004, Pages 874-881

  Dai, Jian ^a,e   Park, Gyungse ^a,f,g,h,i   Perry, Jennifer L ^b,c,j   Il'Ichev, Yuri V ^b,k,l,m   Bow, Daniel A J ^c,n   Pritchard, John B ^c,p,q,r   Faucet, Virginie ^d,s   Pfohl Leszkowicz, Annie ^d,t,u   Manderville, Richard A ^a,o,v,w,x   Simon, John D ^b,p,x,y,z,aa  

^a WAKE FOREST UNIVERSITY   (United States)

^b DUKE UNIVERSITY   (United States)

^c NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

^d LABORATOIRE DE GÉNIE CHIMIQUE   (France)

^e SHANGHAI JIAO TONG UNIVERSITY   (China)

^f Korea University   (South Korea)

^g WAYNE STATE UNIVERSITY   (United States)

^h UNIVERSITY OF NEW HAMPSHIRE   (United States)

ⁱ Pohang University of Science and Technology (POSTECH)   (South Korea)

^j WINTHROP UNIVERSITY   (United States)

^k MOSCOW STATE UNIVERSITY   (Russian Federation)

^l UNIVERSITY OF BASEL   (Switzerland)

^m WICHITA STATE UNIVERSITY   (United States)

ⁿ UNIVERSITY OF ABERDEEN   (United Kingdom)

^o UNIVERSITY OF GUELPH   (Canada)

^p HARVARD UNIVERSITY   (United States)

^q SUNY UPSTATE MEDICAL UNIVERSITY   (United States)

^r MEDICAL UNIVERSITY OF SOUTH CAROLINA   (United States)

^s UNIV MONTPELLIER   (France)

^t Dept of Toxicology and Food Safety   (France)

^u GDEMAR Society

^v QUEEN S UNIVERSITY   (Canada)

^w UNIVERSITY OF VIRGINIA   (United States)

^x University of Montpellier ^*  (United States)

^y WILLIAMS COLLEGE   (United States)

^z UNIVERSITY OF CALIFORNIA   (United States)

^aa UNIVERSITY OF CALIFORNIA   (United States)

more..

Author keywords

[No Author keywords available]

Indexed keywords

HUMAN SERUM ALBUMIN; OCHRATOXIN; ORGANIC ANION TRANSPORTER;

ARTICLE; CARCINOGENICITY; CELL MEMBRANE TRANSPORT; EPITHELIUM CELL; EXPOSURE; FUNGUS; GENOTOXICITY; HUMAN; KIDNEY DISEASE; OXIDATION;

ALBUMINS; AUTORADIOGRAPHY; BIOLOGICAL TRANSPORT; HUMANS; OCHRATOXINS; OXIDATION-REDUCTION; PROTEIN BINDING;

EID: 9444298436     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar0302134     Document Type: Article

References (51)

1. Van der Merwe, K. J.; Steyn, P. S.; Fourie, L. Mycotocins. Part II. The Constitution of Ochratoxins A, B, and C Metabolites of Aspergillus ochraceus, J. Chem. Soc. 1965, 7083-7088.
2. Teren, J.; Varga, J.; Hamari, Z.; Rinyu, E.; Kevei, F. Immunochemical Detection of Ochratoxin A in Black Aspergillus Strains, Mycopathologia 1996, 134, 171-176.
3. Abarca, M. L.; Bragulat, M. R.; Castella, G.; Cabanes, F. J. Ochratoxin A Production by Strains of Aspergillus niger var niger, Appl. Environ. Microbiol. 1994, 60, 2650-2652.
4. Galvano, F.; Piva, A.; Ritieni, A.; Galvano, G. Dietary Strategies to Counteract the Effects of Mycotoxins: A Review, J. Food Prot. 2001, 64, 120-131.
5. Studer-Rohr, I.; Schlatter, J.; Dietrich, D. R. Kinetic Parameters and Intraindividual Fluctuations of Ochratoxin A Plasma Levels in Humans, Arch. Toxicol. 2000, 74, 499-510.
6. Benford, D.; Boyle, C.; Dekant, W.; Fuchs, R.; Gaylor, D. W.; Hard, G.; McGregor, D. B.; Pitt, J. I.; Plestina, R.; Shephard, G.; Solfrizzo, M.; Verger, P. J. P.; Walker, R. Joint Expert Committe on Food Additives, 2001; Vol. 47.
7. Marquardt, R. R.; Frohlich, A. A. A Review of Recent Advances in Understanding Ochratoxicosis, J. Anim. Sci. 1992, 70, 3968-3988.
8. Creppy, E. E. Human Ochratoxicosis, J. Toxicol., Toxin Rev. 1999, 18, 277-293.
9. Krogh, P.; Elling, F.; Friis, C.; Hald, B.; Larsen, A. E.; Lillehoj, E. B.; Madsen, A.; Mortensen, H. P.; Rasmussen, F.; Ravnskov, U. Porcine Nephropathy Induced by Long-Term Ingestion of Ochratoxin A, Vet. Pathol. 1979, 16, 466-475.
10. Simon, P. Chronic Renal Failure: Are There Environmental and Occupational Risk Factors? J. Toxicol., Toxin Rev. 1999, 18, 313-321.
11. Petkova-Bocharova, T.; Chernozemsky, I. N.; Castegnaro, M. Ochratoxin A in Human Blood in Relation to Balkan Endemic Nephropathy and Urinary System Tumours in Bulgaria. Food Addit. Contam. 1998, 5, 299-301.
12. Creppy, E. E.; Kane, A.; Dirheimer, G.; Lafarge-Frayssinet, C.; Mousset, S.; Frayssinet, C. Genotoxicity of Ochratoxin A in Mice: DNA Single-Strand Break Evaluation in Spleen, Liver, and Kidney, Toxicol. Lett. 1985, 28, 29-35.
13. Huff, J. E. Carcinogenicity of Ochratoxin A in Experimental Animals, IARC Sci. Publ. 1991, 229-244.
14. Horvath, A.; Upham, B. L.; Ganev, V.; Trosko, J. E. Determination of the Epigenetic Effects of Ochratoxin in a Human Kidney and a Rat Liver Epithelial Cell Line, Toxicon 2002, 40, 273-282.
15. Peters, T. All About Albumin; Academic Press: New York, 1996.
16. Il'ichev, Y. V.; Perry, J. L.; Simon, J. D. Interaction of Ochratoxin A with Human Serum Albumin. Preferential Binding of the Dianion and pH Effects, J. Phys. Chem. B 2002, 106, 452-459.
17. Il'ichev, Y. V.; Perry, J. L; Rüker, F.; Dockal, M.; Simon, J. D. Interaction of Ochratoxin A with Human Serum Albumin. Binding Sites Localized by Competitive Interactions with the Native Protein and Its Recombinant Fragments, Chem.-Bio. Interact. 2002, 141, 275-293.
18. Chu, F. S. Interaction of Ochratoxin A with Bovine Serum Albumin, Arch. Biochem. Biophys. 1971, 147, 359-366.
19. Uchiyama, S.; Saito, Y.; Uchiyama, M. Protein-Binding of Ochratoxin A and Its Extradability from Proteinaceous Food, J. Food Hyg. Soc. Jpn. 1985, 26, 651-657.
20. Uchiyama, S.; Saito, Y. Protein-Binding Potential of Ochratoxin A in Vitro and Its Fluorescence Enhancement, J. Food Hyg. Soc. Jpn. 1987, 28, 453-460.
21. Perry, J. L.; Christensen, T.; Goldsmith, M. R.; Toone, E. J.; Beratan, D. N.; Simon, J. D. A Binding of Ochratoxin A to Human Serum Albumin Stabilized by a Protein-Ligand Ion Pair, J. Phys. Chem. B 2003, 107, 7884-7888.
22. Perry, J. L.; Goldsmith, M. R.; Peterson, M. A.; Beratan, D. N.; Wozniak, G.; Rüker, F. Simon, J. D. Molecular Details of the Ochratoxin A Binding Site within Human Serum Albumin, J. Phys. Chem. B 2004, in press.
23. Gekle, M.; Silbernagl, S. The Role of the Proximal Tubule in Ochratoxin A Nephrotoxicity in Vivo - Toxodynamic and Toxokinetic Aspects, Renal Physiol. Biochem. 1994, 17, 40-49.
24. Zingerle, M.; Silbernagl, S.; Gekle, M. Reabsorption of the Nephrotoxin Ochratoxin A Along the Rat Nephron in Vivo, J. Pharmacol. Exp. Ther. 1997, 280, 220-244.
25. Welborn, J. R.; Groves, C. E.; Wright, S. H. Peritubular Transport of Ochratoxin A by Single Rabbit Renal Proximal Tubules, J. Am. Soc. Nephrol. 1998, 9, 1973-1982.
26. Groves, C. E.; Nowak, G.; Morales, M. Ochratoxin A Secretion in Primary Cultures of Rabbit Renal Proximal Tubule Cells, J. Am. Soc. Nephrol. 1999, 10, 13-20.
27. Tsuda, M.; Sekine, T.; Takeda, M.; Cha, S. H.; Kanai, Y.; Kimura, M.; Endou, H. Transport of Ochratoxin A by Renal Multispecific Organic Anion Transporter 1. J. Pharmacol. Exp. Ther. 1999, 289, 1301-1305.
28. Jung, K. Y.; Takeda, M.; Kim, D. K.; Tojo, A.; Narikawa, S.; Yoo, B. S.; Hosoyamada, M.; Cha, S. H.; Sekine, T.; Endou, H. Characterization of Ochratoxin A Transport by Human Organic Anion Transporters, Life Sci. 2001, 69, 2123-2135.
29. Simon, J. D.; Perry, J. L.; Il'ichev, Y. V.; Pritchard, J. B.; Bow, D. A. J. Binding of Ochratoxin A to Human Plasma Proteins: Implications in Toxicity Mechanisms, Biophys. J. 2003, 85, 332A.
30. Gautier, J. C.; Holzhaeuser, D.; Markovic, J.; Gremaud, E.; Schilter, B.; Turesky, R. J. Oxidative Damage and Stress Response from Ochratoxin A Exposure in Rats, Free Radical Biol. Med. 2001, 30, 1089-1098.
31. Schaaf, G. J.; Nijmeijer, S. M.; Maas, R. F. M.; Roestenberg, P.; de Groene, E. M.; Fink-Gremmels, J. The Role of Oxidative Stress in the Ochratoxin A-Mediated Toxicity in Proximal Tubular Cells, Biochem. Biophys. Acta 2002, 1588, 149-158.
32. Lebrun, S.; Follmann, W. Detection of Ochratoxin A-Induced DNA Damage in MDCK Cells by Alkaline Single Cell Gel Electrophoresis (Comet Assay), Arch. Toxicol. 2002, 75, 734-741.
33. Pfohl-Leszkowicz, A.; Grosse, Y.; Kane, A.; Creppy, E. E.; Dirheimer, G. Preponderance of DNA-Adducts in Kidney After Ochratoxin A Exposure, in Human Ochratoxicosis and its Pathologies; Creppy, E. E., Castegnaro, M., and Dirheimer, G., Eds.; John Libbey: Montrouge, France, 1993; Vol. 231, pp 199-207.
34. Obrecht-Pflumio, S.; Dirheimer, G. In Vitro DNA and dGMP Adducts Formation Caused by Ochratoxin A, Chem.-Biol. Interact. 2000, 127, 29-44.
35. Obrecht-Pflumio, S.; Dirheimer, G. Horseradish Peroxidase Mediates DNA and Deoxyguanosine 3′-Monophosphate Adduct Formation in the Presence of Ochratoxin A, Arch. Toxicol. 2001, 75, 583-590.
36. Calcutt, M. W.; Gillman, I. G.; Noftle, R. E.; Manderville, R. A. Electrochemical Oxidation of Ochratoxin A: Correlation with 4-Chlorophenol, Chem. Res. Toxicol. 2001, 14, 1266-1272.
37. Gillman, I. G.; Yezek, J. M.; Manderville, R. A. Ochratoxin A Acts as a Photoactivatable DNA Cleaving Agent, Chem. Commun. 1998, 647-648.
38. Il'ichev, Y. V.; Perry, J. L.; Manderville, R. A.; Chignell, C. F.; Simon, J. D. The pH-Dependent Primary Photoreactions of Ochratoxin A, J. Phys. Chem. B, 2001, 105, 11369-11376.
39. Gillman, I. G.; Clark, T. N.; Manderville, R. A. Oxidation of Ochratoxin A by an Fe-Porphyrin System: Model for Enzymatic Activation and DNA Cleavage, Chem. Res. Toxicol. 1999, 12, 1066-1076.
40. Mally, A.; Zepnik, H.; Wanek, P.; Eder, E.; Dingley, K.; Ihmels, H.; Völkel, W.; Dekant, W. Ochratoxin A: Lack of Formation of Covalent DNA Adducts, Chem. Res. Toxicol. 2004, 17, 234-242.
41. Gautier, J. C.; Richoz, J.; Welti, D. H.; Markovik, J.; Gremaud, E.; Guengerich, F. P.; Turesky, R. J. Metabolism of Ochratoxin A: Absence of Formation of Genotoxic Derivatives by Human and Rat Enzymes, Chem. Res. Toxicol. 2001, 14, 34-45.
42. Brow, M. E.; Dai, J.; Park, G.; Wright, M. W.; Gillman, I. G.; Manderville, R. A. Photochemically Catalyzed Reaction of Ochratoxin A with D- and L-Cysteine, Photochem. Photobiol. 2002, 76, 649-656.
43. Manderville, R. A.; Calcutt, M. W.; Dai, J.; Park, G.; Gillman, I. G.; Noftle, R. E.; Mohammed, A. K.; Birincioglu, M.; Dizdaroglu, M.; Rodriguez, H.; Akman, S. A. Stoichiometric Preference in Copper-Promoted Oxidative DNA Damage by Ochratoxin A, J. Inorg. Biochem. 2003, 95, 87-96.
44. Dai, J.; Park, G.; Wright, M. W.; Adams, M.; Akman, S. A.; Manderville, R. A. Detection and Characterization of a Glutathione Conjugate of Ochratoxin A, Chem. Res. Toxicol. 2002, 15, 1581-1588.
45. Dai, J.; Wright, M. W.; Manderville, R. A. Ochratoxin A Forms a Carbon-Bonded C8-Deoxyguanosine Nucleoside Adduct: Implications for C8 Reactivity by a Phenolic Radical, J. Am. Chem. Soc. 2003, 125, 3716-3717.
46. Burrows, C. J.; Muller, J. G. Oxidative Nucleobase Modifications Leading to Strand Scission, Chem. Rev. 1998, 98, 1109-1151.
47. Dai, J.; Wright, M. W.; Manderville, R. A. An Oxygen-Bonded C8-Deoxyguanosine Nucleoside Adduct of Pentachlorophenol by Peroxidase Activation: Evidence for Ambident C8 Reactivity by Phenoxyl Radicals, Chem. Res. Toxicol. 2003, 16, 817-821.
48. Pfohl-Leszkowicz, A.; Faucet, V.; Dai, J.; Manderville, R. A. Evidence for Covalent DNA Adduction by Ochratoxin A Following Chronic Exposure to Rat and Subacute Exposure to Pig, Chem. Res. Toxicol. 2004, 17, 1289-1296.
49. Castegnaro, M.; Mohr, U.; Pfohl-Leszkowicz, A.; Estève, J.; Steinmann, J.; Tillman, J.; Michelon, J.; Bartsch, H. Sex- and Strain-Specific Induction of Renal Tumors by Ochratoxin A in Rats Correlates with DNA Adduction. Int. J. Cancer 1998, 77, 70-75.
50. Pfohl-Leskowicz, A.; Pinelli, E.; Bartsch, H.; Mohr, U.; Castegnaro, M. Sex and Strain Differences in Ochratoxin A Metabolism and DNA Adduction in Two Strains of Rats. Mol. Carcinog. 1998, 23, 76-83.
51. Pfohl-Leszkowicz, A.; Bartsch, H.; Azémar, B.; Mohr, U.; Estève, J.; Castegnaro, M. MESNA Protects Rats against Nephrotoxicity but not Carcinogenicity Induced by Ochratoxin A, Implicating Two Separate Pathways, Facta Universitatis, Series Medicine and Biology 2002, 9, 57-63.