Directing role of organic anion transporters in the excretion of mercapturic acids of alkylated polycyclic aromatic hydrocarbons

Drug Metabolism and Disposition

Volumn 35, Issue 10, 2007, Pages 1824-1831

  Bakhiya, Nadiya ^a   Batke, Monika ^a   Laake, Janet ^a   Monien, Bernhard H ^a   Frank, Heinz ^b   Seidel, Albrecht ^b   Engst, Wolfram ^a   Glatt, Hansruedi ^a  

^a GERMAN INSTITUTE OF HUMAN NUTRITION   (Germany)

^b Biochemical Institute for Environmental Carcinogens   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYMETHYL 8 METHYLPYRENE; 1 METHYLPYRENYL MERCAPTURIC ACID; 1 PYRENEMETHANOL; 1,8 DIMETHYLPYRENYL MERCAPTURIC ACID; 4 AMINOHIPPURIC ACID; ACETYLCYSTEINE; BENZYL ALCOHOL; DIMETHYL SULFOXIDE; ESTRONE SULFATE; METHYL GROUP; ORGANIC ANION TRANSPORTER; ORGANIC ANION TRANSPORTER 1; ORGANIC ANION TRANSPORTER 3; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CELL STRAIN HEK293; CONTROLLED STUDY; DRUG EXCRETION; DRUG FECES LEVEL; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; DRUG URINE LEVEL; ENZYME SPECIFICITY; HUMAN; HUMAN CELL; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; TISSUE CULTURE;

ACETYLCYSTEINE; ANIMALS; CELL LINE; FECES; HUMANS; MALE; ORGANIC ANION TRANSPORT PROTEIN 1; ORGANIC ANION TRANSPORTERS, SODIUM-INDEPENDENT; PYRENES; RATS; RATS, WISTAR;

AVENA; RATTUS;

EID: 34748840493     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.016964     Document Type: Article

References (40)

1. Aslamkhan AG, Han YH, Yang XP, Zalups RK, and Pritchard JB (2003) Human renal organic anion transporter 1-dependent uptake and toxicity of mercuric-thiol conjugates in Madin-Darby canine kidney cells. Mol Pharmacol 63:590-596.
2. Bakhiya N, Bahn A, Burckhardt G, and Wolff N (2003) Human organic anion transporter 3 (hOAT3) can operate as an exchanger and mediate secretory urate flux. Cell Physiol Biochem 13:249-256.
3. Bakhiya N, Batke M, Laake J, Seidel A, Engst W, and Glatt HR (2007) Urinary and faecal excretion of mercapturic acids of alkylated polycyclic aromatic hydrocarbons: directing role of organic anion transporters (OATs). Naunyn-Schmiedeberg's Arch Pharmacol 375:R92-93.
4. Bakhiya N, Stephani M, Bahn A, Ugele B, Seidel A, Burckhardt G, and Glatt HR (2006) Uptake of chemically reactive, DNA-damaging sulfuric acid esters into renal cells by human organic anion transporters. J Am Soc Nephrol 17:1414-1421.
5. Burckhardt BC and Burckhardt G (2003) Transport of organic anions across the basolateral membrane of proximal tubule cells. Rev Physiol Biochem Pharmacol 146:95-158.
6. Commandeur JN, Stijntjes GJ, and Vermeulen NP (1995) Enzymes and transport systems involved in the formation and disposition of glutathione S-conjugates. Role in bioactivation and detoxication mechanisms of xenobiotics. Pharmacol Rev 47:271-330.
7. Dixon M (1953) The determination of enzyme inhibitor constants. Biochem J 55:170-171.
8. Engst W, Landsiedel R, Hermersdörfer H, Doehmer J, and Glatt HR (1999) Benzylic hydroxylation of 1-methylpyrene and 1-ethylpyrene by human and rat cytochromes P450 individually expressed in V79 Chinese hamster cells. Carcinogenesis 20:1777-1785.
9. Eraly SA, Vallon V, Vaughn DA, Gangoiti JA, Richter K, Nagle M, Monte JC, Rieg T, Truong DM, Long JM, et al. (2006) Decreased renal organic anion secretion and plasma accumulation of endogenous organic anions in OAT1 knock-out mice. J Biol Chem 281:5072-5083.
10. Glatt HR (2000) Sulfotransferases in the bioactivation of xenobiotics. Chem-Biol Interact 129:141-170.
11. Glatt HR (2005) Activation and inactivation of carcinogens by human sulfotransferases, in Human Cytosolic Sulfotransferases (Pacifici GM and Coughtrie MWH eds) pp 281-306. Taylor & Francis, London.
12. Glatt HR, Henschler R, Frank H, Seidel A, Yang C, Abu-Shqara E, and Harvey RG (1993) Sulfotransferase-mediated mutagenicity of 1-hydroxymethylpyrene and 4H-cyclopenta[def-]chrysen-4-ol and its enhancement by chloride anions. Carcinogenesis 14:599-602.
13. Glatt HR, Schneider H, and Seidel A (2007) Polycyclische aromatische Kohlenwasserstoffe, in Handbuch der Lebensmitteltoxikologie (Dunkelberg H, Gebel T, and Hartwig A eds), pp 1121-1155. Wiley-VCH Verlag, Weinheim.
14. Harvey RG, Pataki J, and Lee H (1984) The Friedel-Crafts acylation and benzoylation of pyrene. Org Prep Proc Int 16:144-148.
15. Haufroid V and Lison D (2005) Mercapturic acids revisited as biomarkers of exposure to reactive chemicals in occupational toxicology: a minireview. Int Arch Occup Environ Health 78:343-354.
16. Hirom PC, Millburn P, Smith RL, and Williams RT (1972) Species variations in the threshold molecular-weight factor for the biliary excretion of organic anions. Biochem J 129:1071-1077.
17. Inoue M, Okajima K, and Morino Y (1981) Renal transtubular transport of mercapturic acid in vivo. Biochim Biophys Acta 641:122-128.
18. Inoue M, Okajima K, and Morino Y (1982) Metabolic coordination of liver and kidney in mercapturic acid biosynthesis in vivo. Hepatology 2:311-316.
19. Inoue M, Okajima K, and Morino Y (1984) Hepato-renal cooperation in biotransformation, membrane transport, and elimination of cysteine S-conjugates of xenobiotics. J Biochem (Tokyo) 95:247-254.
20. Koh AS, Simmons-Willis TA, Pritchard JB, Grassl SM, and Ballatori N (2002) Identification of a mechanism by which the methylmercury antidotes N-acetylcysteine and dimercaptopropanesulfonate enhance urinary metal excretion: transport by the renal organic anion transporter 1. Mol Pharmacol 62:921-926.
21. Lock EA, Odum J, and Ormond P (1986) Transport of N-acetyl-S-pentachloro-1,3-butadienylcysteine by rat renal cortex. Arch Toxicol 59:12-15.
22. Luch A (2005) The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons. Imperial College Press, London.
23. Ma L, Kuhlow A, and Glatt HR (2002) Ethanol enhances the activation of 1-hydroxymethylpyrene to DNA adduct-forming species in the rat. Polycyclic Aromat Compds 22:933-946.
24. Ma L, Landsiedel R, Seidel A, and Glatt HR (2000) Detection of mercapturic acids and nucleoside adducts in blood, urine and faeces of rats treated with 1-hydroxymethylpyrene. Polycyclic Aromat Compds 21:135-149.
25. Motojima M, Hosokawa A, Yamato H, Muraki T, and Yoshioka T (2002) Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake. Br J Pharmacol 135:555-563.
26. Okajima K, Inoue M, Itoh K, Nagase S, and Morino Y (1985) Role of plasma albumin in renal elimination of a mercapturic acid. Analyses in normal and mutant analbuminemic rats. Eur J Biochem 150:195-199.
27. Pombrio JM, Giangreco A, Li L, Wempe MF, Anders MW, Sweet DH, Pritchard JB, and Ballatori N (2001) Mercapturic acids (N-acetylcysteine S-conjugates) as endogenous substrates for the renal organic anion transporter 1. Mol Pharmacol 60:1091-1099.
28. Race JE, Grassl SM, Williams WJ, and Holtzman EJ (1999) Molecular cloning and characterization of two novel human renal organic anion transporters (hOAT1 and hOAT3). Biochem Biophys Res Commun 255:508-514.
29. Rice JE, Rivenson A, Braley J, and LaVoie EJ (1987) Methylated derivatives of pyrene and fluorene: evaluation of genotoxicity in the hepatocyte/DNA repair test and tumorigenic activity in newborn mice. J Toxicol Environ Health 21:525-532.
30. Sekine T, Cha SH, and Endou H (2000) The multispecific organic anion transporter (OAT) family. Pflugers Arch 440:337-350.
31. Stevens JL and Jones DP (1989) The mercapturic acid pathway: biosynthesis, intermediary metabolism, and physiological disposition, in Glutathione: Chemical, Biochemical, and Medical Aspects (Dolphin D, Avramovic O, and Poulson R eds) pp 45-84. John Wiley and Sons, New York.
32. Sugawara M, Mochizuki T, Takekuma Y, and Miyazaki K (2005) Structure-affinity relationship in the interactions of human organic anion transporter 1 with caffeine, theophylline, theobromine and their metabolites. Biochim Biophys Acta 1714:85-92.
33. Surh YJ and Miller JA (1994) Roles of electrophilic sulfuric acid ester metabolites in mutagenesis and carcinogenesis by some polynuclear aromatic hydrocarbons. Chem-Biol Interact 92:351-362.
34. Sweet DH (2005) Organic anion transporter (Slc22a) family members as mediators of toxicity. Toxicol Appl Pharmacol 204:198-215.
35. + gradient. Am J Physiol Renal Physiol 284:F763-F769.
36. Takeda M, Hosoyamada M, Cha SH, Sekine T, and Endou H (2000) Hydrogen peroxide downregulates human organic anion transporters in the basolateral membrane of the proximal tubule. Life Sci 68:679-687.
37. Takeda M, Narikawa S, Hosoyamada M, Cha SH, Sekine T, and Endou H (2001) Characterization of organic anion transport inhibitors using cells stably expressing human organic anion transporters. Eur J Pharmacol 419:113-120.
38. Van Aubel RA, Masereeuw R, and Russel FG (2000) Molecular pharmacology of renal organic anion transporters. Am J Physiol Renal Physiol 279:F216-F232.
39. Wright SH and Dantzler WH (2004) Molecular and cellular physiology of renal organic cation and anion transport. Physiol Rev 84:987-1049.
40. Zalups RK and Ahmad S (2005) Transport of N-acetylcysteine S-conjugates of methylmercury in Madin-Darby canine kidney cells stably transfected with human isoform of organic anion transporter 1. J Pharmacol Exp Ther 314:1158-1168.