Renal organic anion transporters OAT1 and OAT3 mediate the cellular accumulation of 5-sulfooxymethylfurfural, a reactive, nephrotoxic metabolite of the Maillard product 5-hydroxymethylfurfural

Biochemical Pharmacology

Volumn 78, Issue 4, 2009, Pages 414-419

  Bakhiya, Nadiya ^a   Monien, Bernhard ^a   Frank, Heinz ^b   Seidel, Albrecht ^b   Glatt, Hansruedi ^a  

^a GERMAN INSTITUTE OF HUMAN NUTRITION   (Germany)

^b Prof Dr Gernot Grimmer Foundation   (Germany)

Author keywords

5 Hydroxymethylfurfural; 5 Sulfooxymethylfurfural; Nephrotoxicity; Organic anion transporters

Indexed keywords

4 AMINOHIPPURIC ACID; 5 HYDROXYMETHYLFURFURAL; 5 SULFOOXYMETHYLFURFURAL; CARCINOGEN; ESTRONE SULFATE; MUTAGENIC AGENT; ORGANIC ANION TRANSPORTER 1; ORGANIC ANION TRANSPORTER 3; PROBENECID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; EMBRYO; GLYCATION; HUMAN; HUMAN CELL; KIDNEY CELL; KIDNEY NECROSIS; KIDNEY PROXIMAL TUBULE; NEPHROTOXICITY; PATHOGENESIS; PRIORITY JOURNAL; PROTEIN EXPRESSION; TOXICOKINETICS;

CELL LINE; CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; EPITHELIAL CELLS; FURALDEHYDE; HUMANS; KIDNEY; KIDNEY TUBULES, PROXIMAL; MALE; ORGANIC ANION TRANSPORT PROTEIN 1; ORGANIC ANION TRANSPORTERS, SODIUM-INDEPENDENT;

EID: 67349206640     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2009.04.017     Document Type: Article

References (27)

1. Mauron J. The Maillard reaction in food; a critical review from the nutritional standpoint. Prog Food Nutr Sci 5 (1981) 5-35
2. Antal Jr. M.J., Mok W.S., and Richards G.N. Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from d-fructose and sucrose. Carbohydr Res 199 (1990) 91-109
3. Bachmann S., Meier M., and Känzig A. 5-Hydroxymethyl-2-furfural (HMF) in Lebensmitteln. Lebensmittelchemie 51 (1997) 49-50
4. Murkovic M., and Pichler N. Analysis of 5-hydroxymethylfurfual in coffee, dried fruits and urine. Mol Nutr Food Res 50 (2006) 842-846
5. Husøy T., Haugen M., Murkovic M., Jöbstl D., Stølen L.H., Bjellaas T., et al. Dietary exposure to 5-hydroxymethylfurfural from Norwegian food and correlations with urine metabolites of short-term exposure. Food Chem Toxicol 46 (2008) 3697-3702
6. Ulbricht R.J., Northup S.J., and Thomas J.A. A review of 5-hydroxymethylfurfural (HMF) in parenteral solutions. Fundam Appl Toxicol 4 (1984) 843-853
7. Janzowski C., Glaab V., Samimi E., Schlatter J., and Eisenbrand G. 5-Hydroxymethylfurfural: assessment of mutagenicity. DNA-damaging potential and reactivity towards cellular glutathione. Food Chem Toxicol 38 (2000) 801-809
8. Glatt H.R., and Sommer Y. Health risks by 5-hydroxymethylfurfural (HMF) and related compounds. In: Skog K., and Alexander J. (Eds). Acrylamide and other health hazardous compounds in heat-treated foods (2006), Woodhead Publishing, Cambridge 328-357
9. Zhang X.M., Chan C.C., Stamp D., Minkin S., Archer M.C., and Bruce W.R. Initiation and promotion of colonic aberrant crypt foci in rats by 5-hydroxymethyl-2-furaldehyde in thermolyzed sucrose. Carcinogenesis 14 (1993) 773-775
10. Surh Y.J., Liem A., Miller J.A., and Tannenbaum S.R. 5-Sulfooxymethylfurfural as a possible ultimate mutagenic and carcinogenic metabolite of the Maillard reaction product, 5-hydroxymethylfurfural. Carcinogenesis 15 (1994) 2375-2377
11. 1 mice (gavage studies). Natl Toxicol Program Tech Report Series 2008 (draft available at http://ntp.niehs.nih.gov/).
12. Surh Y.J., and Tannenbaum S.R. Activation of the Maillard reaction product 5-(hydroxymethyl)furfural to strong mutagens via allylic sulfonation and chlorination. Chem Res Toxicol 7 (1994) 313-318
13. Russel F.G., Masereeuw R., and van Aubel R.A. Molecular aspects of renal anionic drug transport. Annu Rev Physiol 64 (2002) 563-594
14. Burckhardt B.C., and Burckhardt G. Transport of organic anions across the basolateral membrane of proximal tubule cells. Rev Physiol Biochem Pharmacol 146 (2003) 95-158
15. Robertson E.E., and Rankin G.O. Human renal organic anion transporters: characteristics and contributions to drug and drug metabolite excretion. Pharmacol Ther 109 (2006) 399-412
16. Sweet D.H. Organic anion transporter (Slc22a) family members as mediators of toxicity. Toxicol Appl Pharmacol 204 (2005) 198-215
17. Bakhiya N., Stephani M., Bahn A., Ugele B., Seidel A., Burckhardt G., et al. Uptake of chemically reactive, DNA-damaging sulfuric acid esters into renal cells by human organic anion transporters. J Am Soc Nephrol 17 (2006) 1414-1421
18. Dixon M. The determination of enzyme inhibitor constants. Biochem J 55 (1953) 170-171
19. Jellum E., Borresen H.C., and Eldjarn L. The presence of furan derivatives in patients receiving fructose-containing solutions intravenously. Clin Chim Acta 47 (1973) 191-201
20. 14C]-5-hydroxymethyl-2-furaldehyde administered orally or intravenously to rats. J Toxicol Environ Health 22 (1987) 79-89
21. Godfrey V.B., Chen L.J., Griffin R.J., Lebetkin E.H., and Burka L.T. Distribution and metabolism of (5-hydroxymethyl)furfural in male F344 rats and B6C3F1 mice after oral administration. J Toxicol Environ Health A 57 (1999) 199-210
22. Monien BH, Frank H, Seidel A, Glatt HR. Convertion of the common food constituent 5-hydroxymethylfurfural into a mutagenic and carcinogenic sulfuric acid ester in the mouse in vivo. Chem Res Toxicol. 2009 Apr 22. [Epub ahead of print].
23. Glatt H.R. Sulphotransferases. In: Ioannides C. (Ed). Handbook of enzyme systems that metabolise drugs and other xenobiotics (2002), John Wiley & Sons, Sussex 353-439
24. Teubner W., Meinl W., Florian S., Kretzschmar M., and Glatt H. Identification and localization of soluble sulfotransferases in the human gastrointestinal tract. Biochem J 404 (2007) 207-215
25. 1 mice (inhalation studies). Natl Toxicol Program Tech Report Series 1999:1-248.
26. Glatt H.R., Meinl W., Kuhlow A., and Ma L. Metabolic formation, distribution and toxicological effects of reactive sulphuric acid esters. Nova Acta Leopoldina 329 (2003) 151-161
27. Martel C.L., and Lara P.N. Renal cell carcinoma: current status and future directions. Crit Rev Oncol Hematol 45 (2003) 177-190