In vivo relevance of Mrp2-mediated biliary excretion of the Amanita mushroom toxin demethylphalloin

Biochimica et Biophysica Acta - Biomembranes

Volumn 1768, Issue 9, 2007, Pages 2070-2077

  Gavrilova, Olga ^a   Geyer, Joachim ^a   Petzinger, Ernst ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

MULTIDRUG RESISTANCE PROTEIN 2; PHALLOIDIN; PHTHALIC ACID DIMETHYL ESTER; TOXIN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BILIARY EXCRETION; CANNULATION; CHOLESTASIS; CONTROLLED STUDY; GALLBLADDER; IN VIVO STUDY; KNOCKOUT MOUSE; LIVER CELL; MALE; MOUSE; MUSHROOM; NONHUMAN; PRIORITY JOURNAL; RAT; TRANSGENIC MOUSE; WILD TYPE;

ALKALOIDS; AMANITA; ANIMALS; BILE; LIVER; MALE; MICE; MICE, KNOCKOUT; MICROFILAMENT PROTEINS; RATS; RATS, WISTAR;

AMANITA; ANIMALIA; BASIDIOMYCOTA; MUS; MUS MUSCULUS; RATTUS; RATTUS NORVEGICUS;

EID: 34548489866     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2007.07.006     Document Type: Article

References (47)

1. Wieland T., and Wieland O. Chemistry and toxicology of the toxins of Amanita phalloides. Pharmacol. Rev. 11 (1959) 87-107
2. Petzinger E., and Frimmer M. Energy linked uptake of demethylphalloin by isolated rat liver cells. Naunyn-Schmiedeberg's Arch. Pharmacol. 319 (1982) 87-92
3. Petzinger E., and Frimmer M. Driving forces in hepatocellular uptake of phalloidin and cholate. Biochim. Biophys. Acta 778 (1984) 539-548
4. Münter K., Mayer D., and Faulstich H. Characterization of a transporting system in rat hepatocytes. Studies with competitive and non-competitive inhibitors of phalloidin transport. Biochim. Biophys. Acta 860 (1986) 91-98
5. Lengsfeld A.M., Low I., Wieland T., Dancker P., and Hasselbach W. Interaction of phalloidin with actin. Proc. Natl. Acad. Sci. U. S. A. 71 (1974) 2803-2807
6. Gabbiani G., Montesano R., Tuchweber B., Salas M., and Orci L. Phalloidin-induced hyperplasia of actin filaments in rat hepatocytes. Lab. Invest. 33 (1975) 562-569
7. Wieland T. Modification of actins by phallotoxins. Naturwissenschaften 64 (1977) 303-309
8. Jahn W., Faulstich H., Deboben A., and Wieland T. Formation of actin clusters in rat liver parenchymal cells on phalloidin poisoning as visualized by a fluorescent phallotoxin. Z. Naturforsch. 35 (1980) 467-469
9. Faulstich H., Münter K., and Mayer D. Phallodin action. In: Keppler D., Popper H., Bianchi L., and Reutter W. (Eds). Mechanisms of Hepatocyte Injury and Death (1984), MTP-Press, Lancaster 183-192
10. Frimmer M., Petzinger E., Rufeger U., and Veil L.B. The role of bile acids in phalloidin poisoning. Naunyn-Schmiedeberg's Arch. Pharmacol. 301 (1977) 145-147
11. Petzinger E. Competitive inhibition of the uptake of demethylphalloin by cholic acid in isolated hepatocytes. Evidence for a transport competition rather than a binding competition. Naunyn-Schmiedeberg's Arch. Pharmacol. 316 (1981) 345-349
12. 3H-demethylphalloin uptake in isolated rat hepatocytes under various experimental conditions. Naunyn-Schmiedeberg's Arch. Pharmacol. 307 (1979) 275-281
13. 14C-cholate. Naunyn-Schmiedeberg's Arch. Pharmacol. 313 (1980) 85-89
14. Petzinger E., Ziegler K., and Frimmer M. Occurrence of a multispecific transporter for the hepatocellular accumulation of bile acids and various cyclopeptides. In: Paumgartner G., Stiehl A., and Gerok W. (Eds). Bile acids and the Liver (1987), MTP-Press, Lancaster 111-124
15. Frimmer M., and Ziegler K. The transport of bile acids in liver cells. Biochim. Biophys. Acta 947 (1988) 75-99
16. Hagenbuch B., and Meier P.J. The superfamily of organic anion transporting polypeptides. Biochim. Biophys. Acta 1609 (2003) 1-18
17. Cattori V., van Montfoort J.E., Stieger B., Landmann L., Meijer D.K., Winterhalter K.H., Meier P.J., and Hagenbuch B. Localization of organic anion transporting polypeptide 4 (Oatp4) in rat liver and comparison of its substrate specificity with Oatp1, Oatp2 and Oatp3. Pflügers Arch. 443 (2001) 188-195
18. König J., Cui Y., Nies A.T., and Keppler D. A novel human organic anion transporting polypeptide localized to the basolateral hepatocyte membrane. Am. J. Physiol.: Gasterointest. Liver Physiol. 278 (2000) G156-G164
19. König J., Cui Y., Nies A.T., and Keppler D. Localization and genomic organization of a new hepatocellular organic anion transporting polypeptide. J. Biol. Chem. 275 (2000) 23161-23168
20. Fehrenbach T., Cui Y., and H.Faulstich D. Characterization of the transport of the bicyclic peptide phalloidin by human hepatic transport proteins. Naunyn-Schmiedeberg's Arch. Pharmacol. 368 (2003) 415-420
21. Meier-Abt F., Faulstich H., and Hagenbuch B. Identification of phalloidin uptake systems of rat and human liver. Biochim. Biophys. Acta 1664 (2004) 64-69
22. 3H-desmethylphalloin. Liebigs Ann. Chem. 725 (1969) 238-240
23. Puchinger H., and Wieland T. Search for some metabolites from poisoning by desmethylphalloin (DMP). Eur. J. Biochem. 11 (1969) 1-6
24. Barriault C., Petit J.L., Gascon-Barre M., Huet P.M., Yousef I.M., and Tuchweber B. Effect of phalloidin on cholestasis, hemodynamics, and microcirculation in isolated perfused rat liver. Hepatology 23 (1996) 294-302
25. Loranger A., Barriault C., Yousef I.M., and Tuchweber B. Structural and functional alterations of hepatocytes during transient phalloidin-induced cholestasis in the rat. Toxicol. Appl. Pharmacol. 137 (1996) 100-111
26. Paulusma C.C., van Geer M.A., Evers R., Heijn M., Ottenhoff R., Borst P., and Oude Elferink R.P. Canalicular multispecific organic anion transporter/multidrug resistance protein 2 mediates low-affinity transport of reduced glutathione. Biochem. J. 338 (1999) 393-401
27. Lischka K., Starke D., Failing K., Herling A., Kramer W., and Petzinger E. Hepatobiliary elimination of bile acid-modified oligodeoxynucleotides in Wistar and TR- rats: evidence for mrp2 as carrier for oligodeoxynucleotides. Biochem. Pharmacol. 66 (2003) 565-577
28. Dubin M., Maurice M., Feldmann G., and Erlinger S. Phalloidin-induced cholestasis in the rat: relation to changes in microfilaments. Gastroenterology 75 (1978) 450-455
29. Cooper J.A. Effects of cytochalasin and phalloidin on actin. J. Cell Biol. 105 (1987) 1473-1478
30. Rost D., Kartenbeck J., and Keppler D. Changes in the localization of the rat canalicular conjugate export pump Mrp2 in phalloidin-induced cholestasis. Hepatology 29 (1999) 814-821
31. Ohashi M., Sano N., and Takikawa H. Effects of phalloidin on the biliary excretion of cholephilic compounds in rats. Pharmacology 66 (2002) 31-35
32. Wieland T. Amatoxins and phallotoxins - Structure and toxicity. In: Voelter V., and Weitzel G. (Eds). Structure and Activity of Natural Peptides (1981), Walter de Gruyter Publisher, Berlin, New York 23-40
33. Lorenzini I., Sakisaka S., Meier P.J., and Boyer J.L. Demonstration of a transcellular vesicle pathway for biliary excretion of inulin in rat liver. Gastroenterology 91 (1986) 1278-1299
34. Johnson B.M., Zhang P., Schuetz J.D., and Brower K.L. Characterization of transport protein expression in multidrug resistance-associated protein (mrp) 2-deficient rats. Drug Metab. Dispos. 34 (2006) 556-562
35. Hooiveld G.J., van Montfoort J.E., Meijer D.K., and Müller M. Function and regulation of ATP-binding cassette transport proteins involved in hepatobiliary transport. Eur. J. Pharm. Sci. 12 (2001) 525-543
36. Chandra P., and Brouwer K.L. The complexities of hepatic drug transport: current knowledge and emerging concepts. Pharm. Res. 21 (2004) 719-735
37. Haimeur A., Conseil G., Deeley R.G., and Cole S.P. The MRP-related and BCRP/ABCG2 multidrug resistance proteins: biology, substrate specificity and regulation. Curr. Drug Metab. 5 (2004) 21-53
38. Shitara Y., Sato H., and Sugiyama Y. Evaluation of drug-drug interaction in the hepatobiliary and renal transport of drugs. Annu. Rev. Pharmacol. Toxicol. 45 (2005) 689-723
39. Petzinger E., and Geyer J. Drug transporters in pharmacokinetics. Naunyn-Schmiedeberg's Arch. Pharmacol. 372 (2006) 465-475
40. Rehbinder D., G.Loeffler O., and Wieland T. Studies on the mechanism of the poisonous effect of phalloidin with poisons labelled with radioactive substances. Hoppe Seylers Z.Physiol.Chem. 331 (1963) 132-142
41. Fürlinger E., and Wolfbeis O.S. The absorption, fluorescence and phosphorescence of phalloidin and α-amanitin. Biochim. Biophys. Acta 760 (1983) 411-414
42. Shin H.C., Kato Y., Yamada T., Niinuma K., Hisaka A., and Sugiyama Y. Hepatobiliary transport mechanism for the cyclopentapeptide endothelin antagonist BQ-123. Am. J. Physiol. 272 (1997) G979-G986
43. Letschert K., Komatsu M., Humel-Eisenbeis J., and Keppler D. Vectorial transport of the peptide CCK-8 by double transfected MDCKII cells stably expressing the organic anion transporter OATP1B3 (OATP8) and the export pump ABCC2. J. Pharmacol. Exp. Ther. 313 (2005) 549-556
44. Kopplow K., Letschert K., König J., Walter B., and Keppler D. Human hepatobiliary transport of organic anions analyzed by quadruple-transfected cells. Mol. Pharmacol. 68 (2005) 1031-1038
45. Kivistö K.T., Grisk O., Hofmann U., Meissner K., Möritz K.U., Ritter C., Arnold K.A., Lütjohann D., von Bergmann K., Klöting I., Eichelbaum M., and Kroemer H.K. Disposition of oral and intravenous pravastatin in MRP2-deficient TR- rats. Drug Metab. Dispos. 33 (2005) 1593-1596
46. Kim M.S., Liu D.Q., Strauss J.R., Capodanno I., Yao Z., Fenyk-Melody J.E., Franklin R.B., and Vincent S.H. Metabolism and disposition of gemfibrozil in Wistar and multidrug resistance-associated protein 2-deficient TR- rats. Xenobiotica 33 (2003) 1027-1042
47. Zamek-Gliszczynski M.J., Xiong H., Patel N.J., Turncliff R.Z., Pollack G.M., and Brouwer K.L. Pharmacokinetics of 5 (and 6)-carboxy-2′,7′-dichlorofluorescein and its diacetate promoiety in the liver. J. Pharmacol. Exp. Ther. 304 (2003) 801-809