Characterization of the inhibitory effects of N-butylpyridinium chloride and structurally related ionic liquids on organic cation transporters 1/2 and human toxic extrusion transporters 1/2-K in vitro and in vivo

Drug Metabolism and Disposition

Volumn 39, Issue 9, 2011, Pages 1755-1761

  Cheng, Yaofeng ^a   Martinez Guerrero, Lucy J ^a   Wright, Stephen H ^a   Kuester, Robert K ^a   Hooth, Michelle J ^b   Sipes, I Glenn ^a  

^a UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

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

Author keywords

[No Author keywords available]

Indexed keywords

1 BUTYLPYRIDINIUM CHLORIDE; 1 METHYL 3 BUTYLIMIDAZOLIUM CHORIDE; CARRIER PROTEIN; IONIC LIQUID; METFORMIN; MULTIDRUG AND TOXIC EXTRUSION TRANSPORTER 1; MULTIDRUG AND TOXIC EXTRUSION TRANSPORTER 2; N BUTYL N METHYLPYRROLIDINIUM CHLORIDE; ORGANIC CATION TRANSPORTER 1; ORGANIC CATION TRANSPORTER 2; TETRYLAMMONIUM; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CHEMICAL STRUCTURE; CHO CELL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG HALF LIFE; DRUG METABOLISM; DRUG TISSUE LEVEL; DRUG TRANSPORT; IC 50; IN VITRO STUDY; IN VIVO STUDY; INHIBITION KINETICS; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; TOXICOKINETICS;

ANIMALS; CATECHOLAMINE PLASMA MEMBRANE TRANSPORT PROTEINS; CHO CELLS; CRICETINAE; CRICETULUS; HUMANS; IONIC LIQUIDS; MALE; METFORMIN; ORGANIC CATION TRANSPORT PROTEINS; PYRIDINIUM COMPOUNDS; RATS; RATS, INBRED F344;

CRICETULUS GRISEUS; RATTUS;

EID: 80051974537     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.110.035865     Document Type: Article

References (42)

1. Baker G.A., Baker S.N., Pandey S, and Bright F.V. (2005) An analytical view of ionic liquids. Analyst 130:800-808. (Pubitemid 40880099)
2. Bednarczyk D., Ekins S., Wikel JH, and Wright S.H. (2003) Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol 63:489-498. (Pubitemid 36297318)
3. Cheng Y., Wright S.H., Hooth MJ, and Sipes I.G. (2009) Characterization of the disposition and toxicokinetics of N-butylpyridinium chloride in male F-344 rats and female B6C3F1 mice and its transport by organic cation transporter 2. Drug Metab Dispos 37:909-916.
4. Cho C.W., Pham T.P., Jeon Y.C., Vijayaraghavan K., Choe WS, and Yun Y.S. (2007) Toxicity of imidazolium salt with anion bromide to a phytoplankton Selenastrum capricornutum: effect of alkyl- Chain length. Chemosphere 69:1003-1007. (Pubitemid 47410266)
5. Choi M.K., Jin Q.R., Jin H.E., Shim C.K., Cho D.Y., Shin JG, and Song I.S. (2007) Effects of tetraalkylammonium compounds with different affinities for organic cation transporters on the pharmacokinetics of metformin. Biopharm Drug Dispos 28:501-510.
6. Choi MK and Song I.S. (2008) Organic cation transporters and their pharmacokinetic and pharmacodynamic consequences. Drug Metab Pharmacokinet 23:243-253.
7. Choi Y.H., Lee U., Lee BK, and Lee M.G. (2010) Pharmacokinetic interaction between itraconazole and metformin in rats: Competitive inhibition of metabolism of each drug by each other via hepatic and intestinal CYP3A1/2. Br J Pharmacol 161:815-829.
8. Couling D.J., Bernot R.J., Docherty K.M., Dixon JK, and Maginn E.J. (2005) Assessing the factors responsible for ionic liquid toxicity to aquatic organism via quantitative structure- Property relationship modeling. Green Chem 8:82-90. (Pubitemid 43485029)
9. Dresser M.J., Xiao G., Leabman M.K., Gray AT, and Giacomini K.M. (2002) Interactions of n- Tetraalkylammonium compounds and biguanides with a human renal organic cation transporter (hOCT2). Pharm Res 19:1244-1247. (Pubitemid 34985011)
10. Groves C.E., Evans K.K., Dantzler WH, and Wright S.H. (1994) Peritubular organic cation transport in isolated rabbit proximal tubules. Am J Physiol 266:F450-F458.
11. Jonker J.W., Wagenaar E., Van Eijl S, and Schinkel A.H. (2003) Deficiency in the organic cation transporters 1 and 2 (Oct1/Oct2 [Slc22a1/Slc22a2]) in mice abolishes renal secretion of organic cations. Mol Cell Biol 23:7902-7908. (Pubitemid 37271485)
12. Knudsen G.A., Cheng Y., Kuester R.K., Hooth MJ, and Sipes I.G. (2009) Effects of dose and route on the disposition and kinetics of 1-butyl-1-methylpyrrolidinium chloride in male F-344 rats. Drug Metab Dispos 37:2171-2177.
13. Koepsell H., Lips K, and Volk C. (2007) Polyspecific organic cation transporters: Structure, function, physiological roles, and biopharmaceutical implications. Pharm Res 24:1227-1251. (Pubitemid 46876495)
14. Latała A., Stepnowski P., Nedzi M, and Mrozik W. (2005) Marine toxicity assessment of imidazolium ionic liquids: Acute effects on the Baltic algae Oocystis submarina and Cyclotella meneghiniana. Aquat Toxicol 73:91-98. (Pubitemid 40693929)
15. +-D-glucose cotransport in human intestinal brush-border membrane vesicles using a fast sampling, rapid filtration apparatus. J Membr Biol 122:127-141.
16. Matsumoto M., Mochiduki K, and Kondo K. (2004) Toxicity of ionic liquids and organic solvents to lactic acid- Producing bacteria. J Biosci Bioeng 98:344-347. (Pubitemid 40013199)
17. Matsuzaki T., Morisaki T., Sugimoto W., Yokoo K., Sato D., Nonoguchi H., Tomita K., Terada T., Inui K., Hamada A., et al. (2008) Altered pharmacokinetics of cationic drugs caused by down- Regulation of renal rat organic cation transporter 2 (Slc22a2) and rat multidrug and toxin extrusion 1 (Slc47a1) in ischemia/reperfusion- Regulation of renal rat organic cation transporter 2 (Slc22a2) and rat multidrug and toxin extrusion 1 (Slc47a1) in ischemia/reperfusionInduced acute kidney injury. Drug Metab Dispos 36:649-654. (Pubitemid 351468369)
18. Motohashi H., Sakurai Y., Saito H., Masuda S., Urakami Y., Goto M., Fukatsu A., Ogawa O, and Inui K. (2002) Gene expression levels and immunolocalization of organic ion transporters in the human kidney. J Am Soc Nephrol 13:866-874. (Pubitemid 34274082)
19. Nies A.T., Koepsell H., Damme K, and Schwab M. (2011) Organic cation transporters (OCTs, MATEs), in vitro and in vivo evidence for the importance in drug therapy. Handb Exp Pharmacol 201:105-167.
20. Okuda M., Saito H., Urakami Y., Takano M, and Inui K. (1996) cDNA cloning and functional expression of a novel rat kidney organic cation transporter, OCT2. Biochem Biophys Res Commun 224:500-507. (Pubitemid 26268216)
21. Pinto P.C., Saraiva ML, and Lima J.L. (2008) Oxidoreductase behavior in ionic liquids: A review. Anal Sci 24:1231-1238.
22. Plechkova NV and Seddon K.R. (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123-150.
23. Pretti C., Chiappe C., Baldetti I., Brunini S., Monni G, and Intorre L. (2009) Acute toxicity of ionic liquids for three freshwater organisms: Pseudokirchneriella subcapitata, Daphnia magna and Danio rerio. Ecotoxicol Environ Saf 72:1170-1176.
24. Ranke J., Mölter K., Stock F., Bottin-Weber U., Poczobutt J., Hoffmann J., Ondruschka B., Filser J, and Jastorff B. (2004) Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST- 1 cell viability assays. Ecotoxicol Environ Saf 58:396-404. (Pubitemid 38833689)
25. Ranke J., Müller A., Bottin-Weber U., Stock F., Stolte S., Arning J., Störmann R, and Jastorff B. (2007) Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity. Ecotoxicol Environ Saf 67:430-438. (Pubitemid 46836730)
26. Rogers RD and Seddon K.R. (2003) Chemistry ionic liquids - Solvents for the future? Science 302:792-793. (Pubitemid 37339605)
27. RowlandMand Tozer NH (1995) Clinical Pharmacokinetics, Concepts and Applications, 3rd ed. Lippincott Williams & Wilkins, Philadelphia.
28. Schäli C., Schild L., Overney J, and Roch-Ramel F. (1983) Secretion of tetraethylammonium by proximal tubules of rabbit kidneys. Am J Physiol 245:F238-F246. (Pubitemid 13031341)
29. Scheen A.J. (1996) Clinical pharmacokinetics of metformin. Clin Pharmacokinet 30:359-371.
30. Sipes I.G., Knudsen GA, and Kuester R.K. (2008) The effects of dose and route on the toxicokinetics and disposition of 1-butyl-3- Butyl3Methylimidazolium chloride in male F- Butyl3Methylimidazolium chloride in male F344 rats and female B6C3F1 mice. Drug Metab Dispos 36:284-293. (Pubitemid 351185740)
31. Stasiewicz M., Mulkiewicz E., Tomczak-Wandzel R., Kumirska J., Siedlecka E.M., Gołebiowski M., Gajdus J., Czerwicka M, and Stepnowski P. (2008) Assessing toxicity and biodegradation of novel, environmentally benign ionic liquids (1-alkoxymethyl-3-hydroxypyridinium chloride, saccharinate and acesulfamates) on cellular and molecular level. Ecotoxicol Environ Saf 71:157-165.
32. Stock F., Hoffmann J., Ranke J., Stormann R., Ondruschka B, and Jastorff B. (2004) Effects of ionic liquids on the acetylcholinesterase - A structure- A structureActivity relationship consideration. Green Chem 6:286-290. (Pubitemid 38962185)
33. Suhre W.M., Ekins S., Chang C., Swaan PW, and Wright S.H. (2005) Molecular determinants of substrate/inhibitor binding to the human and rabbit renal organic cation transporters hOCT2 and rbOCT2. Mol Pharmacol 67:1067-1077. (Pubitemid 40410407)
34. Tanihara Y., Masuda S., Sato T., Katsura T., Ogawa O, and Inui K. (2007) Substrate specificity of MATE1 and MATE2- K, human multidrug and toxin extrusions/H+-organic cation antiporters. Biochem Pharmacol 74:359-371. (Pubitemid 46890818)
35. +/organic cation antiporter MATE1. Pharm Res 23:1696-1701.
36. Tsuda M., Terada T., Mizuno T., Katsura T., Shimakura J, and Inui K. (2009) Targeted disruption of the multidrug and toxin extrusion 1 (mate1) gene in mice reduces renal secretion of metformin. Mol Pharmacol 75:1280-1286.
37. Ullrich K.J. (1997) Renal transporters for organic anions and organic cations. Structural requirements for substrates. J Membr Biol 158:95-107.
38. Walker L.A., Gellai M, and Valtin H. (1986) Renal response to pentobarbital anesthesia in rats: effect of interrupting the renin- Angiotensin system. J Pharmacol Exp Ther 236:721-728. (Pubitemid 16080071)
39. Welton T. (1999) Room-temperature ionic liquids. Solvent for synthesis and catalysis. Chem Rev 99:2017-2084.
40. Yang Z., Yue Y.J., Huang W.C., Zhuang X.M., Chen ZT, and Xing M. (2009) Importance of the ionic nature of ionic liquids in affecting enzyme performance. J Biochem 145:355-364.
41. Yu M., Wang S.H., Luo Y.R., Han Y.W., Li X.Y., Zhang BJ, and Wang J.J. (2009) Effects of the 1-alkyl-3-methylimidazolium bromide ionic liquids on the antioxidant defense system of Daphnia magna. Ecotoxicol Environ Saf 72:1798-1804.
42. Zhao D., Liao Y, and Zhang Z. (2007) Toxicity of ionic liquids. Clean Soil Air Water 35:42-48. (Pubitemid 46578530)