Prediction of drug-induced intrahepatic cholestasis: in vitro screening and QSAR analysis ofdrugs inhibiting the human bile salt export pump

Bibliography

• SERVICE RF: Surviving the blockbuster syndrome. Science (2004) 303(5665):1796-1799.
   PubMed Web of Science ®Google Scholar
• SZUROMI P, VINSON V, MARSHALL E: Rethinking drug discovery. Science (2004) 303:1795.
   Web of Science ®Google Scholar
• MERVIS J: Productivity counts – but the definition is key. Science (2005) 309(5735):726.
   Google Scholar
• ISHIKAWA T, YOSHIKAWA M: ABC transporters: a new approach to toxicogenomics. Inoue T, Pennie WD (Eds), Springer, Tokyo (2003):109-114.
   Google Scholar
• ISHIKAWA T, IKEGAMI Y, SANO K, NAKAGAWA H, SAWADA S: Transport mechanism-based drug molecular design: novel camptothecin analogues to circumvent ABCG2-associated drug resistance of human tumor cells. Curr. Pharm. Des. (2006) 12(3):313-325.
   PubMed Web of Science ®Google Scholar
• ISHIKAWA T: The ATP-dependent glutathione S-conjugate export pump. Trends Biochem. Sci. (1992) 17(11):463-468.
   PubMed Web of Science ®Google Scholar
• NATHANSON MH, BOYER JL: Mechanisms and regulation of bile secretion. Hepatology (1991) 14(3):551-566.
   PubMed Web of Science ®Google Scholar
• TRAUNER M, BOYER JL: Bile salt transporters: molecular characterization, function, and regulation. Physiol. Rev. (2003) 83(2):633-671.
   PubMed Web of Science ®Google Scholar
• KULLAK-UBLICK GA, STIEGER B, MEIER PJ: Enterohepatic bile salt transporters in normal physiology and liver disease. Gastroenterology (2004) 126(1):322-342.
   PubMed Web of Science ®Google Scholar
• CAREY MC, SMALL DM: The physical chemistry of cholesterol solubility in bile. Relationship to gallstone formation and dissolution in man. J. Clin. Invest. (1978) 61(4):998-1026.
   PubMed Web of Science ®Google Scholar
• HIGUCHI H, GORES GJ: Bile acid regulation of hepatic physiology: IV. Bile acids and death receptors. Am. J. Physiol. Gastrointest. Liver Physiol. (2003) 284(5):G734-G738.
   PubMed Web of Science ®Google Scholar
• ISHIKAWA T: Multidrug Resistance: Genetics of ABC Transporters. In: Nature Encyclopedia of the Human Genome. Cooper DN (Ed.), Nature Publishing Group, London, UK (2003):154-160.
   Google Scholar
• MEIER PJ, STIEGER B: Bile salt transporters. Ann. Rev. Physiol. (2002) 64:635-661.
   PubMed Web of Science ®Google Scholar
• KULLAK-UBLICK GA, STIEGER B, HAGENBUCH B, MEIER PJ: Hepatic transport of bile salts. Semin. Liver Dis. (2000) 20(3):273-292.
   PubMed Web of Science ®Google Scholar
• HOFMANN AF: Bile acids: the good, the bad, and the ugly. News Physiol. Sci. (1999) 14:24-29.
   PubMedGoogle Scholar
• WANG W, XUE S, INGLES SA et al.: An association between genetic polymorphisms in the ileal sodium-dependent bile acid transporter gene and the risk of colorectal adenomas. Cancer Epidemiol. Biomarkers Prev. (2001) 10(9):931-936.
   PubMed Web of Science ®Google Scholar
• KRAMER W, GIRBIG F, GLOMBIK H et al.: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J. Biol. Chem. (2001) 276(38):36020-36027.
   PubMed Web of Science ®Google Scholar
• CRADDOCK AL, LOVE MW, DANIEL RW et al.: Expression and transport properties of the human ileal and renal sodium-dependent bile acid transporter. Am. J. Physiol. (1998) 274(1 Pt 1):G157-G169.
   PubMed Web of Science ®Google Scholar
• DAWSON PA, HUBBERT M, HAYWOOD J et al.: The heteromeric organic solute transporter alpha–beta, Ostalpha–Ostbeta, is an ileal basolateral bile acid transporter. J. Biol. Chem. (2005) 280(8):6960-6968.
   PubMed Web of Science ®Google Scholar
• WOLKOFF AW, COHEN DE: Bile acid regulation of hepatic physiology: I. Hepatocyte transport of bile acids. Am. J. Physiol. Gastrointest. Liver Physiol. (2003) 284(2):G175-G179.
   PubMed Web of Science ®Google Scholar
• HAGENBUCH B, MEIER PJ: Molecular cloning, chromosomal localization, and functional characterization of a human liver Na+/bile acid cotransporter. J. Clin. Invest. (1994) 93(3):1326-1331.
   PubMed Web of Science ®Google Scholar
• KONIG J, CUI Y, NIES AT, KEPPLER D: A novel human organic anion transporting polypeptide localized to the basolateral hepatocyte membrane. Am. J. Physiol. Gastrointest. Liver Physiol. (2000) 278(1):G156-G164.
   PubMed Web of Science ®Google Scholar
• HSIANG B, ZHU Y, WANG Z et al.: A novel human hepatic organic anion transporting polypeptide (OATP2). Identification of a liver-specific human organic anion transporting polypeptide and identification of rat and human hydroxymethylglutaryl-CoA reductase inhibitor transporters. J. Biol. Chem. (1999) 274(52):37161-37168.
   PubMed Web of Science ®Google Scholar
• ABE T, KAKYO M, TOKUI T et al.: Identification of a novel gene family encoding human liver-specific organic anion transporter LST-1. J. Biol. Chem. (1999) 274(24):17159-17163.
   PubMed Web of Science ®Google Scholar
• CUI Y, KONIG J, LEIER I, BUCHHOLZ U, KEPPLER D: Hepatic uptake of bilirubin and its conjugates by the human organic anion transporter SLC21A6. J. Biol. Chem. (2001) 276(13):9626-9630.
   PubMed Web of Science ®Google Scholar
• KULLAK-UBLICK GA, ISMAIR MG, STIEGER B et al.: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology (2001) 120(2):525-533.
   PubMed Web of Science ®Google Scholar
• FAUBION WA, GUICCIARDI ME, MIYOSHI H et al.: Toxic bile salts induce rodent hepatocyte apoptosis via direct activation of Fas. J. Clin. Invest. (1999) 103(1):137-145.
   PubMed Web of Science ®Google Scholar
• NAKATA K, TANAKA Y, NAKANO T et al.: Nuclear receptor-mediated xenobiotic procession loops in phase I, II, and III xenobiotic metabolizing systems. Drug Metab. Pharmacokinet. (2006) 21:437-457.
   PubMed Web of Science ®Google Scholar
• SUCHY FJ, ANANTHANARAYANAN M: Bile salt excretory pump: biology and pathobiology. J. Pediatr. Gastroenterol. Nutr. (2006) 43(1 Suppl.):S10-S16.
   PubMed Web of Science ®Google Scholar
• CHIANG JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am. J. Physiol. Gastrointest. Liver Physiol. (2003) 284(3):G349-G356.
   PubMed Web of Science ®Google Scholar
• CHILDS S, YEH RL, GEORGES E, LING V: Identification of a sister gene to P-glycoprotein. Cancer Res. (1995) 55(10):2029-2034.
   PubMed Web of Science ®Google Scholar
• GERLOFF T, STIEGER B, HAGENBUCH B et al.: The sister of P-glycoprotein represents the canalicular bile salt export pump of mammalian liver. J. Biol. Chem. (1998) 273(16):10046-10050.
   PubMed Web of Science ®Google Scholar
• WANG R, SALEM M, YOUSEF IM et al.: Targeted inactivation of sister of P-glycoprotein gene (spgp) in mice results in nonprogressive but persistent intrahepatic cholestasis. Proc. Natl. Acad. Sci. USA (2001) 98(4):2011-2016.
   PubMed Web of Science ®Google Scholar
• BORST P, ELFERINK RO: Mammalian ABC transporters in health and disease. Ann. Rev. Biochem. (2002) 71:537-592.
   PubMed Web of Science ®Google Scholar
• STRAUTNIEKS SS, BULL LN, KNISELY AS et al.: A gene encoding a liver-specific ABC transporter is mutated in progressive familial intrahepatic cholestasis. Nat. Genet. (1998) 20(3):233-238.
   PubMed Web of Science ®Google Scholar
• ARRESE M, ANANTHANARAYANAN M: The bile salt export pump: molecular properties, function and regulation. Pflugers Arch. (2004) 449(2):123-131.
   PubMed Web of Science ®Google Scholar
• NOE J, STIEGER B, MEIER PJ: Functional expression of the canalicular bile salt export pump of human liver. Gastroenterology (2002) 123(5):1659-1666.
   PubMed Web of Science ®Google Scholar
• WANG L, SOROKA CJ, BOYER JL: The role of bile salt export pump mutations in progressive familial intrahepatic cholestasis type II. J. Clin. Invest. (2002) 110(7):965-972.
   PubMed Web of Science ®Google Scholar
• PAULI-MAGNUS C, LANG T, MEIER Y et al.: Sequence analysis of bile salt export pump (ABCB11) and multidrug resistance P-glycoprotein 3 (ABCB4, MDR3) in patients with intrahepatic cholestasis of pregnancy. Pharmacogenetics (2004) 14(2):91-102.
   PubMedGoogle Scholar
• LAM CW, CHEUNG KM, TSUI MS et al.: A patient with novel ABCB11 gene mutations with phenotypic transition between BRIC2 and PFIC2. J. Hepatol. (2006) 44(1):240-242.
   PubMed Web of Science ®Google Scholar
• MEIER Y, PAULI-MAGNUS C, ZANGER UM et al.: Interindividual variability of canalicular ATP-binding-cassette (ABC)-transporter expression in human liver. Hepatology (2006) 44(1):62-74.
   PubMed Web of Science ®Google Scholar
• STIEGER B, MEIER Y, MEIER PJ: The bile salt export pump. Pflugers Arch. (2006) (In Press).
   PubMedGoogle Scholar
• NOE J, KULLAK-UBLICK GA, JOCHUM W et al.: Impaired expression and function of the bile salt export pump due to three novel ABCB11 mutations in intrahepatic cholestasis. J. Hepatol. (2005) 43(3):536-543.
   PubMed Web of Science ®Google Scholar
• PAULI-MAGNUS C, KERB R, FATTINGER K et al.: BSEP and MDR3 haplotype structure in healthy Caucasians, primary biliary cirrhosis and primary sclerosing cholangitis. Hepatology (2004) 39(3):779-791.
   PubMed Web of Science ®Google Scholar
• VAN MIL SW, VAN DER WOERD WL, VAN DER BRUGGE G et al.: Benign recurrent intrahepatic cholestasis type 2 is caused by mutations in ABCB11. Gastroenterology (2004) 127(2):379-384.
   PubMed Web of Science ®Google Scholar
• GOTO K, SUGIYAMA K, SUGIURA T et al.: Bile salt export pump gene mutations in two Japanese patients with progressive familial intrahepatic cholestasis. J. Pediatr. Gastroenterol. Nutr. (2003) 36(5):647-650.
   PubMed Web of Science ®Google Scholar
• JANSEN PL, STRAUTNIEKS SS, JACQUEMIN E et al.: Hepatocanalicular bile salt export pump deficiency in patients with progressive familial intrahepatic cholestasis. Gastroenterology (1999) 117(6):1370-1379.
   PubMed Web of Science ®Google Scholar
• KUBITZ R, KEITEL V, SCHEURING S, KOHRER K, HAUSSINGER D: Benign recurrent intrahepatic cholestasis associated with mutations of the bile salt export pump. J. Clin. Gastroenterol. (2006) 40(2):171-175.
   PubMed Web of Science ®Google Scholar
• SUMMERSKILL WH, WALSHE JM: Benign recurrent intrahepatic ‘obstructive’ jaundice. Lancet (1959) 2:686-690.
   PubMed Web of Science ®Google Scholar
• VALLEJO M, BRIZ O, SERRANO MA, MONTE MJ, MARIN JJ: Potential role of trans-inhibition of the bile salt export pump by progesterone metabolites in the etiopathogenesis of intrahepatic cholestasis of pregnancy. J. Hepatol. (2006) 44(6):1150-1157.
   PubMed Web of Science ®Google Scholar
• SMIT JJ, SCHINKEL AH, OUDE ELFERINK RP et al.: Homozygous disruption of the murine mdr2 P-glycoprotein gene leads to a complete absence of phospholipid from bile and to liver disease. Cell (1993) 75(3):451-462.
   PubMed Web of Science ®Google Scholar
• PAULI-MAGNUS C, MEIER PJ: Hepatobiliary transporters and drug-induced cholestasis. Hepatology (2006) 44(4):778-787.
   PubMed Web of Science ®Google Scholar
• WANG EJ, CASCIANO CN, CLEMENT RP, JOHNSON WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm. Res. (2003) 20(4):537-544.
   PubMed Web of Science ®Google Scholar
• STIEGER B, FATTINGER K, MADON J, KULLAK-UBLICK GA, MEIER PJ: Drug- and estrogen-induced cholestasis through inhibition of the hepatocellular bile salt export pump (Bsep) of rat liver. Gastroenterology (2000) 118(2):422-430.
   PubMed Web of Science ®Google Scholar
• NOE J, HAGENBUCH B, MEIER PJ, ST-PIERRE MV: Characterization of the mouse bile salt export pump overexpressed in the baculovirus system. Hepatology (2001) 33(5):1223-1231.
   PubMed Web of Science ®Google Scholar
• KOSTRUBSKY SE, STROM SC, KALGUTKAR AS et al.: Inhibition of hepatobiliary transport as a predictive method for clinical hepatotoxicity of nefazodone. Toxicol. Sci. (2006) 90(2):451-459.
   PubMed Web of Science ®Google Scholar
• HORIKAWA M, KATO Y, TYSON CA, SUGIYAMA Y: Potential cholestatic activity of various therapeutic agents assessed by bile canalicular membrane vesicles isolated from rats and humans. Drug Metab. Pharmacokinet. (2003) 18(1):16-22.
   PubMedGoogle Scholar
• FUNK C, PONELLE C, SCHEUERMANN G, PANTZE M: Cholestatic potential of troglitazone as a possible factor contributing to troglitazone-induced hepatotoxicity: in vivo and in vitro interaction at the canalicular bile salt export pump (Bsep) in the rat. Mol. Pharmacol. (2001) 59(3):627-635.
   PubMed Web of Science ®Google Scholar
• FUNK C, PANTZE M, JEHLE L et al.: Troglitazone-induced intrahepatic cholestasis by an interference with the hepatobiliary export of bile acids in male and female rats. Correlation with the gender difference in troglitazone sulfate formation and the inhibition of the canalicular bile salt export pump (Bsep) by troglitazone and troglitazone sulfate. Toxicology (2001) 167(1):83-98.
   PubMed Web of Science ®Google Scholar
• FATTINGER K, FUNK C, PANTZE M et al.: The endothelin antagonist bosentan inhibits the canalicular bile salt export pump: a potential mechanism for hepatic adverse reactions. Clin. Pharmacol. Ther. (2001) 69(4):223-231.
   PubMed Web of Science ®Google Scholar
• BYRNE JA, STRAUTNIEKS SS, MIELI-VERGANI G et al.: The human bile salt export pump: characterization of substrate specificity and identification of inhibitors. Gastroenterology (2002) 123(5):1649-1658.
   PubMed Web of Science ®Google Scholar
• HIRANO M, MAEDA K, HAYASHI H, KUSUHARA H, SUGIYAMA Y: Bile salt export pump (BSEP/ABCB11) can transport a nonbile acid substrate, pravastatin. J. Pharmacol. Exp. Ther. (2005) 314(2):876-882.
   PubMed Web of Science ®Google Scholar
• ISHIKAWA T, SAKURAI A, KANAMORI Y et al.: High-speed screening of human ATP-binding cassette transporter function and genetic polymorphisms: new strategies in pharmacogenomics. Methods Enzymol. (2005) 400:485-510.
   PubMed Web of Science ®Google Scholar
• HIRANO H, KURATA A, ONISHI Y et al.: High-speed screening and QSAR analysis of human ATP-binding cassette transporter ABCB11 (bile salt export pump) to predict drug-induced intrahepatic cholestasis. Mol. Pharm. (2006) 3(3):252-265.
   PubMed Web of Science ®Google Scholar
• ISHIKAWA T, ONISHI Y, HIRANO H et al.: Pharmacogenomics of drug transporters: a new approach to functional analysis of the genetic polymorphisms of ABCB1 (P-glycoprotein/MDR1). Biol. Pharm. Bull. (2004) 27(7):939-948.
   PubMed Web of Science ®Google Scholar
• ISHIKAWA T, HIRANO H, ONISHI Y, SAKURAI A, TARUI S: Functional evaluation of ABCB1 (P-glycoprotein) polymorphisms: high-speed screening and structure–activity relationship analyses. Drug Metab. Pharmacokinet. (2004) 19(1):1-14.
   PubMedGoogle Scholar
• HANSCH C: Quantitative structure-activity relationships and the unnamed science. Acc. Chem. Res. (1993) 26(4):147-153.
   Web of Science ®Google Scholar
• HANSCH C: The physicochemical approach to drug design and discovery (QSAR). Drug Dev. Res. (1981) 1(4):267-309.
   Web of Science ®Google Scholar
• FUJITA T: Application of quantitative structure–activity relationship in drug design. Acta Pharm. Jugosl. (1987) 37:43-51.
   Google Scholar
• SAITO H, HIRANO H, NAKAGAWA H et al.: A new strategy of high-speed screening and quantitative structure–activity relationship analysis to evaluate human ATP-binding cassette transporter ABCG2–drug interactions. J. Pharmacol. Exp. Ther. (2006) 317(3):1114-1124.
   PubMed Web of Science ®Google Scholar
• MASUBUCHI Y: Metabolic and non-metabolic factors determining troglitazone hepatotoxicity: a review. Drug Metab. Pharmacokinet. (2006) 21(5):347-356.
   PubMed Web of Science ®Google Scholar
• SMITH MT: Mechanisms of troglitazone hepatotoxicity. Chem. Res. Toxicol. (2003) 16(6):679-687.
   PubMed Web of Science ®Google Scholar
• PARK BK, KITTERINGHAM NR, MAGGS JL, PIRMOHAMED M, WILLIAMS DP: The role of metabolic activation in drug-induced hepatotoxicity. Ann. Rev. Pharmacol. Toxicol. (2005) 45:177-202.
   PubMed Web of Science ®Google Scholar
• KAPLOWITZ N: Idiosyncratic drug hepatotoxicity. Nat. Rev. Drug Discov. (2005) 4(6):489-499.
   PubMed Web of Science ®Google Scholar
• AUSTIN CP, BRADY LS, INSEL TR, COLLINS FS: NIH Molecular Libraries Initiative. Science (2004) 306(5699):1138-1139.
   PubMed Web of Science ®Google Scholar