Stereoselectivity of chiral drug transport: a focus on enantiomer–transporter interaction

References

• Akamine Y, Miura M, Sunagawa S, et al. (2010). Influence of drug-transporter polymorphisms on the pharmacokinetics of fexofenadine enantiomers. Xenobiotica 40:782–789
   PubMed Web of Science ®Google Scholar
• Akamine Y, Miura M, Yasui-Furukori N, et al. (2012). Carbamazepine differentially affects the pharmacokinetics of fexofenadine enantiomers. Br J Clin Pharmacol 73:478–481
   PubMed Web of Science ®Google Scholar
• Barraud de Lagerie S, Comets E, Gautrand C, et al. (2004). Cerebral uptake of mefloquine enantiomers with and without the P-gp inhibitor elacridar (GF1210918) in mice. Br J Pharmacol 141:1214–1222
   PubMed Web of Science ®Google Scholar
• Bhatia P, Kolinski M, Moaddel R, et al. (2008). Determination and modelling of stereoselective interactions of ligands with drug transporters: A key dimension in the understanding of drug disposition. Xenobiotica 38:656–675
   PubMed Web of Science ®Google Scholar
• Bhatia PA, Moaddel R, Wainer IW. (2010). The synthesis and characterization of cellular membrane affinity chromatography columns for the study of human multidrug resistant proteins MRP1, MRP2 and human breast cancer resistant protein BCRP using membranes obtained from Spodoptera frugiperda (Sf9) insect cells. Talanta 81:1477–1481
   PubMed Web of Science ®Google Scholar
• Campo VL, Bernardes LS, Carvalho I. (2009). Stereoselectivity in drug metabolism: molecular mechanisms and analytical methods. Curr Drug Metab 10:188–205
   PubMed Web of Science ®Google Scholar
• Choong E, Dobrinas M, Carrupt PA, Eap CB. (2010). The permeability P-glycoprotein: A focus on enantioselectivity and brain distribution. Expert Opin Drug Metab Toxicol 6:953–965
   PubMed Web of Science ®Google Scholar
• Crettol S, Digon P, Golay KP, et al. (2007). In vitro P-glycoprotein-mediated transport of (R)-, (S)-, (R,S)-methadone, LAAM and their main metabolites. Pharmacology 80:304–311
   PubMed Web of Science ®Google Scholar
• Damme K, Nies AT, Schaeffeler E, Schwab M. (2011). Mammalian MATE (SLC47A) transport proteins: impact on efflux of endogenous substrates and xenobiotics. Drug Metab Rev 43:499–523
   PubMed Web of Science ®Google Scholar
• Gaj CL, Anyanwutaku I, Chang YH, Cheng YC. (1998). Decreased drug accumulation without increased drug efflux in a novel MRP-overexpressing multidrug-resistant cell line. Biochem Pharmacol 55:1199–1211
   PubMed Web of Science ®Google Scholar
• Gross AS, Somogyi AA. (1994). Interaction of the stereoisomers of basic drugs with the uptake of tetraethylammonium by rat renal brush-border membrane vesicles. J Pharmacol Exp Ther 268:1073–1080
   PubMed Web of Science ®Google Scholar
• Gu Y, Wang GJ, Wu XL, et al. (2010). Intestinal absorption mechanisms of ginsenoside Rh2: stereoselectivity and involvement of ABC transporters. Xenobiotica 40:602–612
   PubMed Web of Science ®Google Scholar
• He Y, Zeng S. (2006). Determination of the stereoselectivity of chiral drug transport across Caco-2 cell monolayers. Chirality 18:64–69
   PubMed Web of Science ®Google Scholar
• He Y, Liu Y, Zeng S. (2010). Stereoselective and multiple carrier-mediated transport of cetirizine across Caco-2 cell monolayers with potential drug interaction. Chirality 22:684–692
   PubMed Web of Science ®Google Scholar
• Hillgren KM, Keppler D, Zur AA, et al. (2013). Emerging transporters of clinical importance: An update from the International Transporter Consortium. Clin Pharmacol Ther 94:52–63
   PubMed Web of Science ®Google Scholar
• Honjo H, Uwai Y, Aoki Y, Iwamoto K. (2011). Stereoselective inhibitory effect of flurbiprofen, ibuprofen and naproxen on human organic anion transporters hOAT1 and hOAT3. Biopharm Drug Dispos 32:518–524
   PubMed Web of Science ®Google Scholar
• Ito S, Kusuhara H, Kumagai Y, et al. (2012). N-methylnicotinamide is an endogenous probe for evaluation of drug-drug interactions involving multidrug and toxin extrusions (MATE1 and MATE2-K). Clin Pharmacol Ther 92:635–641
   PubMed Web of Science ®Google Scholar
• Karlsson L, Carlsson B, Hiemke C, et al. (2013). Altered brain concentrations of citalopram and escitalopram in P-glycoprotein deficient mice after acute and chronic treatment. Eur Neuropsychopharmacol 23:1636–1644
   PubMed Web of Science ®Google Scholar
• Kusuhara H, Miura M, Yasui-Furukori N, et al. (2013). Effect of coadministration of single and multiple doses of rifampicin on the pharmacokinetics of fexofenadine enantiomers in healthy subjects. Drug Metab Dispos 41:206–213
   PubMed Web of Science ®Google Scholar
• Menter A, Thrash B, Cherian C, et al. (2012). Intestinal transport of aminopterin enantiomers in dogs and humans with psoriasis is stereoselective: evidence for a mechanism involving the proton-coupled folate transporter. J Pharmacol Exp Ther 342:696–708
   PubMed Web of Science ®Google Scholar
• Mitsuoka K, Tamai I, Morohashi Y, et al. (2009). Direct evidence for efficient transport and minimal metabolism of L-cephalexin by oligopeptide transporter 1 in budded baculovirus fraction. Biol Pharm Bull 32:1459–1461
   PubMed Web of Science ®Google Scholar
• Moaddel R, Ravichandran S, Bighi F, et al. (2007). Pharmacophore modelling of stereoselective binding to the human organic cation transporter (hOCT1). Br J Pharmacol 151:1305–1314
   PubMed Web of Science ®Google Scholar
• Moaddel R, Bighi F, Yamaguchi R, et al. (2010). Stereoselective binding of chiral ligands to single nucleotide polymorphisms of the human organic cation transporter-1 determined using cellular membrane affinity chromatography. Anal Biochem 401:148–153
   PubMed Web of Science ®Google Scholar
• Motohashi H, Inui K. (2013). Multidrug and toxin extrusion family SLC47: Physiological, pharmacokinetic and toxicokinetic importance of MATE1 and MATE2-K. Mol Aspects Med 34:661–668
   PubMed Web of Science ®Google Scholar
• Narawa T, Itoh T. (2010). Stereoselective transport of amethopterin enantiomers by the proton-coupled folate transporter. Drug Metab Pharmacokinet 25:283–289
   PubMed Web of Science ®Google Scholar
• Ni Z, Bikadi Z, Rosenberg MF, Mao Q. (2010). Structure and function of the human breast cancer resistance protein (BCRP/ABCG2). Curr Drug Metab 11:603–617
   PubMed Web of Science ®Google Scholar
• Nikisch G, Eap CB, Baumann P. (2008). Citalopram enantiomers in plasma and cerebrospinal fluid of ABCB1 genotyped depressive patients and clinical response: A pilot study. Pharmacol Res 58:344–347
   PubMed Web of Science ®Google Scholar
• Niwa T, Murayama N, Yamazaki H. (2011). Stereoselectivity of human cytochrome p450 in metabolic and inhibitory activities. Curr Drug Metab 12:549–569
   PubMed Web of Science ®Google Scholar
• Ott RJ, Giacomini KM. (1993). Stereoselective interactions of organic cations with the organic cation transporter in OK cells. Pharm Res 10:1169–1173
   PubMed Web of Science ®Google Scholar
• Perrotton T, Trompier D, Chang XB, et al. (2007). (R)- and (S)-verapamil differentially modulate the multidrug-resistant protein MRP1. J Biol Chem 282:31542–31548
   PubMed Web of Science ®Google Scholar
• Pham YT, Régina A, Farinotti R, et al. (2000). Interactions of racemic mefloquine and its enantiomers with P-glycoprotein in an immortalised rat brain capillary endothelial cell line, GPNT. Biochim Biophys Acta 1524:212–219
   PubMed Web of Science ®Google Scholar
• Sakugawa T, Miura M, Hokama N, et al. (2009). Enantioselective disposition of fexofenadine with the P-glycoprotein inhibitor verapamil. Br J Clin Pharmacol 67:535–540
   PubMed Web of Science ®Google Scholar
• Shen S, He Y, Zeng S. (2007). Stereoselective regulation of MDR1 expression in Caco-2 cells by cetirizine enantiomers. Chirality 19:485–490
   PubMed Web of Science ®Google Scholar
• Staud F, Cerveny L, Ahmadimoghaddam D, Ceckova M. (2013). Multidrug and toxin extrusion proteins (MATE/SLC47); role in pharmacokinetics. Int J Biochem Cell Biol 45:2007–2011
   PubMed Web of Science ®Google Scholar
• Sun S, Chen Z, Li L, et al. (2012). The two enantiomers of tetrahydropalmatine are inhibitors of P-gp, but not inhibitors of MRP1 or BCRP. Xenobiotica 42:1197–1205
   PubMed Web of Science ®Google Scholar
• Tateishi T, Miura M, Suzuki T, Uno T. (2008). The different effects of itraconazole on the pharmacokinetics of fexofenadine enantiomers. Br J Clin Pharmacol 65:693–700
   PubMed Web of Science ®Google Scholar
• Tian Y, He Y, Hu HH, et al. (2012). Determination of the enantioselectivity of six chiral aryloxy aminopropanol drugs transport across Caco-2 cell monolayers. Acta Pharmaceutica Sinica B 2:168–173
   Google Scholar
• Togami K, Tosaki Y, Chono S, et al. (2013). Enantioselective uptake of fexofenadine by Caco-2 cells as model intestinal epithelial cells. J Pharm Pharmacol 65:22–29
   PubMed Web of Science ®Google Scholar
• Wainer IW. (2008). Investigation of molecular recognition in biological systems using cellular membrane affinity chromatography. Chim Oggi 26:19–22
   PubMed Web of Science ®Google Scholar
• Wang L, Leggas M, Empey PE, McNamara PJ. (2012). Stereoselective interaction of pantoprazole with ABCG2. II. In vitro flux analysis. Drug Metab Dispos 40:1024–1031
   PubMed Web of Science ®Google Scholar
• Wang L, McNamara PJ. (2012). Stereoselective interaction of pantoprazole with ABCG2. I. Drug accumulation in rat milk. Drug Metab Dispos 40:1018–1023
   PubMed Web of Science ®Google Scholar
• Wang Y, Cao J, Wang X, Zeng S. (2010). Stereoselective transport and uptake of propranolol across human intestinal Caco-2 cell monolayers. Chirality 22:361–368
   PubMed Web of Science ®Google Scholar
• Wenzel U, Thwaites DT, Daniel H. (1995). Stereoselective uptake of beta-lactam antibiotics by the intestinal peptide transporter. Br J Pharmacol 116:3021–3027
   PubMed Web of Science ®Google Scholar
• Wong IL, Chan KF, Tsang KH, et al. (2009). Modulation of multidrug resistance protein 1 (MRP1/ABCC1)-mediated multidrug resistance by bivalent apigenin homodimers and their derivatives. J Med Chem 52:5311–5322
   PubMed Web of Science ®Google Scholar
• Yonezawa A, Inui K. (2011). Importance of the multidrug and toxin extrusion MATE/SLC47A family to pharmacokinetics, pharmacodynamics/toxicodynamics and pharmacogenomics. Br J Pharmacol 164:1817–1825
   PubMed Web of Science ®Google Scholar
• Zhang J, Zhou F, Niu F, et al. (2012). Stereoselective regulations of P-glycoprotein by ginsenoside Rh2 epimers and the potential mechanisms from the view of pharmacokinetics. PLoS One 7:e35768
   PubMed Web of Science ®Google Scholar
• Zheng XL, Yu QQ, Wang Y, Zeng S. (2013). Stereoselective accumulation of propranolol enantiomers in K562 and K562/ADR cells. Chirality 25:361–364
   PubMed Web of Science ®Google Scholar