Transport of lamivudine [(-)-/β-L-2′,3′-dideoxy-3′- thiacytidine] and high-affinity interaction of nucleoside reverse transcriptase inhibitors with human organic cation transporters 1, 2, and 3

Journal of Pharmacology and Experimental Therapeutics

Volumn 329, Issue 1, 2009, Pages 252-261

  Minuesa, Gerard ^a   Volk, Christopher ^b   Molina Arcas, Míriam ^c   Gorboulev, Valentin ^b   Erkizia, Itziar ^a   Arndt, Petra ^b   Clotet, Bonaventura ^a   Pastor Anglada, Marçal ^c   Koepsell, Hermann ^b   Martinez Picado, Javier ^a,d,e  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c INSTITUTO DE SALUD CARLOS III   (Spain)

^d INSTITUCIÓ CATALANA DE RECERCA I ESTUDIS AVANÇATS ICREA   (Spain)

^e HOSPITAL UNIVERSITARI GERMANS TRIAS I PUJOL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ABACAVIR; EMTRICITABINE; LAMIVUDINE; ORGANIC CATION TRANSPORTER 1; ORGANIC CATION TRANSPORTER 2; ORGANIC CATION TRANSPORTER 3; TENOFOVIR DISOPROXIL; ZIDOVUDINE;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; BINDING SITE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG INHIBITION; DRUG PROTEIN BINDING; IC 50; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALS; ANTI-HIV AGENTS; BINDING SITES; BIOLOGICAL TRANSPORT, ACTIVE; CHO CELLS; CRICETINAE; CRICETULUS; DIDEOXYNUCLEOSIDES; DRUG INTERACTIONS; HUMANS; KINETICS; LAMIVUDINE; ORGANIC ANION TRANSPORT PROTEIN 1; ORGANIC ANION TRANSPORTERS, SODIUM-INDEPENDENT; REVERSE TRANSCRIPTASE INHIBITORS; TRANSFECTION; ZIDOVUDINE;

EID: 63849083391     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.108.146225     Document Type: Article

References (39)

1. Chen R and Nelson JA (2000) Role of organic cation transporters in the renal secretion of nucleosides. Biochem Pharmacol 60:215-219.
2. Cinatl J Jr, Cinatl J, Rabenau H, Doerr HW, and Weber B (1994) Failure of antiretroviral therapy: role of viral and cellular factors. Intervirology 37:307-314.
3. Corzo J (2006) Time, the forgotten dimension of ligand binding teaching. Biochem Mol Biol Educ 34:413-416.
4. Cihlar T, Ho ES, Lin DC, and Mulato AS (2001) Human renal organic anion transporter 1 (hOAT1) and its role in the nephrotoxicity of antiviral nucleotide analogs. Nucleosides Nucleotides Nucleic Acids 20:641-648.
5. Errasti-Murugarren E, Pastor-Anglada M, and Casado FJ (2007) Role ofCnt3 in the transepithelial flux of nucleosides and nucleoside-derived drugs. J Physiol 582:1249-1260.
6. Ford J, Khoo SH, and Back DJ (2004) The intracellular pharmacology of antiretroviral protease inhibitors. J Antimicrob Chemother 54:982-990.
7. Fridland A, Connelly MC, and Robbins BL (2000) Cellular factors for resistance against antiretroviral agents. Antivir Ther 5:181-185.
8. Gorboulev V, Shatskaya N, Volk C, and Koepsell H (2005) Subtype-specific affinity for corticosterone of rat organic cation transporters rOCT1 and rOCT2 depends on three amino acids within the substrate binding region. Mol Pharmacol 67:1612-1619.
9. Gorbunov D, Gorboulev V, Shatskaya N, Mueller T, Bamberg E, Friedrich T, and Koepsell H (2008) High-affinity cation binding to organic cation transporter 1 induces movement of helix 11 and blocks transport after mutations in a modeled interaction domain between two helices. Mol Pharmacol 73:50-61.
10. Hong M, Schlichter L, and Bendayan R (2001) Anovel zidovudine uptake system in microglia. J Pharmacol Exp Ther 296:141-149.
11. Janneh O, Jones E, Chandler B, Owen A, and Khoo SH (2007) Inhibition of P-glycoprotein and multidrug resistance-associated proteins modulates the intracellular concentration of lopinavir in cultured CD4 T cells and primary human lymphocytes. J Antimicrob Chemother 60:987-993.
12. Jung N, Lehmann C, Rubbert A, Knispel M, Hartmann P, van Lunzen J, Stellbrink HJ, Faetkenheuer G, and Taubert D (2008) Relevance of the organic cation transporters 1 and 2 for antiretroviral therapy in HIV infection. Drug Metab Dispos 36:1616-1623.
13. Kock K, Grube M, Jedlitschky G, Oevermann L, Siegmund W, Ritter CA, and Kroemer HK (2007) Expression of adenosine triphosphate-binding cassette (ABC) drug transporters in peripheral blood cells: relevance for physiology and pharmacotherapy. Clin Pharmacokinet 46:449-470.
14. Koepsell H (2004) Polyspecific organic cation transporters: their functions and interactions with drugs. Trends Pharmacol Sci 25:375-381.
15. Koepsell H, Lips K, and Volk C (2007) Polyspecific organic cation transporters: structure, function, physiological roles, and biopharmaceutical implications. Pharm Res 24:1227-1251.
16. McRae MP, Lowe CM, Tian X, Bourdet DL, Ho RH, Leake BF, Kim RB, Brouwer KL, and Kashuba AD (2006) Ritonavir, saquinavir, and efavirenz, but not nevirapine, inhibit bile acid transport in human and rat hepatocytes. J Pharmacol Exp Ther 318:1068-1075.
17. Minuesa G, Purcet S, Erkizia I, Molina-Arcas M, Bofill M, Izquierdo-Useros N, Casado FJ, Clotet B, Pastor-Anglada M, and Martinez-Picado J (2008) Expression and functionality of anti-human immunodeficiency virus and anticancer drug uptake transporters in immune cells. J Pharmacol Exp Ther 324:558-567.
18. Moaddel R, Yamaguchi R, Ho PC, Patel S, Hsu CP, Subrahmanyam V, and Wainer IW (2005) Development and characterization of an immobilized human organic cation transporter based liquid chromatographic stationary phase. J Chromatogr B Analyt Technol Biomed Life Sci 818:263-268.
19. Moore KH, Yuen GJ, Raasch RH, Eron JJ, Martin D, Mydlow PK, and Hussey EK (1996) Pharmacokinetics of lamivudine administered alone and with trimethoprim-sulfamethoxazole. Clin Pharmacol Ther 59:550-558.
20. Nakatani-Freshwater T, Babayeva M, Dontabhaktuni A, and Taft DR (2006) Effects of trimethoprim on the clearance of apricitabine, a deoxycytidine analog reverse transcriptase inhibitor, and lamivudine in the isolated perfused rat kidney. J Pharmacol Exp Ther 319:941-947.
21. Owen A, Pirmohamed M, Khoo SH, and Back DJ (2006) Pharmacogenetics of HIV therapy. Pharmacogenet Genomics 16:693-703.
22. Pastor-Anglada M, Molina-Arcas M, Casado FJ, Bellosillo B, Colomer D, and Gil J (2004) Nucleoside transporters in chronic lymphocytic leukaemia. Leukemia 18:385-393.
23. Purcet S, Minuesa G, Molina-Arcas M, Erkizia I, Casado FJ, Clotet B, Martinez-Picado J, and Pastor-Anglada M (2006) 3′-Azido-2′,3′- dideoxythymidine (zidovudine) uptake mechanisms in T lymphocytes. Antivir Ther 11:803-811.
24. Rodríguez Nóvoa S, Barreiro P, Rendón A, Barrios A, Corral A, Jiménez-Nacher I, González-Lahoz J, and Soriano V (2006) Plasma levels of atazanavir and the risk of hyperbilirubinemia are predicted by the 3435C →T polymorphism at the multidrug resistance gene 1. Clin Infect Dis 42:291-295.
25. Rotger M, Tegude H, Colombo S, Cavassini M, Furrer H, Decosterd L, Blievernicht J, Saussele T, Günthard HF, Schwab M, et al. (2007) Predictive value of known and novel alleles of CYP2B6 for efavirenz plasma concentrations in HIV-infected individuals. Clin Pharmacol Ther 81:557-566.
26. Shehu-Xhilaga M, Tachedjian G, Crowe SM, and Kedzierska K (2005) Antiretroviral compounds: mechanisms underlying failure of HAART to eradicate HIV-1. Curr Med Chem 12:1705-1719.
27. Shu Y, Sheardown SA, Brown C, Owen RP, Zhang S, Castro RA, Ianculescu AG, Yue L, Lo JC, Burchard EG, et al. (2007) Effect of genetic variation in the organic cation transporter 1 (OCT1) on metformin action. J Clin Invest 117:1422-1431.
28. Sweeney KR, Hsyu PH, Statkevich P, and Taft DR (1995) Renal disposition and drug interaction screening of (-)-2′-deoxy-3′-thiacytidine (3TC) in the isolated perfused rat kidney. Pharm Res 12:1958-1963.
29. Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, and Endou H (2002) Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther 300:918-924.
30. Takubo T, Kato T, Kinami J, Hanada K, and Ogata H (2000a) Effect of lamivudine on uptake of organic cations by rat renal brush-border and basolateral membrane vesicles. J Pharm Pharmacol 52:569-575.
31. Takubo T, Kato T, Kinami J, Hanada K, and Ogata H (2000b) Effect of trimethoprim on the renal clearance of lamivudine in rats. J Pharm Pharmacol 52:315-320.
32. Takubo T, Kato T, Kinami J, Hanada K, and Ogata H (2002) Uptake of lamivudine by rat renal brush border membrane vesicles. J Pharm Pharmacol 54:111-117.
33. Turriziani O and Antonelli G (2004) Host factors and efficacy of antiretroviral treatment. New Microbiol 27:63-69.
34. Uwai Y, Ida H, Tsuji Y, Katsura T, and Inui K (2007) Renal transport of adefovir, cidofovir, and tenofovir by SLC22Afamilymembers (hOAT1, hOAT3, and hOCT2). Pharm Res 24:811-815.
35. Volk C, Gorboulev V, Budiman T, Nagel G, and Koepsell H (2003) Different affinities of inhibitors to the outwardly and inwardly directed substrate binding site of organic cation transporter 2. Mol Pharmacol 64:1037-1047.
36. Wang L, Giannoudis A, Lane S, Williamson P, Pirmohamed M, and Clark RE (2008) Expression of the uptake drug transporter hOCT1 is an important clinical determinant of the response to imatinib in chronic myeloid leukemia. Clin Pharmacol Ther 83:258-264.
37. Yonezawa A, Masuda S, Yokoo S, Katsura T, and Inui K (2006) Cisplatin and oxaliplatin, but not carboplatin and Nedaplatin, are substrates for human organic cation transporters (SLC22A1-3 and multidrug and toxin extrusion family). J Pharmacol Exp Ther 319:879-886.
38. Zhang L, Gorset W, Washington CB, Blaschke TF, Kroetz DL, and Giacomini KM (2000) Interactions of HIV protease inhibitors with a human organic cation transporter in a mammalian expression system. Drug Metab Dispos 28:329-334.
39. Zhang S, Lovejoy KS, Shima JE, Lagpacan LL, Shu Y, Lapuk A, Chen Y, Komori T, Gray JW, Chen X, et al. (2006) Organic cation transporters are determinants of oxaliplatin cytotoxicity. Cancer Res 66:8847-8857.