Effects of 1α,25-dihydroxyvitamin D 3 on transport and metabolism of adefovir dipivoxil and its metabolites in Caco-2 cells

European Journal of Pharmaceutical Sciences

Volumn 46, Issue 3, 2012, Pages 149-166

  Maeng, Han Joo ^a,b   Chapy, Hélène ^a,c   Zaman, Sarah ^a   Sandy Pang, K ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b Inje University   (South Korea)

^c UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

1 ,25 Dihydroxyvitamin D 3 (1,25(OH) 2D 3); Adefovir dipivoxil; Caco 2 cells; Multidrug resistance associated protein 4 (MRP4); P glycoprotein (P gp); Vitamin D receptor (VDR)

Indexed keywords

ADEFOVIR DIPIVOXIL; BREAST CANCER RESISTANCE PROTEIN; CALCITRIOL; GLYCOPROTEIN P; MULTIDRUG RESISTANCE PROTEIN 4; VERAPAMIL; VITAMIN D RECEPTOR;

ARTICLE; CELL LYSATE; CONTROLLED STUDY; DRUG METABOLISM; DRUG PENETRATION; DRUG TRANSPORT; HUMAN; HUMAN CELL; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; WESTERN BLOTTING;

ADENINE; ATP-BINDING CASSETTE TRANSPORTERS; BIOLOGICAL TRANSPORT; CACO-2 CELLS; CELLS, CULTURED; DRUG INTERACTIONS; HUMANS; MULTIDRUG RESISTANCE-ASSOCIATED PROTEINS; NEOPLASM PROTEINS; P-GLYCOPROTEIN; PERMEABILITY; PHOSPHONIC ACIDS; VERAPAMIL; VITAMIN D;

EID: 84859430616     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2012.02.018     Document Type: Article

References (43)

1. M.F. Andreasen, P.A. Kroon, G. Williamson, and M.T. Garcia-Conesa Esterase activity able to hydrolyze dietary antioxidant hydroxycinnamates is distributed along the intestine of mammals J. Agric. Food Chem. 49 2001 5679 5684 (Pubitemid 33089725)
2. P. Annaert, J. Van Gelder, L. Naesens, E. De Clercq, G. Van den Mooter, R. Kinget, and P. Augustijns Carrier mechanisms involved in the transepithelial transport of bis(POM)-PMEA and its metabolites across Caco-2 monolayers Pharm. Res. 15 1998 1168 1173 (Pubitemid 28401705)
3. P. Annaert, R. Kinget, L. Naesens, E. de Clercq, and P. Augustijns Transport, uptake, and metabolism of the bis(pivaloyloxymethyl)-ester prodrug of 9-(2-phosphonylmethoxyethyl)adenine in an in vitro cell culture system of the intestinal mucosa (Caco-2) Pharm. Res. 14 1997 492 496 (Pubitemid 27205010)
4. M.G. Belinsky, P. Guo, K. Lee, F. Zhou, E. Kotova, A. Grinberg, H. Westphal, I. Shchaveleva, A. Klein-Szanto, J.M. Gallo, and G.D. Kruh Multidrug resistance protein 4 protects bone marrow, thymus, spleen, and intestine from nucleotide analogue-induced damage Cancer Res. 67 2007 262 268 (Pubitemid 46142783)
5. M. Buti, and R. Esteban Adefovir dipivoxil Drug Today 39 2003 127 135 (Pubitemid 36514364)
6. Z.S. Chen, K. Lee, S. Walther, R.B. Reftogianis, M. Kuwano, H. Zeng, and C.D. Kruh Analysis of methotrexate and folate transport by multidrug resistance protein 4 (ABCC4): MRP4 is a component of the methotrexate efflux system Cancer Res. 62 2002 3144 3150 (Pubitemid 34602407)
7. 3 via the vitamin D receptor Mol. Pharmacol. 69 2006 1913 1923 (Pubitemid 43894308)
8. 3 upregulates P-glycoprotein activities via the VDR and not in both fxr(-/-) and fxr(+/+) mice, and increased renal and brain efflux of digoxin in mice in vivo J. Pharmacol. Exp. Ther. 337 2011 846 859
9. 3 triggered vitamin D receptor and farnesoid X receptor-like effects in rat intestine and liver in vivo Biopharm. Drug Dispos. 30 2009 457 475
10. 3 on transporters and enzymes of the rat intestine and kidney in vivo Biopharm. Drug Dispos. 31 2010 91 108
11. K.C. Cundy, P. Barditch-Crovo, R.E. Walker, A.C. Collier, D. Ebeling, J. Toole, and H.S. Jaffe Clinical pharmacokinetics of adefovir in human immunodeficiency virus type 1-infected patients Antimicrob. Agents Chemother. 39 1995 2401 2405
12. K.C. Cundy, J.A. Fishback, J.P. Shaw, M.L. Lee, K.F. Soike, G.C. Visor, and W.A. Lee Oral bioavailability of the antiretroviral agent 9-(2-phosphonyl-methoxyethyl)adenine (PMEA) from three formulations of the prodrug bis(pivaloyloxymethyl)-PMEA in fasted male cynomolgus monkeys Pharm. Res. 11 1994 839 843 (Pubitemid 24210618)
13. S. Dallas, L. Schlichter, and R. Bendayan Multidrug resistance protein (MRP) 4- and MRP 5-mediated efflux of 9-(2-phosphonylmethoxyethyl)adenine by microglia J. Pharmacol. Exp. Ther. 309 2004 1221 1229 (Pubitemid 38669713)
14. E. De Clercq Clinical potential of the acyclic nucleoside phosphonates cidofovir, adefovir, and tenofovir in treatment of DNA virus and retrovirus infections Clin. Microbiol. Rev. 16 2003 569 596 (Pubitemid 37296550)
15. 3 and vitamin D analogs, in the Caco-2 cell monolayer J. Pharmacol. Exp. Ther. 330 2009 389 402
16. B. Helliot, B. Panis, E. Frison, E. De Clercq, R. Swennen, P. Lepoivre, and J. Neyts The acyclic nucleoside phosphonate analogues, adefovir, tenofovir and PMEDAP, efficiently eliminate banana streak virus from banana (Musa spp.) Antiviral Res. 59 2003 121 126 (Pubitemid 36934498)
17. T. Imai, M. Imoto, H. Sakamoto, and M. Hashimoto Identification of esterases expressed in Caco-2 cells and effects of their hydrolyzing activity in predicting human intestinal absorption Drug Metab. Dispos. 33 2005 1185 1190 (Pubitemid 41043762)
18. T. Imaoka, H. Kusuhara, M. Adachi, J.D. Schuetz, K. Takeuchi, and Y. Sugiyama Functional involvement of multidrug resistance-associated protein 4 (MRP4/ABCC4) in the renal elimination of the antiviral drugs adefovir and tenofovir Mol. Pharmacol. 71 2007 619 627 (Pubitemid 46147926)
19. C.A. Lee, J.A. Cook, E.L. Reyner, and D.A. Smith P-Glycoprotein related drug interactions: clinical importance and a consideration of disease states Expert Opin. Drug Metab. Toxicol. 6 2010 603 619
20. O.H. Lowry, N.J. Rosebrough, A.L. Farr, and R.J. Randall Protein measurement with the folin phenol reagent J. Biol. Chem. 193 1951 265 275
21. 3 on intestinal transporter function: studies with the rat everted intestinal sac Biopharm. Drug Dispos. 32 2011 112 125
22. R. Margolis, and S. Christakos The nuclear receptor superfamily of steroid hormones and vitamin D gene regulation, an update Ann. NY Acad. Sci. 1192 2010 204 208
23. P.M. Mathias, J.T. Harries, T.J. Peters, and D.P. Muller Studies on the in vivo absorption of micellar solutions of tocopherol and tocopheryl acetate in the rat: demonstration and partial characterization of a mucosal esterase localized to the endoplasmic reticulum of the enterocyte J. Lipid Res. 22 1981 829 837 (Pubitemid 11023707)
24. A. Mennone, C.J. Soroka, S.Y. Cai, K. Harry, M. Adachi, L. Hagey, J.D. Schuetz, and J.L. Boyer Mrp4-/- mice have an impaired cytoprotective response in obstructive cholestasis Hepatology 43 2006 1013 1021 (Pubitemid 43724626)
25. X. Ming, and D.R. Thakker Role of basolateral efflux transporter MRP4 in the intestinal absorption of the antiviral drug adefovir dipivoxil Biochem. Pharmacol. 79 2010 455 462
26. A. Ose, M. Ito, H. Kusuhara, K. Yamatsugu, M. Kanai, M. Shibasaki, M. Hosokawa, J.D. Schuetz, and Y. Sugiyama Limited brain distribution of [3R,4R,5S]-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (Ro 64-0802), a pharmacologically active form of oseltamivir, by active efflux across the blood-brain barrier mediated by organic anion transporter 3 (Oat3/Slc22a8) and multidrug resistance-associated protein 4 (Mrp4/Abcc4). Drug Metab Dispos 37 2009 315 321
27. K.S. Pang, H.-J. Maeng, and J. Fan Interplay of transporters and enzymes in drug and metabolite processing Mol. Pharm. 6 2009 1734 1755
28. S.L. Polsky-Fisher, H. Cao, P. Lu, and C.R. Gibson Effect of cytochrome P-450 chemical inhibitors and monoclonal antibodies on human liver microsomal esterase activity Drug Metab. Dispos. 34 2006 1361 1366 (Pubitemid 44079877)
29. G. Reid, P. Wielinga, N. Zelcer, I. vand der Heijden, A. Kuil, M. de Haas, H. Wijnholds, and P. Borst The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs Proc.Natl. Acad. Sci. USA 100 2003 9244 9249 (Pubitemid 37033914)
30. M. Saeki, K. Kurose, M. Tohkin, and R. Hasegawa Identification of the functional vitamin D response elements in the human MDR1 gene Biochem. Pharmacol. 15 2008 531 542
31. J.D. Schuetz, M.C. Connelly, D. Sun, S.G. Paibir, P.M. Flynn, R.V. Srinivas, A. Kumar, and A. Fridland MRP4: a previously unidentified factor in resistance to nucleoside-based antiviral drugs Nat. Med. 5 1999 1048 1051 (Pubitemid 29439577)
32. J.P. Shaw, M.S. Louie, V.V. Krishnamurthy, M.N. Arimilli, R.J. Jones, A.M. Bidgood, W.A. Lee, and K.C. Cundy Pharmacokinetics and metabolism of selected prodrugs of PMEA in rats Drug Metab. Dispos. 25 1997 362 366 (Pubitemid 27120583)
33. D.Q. Sun, H.S. Wang, M.Y. Ni, B.J. Wang, and R.C. Guo Pharmacokinetics, safety and tolerance of single- and multiple-dose adefovir dipivoxil in healthy Chinese subjects Br. J. Clin. Pharmacol. 63 2007 15 23
34. H. Sun, and K.S. Pang Permeability, transport, and metabolism of solutes in Caco-2 cell monolayers: a theoretical study Drug Metab. Dispos. 36 2008 102 123
35. H. Sun, L. Zhang, E.C. Chow, G. Lin, Z. Zuo, and K.S. Pang A catenary model to study transport and conjugation of baicalein, a bioactive flavonoid, in the Caco-2 cell monolayer: demonstration of substrate inhibition J. Pharmacol. Exp. Ther. 326 2008 117 126 (Pubitemid 351872137)
36. K. Takenaka, J.A. Morgan, G.L. Scheffer, M. Adachi, C.F. Stewart, D. Sun, M. Leggas, K.F. Ejendal, C.A. Hrycyna, and J.D. Schuetz Substrate overlap between Mrp4 and Abcg2/Bcrp affects purine analogue drug cytotoxicity and tissue distribution Cancer Res. 67 2007 6965 6972 (Pubitemid 47105544)
37. 3 Mol. Pharmacol. 60 2001 1399 1406 (Pubitemid 33144911)
38. J. Taipalensuu, H. Törnblom, G. Lindberg, C. Einarsson, F. Sjöqvist, H. Melhus, P. Garberg, B. Sjöström, B. Lundgren, and P. Artursson Correlation of gene expression of ten drug efflux proteins of the ATP-binding cassette transporter family in normal human jejunum and in human intestinal epithelial Caco-2 cell monolayers J. Pharmacol. Exp. Ther. 299 2001 164 170 (Pubitemid 32905131)
39. Q. Tian, J. Zhang, T.M. Tan, E. Chan, W. Duan, S.Y. Chan, U.A. Boelsterli, P.C. Ho, H. Yang, J.S. Bian, M. Huang, Y.Z. Zhu, W. Xiong, X. Li, and S. Zhou Human multidrug resistance associated protein 4 confers resistance to camptothecins Pharm. Res. 22 2005 1837 1853 (Pubitemid 41504337)
40. M.D. Troutman, and D.R. Thakker Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium Pharm. Res. 20 2003 1210 1224 (Pubitemid 36951846)
41. B. Urquhart, R. Tirona, and R. Kim Nuclear receptors and the regulation of drug-metabolizing enzymes and drug transporters: implications for interindividual variability in response to drugs J. Clin. Pharmacol. 47 2007 566 578 (Pubitemid 46632158)
42. S. Xu, J. Weerachayaphorn, S.Y. Cai, C.J. Soroka, and J.L. Boyer Aryl hydrocarbon receptor and NF-E2-related factor 2 are key regulators of human MRP4 expression Am. J. Physiol. Gastrointest. Liver Physiol. 299 2010 126 135
43. Y. Yoshigae, T. Imai, A. Horia, H. Matsukane, and M. Otagiri Species differences in stereoselective hydrolase activity in intestinal mucosa Pharm. Res. 15 1998 626 631 (Pubitemid 28214958)