Significance of peptide transporter 1 in the intestinal permeability of valacyclovir in wild-type and PepT1 knockout mice

Drug Metabolism and Disposition

Volumn 41, Issue 3, 2013, Pages 608-614

  Yang, Bei ^a   Smith, David E ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOHIPPURIC ACID; CEFADROXIL; GLYCYLSARCOSINE; HISTIDINE; PEPTIDE TRANSPORTER 1; TETRYLAMMONIUM; VALACICLOVIR; VALINE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; COLON; CONTROLLED STUDY; DRUG ABSORPTION; DRUG METABOLISM; DRUG PENETRATION; DRUG TRANSPORT; DRUG UPTAKE; DUODENUM; FEMALE; GENOTYPE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ILEUM; IN VIVO STUDY; INTESTINE MUCOSA PERMEABILITY; INTESTINE PERFUSION; JEJUNUM; MALE; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; PLASMA CONCENTRATION-TIME CURVE; PRIORITY JOURNAL;

ACYCLOVIR; ADMINISTRATION, ORAL; ANIMALS; ANTIVIRAL AGENTS; BINDING, COMPETITIVE; BIOTRANSFORMATION; CEFADROXIL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLON; DIPEPTIDES; DUODENUM; ILEUM; INTESTINAL ABSORPTION; INTESTINES; JEJUNUM; MICE; MICE, KNOCKOUT; MODELS, BIOLOGICAL; PERFUSION; PERMEABILITY; REPRODUCIBILITY OF RESULTS; SYMPORTERS; VALINE;

EID: 84874045942     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.112.049239     Document Type: Article

References (47)

1. Adachi Y, Suzuki H, and Sugiyama Y (2003) Quantitative evaluation of the function of small intestinal P-glycoprotein: comparative studies between in situ and in vitro. Pharm Res 20: 1163-1169.
2. Balimane PV, Tamai I, Guo A, Nakanishi T, Kitada H, Leibach FH, Tsuji A, and Sinko PJ (1998) Direct evidence for peptide transporter (PepT1)-mediated uptake of a nonpeptide prodrug, valacyclovir. Biochem Biophys Res Commun 250:246-251.
3. Balimane P and Sinko P (2000) Effect of ionization on the variable uptake of valacyclovir via the human intestinal peptide transporter (hPepT1) in CHO cells. Biopharm Drug Dispos 21: 165-174.
4. Benet LZ, Broccatelli F, and Oprea TI (2011) BDDCS applied to over 900 drugs. AAPS J 13: 519-547.
5. Bhardwaj RK, Herrera-Ruiz D, Eltoukhy N, Saad M, and Knipp GT (2006) The functional evaluation of human peptide/histidine transporter 1 (hPHT1) in transiently transfected COS-7 cells. Eur J Pharm Sci 27:533-542.
6. Bhardwaj RK, Herrera-Ruiz D, Sinko PJ, Gudmundsson OS, and Knipp G (2005) Delineation of human peptide transporter 1 (hPepT1)-mediated uptake and transport of substrates with varying transporter affinities utilizing stably transfected hPepT1/Madin-Darby canine kidney clones and Caco-2 cells. J Pharmacol Exp Ther 314:1093-1100.
7. Brandsch M, Knütter I, and Bosse-Doenecke E (2008) Pharmaceutical and pharmacological importance of peptide transporters. J Pharm Pharmacol 60:543-585.
8. Burnette TC and de Miranda P (1994) Metabolic disposition of the acyclovir prodrug valaciclovir in the rat. Drug Metab Dispos 22:60-64.
9. Dahan A, West BT, and Amidon GL (2009) Segmental-dependent membrane permeability along the intestine following oral drug administration: Evaluation of a triple single-pass intestinal perfusion (TSPIP) approach in the rat. Eur J Pharm Sci 36:320-329.
10. Daniel H (2004) Molecular and integrative physiology of intestinal peptide transport. Annu Rev Physiol 66:361-384.
11. de Miranda P, Krasny HC, Page DA, and Elion GB (1981) The disposition of acyclovir in different species. J Pharmacol Exp Ther 219:309-315.
12. de Miranda P and Burnette TC (1994) Metabolic fate and pharmacokinetics of the acyclovir prodrug valaciclovir in cynomolgus monkeys. Drug Metab Dispos 22:55-59.
13. de Vrueh RL, Smith PL, and Lee CP (1998) Transport of L-valine-acyclovir via the oligopeptide transporter in the human intestinal cell line, Caco-2. J Pharmacol Exp Ther 286: 1166-1170.
14. Ganapathy ME, Huang W, Wang H, Ganapathy V, and Leibach FH (1998) Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem Biophys Res Commun 246:470-475.
15. Granero GE and Amidon GL (2006) Stability of valacyclovir: implications for its oral bioavailability. Int J Pharm 317:14-18.
16. Groneberg DA, Döring F, Eynott PR, Fischer A, and Daniel H (2001) Intestinal peptide transport: ex vivo uptake studies and localization of peptide carrier PEPT1. Am J Physiol Gastrointest Liver Physiol 281:G697-G704.66
17. Guo A, Hu P, Balimane PV, Leibach FH, and Sinko PJ (1999) Interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther 289:448-454.
18. Gupta SV, Gupta D, Sun J, Dahan A, Tsume Y, Hilfinger J, Lee KD, and Amidon GL (2011) Enhancing the intestinal membrane permeability of zanamivir: a carrier mediated prodrug approach. Mol Pharm 8:2358-2367.
19. Han H, de Vrueh RL, Rhie JK, Covitz KM, Smith PL, Lee CP, Oh DM, Sadée W, and Amidon GL (1998) 59-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter. Pharm Res 15:1154-1159.
20. Hatanaka T, Haramura M, Fei YJ, Miyauchi S, Bridges CC, Ganapathy PS, Smith SB, Ganapathy V, and Ganapathy ME (2004) Transport of amino acid-based prodrugs by the Na+-and Cl(-)-coupled amino acid transporter ATB0,+ and expression of the transporter in tissues amenable for drug delivery. J Pharmacol Exp Ther 308:1138-1147.
21. Hatanaka T, Huang W, Nakanishi T, Bridges CC, Smith SB, Prasad PD, Ganapathy ME, and Ganapathy V (2002) Transport of D-serine via the amino acid transporter ATB(0,+) expressed in the colon. Biochem Biophys Res Commun 291:291-295.
22. Hu Y, Smith DE, Ma K, Jappar D, Thomas W, and Hillgren KM (2008) Targeted disruption of peptide transporter Pept1 gene in mice significantly reduces dipeptide absorption in intestine. Mol Pharm 5:1122-1130.
23. Jana S, Mandlekar S, and Marathe P (2010) Prodrug design to improve pharmacokinetic and drug delivery properties: challenges to the discovery scientists. Curr Med Chem 17: 3874-3908.
24. Jappar D (2009) Role of the Proton-Coupled Oligopeptide Transporters in Small Peptide Absorption and Disposition. Doctoral dissertation, University of Michigan, Ann Arbor, M.I.
25. Jappar D, Wu SP, Hu Y, and Smith DE (2010) Significance and regional dependency of peptide transporter (PEPT) 1 in the intestinal permeability of glycylsarcosine: in situ singlepass perfusion studies in wild-type and Pept1 knockout mice. Drug Metab Dispos 38: 1740-1746.
26. Jappar D, Hu Y, and Smith DE (2011) Effect of dose escalation on the in vivo oral absorption and disposition of glycylsarcosine in wild-type and Pept1 knockout mice. Drug Metab Dispos 39: 2250-2257.
27. Kagan L and Hoffman A (2008) Selection of drug candidates for gastroretentive dosage forms: pharmacokinetics following continuous intragastric mode of administration in a rat model. Eur J Pharm Biopharm 69:238-246.
28. Komiya I, Park JY, Kamani A, Ho NFH, and Higuchi WI (1980) Quantitative mechanistic studies in simultaneous fluid flow and intestinal absorption using steroids as model solutes. Int J Pharm 4:249-262.
29. König J (2011) Uptake transporters of the human OATP family: molecular characteristics, substrates, their role in drug-drug interactions, and functional consequences of polymorphisms. Handb Exp Pharmacol 201:1-28.
30. Kou JH, Fleisher D, and Amidon GL (1991) Calculation of the aqueous diffusion layer resistance for absorption in a tube: application to intestinal membrane permeability determination. Pharm Res 8:298-305.
31. Lennernäs H (2007) Animal data: the contributions of the Ussing Chamber and perfusion systems to predicting human oral drug delivery in vivo. Adv Drug Deliv Rev 59:1103-1120.
32. Li FJ, Maag H, and Alfredson T (2008) Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting. J Pharm Sci 97:1109-1134.
33. Ma K, Hu Y, and Smith DE (2011) Peptide transporter 1 is responsible for intestinal uptake of the dipeptide glycylsarcosine: studies in everted jejunal rings from wild-type and Pept1 null mice. J Pharm Sci 100:767-774.
34. Ma K, Hu Y, and Smith DE (2012) Influence of fed-fasted state on intestinal PEPT1 expression and in vivo pharmacokinetics of glycylsarcosine in wild-type and Pept1 knockout mice. Pharm Res 29:535-545.
35. Rubio-Aliaga I and Daniel H (2008) Peptide transporters and their roles in physiological processes and drug disposition. Xenobiotica 38:1022-1042.
36. Sinko PJ and Balimane PV (1998) Carrier-mediated intestinal absorption of valacyclovir, the Lvalyl ester prodrug of acyclovir: 1. Interactions with peptides, organic anions and organic cations in rats. Biopharm Drug Dispos 19:209-217.
37. Smith DE, Clémençon B, and Hediger MA (2013) Proton-coupled oligopeptide transporter family SLC15: physiological, pharmacological and pathological implications. Mol Aspects Med (in press)
38. Soul-Lawton J, Seaber E, On N, Wootton R, Rolan P, and Posner J (1995) Absolute bioavailability and metabolic disposition of valaciclovir, the L-valyl ester of acyclovir, following oral administration to humans. Antimicrob Agents Chemother 39:2759-2764.
39. Sun J, Dahan A, and Amidon GL (2010) Enhancing the intestinal absorption of molecules containing the polar guanidino functionality: a double-targeted prodrug approach. J Med Chem 53:624-632.
40. Sutton SC, Rinaldi MT, and Vukovinsky KE (2001) Comparison of the gravimetric, phenol red, and 14C-PEG-3350 methods to determine water absorption in the rat single-pass intestinal perfusion model. AAPS PharmSci 3:E25.
41. 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.
42. Thwaites DT and Anderson CM (2011) The SLC36 family of proton-coupled amino acid transporters and their potential role in drug transport. Br J Pharmacol 164:1802-1816.
43. Tsume Y, Vig BS, Sun J, Landowski CP, Hilfinger JM, Ramachandran C, and Amidon GL (2008) Enhanced absorption and growth inhibition with amino acid monoester prodrugs of floxuridine by targeting hPEPT1 transporters. Molecules 13:1441-1454.
44. Varma MV, Ambler CM, Ullah M, Rotter CJ, Sun H, Litchfield J, Fenner KS, and El-Kattan AF (2010) Targeting intestinal transporters for optimizing oral drug absorption. Curr Drug Metab 11:730-742.
45. Weller S, Blum MR, Doucette M, Burnette T, Cederberg DM, de Miranda P, and Smiley ML (1993) Pharmacokinetics of the acyclovir pro-drug valaciclovir after escalating single-and multiple-dose administration to normal volunteers. Clin Pharmacol Ther 54:595-605.
46. Yan Z, Sun J, Chang Y, Liu Y, Fu Q, Xu Y, Sun Y, Pu X, Zhang Y, and Jing Y, et al. (2011) Bifunctional peptidomimetic prodrugs of didanosine for improved intestinal permeability and enhanced acidic stability: synthesis, transepithelial transport, chemical stability and pharmacokinetics. Mol Pharm 8:319-329.
47. Yang B, Amidon GL, and Smith DE (2011) Contribution of PEPT1 to the pharmacokinetics of antiviral drug acyclovir after oral administration of its prodrug valacyclovir in wild-type and Pept1 null mice [Abstract]. AAPS J 13 (S2).