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Volumn 86, Issue 2-3, 2003, Pages 279-292

Prodrugs of purine and pyrimidine analogues for the intestinal di/tri-peptide transporter PepT1: Affinity for hPepT1 in Caco-2 cells, drug release in aqueous media and in vitro metabolism

Author keywords

Acyclovir; Affinity for hPepT1; Dipeptide prodrugs; Stability and in vitro metabolism; Valaciclovir

Indexed keywords

ACICLOVIR; CARRIER PROTEIN; DEXTRO GLUTAMINYL ACYCLOVIR ALANINE; DEXTRO GLUTAMINYL[1 (2 HYDROXYETHYL)THYMINE]ALANINE; ESTER; GLUTAMINYL ACYCLOVIR SARCOMINE; GLUTAMINYL[1 (2 HYDROXYETHYL)THYMINE]SARCOMINE; PEPTIDE TRANSPORTER 1; PRODRUG; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; THYMINE DERIVATIVE; UNCLASSIFIED DRUG; VALACICLOVIR;

EID: 12244302902     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0168-3659(02)00413-3     Document Type: Article
Times cited : (29)

References (26)
  • 1
    • 0021089633 scopus 로고
    • Pharmacokinetics of acyclovir after intravenous and oral administration
    • de Miranda P., Blum M.R. Pharmacokinetics of acyclovir after intravenous and oral administration. J. Antimicrob. Chemother. 12:(Suppl. B):1983;29-37.
    • (1983) J. Antimicrob. Chemother. , vol.12 , Issue.SUPPL. B , pp. 29-37
    • De Miranda, P.1    Blum, M.R.2
  • 3
    • 0027768955 scopus 로고
    • Pharmacokinetics of the acyclovir pro-drug valaciclovir after escalating single- and multiple-dose administration to normal volunteers
    • Weller S., Blum M.R., Doucette M., Burnette T., Cederberg D.M., de Miranda P., Smiley M.L. Pharmacokinetics of the acyclovir pro-drug valaciclovir after escalating single- and multiple-dose administration to normal volunteers. Clin. Pharmacol. Ther. 54:(6):1993;595-605.
    • (1993) Clin. Pharmacol. Ther. , vol.54 , Issue.6 , pp. 595-605
    • Weller, S.1    Blum, M.R.2    Doucette, M.3    Burnette, T.4    Cederberg, D.M.5    De Miranda, P.6    Smiley, M.L.7
  • 4
    • 0028883462 scopus 로고
    • Absolute bioavailability and metabolic disposition of valaciclovir, the L-valyl etser of acyclovir, following oral administration to humans
    • Soul-Lawton J., Seaber E., On N., Wootton R., Rolan P., Posner J. Absolute bioavailability and metabolic disposition of valaciclovir, the L-valyl etser of acyclovir, following oral administration to humans. Antimicrob. Agents Chemother. 39:(12):1995;2759-2764.
    • (1995) Antimicrob. Agents Chemother. , vol.39 , Issue.12 , pp. 2759-2764
    • Soul-Lawton, J.1    Seaber, E.2    On, N.3    Wootton, R.4    Rolan, P.5    Posner, J.6
  • 5
    • 0032158915 scopus 로고    scopus 로고
    • Transport of L-valine-acyclovir via the oligopeptide transporter in the human intestinal cell line, Caco-2
    • de Vrueh R.L.A., Smith P.L., Lee C.-P. Transport of L-valine-acyclovir via the oligopeptide transporter in the human intestinal cell line, Caco-2. J. Pharmacol. Exp. Ther. 286:(3):1998;1166-1170.
    • (1998) J. Pharmacol. Exp. Ther. , vol.286 , Issue.3 , pp. 1166-1170
    • De Vrueh, R.L.A.1    Smith, P.L.2    Lee, C.-P.3
  • 6
    • 0031784111 scopus 로고    scopus 로고
    • Cellular uptake mechanism of amino acid ester prodrugs in Caco-2/hPEPT1 cells overexpressing a human peptide transporter
    • Han H.-K., Oh D.-M., Amidon G.L. Cellular uptake mechanism of amino acid ester prodrugs in Caco-2/hPEPT1 cells overexpressing a human peptide transporter. Pharm. Res. 15:(9):1998;1382-1386.
    • (1998) Pharm. Res. , vol.15 , Issue.9 , pp. 1382-1386
    • Han, H.-K.1    Oh, D.-M.2    Amidon, G.L.3
  • 8
    • 0030863826 scopus 로고    scopus 로고
    • Influence of oligopeptide transporter binding affinity upon uptake and transport of D-Asp(Obzl)-Ala and Asp(Obzl)-Sar in filter-grown Caco-2 monolayers
    • Taub M.E., Moss B.A., Steffansen B., Frokjaer S. Influence of oligopeptide transporter binding affinity upon uptake and transport of D-Asp(Obzl)-Ala and Asp(Obzl)-Sar in filter-grown Caco-2 monolayers. Int. J. Pharm. 156:1997;219-228.
    • (1997) Int. J. Pharm. , vol.156 , pp. 219-228
    • Taub, M.E.1    Moss, B.A.2    Steffansen, B.3    Frokjaer, S.4
  • 9
    • 0035845726 scopus 로고    scopus 로고
    • Dipeptide model prodrugs for the intestinal oligopeptide transporter. Affinity for and transport via hPepT1 in the human intestinal Caco-2 cell line
    • Nielsen C.U., Andersen R., Brodin B., Frokjaer S., Taub M.E., Steffansen B. Dipeptide model prodrugs for the intestinal oligopeptide transporter. Affinity for and transport via hPepT1 in the human intestinal Caco-2 cell line. J. Control. Release. 76:(1-2):2001;129-138.
    • (2001) J. Control. Release , vol.76 , Issue.1-2 , pp. 129-138
    • Nielsen, C.U.1    Andersen, R.2    Brodin, B.3    Frokjaer, S.4    Taub, M.E.5    Steffansen, B.6
  • 10
    • 0033017478 scopus 로고    scopus 로고
    • Stability, metabolism and transport of D-Asp(OBzl)-Ala - A model prodrug with affinity for the oligopeptide transporter
    • Steffansen B., Lepist E.-I., Taub M.E., Larsen B.D., Frokjaer S., Lennernäs H. Stability, metabolism and transport of D-Asp(OBzl)-Ala - a model prodrug with affinity for the oligopeptide transporter. Eur. J. Pharm. Sci. 8:1999;67-73.
    • (1999) Eur. J. Pharm. Sci. , vol.8 , pp. 67-73
    • Steffansen, B.1    Lepist, E.-I.2    Taub, M.E.3    Larsen, B.D.4    Frokjaer, S.5    Lennernäs, H.6
  • 12
    • 0035907176 scopus 로고    scopus 로고
    • Model prodrugs for the intestinal oligopeptide transporter: Model drug release in aqueous solution and in various biological media
    • Nielsen C.U., Andersen R., Brodin B., Frokjaer S., Steffansen B. Model prodrugs for the intestinal oligopeptide transporter: model drug release in aqueous solution and in various biological media. J. Control. Release. 73:(1):2001;21-30.
    • (2001) J. Control. Release , vol.73 , Issue.1 , pp. 21-30
    • Nielsen, C.U.1    Andersen, R.2    Brodin, B.3    Frokjaer, S.4    Steffansen, B.5
  • 13
    • 0031033894 scopus 로고    scopus 로고
    • Synthesis of dihydroisoxazole nucleoside and nucleotide analogues
    • Gi H.-J., Xiang Y., Schinazi R.F., Zhao K. Synthesis of dihydroisoxazole nucleoside and nucleotide analogues. J. Org. Chem. 62:(1):1997;88-92.
    • (1997) J. Org. Chem. , vol.62 , Issue.1 , pp. 88-92
    • Gi, H.-J.1    Xiang, Y.2    Schinazi, R.F.3    Zhao, K.4
  • 14
    • 0014275246 scopus 로고
    • N-Vinyl derivatives of substituted pyrimidines and purines
    • Pitha J., Ts'o P.O. N-Vinyl derivatives of substituted pyrimidines and purines. J. Org. Chem. 33:(4):1968;1341-1344.
    • (1968) J. Org. Chem. , vol.33 , Issue.4 , pp. 1341-1344
    • Pitha, J.1    Ts'o, P.O.2
  • 15
    • 0034938085 scopus 로고    scopus 로고
    • Model prodrugs designed for the intestinal peptide transporter. A synthetic approach for coupling of hydroxy-containing compounds to dipeptides
    • Friedrichsen G.M., Nielsen C.U., Steffansen B., Begtrup M. Model prodrugs designed for the intestinal peptide transporter. A synthetic approach for coupling of hydroxy-containing compounds to dipeptides. Eur. J. Pharm. Sci. 14:2001;13-19.
    • (2001) Eur. J. Pharm. Sci. , vol.14 , pp. 13-19
    • Friedrichsen, G.M.1    Nielsen, C.U.2    Steffansen, B.3    Begtrup, M.4
  • 17
    • 0031422606 scopus 로고    scopus 로고
    • Rat jejunal permeability and metabolism of μ-selective tetrapeptides in gastrointestinal fluids from humans and rats
    • Krondahl E., Orzechowski A., Ekström G., Lennernäs H. Rat jejunal permeability and metabolism of μ-selective tetrapeptides in gastrointestinal fluids from humans and rats. Pharm. Res. 14:(12):1997;1780-1785.
    • (1997) Pharm. Res. , vol.14 , Issue.12 , pp. 1780-1785
    • Krondahl, E.1    Orzechowski, A.2    Ekström, G.3    Lennernäs, H.4
  • 18
    • 0032507740 scopus 로고    scopus 로고
    • Drug absorption studies of prodrug esters using the Caco-2 model: Evaluation of ester hydrolysis and transepithelial transport
    • Augustijns P., Annaert P., Heylen P., Van den Mooter G., Kinget R. Drug absorption studies of prodrug esters using the Caco-2 model: evaluation of ester hydrolysis and transepithelial transport. Int. J. Pharm. 166:1998;45-53.
    • (1998) Int. J. Pharm. , vol.166 , pp. 45-53
    • Augustijns, P.1    Annaert, P.2    Heylen, P.3    Van den Mooter, G.4    Kinget, R.5
  • 19
    • 0012554865 scopus 로고
    • Kinetics and mechanism of degradation of mecillinam in aqueous solution
    • Larsen C., Bundgaard H. Kinetics and mechanism of degradation of mecillinam in aqueous solution. Arch. Pharm. Chemi. Sci. 5:1977;66-86.
    • (1977) Arch. Pharm. Chemi. Sci. , vol.5 , pp. 66-86
    • Larsen, C.1    Bundgaard, H.2
  • 21
    • 0036018543 scopus 로고    scopus 로고
    • Transport of peptidomimetic drugs by the intestinal di/tri-peptide transporter, PepT1
    • Brodin B., Nielsen C.U., Steffansen B., Frokjaer S. Transport of peptidomimetic drugs by the intestinal di/tri-peptide transporter, PepT1. Pharmacol. Toxicol. 90:2002;285-296.
    • (2002) Pharmacol. Toxicol. , vol.90 , pp. 285-296
    • Brodin, B.1    Nielsen, C.U.2    Steffansen, B.3    Frokjaer, S.4
  • 22
    • 0023481924 scopus 로고
    • Diketopiperazine formation, hydrolysis, and epimerization of the new dipeptide angiotensin-converting enzyme inhibitor RS-10085
    • Gu L., Strickley R.G. Diketopiperazine formation, hydrolysis, and epimerization of the new dipeptide angiotensin-converting enzyme inhibitor RS-10085. Pharm. Res. 4:(5):1987;392-397.
    • (1987) Pharm. Res. , vol.4 , Issue.5 , pp. 392-397
    • Gu, L.1    Strickley, R.G.2
  • 23
    • 0024243587 scopus 로고
    • Preformulation stability studies of the new dipeptide angiotensin-converting enzyme inhibitor RS-10029
    • Gu L., Strickley R.G. Preformulation stability studies of the new dipeptide angiotensin-converting enzyme inhibitor RS-10029. Pharm. Res. 5:(12):1988;765-771.
    • (1988) Pharm. Res. , vol.5 , Issue.12 , pp. 765-771
    • Gu, L.1    Strickley, R.G.2
  • 24
    • 0028118562 scopus 로고
    • Metabolic disposition of the acyclovir prodrug valaciclovir in the rat
    • Burnette T.C., de Miranda P. Metabolic disposition of the acyclovir prodrug valaciclovir in the rat. Drug Metab. Dispos. 22:(1):1994;60-64.
    • (1994) Drug Metab. Dispos. , vol.22 , Issue.1 , pp. 60-64
    • Burnette, T.C.1    De Miranda, P.2
  • 25
    • 0029076466 scopus 로고
    • Purification and characterization of a rat liver enzyme that hydrolyzes valaciclovir, the L-valyl ester prodrug of acyclovir
    • Burnette T.C., Harrington J.A., Reardon J.E., Merrill B.M., de Miranda P. Purification and characterization of a rat liver enzyme that hydrolyzes valaciclovir, the L-valyl ester prodrug of acyclovir. J. Biol. Chem. 270:(26):1995;15827-15831.
    • (1995) J. Biol. Chem. , vol.270 , Issue.26 , pp. 15827-15831
    • Burnette, T.C.1    Harrington, J.A.2    Reardon, J.E.3    Merrill, B.M.4    De Miranda, P.5
  • 26
    • 0034494463 scopus 로고    scopus 로고
    • Effect of ionization on the variable uptake of valacyclovir via the human intestinal peptide transporter (hPepT1) in CHO cells
    • Balimane P.V., Sinko P.J. Effect of ionization on the variable uptake of valacyclovir via the human intestinal peptide transporter (hPepT1) in CHO cells. Biopharm. Drug Dispos. 21:2000;165-174.
    • (2000) Biopharm. Drug Dispos. , vol.21 , pp. 165-174
    • Balimane, P.V.1    Sinko, P.J.2


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