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Volumn 49, Issue 12, 2006, Pages 3636-3644

Human PEPT1 pharmacophore distinguishes between dipeptide transport and binding

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC G 418; DIPEPTIDE; PEPTIDE TRANSPORTER 1; TRIPEPTIDE; TRYPTOPHAN; TYROSINE;

EID: 33745134044     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0511029     Document Type: Article
Times cited : (114)

References (46)
  • 1
    • 0036710840 scopus 로고    scopus 로고
    • Mammalian peptide transporters as targets for drug delivery
    • Rubio-Aliaga, I.; Daniel, H. Mammalian Peptide Transporters as Targets for Drug Delivery. Trends Pharmacol. Sci. 2002, 23, 434-440.
    • (2002) Trends Pharmacol. Sci. , vol.23 , pp. 434-440
    • Rubio-Aliaga, I.1    Daniel, H.2
  • 3
    • 0037380335 scopus 로고    scopus 로고
    • Current perspectives on established and putative mammalian oligopeptide transporters
    • Herrera-Ruiz, D.; Knipp, G. T. Current Perspectives on Established and Putative Mammalian Oligopeptide Transporters. J. Pharm. Sci. 2003, 92, 691-714.
    • (2003) J. Pharm. Sci. , vol.92 , pp. 691-714
    • Herrera-Ruiz, D.1    Knipp, G.T.2
  • 4
    • 0025757375 scopus 로고
    • The high and low affinity transport systems for dipeptides in kidney brush border membrane respond differently to alterations in pH gradient and membrane potential
    • Daniel, H.; Morse, E. L.; Adibi, S. A. The High and Low Affinity Transport Systems for Dipeptides in Kidney Brush Border Membrane Respond Differently to Alterations in pH Gradient and Membrane Potential. J. Biol. Chem. 1991, 266, 19917-19924.
    • (1991) J. Biol. Chem. , vol.266 , pp. 19917-19924
    • Daniel, H.1    Morse, E.L.2    Adibi, S.A.3
  • 6
    • 0035887256 scopus 로고    scopus 로고
    • Bidirectional electrogenic transport of peptides by the proton-coupled carrier pept1 in xenopus laevis oocytes: Its asymmetry and symmetry
    • Kottra, G.; Daniel, H. Bidirectional Electrogenic Transport of Peptides by the Proton-Coupled Carrier Pept1 in Xenopus Laevis Oocytes: Its Asymmetry and Symmetry. J. Physiol. (London, U.K.) 2001, 536, 495-503.
    • (2001) J. Physiol. (London, U.K.) , vol.536 , pp. 495-503
    • Kottra, G.1    Daniel, H.2
  • 7
    • 0031972453 scopus 로고    scopus 로고
    • Molecular and structural features of the proton-coupled oligopeptide transporter superfamily
    • Fei, Y. J.; Ganapathy, V.; Leibach, F. H. Molecular and Structural Features of the Proton-Coupled Oligopeptide Transporter Superfamily. Prog. Nucleic Acid Res. Mol. Biol. 1998, 58, 239-261.
    • (1998) Prog. Nucleic Acid Res. Mol. Biol. , vol.58 , pp. 239-261
    • Fei, Y.J.1    Ganapathy, V.2    Leibach, F.H.3
  • 8
    • 0031428338 scopus 로고    scopus 로고
    • Localization of peptide transporter in nuclei and lysosomes of the pancreas
    • Bookman, D. E.; Ganapathy, V.; Oblak, T. G.; Leibach, F. H. Localization of Peptide Transporter in Nuclei and Lysosomes of the Pancreas. Int. J. Pancreatol. 1997, 22, 221-225.
    • (1997) Int. J. Pancreatol. , vol.22 , pp. 221-225
    • Bookman, D.E.1    Ganapathy, V.2    Oblak, T.G.3    Leibach, F.H.4
  • 10
    • 0032967296 scopus 로고    scopus 로고
    • 3rd localization of pept1 and pept2 proton-coupled oligopeptide transporter Mrna and protein in rat kidney
    • Shen, H.; Smith, D. E.; Yang, T.; Huang, Y. G.; Schnermann, J. B.; Brosius, F. C., 3rd Localization of Pept1 and Pept2 Proton-Coupled Oligopeptide Transporter Mrna and Protein in Rat Kidney. Am. J. Physiol 1999, 276, F658-665.
    • (1999) Am. J. Physiol , vol.276
    • Shen, H.1    Smith, D.E.2    Yang, T.3    Huang, Y.G.4    Schnermann, J.B.5    Brosius, F.C.6
  • 11
    • 0041353145 scopus 로고    scopus 로고
    • Structure and mechanism of the lactose permease of Escherichia coli
    • Abramson, J.; Smirnova, I.; Kasho, V.; Verner, G.; Kaback, H. R.; Iwata, S. Structure and Mechanism of the Lactose Permease of Escherichia coli. Science 2003, 301, 610-615.
    • (2003) Science , vol.301 , pp. 610-615
    • Abramson, J.1    Smirnova, I.2    Kasho, V.3    Verner, G.4    Kaback, H.R.5    Iwata, S.6
  • 12
    • 0030912006 scopus 로고    scopus 로고
    • Symmetry of H+ binding to the intra- and extracellular side of the H+-coupled oligopeptide cotransporter pept1
    • Nussberger, S.; Steel, A.; Trotti, D.; Romero, M. F.; Boron, W. F.; Hediger, M. A. Symmetry of H+ Binding to the Intra- and Extracellular Side of the H+-Coupled Oligopeptide Cotransporter Pept1. J. Biol. Chem. 1997, 272, 7777-7785.
    • (1997) J. Biol. Chem. , vol.272 , pp. 7777-7785
    • Nussberger, S.1    Steel, A.2    Trotti, D.3    Romero, M.F.4    Boron, W.F.5    Hediger, M.A.6
  • 14
    • 21244441988 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter pept1
    • Biegel, A.; Gebauer, S.; Hartrodt, B.; Brandsch, M.; Neubert, K.; Thondorf, I. Three-Dimensional Quantitative Structure-Activity Relationship Analyses of Beta-Lactam Antibiotics and Tripeptides as Substrates of the Mammalian H+/Peptide Cotransporter Pept1. J. Med. Chem. 2005, 48, 4410-4419.
    • (2005) J. Med. Chem. , vol.48 , pp. 4410-4419
    • Biegel, A.1    Gebauer, S.2    Hartrodt, B.3    Brandsch, M.4    Neubert, K.5    Thondorf, I.6
  • 15
    • 13844310290 scopus 로고    scopus 로고
    • Conformational restrictions in ligand binding to the human intestinal di-/tripeptide transporter: Implications for design of Hpept1 targeted prodrugs
    • Vabeno, J.; Nielsen, C. U.; Steffansen, B.; Lejon, T.; Sylte, I.; Jorgensen, F. S.; Luthman, K. Conformational Restrictions in Ligand Binding to the Human Intestinal Di-/Tripeptide Transporter: Implications for Design of Hpept1 Targeted Prodrugs. Bioorg. Med. Chem. 2005, 13, 1977-1988.
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 1977-1988
    • Vabeno, J.1    Nielsen, C.U.2    Steffansen, B.3    Lejon, T.4    Sylte, I.5    Jorgensen, F.S.6    Luthman, K.7
  • 16
    • 0346366456 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationship analyses of peptide substrates of the mammalian H+/peptide cotransporter pept1
    • Gebauer, S.; Knutter, I.; Hartrodt, B.; Brandsch, M.; Neubert, K.; Thondorf, I. Three-Dimensional Quantitative Structure-Activity Relationship Analyses of Peptide Substrates of the Mammalian H+/Peptide Cotransporter Pept1. J. Med. Chem. 2003, 46, 5725-5734.
    • (2003) J. Med. Chem. , vol.46 , pp. 5725-5734
    • Gebauer, S.1    Knutter, I.2    Hartrodt, B.3    Brandsch, M.4    Neubert, K.5    Thondorf, I.6
  • 17
    • 1242272750 scopus 로고    scopus 로고
    • The proton oligopeptide cotransporter family Slc15 in physiology and pharmacology
    • Daniel, H.; Kottra, G. The Proton Oligopeptide Cotransporter Family Slc15 in Physiology and Pharmacology. Pflugers Arch. 2004, 447, 610-618.
    • (2004) Pflugers Arch. , vol.447 , pp. 610-618
    • Daniel, H.1    Kottra, G.2
  • 19
    • 84962464696 scopus 로고    scopus 로고
    • Minimal molecular determinants of substrates for recognition by the intestinal peptide transporter
    • During, F.; Will, J.; Amasheh, S.; Clauss, W.; Ahlbrecht, H.; Daniel, H. Minimal Molecular Determinants of Substrates for Recognition by the Intestinal Peptide Transporter. J. Biol. Chem. 1998, 273, 23211-23218.
    • (1998) J. Biol. Chem. , vol.273 , pp. 23211-23218
    • During, F.1    Will, J.2    Amasheh, S.3    Clauss, W.4    Ahlbrecht, H.5    Daniel, H.6
  • 20
    • 0032512649 scopus 로고    scopus 로고
    • Evidence for the absolute conformational specificity of the intestinal H+/peptide symporter, pept1
    • Brandsch, M.; Thunecke, F.; Kullertz, G.; Schutkowski, M.; Fischer, G.; Neubert, K. Evidence for the Absolute Conformational Specificity of the Intestinal H+/Peptide Symporter, Pept1. J. Biol. Chem. 1998, 273, 3861-3864.
    • (1998) J. Biol. Chem. , vol.273 , pp. 3861-3864
    • Brandsch, M.1    Thunecke, F.2    Kullertz, G.3    Schutkowski, M.4    Fischer, G.5    Neubert, K.6
  • 21
    • 0842304421 scopus 로고    scopus 로고
    • Phe-gly dipeptidomimetics designed for the di-/tripeptide transporters pept1 and pept2: Synthesis and biological investigations
    • Vabeno, J.; Lejon, T.; Nielsen, C. U.; Steffansen, B.; Chen, W.; Ouyang, H.; Borchardt, R. T.; Luthman, K. Phe-Gly Dipeptidomimetics Designed for the Di-/Tripeptide Transporters Pept1 and Pept2: Synthesis and Biological Investigations. J. Med. Chem. 2004, 47, 1060-1069.
    • (2004) J. Med. Chem. , vol.47 , pp. 1060-1069
    • Vabeno, J.1    Lejon, T.2    Nielsen, C.U.3    Steffansen, B.4    Chen, W.5    Ouyang, H.6    Borchardt, R.T.7    Luthman, K.8
  • 23
    • 0031567719 scopus 로고    scopus 로고
    • Enhancement of the small intestinal uptake of phenylalanylglycine via a H+/oligopeptide transport system by chemical modification with fatty acids
    • Fujita, T.; Morishita, Y.; Ito, H.; Kuribayashi, D.; Yamamoto, A.; Muranishi, S. Enhancement of the Small Intestinal Uptake of Phenylalanylglycine Via a H+/Oligopeptide Transport System by Chemical Modification with Fatty Acids. Life Sci. 1997, 61, 2455-2465.
    • (1997) Life Sci. , vol.61 , pp. 2455-2465
    • Fujita, T.1    Morishita, Y.2    Ito, H.3    Kuribayashi, D.4    Yamamoto, A.5    Muranishi, S.6
  • 26
    • 0028899786 scopus 로고
    • Structural requirements for interaction with the oligopeptide transporter in caco-2 cells
    • Hidalgo, I. J.; Bhatnagar, P.; Lee, C. P.; Miller, J.; Cucullino, G.; Smith, P. L. Structural Requirements for Interaction with the Oligopeptide Transporter in Caco-2 Cells. Pharm. Res. 1995, 12, 317-319.
    • (1995) Pharm. Res. , vol.12 , pp. 317-319
    • Hidalgo, I.J.1    Bhatnagar, P.2    Lee, C.P.3    Miller, J.4    Cucullino, G.5    Smith, P.L.6
  • 27
    • 0030455379 scopus 로고    scopus 로고
    • Metabolism, uptake, and transepithelial transport of the stereoisomers of val-val-val in the human intestinal cell line, caco-2
    • Tamura, K.; Lee, C. P.; Smith, P. L.; Borchardt, R. T. Metabolism, Uptake, and Transepithelial Transport of the Stereoisomers of Val-Val-Val in the Human Intestinal Cell Line, Caco-2. Pharm. Res. 1996, 13, 1663-1667.
    • (1996) Pharm. Res. , vol.13 , pp. 1663-1667
    • Tamura, K.1    Lee, C.P.2    Smith, P.L.3    Borchardt, R.T.4
  • 28
    • 0032695909 scopus 로고    scopus 로고
    • Recognition of L-amino acid ester compounds by rat peptide transporters pept1 and pept2
    • Sawada, K.; Terada, T.; Saito, H.; Hashimoto, Y.; Inui, K. I. Recognition of L-Amino Acid Ester Compounds by Rat Peptide Transporters Pept1 and Pept2. J. Pharmacol. Exp. Ther. 1999, 291, 705-709.
    • (1999) J. Pharmacol. Exp. Ther. , vol.291 , pp. 705-709
    • Sawada, K.1    Terada, T.2    Saito, H.3    Hashimoto, Y.4    Inui, K.I.5
  • 29
    • 0033812060 scopus 로고    scopus 로고
    • Structural requirements for determining the substrate affinity of peptide transporters pept1 and pept2
    • Terada, T.; Sawada, K.; Irie, M.; Saito, H.; Hashimoto, Y.; Inui, K. Structural Requirements for Determining the Substrate Affinity of Peptide Transporters Pept1 and Pept2. Pflugers Arch. 2000, 440, 679-684.
    • (2000) Pflugers Arch. , vol.440 , pp. 679-684
    • Terada, T.1    Sawada, K.2    Irie, M.3    Saito, H.4    Hashimoto, Y.5    Inui, K.6
  • 32
    • 0030946942 scopus 로고    scopus 로고
    • Molecular determinants of recognition for the intestinal peptide carrier
    • Swaan, P. W.; Tukker, J. J. Molecular Determinants of Recognition for the Intestinal Peptide Carrier. J. Pharm. Sci. 1997, 86, 596-602.
    • (1997) J. Pharm. Sci. , vol.86 , pp. 596-602
    • Swaan, P.W.1    Tukker, J.J.2
  • 33
    • 0032466466 scopus 로고    scopus 로고
    • Mapping the binding site of the small intestinal peptide carrier (Pept1) using comparative molecular field analysis
    • Swaan, P. W.; Koops, B. C.; Moret, E. E.; Tukker, J. J. Mapping the Binding Site of the Small Intestinal Peptide Carrier (Pept1) Using Comparative Molecular Field Analysis. Recept. Channels 1998, 6, 189-200.
    • (1998) Recept. Channels , vol.6 , pp. 189-200
    • Swaan, P.W.1    Koops, B.C.2    Moret, E.E.3    Tukker, J.J.4
  • 36
    • 0031008576 scopus 로고    scopus 로고
    • Hydrophobicity regained
    • Karplus, P. A. Hydrophobicity Regained. Protein Sci. 1997, 6, 1302-1307.
    • (1997) Protein Sci. , vol.6 , pp. 1302-1307
    • Karplus, P.A.1
  • 40
    • 0346098120 scopus 로고    scopus 로고
    • The intestinal H+/peptide symporter pept1: Structure-affinity relationships
    • Brandsch, M.; Knutter, I.; Leibach, F. H. The Intestinal H+/Peptide Symporter Pept1: Structure-Affinity Relationships. Eur. J. Pharm. Sci. 2004, 21, 53-60.
    • (2004) Eur. J. Pharm. Sci. , vol.21 , pp. 53-60
    • Brandsch, M.1    Knutter, I.2    Leibach, F.H.3
  • 41
    • 2642602528 scopus 로고    scopus 로고
    • Delta-aminolevulinic acid transport by intestinal and renal peptide transporters and its physiological and clinical implications
    • Doring, F.; Walter, J.; Will, J.; Focking, M.; Boll, M.; Amasheh, S.; Clauss, W.; Daniel, H. Delta-Aminolevulinic Acid Transport by Intestinal and Renal Peptide Transporters and Its Physiological and Clinical Implications. J. Clin. Invest. 1998, 101, 2761-2767.
    • (1998) J. Clin. Invest. , vol.101 , pp. 2761-2767
    • Doring, F.1    Walter, J.2    Will, J.3    Focking, M.4    Boll, M.5    Amasheh, S.6    Clauss, W.7    Daniel, H.8
  • 43
    • 23844467048 scopus 로고    scopus 로고
    • Amino acid ester prodrugs of the anticancer agent gemcitabine: Synthesis. Bioconversion, metabolic bioevasion, and Hpept1-mediated transport
    • Song, X.; Lorenzi, P. L.; Landowski, C. P.; Vig, B. S.; Hilfinger, J. M.; Amidon, G. L. Amino Acid Ester Prodrugs of the Anticancer Agent Gemcitabine: Synthesis. Bioconversion, Metabolic Bioevasion, and Hpept1-Mediated Transport. Mol. Pharm. 2005, 2, 157-167.
    • (2005) Mol. Pharm. , vol.2 , pp. 157-167
    • Song, X.1    Lorenzi, P.L.2    Landowski, C.P.3    Vig, B.S.4    Hilfinger, J.M.5    Amidon, G.L.6
  • 44
    • 0030054574 scopus 로고    scopus 로고
    • Molecular modeling study of structural requirements for the oligopeptide transporter
    • Li, J.; Hidalgo, I. J. Molecular Modeling Study of Structural Requirements for the Oligopeptide Transporter. J. Drug Targeting 1996, 4, 9-17.
    • (1996) J. Drug Targeting , vol.4 , pp. 9-17
    • Li, J.1    Hidalgo, I.J.2


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