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Volumn 14, Issue 2, 2012, Pages 108-114

Synthesis and evaluation of a dipeptide-drug conjugate library as substrates for PEPT1

Author keywords

azidothymidine dipeptide conjugates; click chemistry; competitive inhibition; PEPT1; single pass intestinal perfusion

Indexed keywords

ANTIMETABOLITE; COTRANSPORTER; DIPEPTIDE; SLC15A1 PROTEIN, HUMAN; ZIDOVUDINE;

EID: 84863130592     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co200141b     Document Type: Article
Times cited : (20)

References (38)
  • 1
    • 2342644210 scopus 로고    scopus 로고
    • Molecular and integrative physiology of intestinal peptide transport
    • DOI 10.1146/annurev.physiol.66.032102.144149
    • Daniel, H. Molecular and integrative physiology of intestinal peptide transport Annu. Rev. Physiol. 2004, 66, 361-384 (Pubitemid 40614448)
    • (2004) Annual Review of Physiology , vol.66 , pp. 361-384
    • Daniel, H.1
  • 2
    • 1442351172 scopus 로고    scopus 로고
    • Peptide transporters: Structure, function, regulation and application for drug delivery
    • DOI 10.2174/1389200043489153
    • Terada, T.; Inui, K. Peptide transporters: Structure, function, regulation, and application for drug delivery Curr. Drug Metab. 2004, 5 (1) 85-94 (Pubitemid 38292002)
    • (2004) Current Drug Metabolism , vol.5 , Issue.1 , pp. 85-94
    • Terada, T.1    Inui, K.-I.2
  • 3
    • 0034045632 scopus 로고    scopus 로고
    • Structure and function of eukaryotic peptide transporters
    • DOI 10.1007/s000180050040
    • Meredith, D.; Boyd, C. A. R. Structure and function of eukaryotic peptide transporters Cell. Mol. Life Sci. 2000, 57 (5) 754-778 (Pubitemid 30392034)
    • (2000) Cellular and Molecular Life Sciences , vol.57 , Issue.5 , pp. 754-778
    • Meredith, D.1    Boyd, C.A.R.2
  • 4
    • 0026931216 scopus 로고
    • Peptide absorption: A review of current concepts and future perspectives
    • Webb, K. E., Jr; Matthews, J. C.; DiRienzo, D. B. Peptide absorption: A review of current concepts and future perspectives J. Anim. Sci. 1992, 70 (10) 3248-3257
    • (1992) J. Anim. Sci. , vol.70 , Issue.10 , pp. 3248-3257
    • Webb Jr., K.E.1    Matthews, J.C.2    Dirienzo, D.B.3
  • 5
    • 33846503577 scopus 로고    scopus 로고
    • In; D'Mello, J. P. F. CAB International: Wallingford, U.K. Vol. issue, pp, ISBN 0-85199-654-x.
    • Krehbiel, C. R.; Matthews, J. C. In Amino Acids in Animal Nutrition; D'Mello, J. P. F., Ed.; CAB International: Wallingford, U.K., 2003; Vol. 5, issue 2, pp 41-70, ISBN 0-85199-654-x.
    • (2003) Amino Acids in Animal Nutrition , vol.5 , Issue.2 , pp. 41-70
    • Krehbiel, C.R.1    Matthews, J.C.2
  • 6
    • 0030805221 scopus 로고    scopus 로고
    • Carrier-mediated transport of oligopeptides in the human fibrosarcoma cell line HT1080
    • Nakanishi, T.; Tamai, I.; Sai, Y.; Sasaki, T.; Tsuji, A. Carrier-mediated transport of oligopeptides in the human fibrosarcoma cell line HT1080 Cancer Res. 1997, 57 (18) 4118-4122 (Pubitemid 27427706)
    • (1997) Cancer Research , vol.57 , Issue.18 , pp. 4118-4122
    • Nakanishi, T.1    Tamai, I.2    Sai, Y.3    Sasaki, T.4    Tsuji, A.5
  • 7
    • 0032005174 scopus 로고    scopus 로고
    • An oligopeptide transporter is expressed at high levels in the pancreatic carcinoma cell lines AsPc-1 and Capan-2
    • Gonzalez, D. E.; Covitz, K. M. Y.; Sadee, W.; Mrsny, R. J. An oligopeptide transporter is expressed at high levels in the pancreatic carcinoma cell lines AsPc-1 and Capan-2 Cancer Res. 1998, 58 (3) 519-525 (Pubitemid 28087417)
    • (1998) Cancer Research , vol.58 , Issue.3 , pp. 519-525
    • Gonzalez, D.E.1    Covitz, K.-M.Y.2    Sadee, W.3    Mrsny, R.J.4
  • 8
    • 0037012840 scopus 로고    scopus 로고
    • Breaching the membrane
    • Alper, J. Breaching the membrane Science(Washington, DC, U. S.) 2002, 296 (5569) 838-9
    • (2002) Science(Washington, DC, U. S.) , vol.296 , Issue.5569 , pp. 838-9
    • Alper, J.1
  • 9
    • 2942612987 scopus 로고    scopus 로고
    • Membrane transporter/receptor-targeted prodrug design: Strategies for human and veterinary drug development
    • DOI 10.1016/j.addr.2004.02.006, PII S0169409X04000699, Veterinary Drug Delivery: Part VI
    • Majumdar, S.; Duvvuri, S.; Mitra, A. K. Membrane transporter/receptor- targeted prodrug design: strategies for human and veterinary drug development Adv. Drug Delivery Rev. 2004, 56 (10) 1437-1452 (Pubitemid 38748825)
    • (2004) Advanced Drug Delivery Reviews , vol.56 , Issue.10 , pp. 1437-1452
    • Majumdar, S.1    Duvvuri, S.2    Mitra, A.K.3
  • 10
    • 18044374166 scopus 로고    scopus 로고
    • Targeted delivery to PEPT1-overexpressing cells: Acidic, basic, and secondary floxuridine amino acid ester prodrugs
    • DOI 10.1158/1535-7163.MCT-04-0290
    • Landowski, C. P.; Vig, B. S.; Song, X.; Amidon, G. L. Targeted delivery to PEPT1-overexpressing cells: Acidic, basic, and secondary floxuridine amino acid ester prodrugs Mol. Cancer Ther. 2005, 4 (4) 659-67 (Pubitemid 40601848)
    • (2005) Molecular Cancer Therapeutics , vol.4 , Issue.4 , pp. 659-667
    • Landowski, C.P.1    Vig, B.S.2    Song, X.3    Amidon, G.L.4
  • 11
    • 23844467048 scopus 로고    scopus 로고
    • Amino acid ester prodrugs of the anticancer agent gemcitabine: Synthesis, bioconversion, metabolic bioevasion, and hPEPT1-mediated transport
    • DOI 10.1021/mp049888e
    • 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. Pharmaceutics 2005, 2 (2) 157-167 (Pubitemid 41295363)
    • (2005) Molecular Pharmaceutics , vol.2 , Issue.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
  • 13
    • 23844467048 scopus 로고    scopus 로고
    • Amino acid ester prodrugs of the anticancer agent gemcitabine: Synthesis, bioconversion, metabolic bioevasion, and hPEPT1-mediated transport
    • DOI 10.1021/mp049888e
    • 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. Pharmaceutics 2005, 2 (2) 157-67 (Pubitemid 41295363)
    • (2005) Molecular Pharmaceutics , vol.2 , Issue.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
  • 14
    • 62649140994 scopus 로고    scopus 로고
    • Synthesis, transport, and pharmacokinetics of 5′-amino acid ester prodrugs of 1-β- d -arabinofuranosylcytosine
    • Sun, Y.; Sun, J.; Shi, S.; Jing, Y.; Yin, S.; Chen, Y.; Li, G.; Xu, Y.; He, Z. Synthesis, transport, and pharmacokinetics of 5′-amino acid ester prodrugs of 1-β- d -arabinofuranosylcytosine Mol. Pharmaceutics 2008, 6 (1) 315-325
    • (2008) Mol. Pharmaceutics , vol.6 , Issue.1 , pp. 315-325
    • Sun, Y.1    Sun, J.2    Shi, S.3    Jing, Y.4    Yin, S.5    Chen, Y.6    Li, G.7    Xu, Y.8    He, Z.9
  • 15
    • 48849097095 scopus 로고    scopus 로고
    • Enhanced absorption and growth inhibition with amino acid monoester prodrugs of floxuridine by targeting hPEPT1 transporters
    • Tsume, Y.; Vig, B. S.; Sun, J.; Landowski, C. P.; Hilfinger, J. M.; Ramachandran, C.; Amidon, G. L. Enhanced absorption and growth inhibition with amino acid monoester prodrugs of floxuridine by targeting hPEPT1 transporters Molecules 2008, 13 (7) 1441-54
    • (2008) Molecules , vol.13 , Issue.7 , pp. 1441-54
    • Tsume, Y.1    Vig, B.S.2    Sun, J.3    Landowski, C.P.4    Hilfinger, J.M.5    Ramachandran, C.6    Amidon, G.L.7
  • 16
    • 0034214201 scopus 로고    scopus 로고
    • Synthesis, in vitro anti-breast cancer activity, and intracellular decomposition of amino acid methyl ester and alkyl amide phosphoramidate monoesters of 3'-azido-3'-deoxythymidine (AZT)
    • DOI 10.1021/jm000110g
    • Iyer, V. V.; Griesgraber, G. W.; Radmer, M. R.; McIntee, E. J.; Wagner, C. R. Synthesis, in vitro anti-breast cancer activity, and intracellular decomposition of amino acid methyl ester and alkyl amide phosphoramidate monoesters of 3-azido-3-deoxythymidine (AZT) J. Med. Chem. 2000, 43 (11) 2266-2274 (Pubitemid 30354551)
    • (2000) Journal of Medicinal Chemistry , vol.43 , Issue.11 , pp. 2266-2274
    • Iyer, V.V.1    Griesgraber, G.W.2    Radmer, M.R.3    McIntee, E.J.4    Wagner, C.R.5
  • 17
    • 56049109562 scopus 로고    scopus 로고
    • Enhanced cancer cell growth inhibition by dipeptide prodrugs of floxuridine: Increased transporter affinity and metabolic stability
    • Tsume, Y.; Hilfinger, J. M.; Amidon, G. L. Enhanced cancer cell growth inhibition by dipeptide prodrugs of floxuridine: Increased transporter affinity and metabolic stability Mol. Pharmaceutics 2008, 5 (5) 717-27
    • (2008) Mol. Pharmaceutics , vol.5 , Issue.5 , pp. 717-27
    • Tsume, Y.1    Hilfinger, J.M.2    Amidon, G.L.3
  • 19
    • 48149103948 scopus 로고    scopus 로고
    • Dipeptide derivatives of AZT: Synthesis, chemical stability, activation in human plasma, hPEPT1 affinity, and antiviral activity
    • Santos, C.; Morais, J.; Gouveia, L.; De Clercq, E.; Pannecouque, C.; Nielsen, C. U.; Steffansen, B.; Moreira, R.; Gomes, P. Dipeptide derivatives of AZT: Synthesis, chemical stability, activation in human plasma, hPEPT1 affinity, and antiviral activity ChemMedChem 2008, 3 (6) 970-978
    • (2008) ChemMedChem , vol.3 , Issue.6 , pp. 970-978
    • Santos, C.1    Morais, J.2    Gouveia, L.3    De Clercq, E.4    Pannecouque, C.5    Nielsen, C.U.6    Steffansen, B.7    Moreira, R.8    Gomes, P.9
  • 20
    • 0037380335 scopus 로고    scopus 로고
    • Current perspectives on established and putative mammalian oligopeptide transporters
    • DOI 10.1002/jps.10303
    • Herrera-Ruiz, D.; Knipp, G. T. Current perspectives on established and putative mammalian oligopeptide transporters J. Pharm. Sci. 2003, 92 (4) 691-714 (Pubitemid 36396989)
    • (2003) Journal of Pharmaceutical Sciences , vol.92 , Issue.4 , pp. 691-714
    • Herrera-Ruiz, D.1    Knipp, G.T.2
  • 21
    • 77950543534 scopus 로고    scopus 로고
    • Bioavailability through PepT1: The role of computer modelling in intelligent drug design
    • Foley, D. W.; Rajamanickam, J.; Bailey, P. D.; Meredith, D. Bioavailability through PepT1: The role of computer modelling in intelligent drug design Curr. Comput.-Aided Drug Des. 2010, 6 (1) 68-78
    • (2010) Curr. Comput.-Aided Drug Des. , vol.6 , Issue.1 , pp. 68-78
    • Foley, D.W.1    Rajamanickam, J.2    Bailey, P.D.3    Meredith, D.4
  • 22
    • 40849092489 scopus 로고    scopus 로고
    • Quantitative prediction of oral absorption of PEPT1 substrates based on in vitro uptake into Caco-2 cells
    • Shimizu, R.; Sukegawa, T.; Tsuda, Y.; Itoh, T. Quantitative prediction of oral absorption of PEPT1 substrates based on in vitro uptake into Caco-2 cells Int. J. Pharm. 2008, 354 (1-2) 104-110
    • (2008) Int. J. Pharm. , vol.354 , Issue.1-2 , pp. 104-110
    • Shimizu, R.1    Sukegawa, T.2    Tsuda, Y.3    Itoh, T.4
  • 23
    • 0348109450 scopus 로고    scopus 로고
    • The growing impact of click chemistry on drug discovery
    • DOI 10.1016/S1359-6446(03)02933-7, PII S1359644603029337
    • Kolb, H. C.; Sharpless, K. B. The growing impact of click chemistry on drug discovery Drug Discovery Today 2003, 8 (24) 1128-1137 (Pubitemid 37547919)
    • (2003) Drug Discovery Today , vol.8 , Issue.24 , pp. 1128-1137
    • Kolb, H.C.1    Sharpless, K.B.2
  • 24
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • DOI 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
    • Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective ligation of azides and terminal alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599 (Pubitemid 34803480)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.14 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 25
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: Diverse chemical function from a few good reactions
    • Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Click chemistry: Diverse chemical function from a few good reactions Angew. Chem., Int. Ed. 2001, 40 (11) 2004-2021
    • (2001) Angew. Chem., Int. Ed. , vol.40 , Issue.11 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 26
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • DOI 10.1021/jo011148j
    • Tornoe, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on solid phase:[1,2,3]-triazoles by regiospecific copper (I)-catalyzed 1, 3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 2002, 67 (9) 3057-3064 (Pubitemid 34457265)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.9 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 27
    • 34548566907 scopus 로고    scopus 로고
    • On-resin cyclization of peptide ligands of the Vascular Endothelial Growth Factor Receptor 1 by copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition
    • DOI 10.1016/j.bmcl.2007.07.087, PII S0960894X07009237
    • Goncalves, V.; Gautier, B.; Regazzetti, A.; Coric, P.; Bouaziz, S.; Garbay, C.; Vidal, M.; Inguimbert, N. On-resin cyclization of peptide ligands of the vascular endothelial growth factor receptor 1 by copper(I)-catalyzed 1,3-dipolar azide-alkyne cycloaddition Bioorg. Med. Chem. Lett. 2007, 17 (20) 5590-5594 (Pubitemid 47391317)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.20 , pp. 5590-5594
    • Goncalves, V.1    Gautier, B.2    Regazzetti, A.3    Coric, P.4    Bouaziz, S.5    Garbay, C.6    Vidal, M.7    Inguimbert, N.8
  • 28
    • 0029637161 scopus 로고
    • Chemical instability of protein pharmaceuticals: Mechanisms of oxidation and strategies for stabilization
    • Li, S.; Sch neich, C.; Borchardt, R. T. Chemical instability of protein pharmaceuticals: Mechanisms of oxidation and strategies for stabilization Biotechnol. Bioeng. 1995, 48 (5) 490-500
    • (1995) Biotechnol. Bioeng. , vol.48 , Issue.5 , pp. 490-500
    • Li, S.1    Sch Neich, C.2    Borchardt, R.T.3
  • 31
    • 42949174825 scopus 로고    scopus 로고
    • Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting
    • Li, F. J.; Maag, H.; Alfredson, T. Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting J. Pharm. Sci. 2008, 97 (3) 1109-1134
    • (2008) J. Pharm. Sci. , vol.97 , Issue.3 , pp. 1109-1134
    • Li, F.J.1    Maag, H.2    Alfredson, T.3
  • 32
    • 0031723044 scopus 로고    scopus 로고
    • Overexpression of human intestinal oligopeptide transporter in mammalian cells via adenoviral transduction
    • DOI 10.1023/A:1011993303397
    • Hsu, C. P.; Hilfinger, J. M.; Walter, E.; Merkle, H. P.; Roessler, B. J.; Amidon, G. L. Overexpression of human intestinal oligopeptide transporter in mammalian cells via adenoviral transduction Pharm. Res. 1998, 15 (9) 1376-1381 (Pubitemid 28427924)
    • (1998) Pharmaceutical Research , vol.15 , Issue.9 , pp. 1376-1381
    • Hsu, C.-P.1    Hilfinger, J.M.2    Walter, E.3    Merkle, H.P.4    Roessler, B.J.5    Amidon, G.L.6
  • 33
    • 0025046860 scopus 로고
    • Uptake of the cephalosporin, cephalexin, by a dipeptide transport carrier in the human intestinal cell line, Caco-2
    • DOI 10.1016/0005-2736(90)90309-C
    • Dantzig, A. H.; Bergin, L. Uptake of the cephalosporin, cephalexin, by a dipeptide transport carrier in the human intestinal cell line, Caco-2 Biochim. Biophys. Acta, Biomembr. 1990, 1027 (3) 211-217 (Pubitemid 20279132)
    • (1990) Biochimica et Biophysica Acta - Biomembranes , vol.1027 , Issue.3 , pp. 211-217
    • Dantzig, A.H.1    Bergin, L.2
  • 35
    • 0029022956 scopus 로고
    • Oral absorption of anti-aids nucleoside analogues. 1. Intestinal transport of didanosine in rat and rabbit preparations
    • Sinko, P. J.; Hu, P.; Waclawski, A. P.; Patel, N. R. Oral absorption of anti-aids nucleoside analogues. 1. Intestinal transport of didanosine in rat and rabbit preparations J. Pharm. Sci. 1995, 84 (8) 959-965
    • (1995) J. Pharm. Sci. , vol.84 , Issue.8 , pp. 959-965
    • Sinko, P.J.1    Hu, P.2    Waclawski, A.P.3    Patel, N.R.4
  • 36
    • 0032912781 scopus 로고    scopus 로고
    • High in situ rat intestinal permeability of artemisinin unaffected by multiple dosing and with no evidence of P-glycoprotein involvement
    • Svensson, U. S. H.; Sandstr m, R.; Carlborg; Lennern s, H.; Ashton, M. High in situ rat intestinal permeability of artemisinin unaffected by multiple dosing and with no evidence of P-glycoprotein involvement Drug Metab. Dispos. 1999, 27 (2) 227
    • (1999) Drug Metab. Dispos. , vol.27 , Issue.2 , pp. 227
    • Svensson, U.S.H.1    Sandstr, M.R.2    Carlborg3    Lennern, S.H.4    Ashton, M.5
  • 37
    • 0019133312 scopus 로고
    • Analysis of models for determining intestinal wall permeabilities
    • DOI 10.1002/jps.2600691204
    • Amidon, G. L.; Kou, J.; Elliott, R. L.; Lightfoot, E. N. Analysis of models for determining intestinal wall permeabilities J. Pharm. Sci. 1980, 69 (12) 1369-1373 (Pubitemid 11172811)
    • (1980) Journal of Pharmaceutical Sciences , vol.69 , Issue.12 , pp. 1369-1373
    • Amidon, G.L.1    Kou, J.2    Elliott, R.L.3    Lightfoot, E.N.4
  • 38
    • 34247567472 scopus 로고    scopus 로고
    • Intestinal absorption of novel-dipeptide prodrugs of saquinavir in rats
    • DOI 10.1016/j.ijpharm.2006.11.058, PII S0378517306010362
    • Jain, R.; Duvvuri, S.; Kansara, V.; Mandava, N. K.; Mitra, A. K. Intestinal absorption of novel-dipeptide prodrugs of saquinavir in rats Int. J. Pharm. 2007, 336 (2) 233-240 (Pubitemid 46670646)
    • (2007) International Journal of Pharmaceutics , vol.336 , Issue.2 , pp. 233-240
    • Jain, R.1    Duvvuri, S.2    Kansara, V.3    Mandava, N.K.4    Mitra, A.K.5


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