The development of orally administrable gemcitabine prodrugs with d-enantiomer amino acids: Enhanced membrane permeability and enzymatic stability
Tài liệu tham khảo
van Moorsel, 1997, Gemcitabine: future prospects of single-agent and combination studies, Oncologist, 2, 127, 10.1634/theoncologist.2-3-127
Han, 1998, 5′-Amino acid esters of antiviral nucleosides, acyclovir, and AZT are absorbed by the intestinal PEPT1 peptide transporter, Pharm. Res., 15, 1154, 10.1023/A:1011919319810
Song, 2005, Amino acid ester prodrugs of the anticancer agent gemcitabine: synthesis, bioconversion, metabolic bioevasion, and hPEPT1-mediated transport, Mol. Pharm., 2, 157, 10.1021/mp049888e
Song, 2005, Amino acid ester prodrugs of the antiviral agent 2-bromo-5,6-dichloro-1-(beta-d-ribofuranosyl)benzimidazole as potential substrates of hPEPT1 transporter, J. Med. Chem., 48, 1274, 10.1021/jm049450i
Tolle-Sander, 2004, Increased acyclovir oral bioavailability via a bile acid conjugate, Mol. Pharm., 1, 40, 10.1021/mp034010t
Tsume, 2008, Enhanced cancer cell growth inhibition by dipeptide prodrugs of floxuridine: increased transporter affinity and metabolic stability, Mol. Pharm., 5, 717, 10.1021/mp800008c
Tsume, 2008, Enhanced absorption and growth inhibition with amino acid monoester prodrugs of floxuridine by targeting hPEPT1 transporters, Molecules, 13, 1441, 10.3390/molecules13071441
Kawaguchi, 1985, Specificity of esterases and structure of prodrug esters. II. Hydrolytic regeneration behavior of 5-fluoro-2′-deoxyuridine (FUdR) from 3′,5′-diesters of FUdR with rat tissue homogenates and plasma in relation to their antitumor activity, Chem. Pharm. Bull. (Tokyo), 33, 1652, 10.1248/cpb.33.1652
Landowski, 2005, Floxuridine amino acid ester prodrugs: enhancing Caco-2 permeability and resistance to glycosidic bond metabolism, Pharm. Res., 22, 1510, 10.1007/s11095-005-6156-9
Landowski, 2005, Targeted delivery to PEPT1-overexpressing cells: acidic, basic, and secondary floxuridine amino acid ester prodrugs, Mol. Cancer Ther., 4, 659, 10.1158/1535-7163.MCT-04-0290
Anand, 2003, Interactions of the dipeptide ester prodrugs of acyclovir with the intestinal oligopeptide transporter: competitive inhibition of glycylsarcosine transport in human intestinal cell line-Caco-2, J. Pharmacol. Exp. Therap., 304, 781, 10.1124/jpet.102.044313
Hatanaka, 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. Therap., 308, 1138, 10.1124/jpet.103.057109
Phan, 2003, Intra- and interindividual variabilities of valacyclovir oral bioavailability and effect of coadministration of an hPEPT1 inhibitor, Antimicrob. Agents Chemother., 47, 2351, 10.1128/AAC.47.7.2351-2353.2003
Anand, 2004, Pharmacokinetics of novel dipeptide ester prodrugs of acyclovir after oral administration: intestinal absorption and liver metabolism, J. Pharmacol. Exp. Therap., 311, 659, 10.1124/jpet.104.069997
Meredith, 2000, Modified amino acids and peptides as substrates for the intestinal peptide transporter PepT1, Eur. J. Biochem., 267, 3723, 10.1046/j.1432-1327.2000.01405.x
Nielsen, 2001, 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, 129, 10.1016/S0168-3659(01)00427-8
Satake, 2002, Transepithelial transport of the bioactive tripeptide, Val-Pro-Pro, in human intestinal Caco-2 cell monolayers, Biosci. Biotechnol. Biochem., 66, 378, 10.1271/bbb.66.378
Surendran, 1999, Evidence for overlapping substrate specificity between large neutral amino acid (LNAA) and dipeptide (hPEPT1) transporters for PD 158473, an NMDA antagonist, Pharm. Res., 16, 391, 10.1023/A:1018821718340
Wenzel, 1995, Stereoselective uptake of beta-lactam antibiotics by the intestinal peptide transporter, Br. J. Pharmacol., 116, 3021, 10.1111/j.1476-5381.1995.tb15958.x
Kahramanogullari, 2012, Algorithmic modeling quantifies the complementary contribution of metabolic inhibitions to gemcitabine efficacy, PLoS ONE, 7, e50176, 10.1371/journal.pone.0050176
Veltkamp, 2008, New insights into the pharmacology and cytotoxicity of gemcitabine and 2′,2′-difluorodeoxyuridine, Mol. Cancer Ther., 7, 2415, 10.1158/1535-7163.MCT-08-0137
O’Neill, 2002, Oral cancer treatment: developments in chemotherapy and beyond, Br. J. Cancer, 87, 933, 10.1038/sj.bjc.6600591
Birnie, 1963, Studies of fluorinated pyrimidines. Xviii. The degradation of 5-fluoro-2′-deoxyuridine and related compounds by nucleoside phosphorylase, Biochemistry, 2, 566, 10.1021/bi00903a031
Incecayir, 2013, Comparison of the permeability of metoprolol and labetalol in rat, mouse, and Caco-2 cells: use as a reference standard for BCS classification, Mol. Pharm., 10.1021/mp300410n
Tsume, 2011, The achievement of mass balance by simultaneous quantification of floxuridine prodrug, floxuridine, 5-fluorouracil, 5-dihydrouracil, alpha-fluoro-beta-ureidopropionate, alpha-fluoro-beta-alanine using LC–MS, J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 879, 915, 10.1016/j.jchromb.2011.02.045
Anand, 2002, Current prodrug strategies via membrane transporters/receptors, Expert Opin. Biol. Ther., 2, 607, 10.1517/14712598.2.6.607
Ganapathy, 1998, Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2, Biochem. Biophys. Res. Commun., 246, 470, 10.1006/bbrc.1998.8628
Steingrimsdottir, 2000, Bioavailability of aciclovir after oral administration of aciclovir and its prodrug valaciclovir to patients with leukopenia after chemotherapy, Antimicrob. Agents Chemother., 44, 207, 10.1128/AAC.44.1.207-209.2000
Weller, 1993, Pharmacokinetics of the acyclovir pro-drug valaciclovir after escalating single- and multiple-dose administration to normal volunteers, Clin. Pharmacol. Ther., 54, 595, 10.1038/clpt.1993.196
Eriksson, 2005, HPEPT1 affinity and translocation of selected Gln-Sar and Glu-Sar dipeptide derivatives, Mol. Pharm., 2, 242, 10.1021/mp050015+
Li, 1998, Structure–affinity relationships of Val-Val and Val-Val-Val stereoisomers with the apical oligopeptide transporter in human intestinal Caco-2 cells, J. Drug Target., 5, 317, 10.3109/10611869808997860
Vabeno, 2004, Phe-Gly dipeptidomimetics designed for the di-/tripeptide transporters PEPT1 and PEPT2: synthesis and biological investigations, J. Med. Chem., 47, 1060, 10.1021/jm031022+
Lorenzi, 2005, Amino acid ester prodrugs of 2-bromo-5,6-dichloro-1-(beta-d-ribofuranosyl)benzimidazole enhance metabolic stability in vitro and in vivo, J. Pharmacol. Exp. Therap., 314, 883, 10.1124/jpet.104.082412
Cao, 2012, Advances in research of PepT1-targeted prodrug, Asian J. Pharm. Sci., 7, 110
Tsume, 2012, The feasibility of enzyme targeted activation for amino acid/dipeptide monoester prodrugs of floxuridine; cathepsin D as a potential targeted enzyme, Molecules, 17, 3672, 10.3390/molecules17043672