A biological stabilization technology for peptide drugs: enzymatic introduction of thioether-bridges
Tài liệu tham khảo
Li, 2002, Cyclization strategies in peptide derived drug design, Curr. Top. Med. Chem., 2, 325, 10.2174/1568026023394209
Tugyi, 2005, The effect of cyclization on the enzymatic degradation of herpes simplex virus glycoprotein D derived epitope peptide, J. Pept. Sci., 11, 642, 10.1002/psc.669
Xie, 2004, Lacticin 481: in vitro reconstitution of lantibiotic synthetase activity, Science, 303, 679, 10.1126/science.1092600
Furgerson Ihnken, 2008, In vitro reconstitution and substrate specificity of a lantibiotic protease, Biochemistry, 47, 7352, 10.1021/bi800278n
Zhang, 2007, On the regioselectivity of thioether formation by lacticin 481 synthetase, Org. Lett., 9, 3343, 10.1021/ol071301h
Paul, 2007, Mutants of the zinc ligands of lacticin 481 synthetase retain dehydration activity but have impaired cyclization activity, Biochemistry, 46, 6268, 10.1021/bi7000104
Kuipers, 2004, NisT, the transporter of the lantibiotic nisin, can transport fully modified, dehydrated, and unmodified prenisin and fusions of the leader peptide with non-lantibiotic peptides, J. Biol. Chem., 279, 22176, 10.1074/jbc.M312789200
Kuipers, 2008, Mechanistic dissection of the enzyme complexes involved in the biosynthesis of nisin and lacticin 3147, Appl. Environ. Microbiol., 74, 6591, 10.1128/AEM.01334-08
Rink, 2007, Production of dehydroamino acid-containing peptides by L. lactis, Appl. Environ. Microbiol., 73, 1792, 10.1128/AEM.02350-06
Rink, 2005, Lantibiotic structures as guidelines for the design of peptides that can be modified by lantibiotic enzymes, Biochemistry, 44, 8873, 10.1021/bi050081h
Kuipers, 2006, Sec-mediated transport of post-translationally dehydrated peptides in Lactococcus lactis, Appl. Environ. Microbiol., 72, 7626, 10.1128/AEM.01802-06
Kuipers, A. et al. (2009) Translocation of a thioether-bridged azurin peptide fragment via the Sec pathway in L. lactis. Epub ahead of print
Okeley, 2000, Facile chemoselective synthesis of dehydroalanine-containing peptides, Org. Lett., 2, 3603, 10.1021/ol006485d
Kluskens, 2005, Post-translational modification of therapeutic peptides by NisB, the dehydratase of the lantibiotic nisin, Biochemistry, 44, 12827, 10.1021/bi050805p
Rink, 2007, NisC, the cyclase of the lantibiotic nisin, can catalyze cyclization of designed non-lantibiotic peptides, Biochemistry, 46, 13179, 10.1021/bi700106z
Rink, 2007, Dissection and modulation of the four distinct activities of nisin by mutagenesis of rings A and B and by C-terminal truncation, Appl. Environ. Microbiol., 73, 5809, 10.1128/AEM.01104-07
Bierbaum, 1996, Engineering of a novel thioether-bridge and role of modified residues in the lantibiotic Pep5, Appl. Environ. Microbiol., 62, 385, 10.1128/AEM.62.2.385-392.1996
Ösapay, 1997, Lanthionine–somatostatin analogs: synthesis, characterization, biological activity and enzymatic studies, J. Med. Chem., 40, 2241, 10.1021/jm960850i
Rew, 2002, Synthesis and biological activities of cyclic lanthionine enkephalin analogues: delta-opioid receptor selective ligands, J. Med. Chem., 45, 3746, 10.1021/jm020108k
Kluskens, 2008, Angiotensin-(1–7) with thioether-bridge: an ACE-resistant, potent Ang-(1–7) analogue, J. Pharmacol. Exp. Ther., 328, 849, 10.1124/jpet.108.146431
Haas, M. et al. (2008) Cyclic angiotensin analogues. Patent Application WO 2008/018792A2
Jain, 2008, PEGylation: an approach for drug delivery, Crit. Rev. Ther. Drug Carrier Syst., 25, 403, 10.1615/CritRevTherDrugCarrierSyst.v25.i5.10
de Kort, 2008, Conjugation of ATIII-binding pentasaccharides to extend the half-life of proteins: long-acting insulin, Chem. Med. Chem., 3, 1189, 10.1002/cmdc.200800053
Tiessen, 2008, Pharmacokinetics and tolerability of a novel long-acting glucagon-like peptide-1 analog, CJC-1131, in healthy and diabetic subjects, Int. J. Clin. Pharmacol. Ther., 46, 443, 10.5414/CPP46443
Han, 2000, Targeted prodrug design to optimize drug delivery, AAPS Pharm. Sci., 2, E6, 10.1208/ps020106
Russell-Jones, 2004, Use of targeting agents to increase uptake and localization of drugs to the intestinal epithelium, J. Drug Target., 12, 113, 10.1080/10611860410001693760
Wang, 2003, Reversible lipidization for the oral delivery of salmon calcitonin, J. Control. Release, 26, 369, 10.1016/S0168-3659(03)00008-7
Tsai, 1997, Synthesis and purification of NB1-palmitoyl insulin, J. Pharm. Sci., 86, 1264, 10.1021/js9701263