Functional polypeptide and hybrid materials: Precision synthesis via α-amino acid N-carboxyanhydride polymerization and emerging biomedical applications

Progress in Polymer Science

Volumn 39, Issue 2, 2014, Pages 330-364

  Deng, Chao ^a   Wu, Jintian ^a   Cheng, Ru ^a   Meng, Fenghua ^a   Klok, Harm Anton ^a,b   Zhong, Zhiyuan ^a  

^a SOOCHOW UNIVERSITY   (China)

^b Institute des Materiaux   (Switzerland)

Author keywords

Amino acid N carboxyanhydride; Biomaterials; Drug release; Gene delivery; NCA polymerization; Polypeptides; Tissue engineering

Indexed keywords

BIOMEDICAL APPLICATIONS; CONTROLLED DRUG RELEASE; DRUG RELEASE; GENE DELIVERY; HIGH MOLECULAR WEIGHT; LARGE-SCALE PRODUCTION; LIVING RADICAL POLYMERIZATION; N-CARBOXYANHYDRIDE;

AMINO ACIDS; BIODEGRADATION; BIOMATERIALS; GENE TRANSFER; HYBRID MATERIALS; LIVING POLYMERIZATION; MEDICAL APPLICATIONS; POLYETHYLENE GLYCOLS; TISSUE ENGINEERING;

POLYPEPTIDES;

EID: 84893699367     PISSN: 00796700     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.progpolymsci.2013.10.008     Document Type: Review

References (251)

1. S. Gomes, I.B. Leonor, J.F. Mano, R.L. Reis, and D.L. Kaplan Natural and genetically engineered proteins for tissue engineering Prog Polym Sci 37 2012 1 17
2. S.K. Maji, M.H. Perrin, M.R. Sawaya, S. Jessberger, K. Vadodaria, R.A. Rissman, P.S. Singru, K.P.R. Nilsson, R. Simon, D. Schubert, D. Eisenberg, J. Rivier, P. Sawchenko, W. Vale, and R. Riek Functional amyloids as natural storage of peptide hormones in pituitary secretory granules Science 325 2009 328 332
3. C.M. Dobson Protein folding and misfolding Nature 426 2003 884 890 (Pubitemid 38056880)
4. J.F. Lutz, and H.G. Boerner Modern trends in polymer bioconjugates design Prog Polym Sci 33 2008 1 39
5. T.J. Deming Synthetic polypeptides for biomedical applications Prog Polym Sci 32 2007 858 875 (Pubitemid 47202019)
6. L. Liu, K. Xu, H. Wang, J.P.K. Tan, W. Fan, S.S. Venkatraman, L. Li, and Y.Y. Yang Self-assembled cationic peptide nanoparticles as an efficient antimicrobial agent Nat Nanotechnol 4 2009 457 463
7. D.W.P.M. Lowik, E.H.P. Leunissen, M. van den Heuvel, M.B. Hansen, and J.C.M. van Hest Stimulus responsive peptide based materials Chem Soc Rev 39 2010 3394 3412
8. J.E. Dueber, G.C. Wu, G.R. Malmirchegini, T.S. Moon, C.J. Petzold, A.V. Ullal, K.L.J. Prather, and J.D. Keasling Synthetic protein scaffolds provide modular control over metabolic flux Nat Biotechnol 27 2009 753 759
9. E.F. Banwell, E.S. Abelardo, D.J. Adams, M.A. Birchall, A. Corrigan, A.M. Donald, M. Kirkland, L.C. Serpell, M.F. Butler, and D.N. Woolfson Rational design and application of responsive alpha-helical peptide hydrogels Nat Mater 8 2009 596 600
10. N.R. Zaccai, B. Chi, A.R. Thomson, A.L. Boyle, G.J. Bartlett, M. Bruning, N. Linden, R.B. Sessions, P.J. Booth, R.L. Brady, and D.N. Woolfson A de novo peptide hexamer with a mutable channel Nat Chem Biol 7 2011 935 941
11. F. Nederberg, Y. Zhang, J.P.K. Tan, K. Xu, H. Wang, C. Yang, S. Gao, X.D. Guo, K. Fukushima, L. Li, J.L. Hedrick, and Y.Y. Yang Biodegradable nanostructures with selective lysis of microbial membranes Nat Chem 3 2011 409 414
12. C. Cai, L. Wang, and J. Lin Self-assembly of polypeptide-based copolymers into diverse aggregates Chem Commun 47 2011 11189 11203
13. Y. Bae, and K. Kataoka Intelligent polymeric micelles from functional poly(ethylene glycol)-poly(amino acid) block copolymers Adv Drug Delivery Rev 61 2009 768 784
14. N. Hadjichristidis, H. Iatrou, M. Pitsikalis, and G. Sakellariou Synthesis of well-defined polypeptide-based materials via the ring-opening polymerization of alpha-amino acid N-carboxyanhydrides Chem Rev 109 2009 5528 5578
15. R. Duncan The dawning era of polymer therapeutics Nat Rev Drug Discov 2 2003 347 360 (Pubitemid 37361705)
16. C. He, X. Zhuang, Z. Tang, H. Tian, and X. Chen Stimuli-sensitive synthetic polypeptide-based materials for drug and gene delivery Adv Healthcare Mater 1 2012 48 78
17. H.A. Klok Peptide/protein-synthetic polymer conjugates: quo vadis Macromolecules 42 2009 7990 8000
18. A. Carlsen, and S. Lecommandoux Self-assembly of polypeptide-based block copolymer amphiphiles Curr Opin Colloid Interface Sci 14 2009 329 339
19. J.N. Cha, G.D. Stucky, D.E. Morse, and T.J. Deming Biomimetic synthesis of ordered silica structures mediated by block copolypeptides Nature 403 2000 289 292 (Pubitemid 30062380)
20. L.A. Canalle, D.W.P.M. Lowik, and J.C.M. van Hest Polypeptide-polymer bioconjugates Chem Soc Rev 39 2010 329 353
21. J.C.M. van Hest, and D.A. Tirrell Protein-based materials, toward a new level of structural control Chem Commun 2001 1897 1904 (Pubitemid 32964507)
22. B. Bacsa, K. Horvati, S. Bosze, F. Andreae, and C.O. Kappe Solid-phase synthesis of difficult peptide sequences at elevated temperatures: a critical comparison of microwave and conventional heating technologies J Org Chem 73 2008 7532 7542
23. T.J. Deming Polypeptide and polypeptide hybrid copolymer synthesis via NCA polymerization Adv Polym Sci 202 2006 1 18
24. H. Tian, Z. Tang, X. Zhuang, X. Chen, and X. Jing Biodegradable synthetic polymers: preparation, functionalization and biomedical application Prog Polym Sci 37 2012 237 280
25. H.R. Kricheldorf Polypeptides and 100 years of chemistry of alpha-amino acid N-carboxyanhydrides Angew Chem Int Ed 45 2006 5752 5784 (Pubitemid 44368810)
26. A.C. Farthing, and R.J.W. Reynolds Anhydro-N-carboxy-dl-beta- phenylalanine Nature 165 1950 647 657
27. D. Coleman, and A.C. Farthing Synthetic polypeptides. 2. Properties of oxazolid-2-5-diones and an initial study of the preparation of polypeptides therefrom J Chem Soc 1950 3218 3222
28. D.S. Poche, M.J. Moore, and J.L. Bowles An unconventional method for purifying the N-carboxyanhydride derivatives of gamma-alkyl-l-glutamates Synth Commun 29 1999 843 854 (Pubitemid 29102528)
29. N.M.B. Smeets, P.L.J. van der Weide, J. Meuldijk, J. Vekemans, and L.A. Hulshof A scalable synthesis of l-leucine-N-carboxyanhydride Org Process Res Dev 9 2005 757 763 (Pubitemid 41784090)
30. J.R. Kramer, and T.J. Deming General method for purification of alpha-amino acid-N-carboxyanhydrides using flash chromatography Biomacromolecules 11 2010 3668 3672
31. T.J. Deming Facile synthesis of block copolypeptides of defined architecture Nature 390 1997 386 389 (Pubitemid 28027315)
32. T.J. Deming Cobalt and iron initiators for the controlled polymerization of alpha-amino acid-N-carboxyanhydrides Macromolecules 32 1999 4500 4502
33. I. Dimitrov, and H. Schlaad Synthesis of nearly monodisperse polystyrene-polypeptide block copolymers via polymerisation of N-carboxyanhydrides Chem Commun 2003 2944 2945 (Pubitemid 37485447)
34. T. Aliferis, H. Iatrou, and N. Hadjichristidis Living polypeptides Biomacromolecules 5 2004 1653 1656 (Pubitemid 39335198)
35. W. Vayaboury, O. Giani, H. Cottet, A. Deratani, and F. Schue Living polymerization of alpha-amino acid N-carboxyanhydrides (NCA) upon decreasing the reaction temperature Macromol Rapid Commun 25 2004 1221 1224
36. H. Lu, and J. Cheng Hexamethyldisilazane-mediated controlled polymerization of alpha-amino acid N-carboxyanhydrides J Am Chem Soc 129 2007 14114 14115 (Pubitemid 350171403)
37. H. Lu, and J. Cheng N-Trimethylsilyl amines for controlled ring-opening polymerization of amino acid N-carboxyanhydrides and facile end group functionalization of polypeptides J Am Chem Soc 130 2008 12562 12563
38. J.A. Hanson, C.B. Chang, S.M. Graves, Z. Li, T.G. Mason, and T.J. Deming Nanoscale double emulsions stabilized by single-component block copolypeptides Nature 455 2008 85 88
39. C.Y. Yang, B. Song, Y. Ao, A.P. Nowak, R.B. Abelowitz, R.A. Korsak, L.A. Havton, T.J. Deming, and M.V. Sofroniew Biocompatibility of amphiphilic diblock copolypeptide hydrogels in the central nervous system Biomaterials 30 2009 2881 2898
40. K. Miyata, R.J. Christie, and K. Kataoka Polymeric micelles for nano-scale drug delivery React Funct Polym 71 2011 227 234
41. J.A. Hanson, and T.J. Deming Functionalized nanoscale through microscale polypeptide stabilized emulsions for display of biomolecules Polym Chem 2 2011 1473 1475
42. A.C. Engler, A. Shukla, S. Puranam, H.G. Buss, N. Jreige, and P.T. Hammond Effects of side group functionality and molecular weight on the activity of synthetic antimicrobial polypeptides Biomacromolecules 12 2011 1666 1674
43. J. Huang, and A. Heise Stimuli responsive synthetic polypeptides derived from N-carboxyanhydride (NCA) polymerisation Chem Soc Rev 42 2013 7373 7390
44. T.J. Deming Polypeptide and polypeptide hybrid copolymer synthesis via NCA polymerization H.A. Klok, S. Helmut, Peptide hybrid polymers 2006 Springer-Verlag Berlin/Heidelberg 1 18
45. H.A. Klok, and S. Lecommandoux Solid-state structure, organization and properties of peptide - synthetic hybrid block copolymers H.A. Klok, H. Schlaad, Peptide hybrid polymers 2006 Springer-Verlag Berlin/Heidelberg 75 111
46. J.R. Hernandez, and H.A. Klok Synthesis and ring-opening (Co) polymerization of l-lysine N-carboxyanhydrides containing labile side-chain protective groups J Polym Sci Part A Polym Chem 41 2003 1167 1187 (Pubitemid 36502779)
47. A. Patchornik, A. Berger, and E. Katchalski Poly-l-histidine J Am Chem Soc 79 1957 5227 5230
48. E.S. Lee, H.J. Shin, K. Na, and Y.H. Bae Poly(l-histidine)-PEG block copolymer micelles and pH-induced destabilization J Control Release 90 2003 363 374 (Pubitemid 36859967)
49. E.S. Lee, K. Na, and Y.H. Bae Super pH-sensitive multifunctional polymeric micelle Nano Lett 5 2005 325 329 (Pubitemid 40308294)
50. E.S. Lee, D. Kim, Y.S. Youn, K.T. Oh, and Y.H. Bae A virus-mimetic nanogel vehicle Angew Chem Int Ed 47 2008 2418 2421
51. A. Berger, J. Noguchi, and E. Katchalski Poly-l-cysteine J Am Chem Soc 78 1956 4483 4488
52. S. Abraham, I. Kim, and C.A. Batt A facile preparative method for aggregation-free gold nanoparticles using poly(styrene-block-cysteine) Angew Chem Int Ed 46 2007 5720 5723 (Pubitemid 47172195)
53. G.J.M. Habraken, C.E. Koning, J.P.A. Heuts, and A. Heise Thiol chemistry on well-defined synthetic polypeptides Chem Commun 2009 3612 3614
54. T. Xing, B. Lai, X. Ye, and L. Yan Disulfide core cross-linked PEGylated polypeptide nanogel prepared by a one-step ring opening copolymerization of N-carboxyanhydrides for drug delivery Macromol Biosci 11 2011 962 969
55. J. Ding, F. Shi, C. Xiao, L. Lin, L. Chen, C. He, X. Zhuang, and X. Chen One-step preparation of reduction-responsive poly(ethylene glycol)-poly (amino acid)s nanogels as efficient intracellular drug delivery platforms Polym Chem 2 2011 2857 2864
56. T. Hayakawa, Y. Kondo, H. Yamamoto, and Y. Murakami The synthesis of poly-l-arginine hydrobromide and copolymers of l-arginine and other amino acids Bull Chem Soc Jpn 42 1969 479 482
57. E.G. Bellomo, M.D. Wyrsta, L. Pakstis, D.J. Pochan, and T.J. Deming Stimuli-responsive polypeptide vesicles by conformation-specific assembly Nat Mater 3 2004 244 248
58. G.D. Fasman, and E.R. Blout The synthesis and the conformation of poly-l-serine and poly-O-acetyl-l-serine J Am Chem Soc 82 1960 2262 2267
59. N.M. Tooney, and G.D. Fasman Synthesis of poly-O-tert-butyl-serine and poly-l-serine Biopolymers 6 1968 81 96
60. M. Deng, J. Wu, C.A. Reinhart-King, and C.C. Chu Biodegradable functional poly(ester amide)s with pendant hydroxyl functional groups: synthesis, characterization, fabrication and in vitro cellular response Acta Biomater 7 2011 1504 1515
61. H. Yamamoto, and T. Hayakawa Letter: sense of helix poly-O,O′- dicarbobenzoxy-l-DOPA in solution Macromolecules 9 1976 532 534
62. M.E. Yu, and T.J. Deming Synthetic polypeptide mimics of marine adhesives Macromolecules 31 1998 4739 4745 (Pubitemid 128565485)
63. E.P. Holowka, and T.J. Deming Synthesis and cross linking of l-DOPA containing polypeptide vesicles Macromol Biosci 10 2010 496 502
64. M. Yu, A.P. Nowak, T.J. Deming, and D.J. Pochan Methylated mono- and diethyleneglycol functionalized polylysines: nonionic, alpha-helical, water-soluble polypeptides J Am Chem Soc 121 1999 12210 12211 (Pubitemid 30027808)
65. J.A. Hanson, Z. Li, and T.J. Deming Nonionic block copolypeptide micelles containing a hydrophobic rac-leucine core Macromolecules 43 2010 6268 6269
66. J. Wang, M.I. Gibson, R. Barbey, S.J. Xiao, and H.A. Klok Nonfouling polypeptide brushes via surface-initiated polymerization of N(epsilon)- oligo(ethylene glycol)succinate-l-lysine N-carboxyanhydride Macromol Rapid Commun 30 2009 845 850
67. J.Y. Hwang, and T.J. Deming Methylated mono- and di(ethylene glycol)-functionalized beta-sheet forming polypeptides Biomacromolecules 2 2001 17 21 (Pubitemid 32707467)
68. C. Chen, Z. Wang, and Z. Li Thermoresponsive polypeptides from pegylated poly-l-glutamates Biomacromolecules 12 2011 2859 2863
69. Y. Cheng, C. He, C. Xiao, J. Ding, X. Zhuang, and X. Chen Versatile synthesis of temperature-sensitive polypeptides by click grafting of oligo(ethylene glycol) Polym Chem 2 2011 2627 2634
70. Y. Liao, and C.M. Dong Synthesis, conformation transition, liquid crystal phase, and self-assembled morphology of thermosensitive homopolypeptide J Polym Sci Part A Polym Chem 50 2012 1834 1843
71. A.C. Engler, Lee Hi, and P.T. Hammond Highly efficient "grafting onto" a polypeptide backbone using click chemistry Angew Chem Int Ed 48 2009 9334 9338
72. A.C. Engler, D.K. Bonner, H.G. Buss, E.Y. Cheung, and P.T. Hammond The synthetic tuning of clickable pH responsive cationic polypeptides and block copolypeptides Soft Matter 7 2011 5627 5637
73. C.S. Xiao, C.W. Zhao, P. He, Z.H. Tang, X.S. Chen, and X.B. Jing Facile synthesis of glycopolypeptides by combination of ring-opening polymerization of an alkyne-substituted N-carboxyanhydride and click "glycosylation" Macromol Rapid Commun 31 2010 991 997
74. Y. Huang, Y. Zeng, J. Yang, Z. Zeng, F. Zhu, and X. Chen Facile functionalization of polypeptides by thiol-yne photochemistry for biomimetic materials synthesis Chem Commun 47 2011 7509 7511
75. H. Tang, and D. Zhang General route toward side-chain-functionalized alpha-helical polypeptides Biomacromolecules 11 2010 1585 1592
76. H. Tang, Y. Li, S.H. Lahasky, S.S. Sheiko, and D. Zhang Core-shell molecular bottlebrushes with helical polypeptide backbone: synthesis, characterization, and solution conformations Macromolecules 44 2011 1491 1499
77. H. Tang, and D. Zhang Multi-functionalization of helical block copoly(alpha-peptide)s by orthogonal chemistry Polym Chem 2 2011 1542 1551
78. A.J. Rhodes, and T.J. Deming Soluble, clickable polypeptides from azide-containing N-carboxyanhydride monomers ACS Macro Lett 2 2013 351 354
79. Y. Zhang, H. Lu, Y. Lin, and J. Cheng Water-soluble polypeptides with elongated, charged side chains adopt ultrastable helical conformations Macromolecules 44 2011 6641 6644
80. H. Tang, L. Yin, H. Lu, and J. Cheng Water-soluble poly(l-serine)s with elongated and charged side-chains: synthesis, conformations, and cell-penetrating properties Biomacromolecules 13 2012 2609 2615
81. J. Huang, G. Habraken, F. Audouin, and A. Heise Hydrolytically stable bioactive synthetic glycopeptide homo- and copolymers by combination of NCA polymerization and click reaction Macromolecules 43 2010 6050 6057
82. J. Sun, and H. Schlaad Thiol-ene clickable polypeptides Macromolecules 43 2010 4445 4448
83. J.R. Kramer, and T.J. Deming Glycopolypeptides via living polymerization of glycosylated-l-lysine N-carboxyanhydrides J Am Chem Soc 132 2010 15068 15071
84. J.R. Kramer, and T.J. Deming Glycopolypeptides with a redox-triggered helix-to-coil transition J Am Chem Soc 134 2012 4112 4115
85. D. Pati, A.Y. Shaikh, S. Hotha, and S. Sen Gupta Synthesis of glycopolypeptides by the ring opening polymerization of O-glycosylated-alpha- amino acid N-carboxyanhydride (NCA) Polym Chem 2 2011 805 811
86. J. Ding, C. Xiao, L. Zhao, Y. Cheng, L. Ma, Z. Tang, X. Zhuang, and X. Chen Poly(l-glutamic acid) grafted with oligo(2-(2-(2-methoxyethoxy)ethoxy) ethyl methacrylate): thermal phase transition, secondary structure, and self-assembly J Polym Sci Part A Polym Chem 49 2011 2665 2676
87. A.J. Rhodes, and T.J. Deming Tandem catalysis for the preparation of cylindrical polypeptide brushes J Am Chem Soc 134 2012 19463 19467
88. H. Lu, Y. Bai, J. Wang, N.P. Gabrielson, F. Wang, Y. Lin, and J. Cheng Ring-opening polymerization of gamma-(4-vinylbenzyl)-l-glutamate N-carboxyanhydride for the synthesis of functional polypeptides Macromolecules 44 2011 6237 6240
89. J. Zhou, P. Chen, C. Deng, F. Meng, R. Cheng, and Z. Zhong A simple and versatile synthetic strategy to functional polypeptides via vinyl sulfone-substituted l-cysteine N-carboxyanhydride Macromolecules 46 2013 6723 6730
90. L. Yan, L. Yang, H. He, X. Hu, Z. Xie, Y. Huang, and X. Jing Photo-cross-linked mPEG-poly(gamma-cinnamyl-l-glutamate) micelles as stable drug carriers Polym Chem 3 2012 1300 1307
91. G. Liu, and C.M. Dong Photoresponsive poly(S-(o-nitrobenzyl)-l-cysteine)- b-PEO from a l-cysteine N-carboxyanhydride monomer: synthesis, self-assembly, and phototriggered drug release Biomacromolecules 13 2012 1573 1583
92. H. Enomoto, B. Nottelet, S. Al Halifa, C. Enjalbal, M. Dupre, J. Tailhades, J. Coudane, G. Subra, J. Martinez, and M. Amblard Synthesis of peptide-grafted comb polypeptides via polymerisation of NCA-peptides Chem Commun 49 2013 409 411
93. M.A. Gauthier, M.I. Gibson, and H.A. Klok Synthesis of functional polymers by post-polymerization modification Angew Chem Int Ed 48 2009 48 58
94. C. Deng, H.Y. Tian, P.B. Zhang, J. Sun, X.S. Chen, and X.B. Jing Synthesis and characterization of RGD peptide grafted poly(ethylene glycol)-b-poly(l-lactide)-b-poly(l-glutamic acid) triblock copolymer Biomacromolecules 7 2006 590 596
95. T. Lu, X. Chen, Q. Shi, Y. Wang, P. Zhang, and X. Jing The immobilization of proteins on biodegradable fibers via biotin-streptavidin bridges Acta Biomater 4 2008 1770 1777
96. T. Lu, J. Sun, X. Chen, P. Zhang, and X. Jing Folate-conjugated micelles and their folate-receptor-mediated endocytosis Macromol Biosci 9 2009 1059 1068
97. C. Deng, X. Chen, J. Sun, T. Lu, W. Wang, and X. Jing RGD peptide grafted biodegradable amphiphilic triblock copolymer poly(glutamic acid)-b-poly(l- lactide)-b-poly(glutamic acid): synthesis and self-assembly J Polym Sci Part A Polym Chem 45 2007 3218 3230 (Pubitemid 47209925)
98. J.X. Ding, X.L. Zhuang, C.S. Xiao, Y.L. Cheng, L. Zhao, C.L. He, Z.H. Tang, and X.S. Chen Preparation of photo-cross-linked pH-responsive polypeptide nanogels as potential carriers for controlled drug delivery J Mater Chem 21 2011 11383 11391
99. V.Z. Sun, Z. Li, T.J. Deming, and D.T. Kamei Intracellular fates of cell-penetrating block copolypeptide vesicles Biomacromolecules 12 2011 10 13
100. M. Nakanishi, J.S. Park, W.D. Jang, M. Oba, and K. Kataoka Study of the quantitative aminolysis reaction of poly(beta-benzyl l-aspartate) (PBLA) as a platform polymer for functionality materials React Funct Polym 67 2007 1361 1372 (Pubitemid 47562878)
101. Arnida, N. Nishiyama, N. Kanayama, W.D. Jang, Y. Yamasaki, and K. Kataoka PEGylated gene nanocarriers based on block catiomers bearing ethylenediamine repeating units directed to remarkable enhancement of photochemical transfection J Control Release 115 2006 208 215 (Pubitemid 44537495)
102. K. Miyata, M. Oba, M. Nakanishi, S. Fukushima, Y. Yamasaki, H. Koyama, N. Nishiyama, and K. Kataoka Polyplexes from poly(aspartamide) bearing 1,2-diaminoethane side chains induce pH-selective, endosomal membrane destabilization with amplified transfection and negligible cytotoxicity J Am Chem Soc 130 2008 16287 16294
103. A. Koide, A. Kishimura, K. Osada, W.D. Jang, Y. Yamasaki, and K. Kataoka Semipermeable polymer vesicle (PICsome) self-assembled in aqueous medium from a pair of oppositely charged block copolymers: physiologically stable micro-/nanocontainers of water-soluble macromolecules J Am Chem Soc 128 2006 5988 5989
104. J. Guo, Y. Huang, X. Jing, and X. Chen Synthesis and characterization of functional poly(gamma-benzyl-l-glutamate) (PBLG) as a hydrophobic precursor Polymer 50 2009 2847 2855
105. J.R. Kramer, and T.J. Deming Preparation of multifunctional and multireactive polypeptides via methionine alkylation Biomacromolecules 13 2012 1719 1723
106. S. Steig, F. Cornelius, P. Witte, B.B.P. Staal, C.E. Koning, A. Heise, and H. Menzel Synthesis of polypeptide based rod-coil block copolymers Chem Commun 2005 5420 5422 (Pubitemid 41689376)
107. G.J.M. Habraken, C.E. Koning, and A. Heise Peptide block copolymers by N-carboxyanhydride ring-opening polymerization and atom transfer radical polymerization: the effect of amide macroinitiators J Polym Sci Part A Polym Chem 47 2009 6883 6893
108. X. Zhang, J. Li, W. Li, and A. Zhang Synthesis and characterization of thermo- and pH-responsive double-hydrophilic diblock copolypeptides Biomacromolecules 8 2007 3557 3567 (Pubitemid 350193757)
109. R.J.I. Knoop, G.J.M. Habraken, N. Gogibus, S. Steig, H. Menzel, C.E. Koning, and A. Heise Synthesis of poly(benzyl glutamate-b-styrene) rod-coil block copolymers by dual initiation in one pot J Polym Sci Part A Polym Chem 46 2008 3068 3077 (Pubitemid 351579060)
110. J. Li, T. Wang, D. Wu, X. Zhang, J. Yan, S. Du, Y. Guo, J. Wang, and A. Zhang Stimuli-responsive zwitterionic block copolypeptides: poly(N- isopropylacrylamide)-block-poly(lysine-co-glutamic acid) Biomacromolecules 9 2008 2670 2676
111. W. Agut, D. Taton, and S. Lecommandoux A versatile synthetic approach to polypeptide based rod-coil block copolymers by click chemistry Macromolecules 40 2007 5653 5661 (Pubitemid 47280837)
112. W. Agut, A. Brulet, C. Schatz, D. Taton, and S. Lecommandoux pH and temperature responsive polymeric micelles and polymersomes by self-assembly of poly[2-(dimethylamino)ethyl methacrylate]-b-poly(glutamic acid) double hydrophilic block copolymers Langmuir 26 2010 10546 10554
113. C. Schatz, S. Louguet, J.F. Le Meins, and S. Lecommandoux Polysaccharide-block-polypeptide copolymer vesicles: towards synthetic viral capsids Angew Chem Int Ed 48 2009 2572 2575
114. K.K. Upadhyay, J.F. Le Meins, A. Misra, P. Voisin, V. Bouchaud, E. Ibarboure, C. Schatz, and S. Lecommandoux Biomimetic doxorubicin loaded polymersomes from hyaluronan-block-poly(gamma-benzyl glutamate) copolymers Biomacromolecules 10 2009 2802 2808
115. W. Agut, R. Agnaou, S. Lecommandoux, and D. Taton Synthesis of block copolypeptides by click chemistry Macromol Rapid Commun 29 2008 1147 1155
116. J. Rao, Y. Zhang, J. Zhang, and S. Liu Facile preparation of well-defined AB(2) Y-shaped miktoarm star polypeptide copolymer via the combination of ring-opening polymerization and click chemistry Biomacromolecules 9 2008 2586 2593
117. S.S. Naik, J.W. Chan, C. Comer, C.E. Hoyle, and D.A. Savin Thiol-yne 'click' chemistry as a route to functional lipid mimetics Polym Chem 2 2011 303 305
118. J.G. Ray, J.T. Ly, and D.A. Savin Peptide-based lipid mimetics with tunable core properties via thiol-alkyne chemistry Polym Chem 2 2011 1536 1541
119. F. Audouin, R.J.I. Knoop, J. Huang, and A. Heise Star polymers by cross-linking of linear poly(benzyl-l-glutamate) macromonomers via free-radical and RAFT polymerization. A simple route toward peptide-stabilized nanoparticles J Polym Sci Part A Polym Chem 48 2010 4602 4610
120. H.A. Klok, J.R. Hernandez, S. Becker, and K. Mullen Star-shaped fluorescent polypeptides J Polym Sci Part A Polym Chem 39 2001 1572 1583 (Pubitemid 32450542)
121. H.Y. Tian, C. Deng, H. Lin, J.R. Sun, M.X. Deng, X.S. Chen, and X.B. Jing Biodegradable cationic PEG-PEI-PBLG hyperbranched block copolymer: synthesis and micelle characterization Biomaterials 26 2005 4209 4217 (Pubitemid 40430847)
122. M. Byrne, P.D. Thornton, S.A. Cryan, and A. Heise Star polypeptides by NCA polymerisation from dendritic initiators: synthesis and enzyme controlled payload release Polym Chem 3 2012 2825 2831
123. Q. Wang, J. Yu, Y. Yan, S. Xu, F. Wang, Q. Li, J. Wang, X. Zhang, and D. Liu Controlled biomimetic silica formation using star-shaped poly(l-lysine) Polym Chem 3 2012 1284 1290
124. C. Fu, L. Lin, H. Shi, D. Zheng, W. Wang, S. Gao, Y. Zhao, H. Tian, X. Zhu, and X. Chen Hydrophobic poly (amino acid) modified PEI mediated delivery of rev-casp-3 for cancer therapy Biomaterials 33 2012 4589 4596
125. J. Xia, L. Chen, J. Chen, H. Tian, F. Li, X. Zhu, G. Li, and X. Chen Hydrophobic polyphenylalanine-grafted hyperbranched polyethylenimine and its in vitro gene transfection Macromol Biosci 11 2011 211 218
126. L. Chen, H. Tian, J. Chen, X. Chen, Y. Huang, and X. Jing Multi-armed poly(l-glutamic acid)-graft-oligoethylenimine copolymers as efficient nonviral gene delivery vectors J Gene Med 12 2010 64 76
127. Z.Y. Li, H.Y. Wang, C. Li, X.L. Zhang, X.J. Wu, S.Y. Qin, X.Z. Zhang, and R.X. Zhuo Porphyrin-functionalized amphiphilic diblock copolypeptides for photodynamic therapy J Polym Sci Part A Polym Chem 49 2011 286 292
128. A.J. Williams, and V.K. Gupta Self-assembly of a rodlike polypeptide on solid surfaces: role of solvent, molecular weight, and time of assembly J Phys Chem B 105 2001 5223 5230 (Pubitemid 35372622)
129. A.J. Williams, and V.K. Gupta Structure and formation of self-assembled monolayers of helical poly (gamma-benzyl l-glutamate) by surface plasmon resonance and infrared spectroscopy Thin Solid Films 423 2003 228 234
130. J. Rodriguez-Hernandez, M. Gatti, and H.A. Klok Highly branched poly(l-lysine) Biomacromolecules 4 2003 249 258 (Pubitemid 36527095)
131. T. Aliferis, H. Iatrou, and N. Hadjichristidis Well-defined linear multiblock and branched polypeptides by linking chemistry J Polym Sci Part A Polym Chem 43 2005 4670 4673 (Pubitemid 41625166)
132. T.B. Ren, W.J. Xia, H.Q. Dong, and Y.Y. Li Sheddable micelles based on disulfide-linked hybrid PEG-polypeptide copolymer for intracellular drug delivery Polymer 52 2011 3580 3586
133. K.R. Brzezinska, S.A. Curtin, and T.J. Deming Polypeptide end-capping using functionalized isocyanates: preparation of pentablock copolymers Macromolecules 35 2002 2970 2976 (Pubitemid 34586521)
134. A. Kros, W. Jesse, G.A. Metselaar, and J. Cornelissen Synthesis and self-assembly of rod-rod hybrid poly(gamma-benzyl l-glutamate)-block- polyisocyanide copolymers Angew Chem Int Ed 44 2005 4349 4352 (Pubitemid 41026366)
135. Z. Tian, M. Wang, A.Y. Zhang, and Z.G. Feng Preparation and evaluation of novel amphiphilic glycopeptide block copolymers as carriers for controlled drug release Polymer 49 2008 446 454
136. J. Huang, C. Bonduelle, J. Thevenot, S. Lecommandoux, and A. Heise Biologically active polymersomes from amphiphilic glycopeptides J Am Chem Soc 134 2012 119 122
137. K.S. Krannig, and H. Schlaad pH-responsive bioactive glycopolypeptides with enhanced helicity and solubility in aqueous solution J Am Chem Soc 134 2012 18542 18545
138. E. Rude, O. Westphal, E. Hurwitz, S. Fuchs, and M. Sela Synthesis and antigenic properties of sugar-polypeptide conjugates Immunochemistry 3 1966 137 151
139. K. Aoi, K. Tsutsumiuchi, and M. Okada Glycopeptide synthesis by an alpha-amino-acid N-carboxyanhydride (NCA) method - ring-opening polymerization of a sugar-substituted NCA Macromolecules 27 1994 875 877
140. M.I. Gibson, G.J. Hunt, and N.R. Cameron Improved synthesis of O-linked, and first synthesis of S-linked, carbohydrate functionalised N-carboxyanhydrides (glycoNCAs) Org Biomol Chem 5 2007 2756 2757 (Pubitemid 47258232)
141. D. Pati, A.Y. Shaikh, S. Das, P.K. Nareddy, M.J. Swamy, S. Hotha, and S.S. Gupta Controlled synthesis of o-glycopolypeptide polymers and their molecular recognition by lectins Biomacromolecules 13 2012 1287 1295
142. D. Pati, N. Kalva, S. Das, G. Kumaraswamy, S. Sen Gupta, and A.V. Ambade Multiple topologies from glycopolypeptide-dendron conjugate self-assembly: nanorods, micelles, and organogels J Am Chem Soc 134 2012 7796 7802
143. K.K. Upadhyay, A.N. Bhatt, A.K. Mishra, B.S. Dwarakanath, S. Jain, C. Schatz, J.F. Le Meins, A. Farooque, G. Chandraiah, A.K. Jain, A. Misra, and S. Lecommandoux The intracellular drug delivery and anti tumor activity of doxorubicin loaded poly(gamma-benzyl l-glutamate)-b-hyaluronan polymersomes Biomaterials 31 2010 2882 2892
144. H. Yu, C. Deng, H. Tian, T. Lu, X. Chen, and X. Jing Chemo-physical and biological evaluation of poly(l-lysine)-grafted chitosan copolymers used for highly efficient gene delivery Macromol Biosci 11 2011 352 361
145. H. Yu, X. Chen, T. Lu, J. Sun, H. Tian, J. Hu, Y. Wang, P. Zhang, and X. Jing Poly(l-lysine)-graft-chitosan copolymers: synthesis, characterization, and gene transfection effect Biomacromolecules 8 2007 1425 1435 (Pubitemid 46865113)
146. C.M. Dong, K.M. Faucher, and E.L. Chaikof Synthesis and properties of biomimetic poIy(l-glutamate)-b-poly(2-acryloyloxyethyllactoside)-b-poly(l- glutamate) triblock copolymers J Polym Sci Part A Polym Chem 42 2004 5754 5765
147. C.M. Dong, X.L. Sun, K.M. Faucher, R.P. Apkarian, and E.L. Chaikof Synthesis and characterization of glycopolymer-polypeptide triblock copolymers Biomacromolecules 5 2004 224 231 (Pubitemid 38181334)
148. Y. Matsumura, and K. Kataoka Preclinical and clinical studies of anticancer agent-incorporating polymer micelles Cancer Sci 100 2009 572 579
149. M. Murakami, H. Cabral, Y. Matsumoto, S. Wu, M.R. Kano, T. Yamori, N. Nishiyama, and K. Kataoka Improving drug potency and efficacy by nanocarrier-mediated subcellular targeting Sci Transl Med 3 2011 64ra2/1-12
150. M. Rafi, H. Cabral, M.R. Kano, P. Mi, C. Iwata, M. Yashiro, K. Hirakawa, K. Miyazono, N. Nishiyama, and K. Kataoka Polymeric micelles incorporating (1,2-diaminocyclohexane) platinum (II) suppress the growth of orthotopic scirrhous gastric tumors and their lymph node metastasis J Control Release 159 2012 189 196
151. H. Yin, E.S. Lee, D. Kim, K.H. Lee, K.T. Oh, and Y.H. Bae Physicochemical characteristics of pH-sensitive poly(l-histidine)-b-poly (ethylene glycol)/poly(l-lactide)-b-poly(ethylene glycol) mixed micelles J Control Release 126 2008 130 138
152. E.S. Lee, K. Na, and Y.H. Bae Polymeric micelle for tumor pH and folate-mediated targeting J Control Release 91 2003 103 113 (Pubitemid 37288881)
153. E.S. Lee, K. Na, and Y.H. Bae Doxorubicin loaded pH-sensitive polymeric micelles for reversal of resistant MCF-7 tumor J Control Release 103 2005 405 418 (Pubitemid 40342538)
154. Z.G. Gao, L. Tian, J. Hu, I.S. Park, and Y.H. Bae Prevention of metastasis in a 4T1 murine breast cancer model by doxorubicin carried by folate conjugated pH sensitive polymeric micelles J Control Release 152 2011 84 89
155. D. Kim, Z.G. Gao, E.S. Lee, and Y.H. Bae In vivo evaluation of doxorubicin-loaded polymeric micelles targeting folate receptors and early endosomal pH in drug-resistant ovarian cancer Mol Pharm 6 2009 1353 1362
156. D. Kim, E.S. Lee, K.T. Oh, Z.G. Gao, and Y.H. Bae Doxorubicin-loaded polymeric micelle overcomes multidrug resistance of cancer by double-targeting folate receptor and early endosomal pH Small 4 2008 2043 2050
157. Y. Bae, S. Fukushima, A. Harada, and K. Kataoka Design of environment-sensitive supramolecular assemblies for intracellular drug delivery: polymeric micelles that are responsive to intracellular pH change Angew Chem Int Ed 42 2003 4640 4643 (Pubitemid 37271305)
158. S.J. Lee, K.H. Min, H.J. Lee, A.N. Koo, H.P. Rim, B.J. Jeon, S.Y. Jeong, J.S. Heo, and S.C. Lee Ketal cross-linked poly(ethylene glycol)-poly(amino acid)s copolymer micelles for efficient intracellular delivery of doxorubicin Biomacromolecules 12 2011 1224 1233
159. R. Cheng, F. Feng, F. Meng, C. Deng, J. Feijen, and Z. Zhong Glutathione-responsive nano-vehicles as a promising platform for targeted intracellular drug and gene delivery J Control Release 152 2011 2 12
160. F. Meng, W.E. Hennink, and Z. Zhong Reduction-sensitive polymers and bioconjugates for biomedical applications Biomaterials 30 2009 2180 2198
161. H. Cabral, M. Nakanishi, M. Kumagai, W.D. Jang, N. Nishiyama, and K. Kataoka A photo-activated targeting chemotherapy using glutathione sensitive camptothecin-loaded polymeric micelles Pharm Res 26 2009 82 92
162. H.Y. Wen, H.Q. Dong, W.J. Xie, Y.Y. Li, K. Wang, G.M. Pauletti, and D.L. Shi Rapidly disassembling nanomicelles with disulfide-linked PEG shells for glutathione-mediated intracellular drug delivery Chem Commun 47 2011 3550 3552
163. T. Thambi, H.Y. Yoon, K. Kim, I.C. Kwon, C.K. Yoo, and J.H. Park Bioreducible block copolymers based on poly(ethylene glycol) and poly(gamma-benzyl l-glutamate) for intracellular delivery of camptothecin Bioconjug Chem 22 2011 1924 1931
164. J. Dai, S. Lin, D. Cheng, S. Zou, and X. Shuai Interlayer-crosslinked micelle with partially hydrated core showing reduction and pH dual sensitivity for pinpointed intracellular drug release Angew Chem Int Ed 50 2011 9404 9408
165. K. Wang, G.F. Luo, Y. Liu, C. Li, S.X. Cheng, R.X. Zhuo, and X.Z. Zhang Redox-sensitive shell cross-linked PEG-polypeptide hybrid micelles for controlled drug release Polym Chem 3 2012 1084 1090
166. L. Wu, Y. Zou, C. Deng, R. Cheng, F. Meng, and Z. Zhong Intracellular release of doxorubicin from core-crosslinked polypeptide micelles triggered by both pH and reduction conditions Biomaterials 34 2013 5262 5272
167. S.S. Naik, J.G. Ray, and D.A. Savin Temperature- and pH-responsive self-assembly of poly(propylene oxide)-b-poly(lysine) block copolymers in aqueous solution Langmuir 27 2011 7231 7240
168. C. Cai, L. Zhang, J. Lin, and L. Wang Self-assembly behavior of pH- and thermosensitive amphiphilic triblock copolymers in solution: experimental studies and self-consistent field theory simulations J Phys Chem B 112 2008 12666 12673
169. W. Agut, A. Brulet, D. Taton, and S. Lecommandoux Thermoresponsive micelles from jeffamine-b-poly(l-glutamic acid) double hydrophilic block copolymers Langmuir 23 2007 11526 11533 (Pubitemid 350132995)
170. H. Arimura, Y. Ohya, and T. Ouchi The formation of biodegradable polymeric micelles from newly synthesized poly(aspartic acid)-block-polylactide AB-type diblock copolymers Macromol Rapid Commun 25 2004 743 747
171. H. Arimura, Y. Ohya, and T. Ouchi Formation of core-shell type biodegradable polymeric micelles from amphiphilic poly(aspartic acid)-block-polylactide diblock copolymer Biomacromolecules 6 2005 720 725 (Pubitemid 40467813)
172. Y. Yang, J. Cai, X. Zhuang, Z. Guo, X. Jing, and X. Chen pH-dependent self-assembly of amphiphilic poly(l-glutamic acid)-block-poly(lactic-co-glycolic acid) copolymers Polymer 51 2010 2676 2682
173. C. Deng, G.Z. Rong, H.Y. Tian, Z.H. Tang, X.S. Chen, and X.B. Jing Synthesis and characterization of poly(ethylene glycol)-b-poly (l-lactide)-b-poly(l-glutamic acid) triblock copolymer Polymer 46 2005 653 659 (Pubitemid 40091758)
174. J. Sun, C. Deng, X. Chen, H. Yu, H. Tian, J. Sun, and X. Jing Self-assembly of polypeptide-containing ABC-type triblock copolymers in aqueous solution and its pH dependence Biomacromolecules 8 2007 1013 1017 (Pubitemid 46488486)
175. C. Deng, X. Chen, H. Yu, J. Sun, T. Lu, and X. Jing A biodegradable triblock copolymer poly(ethylene glycol)-b-poly(l-lactide)-b-poly(l-lysine): synthesis, self-assembly and RGD peptide modification Polymer 48 2007 139 149 (Pubitemid 44918032)
176. E.S. Lee, Z. Gao, D. Kim, K. Park, I.C. Kwon, and Y.H. Bae Super pH-sensitive multifunctional polymeric micelle for tumor pH(e) specific TAT exposure and multidrug resistance J Controlled Release 129 2008 228 236
177. J. Sun, X. Chen, T. Lu, S. Liu, H. Tian, Z. Guo, and X. Jing Formation of reversible shell cross-linked micelles from the biodegradable amphiphilic diblock copolymer poly(l-cysteine)-block-poly(l-lactide) Langmuir 24 2008 10099 10106
178. J. Sun, X. Chen, J. Wei, L. Yan, and X. Jing Application of the biodegradable diblock copolymer poly(l-lactide)-block-poly(l-cysteine): drug delivery and protein conjugation J Appl Polym Sci 118 2010 1738 1742
179. J. Rao, Z. Luo, Z. Ge, H. Liu, and S. Liu "Schizophrenic" micellization associated with coil-to-helix transitions based on polypeptide hybrid double hydrophilic rod-coil diblock copolymer Biomacromolecules 8 2007 3871 3878
180. C. He, C. Zhao, X. Chen, Z. Guo, X. Zhuang, and X. Jing Novel pH- and temperature-responsive block copolymers with tunable pH-responsive range Macromol Rapid Commun 29 2008 490 497
181. C. He, C. Zhao, X. Guo, Z. Guo, X. Chen, X. Zhuang, S. Liu, and X. Jing Novel temperature- and pH-responsive graft copolymers composed of poly(l-glutamic acid) and poly(N-isopropylacrylamide) J Polym Sci Part A Polym Chem 46 2008 4140 4150
182. C. Zhao, X. Zhuang, C. He, X. Chen, and X. Jing Synthesis of novel thermo- and pH-responsive poly(l-lysine)-based copolymer and its micellization in water Macromol Rapid Commun 29 2008 1810 1816
183. C.J. Huang, and F.C. Chang Polypeptide diblock copolymers: syntheses and properties of poly(N-isopropylacrylamide)-b-polylysine Macromolecules 41 2008 7041 7052
184. H. Lu, J. Wang, Y. Bai, J.W. Lang, S. Liu, Y. Lin, and J. Cheng Ionic polypeptides with unusual helical stability Nat Commun 2 2011 206/1-9
185. N.P. Gabrielson, H. Lu, L. Yin, D. Li, F. Wang, and J. Cheng Reactive and bioactive cationic a-helical polypeptide template for nonviral gene delivery Angew Chem Int Ed 51 2012 1143 1147
186. K. Osada, R.J. Christie, and K. Kataoka Polymeric micelles from poly(ethylene glycol)-poly(amino acid) block copolymer for drug and gene delivery J R Soc Interface 6 2009 S325 S339
187. H. Cabral, N. Nishiyama, and K. Kataoka Supramolecular nanodevices: from design validation to theranostic nanomedicine Acc Chem Res 44 2011 999 1008
188. D. Akagi, M. Oba, H. Koyama, N. Nishiyama, S. Fukushima, T. Miyata, H. Nagawa, and K. Kataoka Biocompatible micellar nanovectors achieve efficient gene transfer to vascular lesions without cytotoxicity and thrombus formation Gene Ther 14 2007 1029 1038 (Pubitemid 46965272)
189. K. Itaka, S. Ohba, K. Miyata, H. Kawaguchi, K. Nakamura, T. Takato, U.I. Chung, and K. Kataoka Bone regeneration by regulated in vivo gene transfer using biocompatible polyplex nanomicelles Mol Ther 15 2007 1655 1662 (Pubitemid 47289009)
190. M. Harada-Shiba, I. Takamisawa, K. Miyata, T. Ishii, N. Nishiyama, K. Itaka, K. Kangawa, F. Yoshihara, Y. Asada, K. Hatakeyama, N. Nagaya, and K. Kataoka Intratracheal gene transfer of adrenomedullin using polyplex nanomicelles attenuates monocrotaline-induced pulmonary hypertension in rats Mol Ther 17 2009 1180 1186
191. H. Uchida, K. Miyata, M. Oba, T. Ishii, T. Suma, K. Itaka, N. Nishiyama, and K. Kataoka Odd-even effect of repeating aminoethylene units in the side chain of N-substituted polyaspartamides on gene transfection profiles J Am Chem Soc 133 2011 15524 15532
192. T.C. Lai, Y. Bae, T. Yoshida, K. Kataoka, and G.S. Kwon pH-sensitive multi-PEGylated block copolymer as a bioresponsive pDNA delivery vector Pharm Res 27 2010 2260 2273
193. Y. Lee, S. Fukushima, Y. Bae, S. Hiki, T. Ishii, and K. Kataoka A protein nanocarrier from charge-conversion polymer in response to endosomal pH J Am Chem Soc 129 2007 5362 5363 (Pubitemid 46697615)
194. Y. Lee, K. Miyata, M. Oba, T. Ishii, S. Fukushima, M. Han, H. Koyama, N. Nishiyama, and K. Kataoka Charge-conversion ternary polyplex with endosome disruption moiety: a technique for efficient and safe gene delivery Angew Chem Int Ed 47 2008 5163 5166
195. S. Fukushima, K. Miyata, N. Nishiyama, N. Kanayama, Y. Yamasaki, and K. Kataoka PEGylated polyplex micelles from triblock catiomers with spatially ordered layering of condensed pDNA and buffering units for enhanced intracellular gene delivery J Am Chem Soc 127 2005 2810 2811 (Pubitemid 40349832)
196. J. Deng, N. Gao, Y. Wang, H. Yi, S. Fang, Y. Ma, and L. Cai Self-assembled cationic micelles based on PEG-PLL-PLLeu hybrid polypeptides as highly effective gene vectors Biomacromolecules 13 2012 3795 3804
197. Y.Y. Li, S.H. Hua, W. Xiao, H.Y. Wang, X.H. Luo, C. Li, S.X. Cheng, X.Z. Zhang, and R.X. Zhuo Dual-vectors of anti-cancer drugs and genes based on pH-sensitive micelles self-assembled from hybrid polypeptide copolymers J Mater Chem 21 2011 3100 3106
198. H. Takemoto, A. Ishii, K. Miyata, M. Nakanishi, M. Oba, T. Ishii, Y. Yamasaki, N. Nishiyama, and K. Kataoka Polyion complex stability and gene silencing efficiency with a siRNA-grafted polymer delivery system Biomaterials 31 2010 8097 8105
199. S. Takae, K. Miyata, M. Oba, T. Ishii, N. Nishiyama, K. Itaka, Y. Yamasaki, H. Koyama, and K. Kataoka PEG-detachable polyplex micelles based on disulfide-linked block catiomers as bioresponsive nonviral gene vectors J Am Chem Soc 130 2008 6001 6009 (Pubitemid 351620847)
200. K. Miyata, Y. Kakizawa, N. Nishiyama, A. Harada, Y. Yamasaki, H. Koyama, and K. Kataoka Block catiomer polyplexes with regulated densities of charge and disulfide cross-linking directed to enhance gene expression J Am Chem Soc 126 2004 2355 2361 (Pubitemid 38295715)
201. R.J. Christie, K. Miyata, Y. Matsumoto, T. Nomoto, D. Menasco, T.C. Lai, M. Pennisi, K. Osada, S. Fukushima, N. Nishiyama, Y. Yamasaki, and K. Kataoka Effect of polymer structure on micelles formed between siRNA and cationic block copolymer comprising thiols and amidines Biomacromolecules 12 2011 3174 3185
202. M. Oba, K. Aoyagi, K. Miyata, Y. Matsumoto, K. Itaka, N. Nishiyama, Y. Yarnasaki, H. Koyama, and K. Kataoka Polyplex micelles with cyclic RGD peptide ligands and disulfide cross-links directing to the enhanced transfection via controlled intracellular trafficking Mol Pharm 5 2008 1080 1092
203. M. Sanjoh, K. Miyata, R.J. Christie, T. Ishii, Y. Maeda, F. Pittella, S. Hiki, N. Nishiyama, and K. Kataoka Dual environment-responsive polyplex carriers for enhanced intracellular delivery of plasmid DNA Biomacromolecules 13 2012 3641 3649
204. M.J. Heffernan, and N. Murthy Disulfide-crosslinked polyion micelles for delivery of protein therapeutics Ann Biomed Eng 37 2009 1993 2002
205. M. Naito, T. Ishii, A. Matsumoto, K. Miyata, Y. Miyahara, and K. Kataoka A phenylboronate-functionalized polyion complex micelle for ATP-triggered release of siRNA Angew Chem Int Ed 51 2012 10751 10755
206. F. Meng, and Z. Zhong Polymersomes spanning from nano- to microscales: advanced vehicles for controlled drug delivery and robust vesicles for virus and cell mimicking J Phys Chem Lett 2 2011 1533 1539
207. F. Meng, Z. Zhong, and J. Feijen Stimuli-responsive polymersomes for programmed drug delivery Biomacromolecules 10 2009 197 209
208. J. Sun, X. Chen, C. Deng, H. Yu, Z. Xie, and X. Jing Direct formation of giant vesicles from synthetic polypeptides Langmuir 23 2007 8308 8315 (Pubitemid 47237818)
209. J. Sun, Y. Huang, Q. Shi, X. Chen, and X. Jing Oxygen carrier based on hemoglobin/poly(l-lysine)-block-poly(l-phenylalanine) vesicles Langmuir 25 2009 13726 13729
210. M.S. Kim, K. Dayananda, E.Y. Choi, H.J. Park, J.S. Kim, and D.S. Lee Synthesis and characterization of poly(l-glutamic acid)-block-poly(l- phenylalanine) Polymer 50 2009 2252 2257
211. E.P. Holowka, D.J. Pochan, and T.J. Deming Charged polypeptide vesicles with controllable diameter J Am Chem Soc 127 2005 12423 12428 (Pubitemid 41279271)
212. E.P. Holowka, V.Z. Sun, D.T. Kamei, and T.J. Deming Polyarginine segments in block copolypeptides drive both vesicular assembly and intracellular delivery Nat Mater 6 2007 52 57 (Pubitemid 46041477)
213. H. Iatrou, H. Frielinghaus, S. Hanski, N. Ferderigos, J. Ruokolainen, O. Ikkala, D. Richter, J. Mays, and N. Hadjichristidis Architecturally induced multiresponsive vesicles from formation of gene vehicles, well-defined polypeptides Biomacromolecules 8 2007 2173 2181 (Pubitemid 47108139)
214. W. Dzwolak, T. Muraki, M. Kato, and Y. Taniguchi Chain-length dependence of alpha-helix to beta-sheet transition in polylysine: model of protein aggregation studied by temperature-tuned FTIR spectroscopy Biopolymers 73 2004 463 469 (Pubitemid 38332398)
215. X. Xu, H. Yuan, J. Chang, B. He, and Z. Gu Cooperative hierarchical self-assembly of peptide dendrimers and linear polypeptides into nanoarchitectures mimicking viral capsids Angew Chem Int Ed 51 2012 3130 3133
216. J. Rodriguez-Hernandez, and S. Lecommandoux Reversible inside-out micellization of pH-responsive and water-soluble vesicles based on polypeptide diblock copolymers J Am Chem Soc 127 2005 2026 2027 (Pubitemid 40270489)
217. A. Kishimura, A. Koide, K. Osada, Y. Yamasaki, and K. Kataoka Encapsulation of myoglobin in PEGylated polyion complex vesicles made from a pair of oppositely charged block lonomers: a physiologically available oxygen carrier Angew Chem Int Ed 46 2007 6085 6088 (Pubitemid 47290959)
218. Y. Anraku, A. Kishimura, M. Oba, Y. Yamasaki, and K. Kataoka Spontaneous formation of nanosized unilamellar polyion complex vesicles with tunable size and properties J Am Chem Soc 132 2010 1631 1636
219. K. Osada, H. Cabral, Y. Mochida, S. Lee, K. Nagata, T. Matsuura, M. Yamamoto, Y. Anraku, A. Kishimura, N. Nishiyama, and K. Kataoka Bioactive polymeric metallosomes self-assembled through block copolymer-metal complexation J Am Chem Soc 134 2012 13172 13175
220. M. Le Hellaye, N. Fortin, J. Guilloteau, A. Soum, S. Lecommandoux, and S.M. Guillaume Biodegradable polycarbonate-b-polypeptide and polyester-b-polypeptide block copolymers: synthesis and nanoparticle formation towards biomaterials Biomacromolecules 9 2008 1924 1933
221. C. Sanson, C. Schatz, J.F. Le Meins, A. Brulet, A. Soum, and S. Lecommandoux Biocompatible and biodegradable poly(trimethylene carbonate)-b-poly (l-glutamic acid) polymersomes: size control and stability Langmuir 26 2010 2751 2760
222. C. Sanson, J.F. Le Meins, C. Schatz, A. Soum, and S. Lecommandoux Temperature responsive poly(trimethylene carbonate)-block-poly(l-glutamic acid) copolymer: polymersomes fusion and fission Soft Matter 6 2010 1722 1730
223. H. Oliveira, E. Perez-Andres, J. Thevenot, O. Sandre, E. Berra, and S. Lecommandoux Magnetic field triggered drug release from polymersomes for cancer therapeutics J Control Release 169 2013 165 170
224. H.J. Lee, and Y. Bae Cross-linked nanoassemblies from poly(ethylene glycol)-poly(aspartate) block copolymers as stable supramolecular templates for particulate drug delivery Biomacromolecules 12 2011 2686 2696
225. C. Zhao, X. Gao, P. He, C. Xiao, X. Zhuang, and X. Chen Facile synthesis of thermo- and pH-responsive biodegradable microgels Colloid Polym Sci 289 2011 447 451
226. C. Zhao, P. He, C. Xiao, X. Gao, X. Zhuang, and X. Chen Synthesis of temperature and pH-responsive crosslinked micelles from polypeptide-based graft copolymer J Colloid Interface Sci 359 2011 436 442
227. F. Shi, J. Ding, C. Xiao, X. Zhuang, C. He, L. Chen, and X. Chen Intracellular microenvironment responsive PEGylated polypeptide nanogels with ionizable cores for efficient doxorubicin loading and triggered release J Mater Chem 22 2012 14168 14179
228. A.P. Nowak, V. Breedveld, L. Pakstis, B. Ozbas, D.J. Pine, D. Pochan, and T.J. Deming Rapidly recovering hydrogel scaffolds from self-assembling diblock copolypeptide amphiphiles Nature 417 2002 424 428 (Pubitemid 34563531)
229. A.P. Nowak, V. Breedveld, D.J. Pine, and T.J. Deming Unusual salt stability in highly charged diblock co-polypeptide hydrogels J Am Chem Soc 125 2003 15666 15670 (Pubitemid 37532212)
230. T.J. Deming Polypeptide hydrogels via a unique assembly mechanism Soft Matter 1 2005 28 35
231. L.M. Pakstis, B. Ozbas, K.D. Hales, A.P. Nowak, T.J. Deming, and D. Pochan Effect of chemistry and morphology on the biofunctionality of self-assembling diblock copolypeptide hydrogels Biomacromolecules 5 2004 312 318 (Pubitemid 38404465)
232. A.P. Nowak, J. Sato, V. Breedveld, and T.J. Deming Hydrogel formation in amphiphilic triblock copolypeptides Supramol Chem 18 2006 423 427 (Pubitemid 44174387)
233. Z. Li, and T.J. Deming Tunable hydrogel morphology via self-assembly of amphiphilic pentablock copolypeptides Soft Matter 6 2010 2546 2551
234. B. Song, J. Song, S. Zhang, M.A. Anderson, Y. Ao, C.Y. Yang, T.J. Deming, and M.V. Sofroniew Sustained local delivery of bioactive nerve growth factor in the central nervous system via tunable diblock copolypeptide hydrogel depots Biomaterials 33 2012 9105 9116
235. Y.Y. Choi, M.K. Joo, Y.S. Sohn, and B. Jeong Significance of secondary structure in nanostructure formation and thermosensitivity of polypeptide block copolymers Soft Matter 4 2008 2383 2387
236. H.J. Oh, M.K. Joo, Y.S. Sohn, and B. Jeong Secondary structure effect of polypeptide on reverse thermal gelation and degradation of l/dl-poly(alanine)- poloxamer-l/dl-poly(alanine) copolymers Macromolecules 41 2008 8204 8209
237. B.G. Choi, M.H. Park, S.H. Cho, M.K. Joo, H.J. Oh, E.H. Kim, K. Park, D.K. Han, and B. Jeong Thermal gelling polyalanine-poloxamine-polyalanine aqueous solution for chondrocytes 3D culture: initial concentration effect Soft Matter 7 2011 456 462
238. B.G. Choi, M.H. Park, S.H. Cho, M.K. Joo, H.J. Oh, E.H. Kim, K. Park, D.K. Han, and B. Jeong In situ thermal gelling polypeptide for chondrocytes 3D culture Biomaterials 31 2010 9266 9272
239. Y. Jeong, M.K. Joo, K.H. Bahk, Y.Y. Choi, H.T. Kim, W.K. Kim, H.J. Lee, Y.S. Sohn, and B. Jeong Enzymatically degradable temperature-sensitive polypeptide as a new in-situ gelling biomaterial J Control Release 137 2009 25 30
240. Y. Chen, X.H. Pang, and C.M. Dong Dual stimuli-responsive supramolecular polypeptide-based hydrogel and reverse micellar hydrogel mediated by host-guest chemistry Adv Funct Mater 20 2010 579 586
241. Y. Chen, and C.M. Dong pH-sensitive supramolecular polypeptide-based micelles and reverse micelles mediated by hydrogen-bonding interactions or host-guest chemistry: characterization and in vitro controlled drug release J Phys Chem B 114 2010 7461 7468
242. C. Zhao, X. Zhuang, P. He, C. Xiao, C. He, J. Sun, X. Chen, and X. Jing Synthesis of biodegradable thermo- and pH-responsive hydrogels for controlled drug release Polymer 50 2009 4308 4316
243. Z. Zhang, L. Chen, M. Deng, Y. Bai, X. Chen, and X. Jing Biodegradable thermo- and pH-responsive hydrogels for oral drug delivery J Polym Sci Part A Polym Chem 49 2011 2941 2951
244. H. Peng, Y. Xiao, X. Mao, L. Chen, R. Crawford, and A.K. Whittaker Amphiphilic triblock copolymers of methoxy-poly(ethylene glycol)-b-poly(l- lactide)-b-poly(l-lysine) for enhancement of osteoblast attachment and growth Biomacromolecules 10 2009 95 104
245. P. Zhang, H. Wu, H. Wu, Z. Lu, C. Deng, Z. Hong, X. Jing, and X. Chen RGD-conjugated copolymer incorporated into composite of poly(lactide-co- glycotide) and poly(l-lactide)-grafted nanohydroxyapatite for bone tissue engineering Biomacromolecules 12 2011 2667 2680
246. K. Zhang, Y. Zhang, S. Yan, L. Gong, J. Wang, X. Chen, L. Cui, and J. Yin Repair of an articular cartilage defect using adipose-derived stem cells loaded on a polyelectrolyte complex scaffold based on poly(l-glutamic acid) and chitosan Acta Biomater 9 2013 7276 7288
247. M. Yin, Y. Yuan, C. Liu, and J. Wang Development of mussel adhesive polypeptide mimics coating for in-situ inducing re-endothelialization of intravascular stent devices Biomaterials 30 2009 2764 2773
248. B. Li, B. Jiang, B.M. Boyce, and B.A. Lindsey Multilayer polypeptide nanoscale coatings incorporating IL-12 for the prevention of biomedical device-associated infections Biomaterials 30 2009 2552 2558
249. Z.K. Jiang, S.B.S. Koh, M. Sato, I.C. Atanasov, M. Johnson, Z.H. Zhou, T.J. Deming, and L. Wu Engineering polypeptide coatings to augment gene transduction and in vivo stability of adenoviruses J Control Release 166 2013 75 85
250. L. Yin, Z. Song, K.H. Kim, N. Zheng, N.P. Gabrielson, and J. Cheng Non-viral gene delivery via membrane-penetrating, mannose-targeting supramolecular self-assembled nanocomplexes Adv Mater 25 2013 3063 3070
251. R. Cheng, F. Meng, C. Deng, H.A. Klok, and Z. Zhong Dual and multi-stimuli responsive polymeric nanoparticles for programmed site-specific drug delivery Biomaterials 34 2013 3647 3657