Advances in polymer and polymeric nanostructures for protein conjugation

European Polymer Journal

Volumn 49, Issue 10, 2013, Pages 2906-2918

  González Toro, Daniella C ^a   Thayumanavan, S ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

Covalent conjugation; Nanostructures; Polymer; Protein; Telechelic

Indexed keywords

BIOLOGICAL APPLICATIONS; COVALENT CONJUGATION; FUNCTIONALIZATIONS; POLYMER TECHNOLOGY; PROTEIN CONJUGATES; PROTEIN CONJUGATIONS; SYNTHETIC STRATEGIES; TELECHELICS;

BIOMOLECULES; NANOSTRUCTURES; PROTEINS; SCAFFOLDS (BIOLOGY);

POLYMERS;

EID: 84883897749     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2013.05.002     Document Type: Article

References (87)

1. L. Neutsch, B. Eggenreich, E. Herwig, M. Marchetti-Deschmann, G. Allmaier, and F. Gabor Lectin bioconjugates trigger urothelial cytoinvasion - a glycotargeted approach for improved intravesical drug delivery Eur J Pharm Biopharm 82 2 2012 367 375
2. K.B. Hadley, and P.H. Sato Catalytic activity of administered gulonolactone oxidase polyethylene-glycol conjugates Enzyme 42 4 1989 225 234
3. F.M. Veronese Peptide and protein PEGylation: a review of problems and solutions Biomaterials 22 5 2001 405 417
4. O. Schiavon, P. Caliceti, P. Ferruti, and F.M. Veronese Therapeutic proteins: a comparison of chemical and biological properties of uricase conjugated to linear or branched poly(ethylene glycol) and poly(N- acryloylmorpholine) IL Farmaco 55 4 2000 264 269
5. R. Hartmann-Petersen, and C. Gordon Quantifying protein-protein interactions in the ubiquitin pathway by surface plasmon resonance Methods Enzymol 399 2005 164 177
6. K.E. Sapsford, I.L. Medintz, J.P. Golden, J.R. Deschamps, H.T. Uyeda, and H. Mattoussi Surface-immobilized self-assembled protein-based quantum dot nanoassemblies Langmuir 20 18 2004 7720 7728
7. J. Zimmermann, M. Kwak, and A. Hermann Amphiphilic DNAblock copolymers: nucleic acid-polymer hybrid materials for diagnostics and biomedicine Methods Mol Biol 751 2011 239 266
8. P. Baumann, P. Tanner, O. Onaca, and C.G. Palivan Bio-decorated polymer membranes: a new approach in diagnostics and therapeutics Polymers 3 2011 173 192
9. E.N. Savariar, S. Ghosh, D.C. Gonzalez, and S. Thayumanavan Disassembly of non-covalent amphiphilic polymers with proteins and utility in pattern sensing J Am Chem Soc 130 16 2008 5416 5417
10. D.C. Gonzalez-Toro, E.N. Savariar, and S. Thayumanavan Fluorescence patterns from supramolecular polymer assembly and disassembly for sensing metallo and nonmetalloproteins J Am Chem Soc 131 22 2009 7708 7716
11. C. Boyer, X. Huang, M.R. Whittaker, V. Bulmus, and T.P. Davis An overview of protein-polymer particles Soft Matter 7 5 2011 1599 1614
12. N. Rodthongkum, R. Ramireddy, S. Thayumanavan, and R.W. Vachet Selective enrichment and sensitive detection of peptide and protein biomarkers in human serum using polymeric reverse micelles and MALDI-MS Analyst 137 4 2012 1024 1030
13. N. Rodthongkum, Y. Chen, S. Thayumanavan, and R.W. Vachet MALDI-MS signal enhancement of peptides after selective extraction with polymeric reverse micelles Anal Chem 82 9 2010 3686 3691
14. M.A. Azagarsamy, A. Gomez-Escudero, V. Yesilyurt, R.W. Vachet, and S. Thayumanavan Amphiphilic nanoassemblies for the detection of peptides and proteins using fluorescence and mass spectrometry Analyst 134 4 2009 635 649
15. E.A. Wang Bone Morphonetic Proteins (BMPs): therapeutic potential in healing bony defect Trends Biotechnol 11 9 1993 379 383
16. J. Löfbloom, J. Feldwisch, V. Tolmachev, J. Carlsson, S. Stahl, and F.Y. Frejd Affibody molecules: engineered proteins for therapeutic. diagnostic and biotechnological applications FEBES Lett 584 12 2010 2670 2680
17. S.P. Baldwin, and W.M. Saltzman Materials for protein delivery in tissue engineering Adv Drug Deliv Rev 33 1-2 1998 71 86
18. J. Kalia, and R.T. Raines Advances in bioconjugation Curr Org Chem 14 2 2010 138 147
19. R.M. Broyer, G.N. Grover, and H.D. Maynard Emerging synthetic approaches for protein-polymer conjugations Chem Commun 47 8 2011 2212 2226
20. T. Cha, A. Guo, and X.Y. Zhu Enzymatic activity on a chip: the critical role of protein orientation Proteomics 5 2 2005 416 419
21. F.M. Veronese, and G. Pasut PEGylation, successful approach to drug delivery Discov Today 10 21 2005 1451 1458
22. D. Bontempo, K.L. Heredia, B.A. Fish, and H.D. Maynard Cysteine-reactive polymers synthesized by atom transfer radical polymerization for conjugation to proteins J Am Chem Soc 126 47 2004 15372 15373
23. R.L. Lundblad Techniques in protein modification 1995 CRC Press Boca Raton, FL
24. A. Chilkoti, G. Chen, P.S. Stayton, and A.S. Hoffman Site-specific conjugation of a temperature-sensitive polymer to a genetically-engineered protein Biocong Chem 5 6 1994 504 507
25. B.D. Olsen, J.A. Kornfield, and D.A. Tirrell Yielding behavior in injectable hydrogels from telechelic proteins Macromolecules 43 21 2010 9094 9099
26. S.A. Maskarinec, and D.A. Tirrell Protein engineering approaches to biomaterials design Curr Opin Biotechnol 16 4 2005 422 426
27. S. Rana, Y.-C. Yehand, and V.M. Rotello Engineering the nanoparticle-protein interface: application and possibilities Curr Opin Chem Biol 14 6 2010 828 834
28. S. Thompson Small-molecule-protein conjugation procedures Methods Mol Med 94 2004 255 265
29. G.N. Grover, and H.D. Maynard Protein-polymer conjugates: synthetic approaches by controlled radical polymerizations and interesting applications Curr Opin Chem Biol 14 6 2010 818 827
30. B. Le Droumaguet, and J. Nicolas Recent advances in the design of bioconjugates from controlled/living radical polymerization Polym Chem 1 5 2010 563 598
31. R.M. Broyer, G.N. Grover, and H.D. Maynard Emerging synthetic approaches for protein-polymer conjugations Chem Commun 47 8 2011 2212 2226
32. M. Ratner Progress with PEGylation Nat Biotechnol 8 4 1990 279 281
33. Y. Kodera, A. Matsushima, M. Hiroto, H. Nishimura, A. Ishii, and T. Ueno PEGylation of proteins and bioactive substances for medical and technical applications Prog Polym Sci 23 7 1998 1233 1271
34. M.J. Joralemon, S. McRae, and T. Emrick PEGylated polymers for medicine: from conjugation to self-assembled systems Chem Commun 46 9 2010 1377 1393
35. G. Pasut, and F.M. Veronese State of the art in PEGylation: the great versatility achieved after forty years of research J Controlled Release 161 2 2012 461 472
36. J.M. Harris, N.E. Martin, and M. Modi PEGylation - a novel process for modifying pharmacokinetics Clin Pharmacokin 40 7 2001 539 551
37. L. Tao, M. Giuseppe, F. Lecolley, and D.M. Haddleton α-Aldehyde terminally functional methacrylic polymers from living radical polymerization: application in protein conjugation "Pegylation" J Am Chem Soc 126 41 2004 13220 13221
38. G.N. Grover, J. Lee, N.M. Matsumoto, and H.D. Maynard Aminooxy and pyridyl disulfide telechelic poly(poly(ethylene glycol)acrylate) by RAFT polymerization Macromolecules 45 12 2012 4958 4965
39. J. Lai, D. Filla, and R. Shea Functional polymers from novel carboxyl-terminated trithiocarbones as highly efficient RAFT agents Macromolecules 35 18 2002 6754 6756
40. B. Iskin, G. Yilmaz, and Y. Yagci Telechelic polymers by visible light induced radical coupling Macromol Chem Phys 214 1 2013 94 98
41. R.B. Bdkhe, S.J. Stafslien, N. Cilz, J. Daniels, S.E.M. Thompson, and M.E. Callow Polyurethanes with amphiphilic surfaces made using telechelic functional PDMS having orthogonal acid functional groups Prog Org Coat 75 1-2 2012 38 48
42. K.L. Heredia, D. Bontempo, T. Ly, J.T. Byers, S. Halstenberg, and H.D. Maynard In situ preparation of protein-"smart" polymer conjugates with retention of bioactivity J Am Chem Soc 127 48 2005 16955 16960
43. E.F. Osserman, R.E. Canfield, and S. Begchok Lysozyme 1974 Academic press New York
44. B. Treetarnmathurot, L. Dieudonné, E. Ferguson, D. Schmaljohann, R. Duncan, and R. Wiwattanapatapee Dextrin-trypsin and ST-HPMA-trypsin conjugates: enzyme activity, autolysis and thermal stability Int J Pharm 373 1-2 2009 68 76
45. L. Tao, G. Chen, L. Zhao, J. Xu, E. Huang, and A. Liu Protein release from biodegradable PolyHPMA-lysozyme conjugates resulting in bioactivity enhancement Chem Asian J 6 6 2011 1398 1404
46. N.J. Mariananyagam, M. Sunde, and J.M. Matthews The power of two: protein dimerization in biology Trends Biochem Sci 29 11 2004 618 625
47. Y.-Z. You, D.S. Manickam, Q.-H. Zhou, and D. Oupicky A versatile approach to reducible vinyl polymers via oxidation of telechelic polymers prepared by reversible addition fragmentation chain transfer polymerization Biomacromolecules 8 6 2007 2038 2044
48. C.R. Bertozzi, and M.D. Bednarski The synthesis of heterobifunctional linkers for the conjugation of ligands to molecular probes J Org Chem 56 56 1991 4326 4329
49. S.S. Iyer, A.S. Anderson, S. Reed, B. Swanson, and J.G. Schmidt Synthesis of orthogonal end functionalized oligoethylene glycols of defined lengths Tetrahedron Lett 45 22 2004 4285 4288
50. L. Tao, C.S. Kaddis, R.R.O. Loo, and G.N. Grover Synthetic approach to homodimeric protein-polymer conjugates Chem Commun 16 2009 2148 2150
51. R.H. Kramer, and J.W. Karpen Spanning binding sites on allosteric proteins with polymer-linked ligand dimers Nature 395 6703 1998 710 713
52. B.D. Mather, K. Viswananthan, K.M. Miller, and T.E. Long Michael addition reactions in macromolecular design for emerging technologies Prog Polym Sci 31 5 2006 487 531
53. J. Yang, K. Luo, H. Pan, P. Kopečková, and J. Kopeček Synthesis of biodegradable multiblock copolymers by click coupling of RAFT-generated heterotelechelic polyHPMA conjugates React Funct Polym 71 3 2011 294 302
54. J. Kopeček Polymer-drug conjugates: origins, progress to date and future directions Adv Drug Deliv Rev 65 1 2013 49 59
55. U. Masfeld, A. Winter, M.D. Hager, R. Hoogenboom, W. Günther, and U.S. Schubert Orthogonal self-assembly of stimuli-responsive supramolecular polymers using one-step prepared heterotelechelic building blocks Polym Chem 4 1 2013 113 123
56. K.L. Heredia, L. Tao, G.N. Grover, and H.D. Maynard Heterotelechelic polymers for capture and release of protein-polymer conjugates Polym Chem 1 2 2010 168 170
57. J. Liu, H. Liu, V. Bulmus, L. Tao, C. Boyer, and T. Davis A simple methodology for the synthesis of heterotelechelic protein-polymer-polymer- biomolecule conjugates J Polym Sci Pol Chem 48 6 2010 1399 1405
58. C. Boyer, J. Liu, V. Bulmus, T.P. Davis, B. Barner-Kowollik, and M.H. Stenzel Direct synthesis of well-defined heterotelechelic polymers for bioconjugations Macromolecules 41 15 2008 5641 5650
59. K.L. Heredia, G.N. Grover, G.N. Tao, L. Tao, and H.D. Maynard Synthesis of heterotelechelic polymers for conjugation of two different proteins Macromolecules 42 7 2009 2360 2367
60. L. Tao, J. Liu, and T.P. Davis Branched polymer-protein conjugates made from mid-chain-functional P(HPMA) Biomacromolecules 10 10 2009 2847 2851
61. F.M. Veronese, C. Monfardini, P. Caliceti, O. Schiavon, M.D. Scrawen, and D. Beer Improvement of pharmacokinetic, immunological and stability properties of asparaginase by conjugation to linear and branched monomethoxy poly(ethylene glycol) J Controlled Rel 40 3 1996 199 209
62. W. Gao, W. Liu, T. Christensen, M.R. Zalutsky, and A. Chilkoti In situ growth of a PEG-like polymer from the C terminus of an intein fusion protein improves pharmacokinetics and tumor accumulation PNAS 107 38 2010 16432 16437
63. S. Brocchini, A. Godwin, S. Balan, J.-W. Choi, M. Zloh, and S. Shaunak Disulfide bridge based PEGylation of protein Adv Drug Deliv Rev 60 1 2008 3 12
64. Y. Nojima, Y. Suzuki, I. Kazuma, T. Shiga, A. Iwata, and T. Fujimoto Development of poly(ethylene glycol) conjugated lactoferrin for oral administration Bioconjugate Chem 19 11 2008 2253 2259
65. L. Tao, C.S. Kaddis, R.R.O. Loo, G.N. Grover, J.A. Loo, and H.O. Maynard Synthesis of maleimide-end-functionalized star polymers and multimeric protein-polymer conjugates Macromolecules 42 21 2009 8028 8033
66. A.K. Iyer, G. Khaled, J. Fang, and H. Maeda Exploiting the enhanced permeability and retention effect for tumor targeting Drug Discov Today 11 17-18 2006 812 818
67. Y. Lee, T. Ishii, H. Cabral, H.J. Kim, J.-H. Seo, and N. Nishiyama Change-conversional polyionic complex micelles-efficient nanocarriers for protein delivery into cytoplasm Angew Chem Int 48 29 2009 5309 5312
68. A. Verma, J.M. Simard, J.W.E. Worrall, and V.M. Rotello Tunable reactivation of nanoparticle-inhibited β-galactosidase by glutathione at intracellular concentrations J Am Chem Soc 126 43 2004 13987 13991
69. T. Akagi, T. Kaneko, T. Kida, and M. Akashi Multifunctional conjugation of proteins on/into bio-nanoparticles prepared by amphiphilic poly(γ - glutamic acid) J Biomater Sci Polymer Edn 17 8 2006 875 892
70. D. Gonzalez-Toro, J.-H. Ryu, R. Chacko, J. Zhuang, and S. Thayumanavan Concurrent binding and delivery of proteins and lipophilic small molecules using polymeric nanogels J Am Chem Soc 134 16 2012 6964 6967
71. B.S. Sandanaraj, D.R. Vutukuri, J.M. Simard, A. Klaikherd, R. Hong, and V.M. Rotello Noncovalent modification of chymotrypsin surface using an amphiphilic polymer scaffold: implications in modulating protein function J Am Chem Soc 127 30 2005 10693 10698
72. S.B. Sandanaraj, H. Bayraktar, K. Krishnamoorthy, M. Knapp, and S. Thayumanavan Recognition and modulation of cytochrome c's redox properties using an amphiphilic homopolymer Langmuir 23 7 2007 3891 3897
73. K. Velonia Protein-polymer amphiphilic chimeras: recent advances and future challenges Polym Chem 1 7 2010 944 952
74. K. Velonia, A.E. Rowan, and R.J.M. Nolte Lipase polystyrene giant amphiphiles J Am Chem Soc 124 16 2002 4224 4225
75. B. Le Droumaguet, and K. Velonia In situ ATRP-mediated hierarchical formation of giant amphiphile bioreactors Angew Chem, Int Ed 47 33 2008 6263 6266
76. E. Daskalaki, B. Le Droumaguet, D. Gérard, and K. Velonia Multifunctional giant amphiphiles via simultaneous copper(I)-catalized azide-alkyne cycloadition and living radical polymerization Chem Commun 48 2012 1586 1588
77. S.F.M. Van Dongen, M. Nallani, J.J.L.M. Cornelissen, R.J.M. Nolte, and J.C.M. van Hest A three-enzyme cascade reaction through positional assembly of enzymes in a polymersome nanoreactor Chem Eur J 15 5 2009 1107 1114
78. L. Zhang, Z. Lu, X. Li, Y. Deng, F. Zhang, and C. Ma Methoxy poly(ethylene flycol) conjugated denatured bovine serum albumin micelles for effective delivery of camptothecin Polym Chem 3 8 2012 1958 1961
79. S. Jung, S. Hug, Y.-P. Cheon, and S. Park Intracellular protein delivery by glucose-coated polymeric beads Chem Commun 33 2009 5003 5005
80. H.J. Freisleben, H.J. Fürstenberger, S. Deisinger, K.B. Freisleben, N. Wiernsperger, and G. Zimmer Interaction of glucose and metformin with isolated red cell membrane Arzneimittelforschung 46 8 1996 773 778
81. M. Breuken, E.H.M. Lempens, R.P. Temming, B.A. Helms, E.W. Meijer, and M. Merkx Collagen targeting using multivalent protein-functionalized dendrimers Bioorgan Med Chem 19 3 2011 1062 1071
82. E.H.M. Lempens, B.A. Helms, A.R. Bayles, M. Merkx, and E.W. Meijer A versatile, modular platform for multivalent peptide ligands based on a dendritic wedge Eur J Org Chem 2010 1 2010 111 119
83. S.W.A. Reulen, P.Y.W. Dankers, P.H.H. Bomans, E.W. Meijer, and M. Merkx Collagen targeting using protein-functionalized micelles: the strength of multiple weak interactions J Am Chem Soc 131 21 2009 7304 7312
84. L. Van Baal, H. Malda, S.A. Synowsky, J.L. Van Dongen, T.M. Hackeng, and M. Merkx Multivalent peptide and protein dendrimers using native chemical ligation Angew Chem, Int Ed 44 32 2005 5052 5057
85. J. Kim, and J.W. Grate Single-enzyme nanoparticles armored by a nanometer-scale organic/inorganic network Nano Lett 3 9 2003 1219 1222
86. M. Yan, J. Ge, L. Zheng, and P. Ouyang Encapsulation of single enzyme in nanogel with enhanced biocatalytic activity and stability J Am Chem Soc 128 34 2006 11008 11009
87. M. Yan, J. Du, Z. Gu, M. Liang, Y. Hu, and W. Zhang A novel intracellular protein delivery platform based on single-protein nanocapsules Nat Nanotechnol 5 1 2010 48 53