Protein-Polymer Conjugates
First published: 15 September 2011
Abstract
This chapter focuses on the design and applications of protein-polymer conjugates. Protein-polymer conjugates are synthesized by conjugating a polymer chain or many polymer chains onto a protein. The site of conjugation, protein, polymer, and stoichiometry are important criteria when designing a protein-polymer conjugate. The important structural aspects and functions of proteins, such as hierarchical structure and activity, are discussed. The various methods of site-specific conjugation, “grafting to”, “grafting from” and cofactor reconstitution, are included along the pros and cons of each method. Conjugates synthesized by random conjugation are also discussed. The specific reactions used for protein attachment are not included, as numerous synthetic reviews exist; however, a broad overview of the field is presented. Novel conjugate structures can be synthesized by attaching synthetic peptide sequences onto polymers. In addition to design considerations, the range of applications from drug delivery systems to biosensors are discussed. This chapter aims to aid in furthering the knowledge and growth of the synergistic combination of proteins and polymers.
Cited Publications
- 1 H. Klok, J. Polym. Sci., Part A: Polym. Chem. 43 (1), 1–17 (2005).
- 2 C. Boyer, X. Huang, M. R. Whittaker, V. Bulmus and T. P. Davis, Soft Matter 7, 1599–1614 (2010).
- 3 K. Heredia and H. Maynard, Org. Biomol. Chem. 5, 45–53 (2007).
- 4 I. Gill and A. Ballesteros, Trends Biotechnol. 18 (11), 469–479 (2000).
- 5 P. Thordarson, B. Le Droumaguet and K. Velonia, Appl. Biochem. Microbiol. 73 (2), 243–254 (2006).
- 6 G. S. Manning, Q. Rev. Biophys. 11 (02), 179–246 (1978).
- 7 D. Stigter, Biophys. J. 69 (2), 380–388 (1995).
- 8 H. Larsericsdotter, S. Oscarsson and J. Buijs, J. Colloid Interface Eci. 237 (1), 98–103 (2001).
- 9 G. Das and K. Prabhu, Enzyme Microb. Technol. 12 (8), 625–630 (1990).
- 10 C. A. Haynes and W. Norde, Colloids Surf., B 2 (6), 517–566 (1994).
- 11 M. R. Duff Jr and C. V. Kumar, Langmuir 25 (21), 12635–12643 (2009).
- 12
H. Y. Erbil,
Surface chemistry of solid and liquid interfaces,
Wiley-Blackwell,
(2006).
10.1002/9781444305401 Google Scholar
- 13 W. Y. Chen, H. M. Huang, C. C. Lin, F. Y. Lin and Y. C. Chan, Langmuir 19 (22), 9395–9403 (2003).
- 14 A. Revzin, The Biology of nonspecific DNA-protein interactions, CRC, (1990).
- 15 S. Kidoaki and T. Matsuda, Langmuir 15 (22), 7639–7646 (1999).
- 16 R. G. Chapman, E. Ostuni, L. Yan and G. M. Whitesides, Langmuir 16 (17), 6927–6936 (2000).
- 17 A. Abuchowski, T. Van Es, N. Palczuk and F. Davis, J. Biol. Chem. 252 (11), 3578 (1977).
- 18 F. Veronese and G. Pasut, Drug Discovery Today 10 (21), 1451–1458 (2005).
- 19 P. Caliceti and F. Veronese, Adv. Drug Delivery Rev. 55 (10), 1261–1277 (2003).
- 20 F. Veronese, Biomaterials 22 (5), 405–417 (2001).
- 21 G. Moad, E. Rizzardo and S. H. Thang, Polymer 49 (5), 1079–1131 (2008).
- 22 R. Barbey, L. Lavanant, D. Paripovic, N. Schuwer, C. Sugnaux, S. Tugulu and H. A. Klok, Chem. Rev. 109 (11), 5437–5527 (2009).
- 23 A. W. York, S. E. Kirkland and C. L. McCormick, Adv. Drug Delivery Rev. 60 (9), 1018–1036 (2008).
- 24 W. A. Braunecker and K. Matyjaszewski, Prog. Polym. Sci. 32 (1), 93–146 (2007).
- 25 M. Hillmyer, Curr. Opin. 4 (6), 559–564 (1999).
- 26 E. Saurer, R. Flessner, S. Sullivan, M. Prausnitz and D. Lynn, Biomacromolecules 101–114 (2010).
- 27 M. Macdonald, N. M. Rodriguez, R. Smith and P. T. Hammond, J. Controlled Release 131 (3), 228–234 (2008).
- 28 R. G. Krishna and F. Wold, 67 (1993).
- 29 R. Smith and D. Hansen, J. Am. Chem. Soc 120 (35), 8910–8913 (1998).
- 30 C. Walsh, Posttranslational Modification of Proteins: Expanding Nature's Inventory, Roberts & Company Publishers, Greenwood Vilage (2006).
- 31 D. Voet, J. G. Voet and C. W. Pratt, Fundamentals of biochemistry: life at the molecular level, Wiley Hoboken, NJ, (2006).
- 32 C. H. Haigler and P. J. Weimer, Biosynthesis and biodegradation of cellulose, CRC, (1991).
- 33 P. Bornstein and K. A. Piez, J. Clin. Invest. 43 (9), 1813 (1964).
- 34 A. Hoffman and P. Stayton, Prog. Polym. Sci. 32 (8-9), 922–932 (2007).
- 35 V. Thilakarathne, V. A. Briand, R. M. Kasi and C. V. Kumar, in preparation (2011).
- 36
Z. Ding,
G. Chen and
A. S. Hoffman,
J. Biomed. Mater. Res., Part A
39
(3),
498–505
(1998).
10.1002/(SICI)1097-4636(19980305)39:3<498::AID-JBM22>3.0.CO;2-5 CAS PubMed Web of Science® Google Scholar
- 37 K. Velonia, A. Rowan and R. Nolte, J. Am. Chem. Soc 124 (16), 4224–4225 (2002).
- 38 H. Klok, Macromolecules 42 (21), 7990–8000 (2009).
- 39 K. L. Heredia, D. Bontempo, T. Ly, J. T. Byers, S. Halstenberg and H. D. Maynard, J. Am. Chem. Soc 127 (48), 16955–16960 (2005).
- 40 R. M. Broyer, G. N. Grover and H. D. Maynard, Chem. Commun. (2011).
- 41 K. Heredia and H. Maynard, Org. Biomol. Chem. (2006).
- 42 B. Lele, H. Murata, K. Matyjaszewski and A. Russell, Biomacromolecules 6 (6), 3380–3387 (2005).
- 43 M. Gauthier and H. Klok, Chem. Commun. 2008 (23), 2591–2611 (2008).
- 44 M. Roberts, M. Bentley and J. Harris, Adv. Drug Delivery Rev. 54 (4), 459–476 (2002).
- 45 J. Nicolas, G. Mantovani and D. Haddleton, Macromol. Rapid Commun. 28 (10), 1083–1111 (2007).
- 46 D. Bontempo, K. L. Heredia, B. A. Fish and H. D. Maynard, J. Am. Chem. Soc 126 (47), 15372–15373 (2004).
- 47 F. Lecolley, L. Tao, G. Mantovani, I. Durkin, S. Lautru and D. M. Haddleton, Chem. Commun. (18), 2026 (2004).
- 48 D. Bontempo and H. D. Maynard, J. Am. Chem. Soc. 127 (18), 6508–6509 (2005).
- 49
J. Liu,
V. Bulmus,
D. L. Herlambang,
C. Barner Kowollik,
M. H. Stenzel and
T. P. Davis,
Angew. Chem.
119
(17),
3159–3163
(2007).
10.1002/ange.200604922 Google Scholar
- 50 D. Voet, J. Voet and C. Pratt, Fundamentals of biochemistry, Wiley New York, (1999).
- 51 M. Boerakker, N. Botterhuis, P. Bomans, P. Frederik, E. Meijer, R. Nolte and N. Sommerdijk, Chemistry: A European Journal 12 (23), 6071–6080 (2006).
- 52
M. Boerakker,
J. Hannink,
P. Bomans,
P. Frederik,
R. Nolte,
E. Meijer and
N. Sommerdijk,
Angew. Chem.
114
(22),
4413–4415
(2002).
10.1002/1521-3757(20021115)114:22<4413::AID-ANGE4413>3.0.CO;2-L Google Scholar
- 53 A. J. Link, M. L. Mock and D. A. Tirrell, Curr. Opin. Biotechnol. 14 (6), 603–609 (2003).
- 54 T. Shimoboji, Z. Ding, P. Stayton and A. Hoffman, Bioconjugate Chem. 13 (5), 915–919 (2002).
- 55 G. D. Meredith, H. Y. Wu and N. L. Allbritton, Bioconjugate Chem. 15 (5), 969–982 (2004).
- 56 D. R. W. Hodgson and J. M. Sanderson, Chem. Soc. Rev. 33 (7), 422–430 (2004).
- 57 C. Boyer, J. Liu, V. Bulmus, T. P. Davis, C. Barner-Kowollik and M. H. Stenzel, Macromolecules 41 (15), 5641–5650 (2008).
- 58 C. Boyer, V. Bulmus, J. Liu, T. P. Davis, M. H. Stenzel and C. Barner-Kowollik, J. Am. Chem. Soc. 129 (22), 7145–7154 (2007).
- 59 T. Sookkumnerd, J. T. Hsu and Y. Ito, J. Liq. Chromatogr. Relat. Technol. 23 (13), 1973–1979 (2000).
- 60 Z. Ding, J. Cynthia, Y. Hayashi, E. V. Bulmus, A. S. Hoffman and P. S. Stayton, Bioconjugate Chem. 10 (3), 395–400 (1999).
- 61 Z. Ding, R. B. Fong, C. J. Long, P. S. Stayton and A. S. Hoffman, Nature 411 (6833), 59–62 (2001).
- 62 R. Gaspar and R. Duncan, Adv. Drug Delivery Rev. 61 (13), 1220–1231 (2009).
- 63 J. L. Drury and D. J. Mooney, Biomaterials 24 (24), 4337–4351 (2003).
- 64 J. Kopecek, Biomaterials 28 (34), 5185–5192 (2007).
- 65 D. Tada, T. Tanabe, A. Tachibana and K. Yamauchi, J. Biosci. Bioeng. 100 (5), 551–555 (2005).
- 66 J. Kopecek, A. Tang, C. Wang and R. J. Stewart, 174, 31–42 (2001).
- 67 M. Gonen-Wadmany, L. Oss-Ronen and D. Seliktar, Biomaterials 28 (26), 3876–3886 (2007).
- 68 I. Gill and A. Ballesteros, Biotechnol. Bioeng. 70 (4), 400–410 (2000).
- 69 Y. Shachaf, M. Gonen-Wadmany and D. Seliktar, Biomaterials 31 (10), 2836–2847 (2010).
- 70 D. Martorell, F. Cespedes, E. Martìnez-Fàbregas and S. Alegret, Anal. Chim. Acta 290 (3), 343–348 (1994).
- 71 M. Santandreu, S. Solé, E. Fàbregas and S. Alegret, Biosens. Bioelectron. 13 (1), 7–17 (1998).
- 72 G. Vandermeulen and H. Klok, Macromol. Biosci. 4 (4), 383–398 (2004).
- 73 K. Rajagopal and J. Schneider, Curr. Opin. Struct. Biol. 14 (4), 480–486 (2004).
- 74 T. Deming, Adv. Drug Delivery Rev. 54 (8), 1145–1155 (2002).
- 75 P. Michal Pechar, Macromol. Biosci. 2 (5), 199–206 (2002).
- 76 G. Vandermeulen, C. Tziatzios and H. Klok, Macromolecules 36 (11), 4107–4114 (2003).
- 77 H. Klok, J. Langenwalter and S. Lecommandoux, Macromolecules 33 (21), 7819–7826 (2000).
- 78 P. Papadopoulos, G. Floudas, I. Schnell, T. Aliferis, H. Iatrou and N. Hadjichristidis, Biomacromolecules 6 (4), 2352–2361 (2005).
- 79 P. Papadopoulos, G. Floudas, H. Klok, I. Schnell and T. Pakula, Biomacromolecules 5 (1), 81–91 (2004).
- 80 C. Li, Adv. Drug Delivery Rev. 54 (5), 695–713 (2002).
- 81 A. Nowak, V. Breedveld, L. Pakstis, B. Ozbas, D. Pine, D. Pochan and T. Deming, Nature 417 (6887), 424–428 (2002).
- 82 C. Yang, B. Song, Y. Ao, A. Nowak, R. Abelowitz, R. Korsak, L. Havton, T. Deming and M. Sofroniew, Biomaterials 30 (15), 2881–2898 (2009).
- 83 M. Charati and K. Kiick, Polym. Chem. 1 (8), 1160–1170 (2010).
- 84 S. Grieshaber, A. Farran, S. Lin-Gibson, K. Kiick and X. Jia, Macromolecules 42 (7), 2532–2541 (2009).
- 85 K. Gebhardt, S. Ahn, G. Venkatachalam and D. Savin, J. Colloid Interface Eci. 317 (1), 70–76 (2008).
- 86 H. Lu, J. Wang, Y. Lin and J. Cheng, J. Am. Chem. Soc. 131 (38), 13582–13583 (2009).
- 87 H. Lu, J. Wang, Y. Bai, J. W. Lang, S. Liu, Y. Lin and J. Cheng, Nat. Commun. 2 206 (2011).
- 88 M. Vicent and R. Duncan, Trends Biotechnol. 24 (1), 39–47 (2006).
- 89 H. Maeda, Adv. Drug Delivery Rev. 6 (2), 181–202 (1991).
- 90 R. Duncan, Nat. Rev. Cancer 6 (9), 688–701 (2006).
- 91 H. Maeda, Adv. Drug Delivery Rev. 46 (1-3), 169–185 (2001).
- 92 Y. Luo, N. J. Bernshaw, Z. R. Lu, J. Kopecek and G. D. Prestwich, Pharm. Res. 19 (4), 396–402 (2002).
- 93 F. Veronese, B. Sacca, P. P. De Laureto, M. Sergi, P. Caliceti, O. Schiavon and P. Orsolini, Bioconjugate Chem. 12 (1), 62–70 (2001).
- 94 R. Duncan, Nat. Rev. Drug Discovery 2 (5), 347–360 (2003).
- 95 R. Duncan and F. Spreafico, Clin. Pharm. 27 (4), 290 (1994).
- 96 L. G. Griffith and G. Naughton, Science 295 (5557), 1009 (2002).
- 97 B. S. Kim and D. J. Mooney, Trends Biotechnol. 16 (5), 224–230 (1998).
- 98 M. S. Shoichet, Macromolecules 43 (2), 581–591 (2009).
- 99 M. Goldberg, R. Langer and X. Jia, J. Biomater. Sci. Polym. Ed. 18 (3), 241–268 (2007).
- 100 M. Martina and D. W. Hutmacher, Polym. Int. 56 (2), 145–157 (2007).
- 101 S. P. Baldwin and W. Mark Saltzman, Adv. Drug Delivery Rev. 33 (1–2), 71–86 (1998).
- 102 T. Nie, A. Baldwin, N. Yamaguchi and K. L. Kiick, J. Controlled Release 122 (3), 287–296 (2007).
- 103 A. Alayash, Nat. Biotechnol. 17 (6), 545–549 (1999).
- 104 H. Sakai, M. Yuasa, H. Onuma, S. Takeoka and E. Tsuchida, Bioconjugate Chem. 11 (1), 56–64 (2000).
- 105 C. Alarcon, S. Pennadam and C. Alexander, Chem. Soc. Rev. 34 (3), 276–285 (2005).
- 106 D. Schmaljohann, Adv. Drug Delivery Rev. 58 (15), 1655–1670 (2006).
- 107 A. Hoffman, Clin. Chem. 46 (9), 1478 (2000).
- 108 A. Chilkoti, G. Chen, P. Stayton and A. Hoffman, Bioconjugate Chem. 5 (6), 504–507 (1994).
- 109 C. Lackey, N. Murthy, O. Press, D. Tirrell, A. Hoffman and P. Stayton, Bioconjugate Chem. 10 (3), 401–405 (1999).
- 110 S. Kulkarni, C. Schilli, B. Grin, A. Müller, A. Hoffman and P. Stayton, Biomacromolecules 7 (10), 2736–2741 (2006).
- 111 A. Hoffman, P. Stayton, V. Bulmus, G. Chen, J. Chen, C. Cheung, A. Chilkoti, Z. Ding, L. Dong and R. Fong, J. Biomed. Mater. Res., Part A 52 (4), 577–586 (2000).
- 112 T. Shimoboji, E. Larenas, T. Fowler, A. Hoffman and P. Stayton, Bioconjugate Chem. 14 (3), 517–525 (2003).
- 113 J. Chen, H. Yang and A. Huffman, Biomaterials 11 (9), 625–630 (1990).
- 114 N. Lavignac, M. Lazenby, J. Franchini, P. Ferruti and R. Duncan, Int. J. Pharm. 300 (1-2), 102–112 (2005).
- 115
S. Itaru Hamachi,
Eur. J. Org. Chem.
1999(3),
539–549
(1999).
10.1002/(SICI)1099-0690(199903)1999:3<539::AID-EJOC539>3.0.CO;2-F Google Scholar
- 116 L. Fruk, C. Kuo, E. Torres and C. Niemeyer, Agnew. Chem. Int. Ed. 48 (9), 1550–1574 (2009).
- 117 A. Arslan, H. Kuzu and M. Altikatoglu, J. Carbohydr. Chem. 29 (5), 222–235
- 118 R. Dutra, G. Coelho, V. Silva, W. Ledingham and J. L. L. Filho, Biotechnol. Lett. 22 (7), 579–583 (2000).
