Full Paper
Functional Brush-Decorated Poly(globalide) Films by ARGET-ATRP for Bioconjugation
Zeliha Ates,
Fabrice Audouin,
Amy Harrington,
Brendan O'Connor,
Andreas Heise,
Zeliha Ates
School of Chemical Sciences, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorFabrice Audouin
School of Chemical Sciences, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorAmy Harrington
School of Biotechnology, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorBrendan O'Connor
School of Biotechnology, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorCorresponding Author
Andreas Heise
School of Chemical Sciences, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorZeliha Ates,
Fabrice Audouin,
Amy Harrington,
Brendan O'Connor,
Andreas Heise,
Zeliha Ates
School of Chemical Sciences, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorFabrice Audouin
School of Chemical Sciences, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorAmy Harrington
School of Biotechnology, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorBrendan O'Connor
School of Biotechnology, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorCorresponding Author
Andreas Heise
School of Chemical Sciences, Dublin City University, Dublin 9, Ireland
Search for more papers by this authorAbstract
Formation of hydroxyl functionalized poly(macrolactone) films was achieved by a combination of enzymatic ring opening polymerization of globalide and thiol-ene coupling reactions. Reaction with α-bromoisobutyryl bromide yielded ATRP initiator functional films. Efficient activator regeneration by electron transfer (ARGET) ATRP was employed for the polymerization of tert-butyl acrylate (tBA) and NIPAM from the initiator decorated surfaces. Deprotection of the tert-butyl ester decorated polymer films yielded carboxylic acid groups for convenient attachment of biomolecule. The successful conjugation of green fluorescent protein (eGFP) and active enzyme chitobiase (Chb) on densely poly(acrylic acid)-functionalized polyester films is demonstrated.
References
- 1 H. Seyednejad, A. H. Ghassemi, C. F. van Nostrum, T. Vermonden, W. E. Hennink, J. Control. Release 2011, 152, 168.
- 2 Y.-C. Yoo, H.-Y. Kim, F.-L. Jin, S.-J. Park, Macromol. Res. 2013, 21, 687.
- 3 C. Jerome, A. Aqil, S. Voccia, D. E. Labaye, V. Maquet, S. Gautier, O. E. Bertrand, R. Jerome, J. Biomed. Mater. Res. A 2006, 76, 521.
- 4 D. Chan-Seng, T. Ranganathan, X. Zhang, Y. Tang, Q. Lin, L. Kleiner, T. Emrick, Drug Deliv. 2009, 16, 304.
- 5 B. M. Holzapfel, F. Wagner, D. Loessner, N. P. Holzapfel, L. Thibaudeau, R. Crawford, M. T. Ling, J. A. Clements, P. J. Russell, D. W. Hutmacher, Biomaterials 2014, 35, 4108.
- 6 Y. Sun, Z. Xing, Y. Xue, K. Mustafa, A. Finne-Wistrand, A. C. Albertsson, Biomacromolecules 2014, 15, 1259.
- 7 Y. Sun, A. Finne-Wistrand, A. C. Albertsson, Z. Xing, K. Mustafa, W. J. Hendrikson, D. W. Grijpma, L. Moroni, J. Biomed. Mater. Res. A 2012, 100, 2739.
- 8 M. Tang, M. Purcell, J. A. M. Steele, K.-Y. Lee, S. McCullen, K. M. Shakesheff, A. Bismarck, M. M. Stevens, S. M. Howdle, C. K. Williams, Macromolecules 2013, 46, 8136.
- 9 J. Undin, A. Finne-Wistrand, A. C. Albertsson, Biomacromolecules 2013, 14, 2095.
- 10 Y. Du, X. Chen, y. Hang Koh, B. Lei, Mater. Lett. 2014, 122, 62.
- 11 D. Pepic, M. S. Nikolic, S. Grujic, M. Lausevic, J. Djonlagic, J. Microencapsulation 2013, 30, 151.
- 12 A. Cammarano, G. Luca, E. Amendola, Cent. Eur. J. Chem. 2012, 11, 35.
- 13 D. Yan, J. Jones, X. Y. Yuan, X. H. Xu, J. Sheng, J. C. Lee, G. Q. Ma, Q. S. Yu, J. Biomed. Mater. Res. A 2013, 101, 963.
- 14 A. Martins, E. D. Pinho, S. Faria, I. Pashkuleva, A. P. Marques, R. L. Reis, N. M. Neves, Small 2009, 5, 1195.
- 15 H. Park, Y. K. Lee, J. S. Lee, E. K. Park, H. W. Park, Macromol. Res. 2007, 15.
- 16 M. B. Olde Riekerink, J. G. A. Terlingen, G. H. M. Engbers, J. Feijen, Langmuir 1999, 15, 4847.
- 17 Y. Wan, X. Qu, J. Lu, C. Zhu, L. Wan, J. Yang, J. Bei, S. Wang, Biomaterials 2004, 25, 4777.
- 18 A. Bozzi, T. Yuranova, J. Kiwi, J. Photochem. Photobiol. A 2005, 172, 27.
- 19 S. Edmondson, V. L. Osborne, W. T. Huck, Chem. Soc. Rev. 2004, 33, 14.
- 20 H.-I. Lee, J. Pietrasik, S. S. Sheiko, K. Matyjaszewski, Prog. Polym. Sci. 2010, 35, 24.
- 21 R. Barbey, L. Lavanant, D. Paripovic, N. Schuwer, C. Sugnaux, S. Tugulu, H. A. Klok, Chem. Rev. 2009, 109, 5437.
- 22 Y. K. Jhon, S. Arifuzzaman, A. E. Ozcam, D. J. Kiserow, j. Genzer, Langmuir 2012, 28, 872.
- 23 P. Ye, H. Dong, M. Zhong, K. Matyjaszewski, Macromolecules 2011, 44, 2253.
- 24 J. Choi, H. Dong, K. Matyjaszewski, R. M. Bockstaller, J. Am. Chem. Soc. 2010, 132, 12537.
- 25 Y. Liu, V. Klep, B. Zdyrko, I. Luzinov, Langmuir 2005, 21, 11806.
- 26 S. Ohno, K. Matyjaszewski, J. Polym. Sci. A: Polym. Chem. 2006, 44, 5454.
- 27 S. Yuan, G. Xiong, X. Wang, S. Zhang, C. Choong, J. Mater. Chem. 2012, 22, 13039.
- 28 F. J. Xu, Z. H. Wang, W. T. Yang, Biomaterials 2010, 31, 3139.
- 29 B. Lebedev, A. Yevstropov, Makromol. Chem. 1984, 185, 1235.
- 30 M. L. Focarete, M. Scandola, A. Kumar, R. A. Gross, J. Polym. Sci., Part B: Polym. Phys. 2001, 39, 1721.
- 31 P. Skoglund, A. Fransson, Polymer 1998, 39, 3143.
- 32 A. R. Gross, A. Kumar, B. Kalra, Chem. Rev. 2001, 101, 2097.
- 33 M. Bouyahyi, R. Duchateau, Macromolecules 2014, 47, 517.
- 34 I. van der Meulen, E. Gubbels, S. Huijser, Rl. Sablong, C. E. Koning, A. Heise, R. Duchateau, Macromolecules 2011, 44, 4301.
- 35 J. Cai, C. Liu, M. Cai, J. Zhu, F. Zuo, B. S. Hsiao, R. A. Gross, Polymer 2010, 51, 1088.
- 36 H. Uyama, K. Takeya, N. Hoshi, S. Kobayashi, Macromolecules 1995, 28, 7046.
- 37 A. Kumar, B. Kalra, A. Dekhterman, R. A. Gross, Macromolecules 2000, 33, 6303.
- 38 K. S. Bisht, L. A. Henderson, R. A. Gross, D. L. Kaplan, G. Swift, Macromolecules 1997, 30, 2705.
- 39 M. de Geus, I. van der Meulen, B. Goderis, K. van Hecke, M. Dorschu, H. van der Werff, C. E. Koning, A. Heise, Polym. Chem. 2010, 1, 525.
- 40 I. van der Meulen, M. de Geus, J. A. E. Joosten, H. Antheunis, E. C. Koning, R. Deumens, A. Heise, Biomacromolecules 2008, 9, 3404.
- 41 M. Bouyahyi, M. P. F. Pepels, A. Heise, R. Duchateau, Macromolecules 2012, 45, 3356.
- 42 M. Bouyahyi, R. Duchateau, Macromolecules 2014, 47, 517.
- 43 Z. Ates, A. Heise, Polym. Chem. 2014, 5, 2936.
- 44 Z. Ates, P. D. Thornton, A. Heise, Polym. Chem. 2011, 2, 309.
- 45 F. Audouin, A. Heise, Eur. Polym. J. 2013, 49, 1073.
- 46 C. M. Hui, J. Pietrasik, M. Schmitt, C. Mahoney, J. Choi, M. R. Bockstaller, K. Matyjaszewski, Chem. Mater. 2014, 26, 745.
- 47 J. Pyun, T. Kowalewski, K. Matyjaszewski, Macromol. Rapid Commun. 2003, 24, 1043.
- 48 V. N. Tsarevsky, K. Matyjaszewski, Chem. Rev. 2007, 107, 2270.
- 49 W. Jakubowski, K. Matyjaszewski, Macromolecules 2005, 38, 4139.
- 50 J. Kim, W. Huang, M. D. Miller, G. L. Baker, M. L. Bruening, J. Polym. Sci. A: Polym. Chem. 2003, 41, 386.
- 51 E. Marutani, S. Yamamoto, T. Ninjbadgar, Y. Tsujii, T. Fukuda, M. Takano, Polymer 2004, 45, 2231.
- 52 B. C. Gorman, J. R. Petrie, J. Jan Genzer, Macromolecules 2008, 41, 4856.
- 53 J. R. Schaefgek, I. M. Sarasohn, J. Polym. Sci. 1962, 58, 1049.
- 54 C. Porsch, S. Hansson, N. Nordgren, E. Malmström, Polym. Chem. 2011, 2, 1114.
- 55 M. A. Cooperstein, H. E. Canavan, Langmuir 2010, 26, 7695.
- 56 M. Teodorescu, K. Matyjaszewski, Macromolecules 1999, 32, 4826.
- 57 M. Teodorescu, K. Matyjaszewski, Macromol. Rapid Commun. 2000, 21, 190.
- 58 R. J. Spencer, G. J. N. Delaet, A. Toy-Palmer, V. V. Antonenko, M. Goodman, J. Org. Chem. 1993, 58, 1635.
- 59 Y. Wu, C. D. Limburg, E. D. Wilkinson, J. M. Vaal, S. G. Hamilton, Tetrahedron Lett. 2000, 41.
- 60 J. M. Goddard, J. H. Hotchkiss, Prog. Polym. Sci. 2007, 32, 698.
- 61 H. Jiang, F. J. Xu, Chem. Soc. Rev. 2013, 42, 3394.
- 62 F. J. Xu, K. G. Neoh, E. T. Kang, Prog. Polym. Sci. 2009, 34, 719.
- 63 F. Yang, G. L. Moss, N. G. Phillips, Nat. Biotechnol. 1996, 14, 1246.
- 64 E. Duchaud, C. Rusniok, L. Frangeul, C. Buchrieser, A. Givaudan, S. Taourit, S. Bocs, C. Boursaux-Eude, M. Chandler, J. F. Charles, E. Dassa, R. Derose, S. Derzelle, G. Freyssinet, S. Gaudriault, C. Medigue, A. Lanois, K. Powell, P. Siguier, R. Vincent, V. Wingate, M. Zouine, P. Glaser, N. Boemare, A. Danchin, F. Kunst, Nat. Biotechnol. 2003, 21, 1307.
- 65 R. N. Tharanathan, F. S. Kittur, Crit. Rev. Food Sci. 2003, 43, 61.
