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Thiol coupling based synthesis of temperature-sensitivepolymer–peptide conjugates with controlled architecture.

Published online by Cambridge University Press:  18 May 2012

Jean-Baptiste Guilbaud
Affiliation:
School of Materials, The University of Manchester, Manchester, M1 7HS, UK
Aline F. Miller
Affiliation:
CEAS, The University of Manchester, Manchester, M60 1QD, UK
Alberto Saiani
Affiliation:
School of Materials, The University of Manchester, Manchester, M1 7HS, UK
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Abstract

A synthetic strategy to couple selectively an ionic complementary thiolmodified octapeptide, that is able to gel at low temperature, to thethermoresponsive polymer poly(N-isopropylacrylamide) (pNIPAAm) withcontrolled molecular weight and narrow polydispersity is described. Thepolymer was synthesized by atom transfer radical polymerization (ATRP)affording halogen functionalized chain ends. This allowed subsequentcoupling to a thiol terminated ionic complementary octapeptide via nucleophile substitution. Results indicated that thepeptide was covalently attached to the polymer and that both thecoil-globule phase transition of pNIPAAm and the gelation properties of thepeptide were retained in the conjugated product. This method provides aversatile route for the synthesis of a range of bioconjugate materials withcontrolled architecture and dual self-assembling and thermoresponsivebehavior.

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Copyright
Copyright © Materials Research Society 2012

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References

REFERENCES

1.Mei, Y., Beers, K. L., Byrd, H. C. M., Vanderhart, D. L. and Washburn, N. R., J. Am. Chem. Soc. 126 (11), 34723476 (2004).CrossRefGoogle Scholar
2.Klok, H. A., Vandermeulen, G. W. M., Nuhn, H., Rosler, A., Hamley, I. W., Castelletto, V., Xu, H. and Sheiko, S. S., Faraday Discuss. 128, 2941 (2005).CrossRefGoogle Scholar
3.Stoica, F., Alexander, C., Tirelli, N., Miller, A. F. and Saiani, A., Chem. Commun. (37), 44334435 (2008).CrossRefGoogle Scholar
4.Matyjaszewski, K. and Xia, J. H., Chem. Rev. 101 (9), 29212990 (2001).CrossRefGoogle Scholar
5.Sarin, V. K., Kent, S. B. H., Tam, J. P. and Merrifield, R. B., Anal. Biochem. 117 (1), 147157 (1981).CrossRefGoogle Scholar
6.Boothroyd, S., Saiani, A. and Miller, A. F., Macromol. Symp. 273, 139145 (2008).CrossRefGoogle Scholar
7.Saiani, A., Mohammed, A., Frielinghaus, H., Collins, R., Hodson, N., Kielty, C. M., Sherratt, M. J. and Miller, A. F., Soft Matter 5 (1), 193202 (2009).CrossRefGoogle Scholar
8.Xia, Y., Yin, X. C., Burke, N. A. D. and Stover, H. D. H., Macromolecules 38 (14), 59375943 (2005).CrossRefGoogle Scholar
9.Ye, J. D. and Narain, R., J. Phys. Chem. B 113 (3), 676681 (2009).CrossRefGoogle Scholar
10.Zhu, H. H., Yalcin, T. and Li, L., J. Am. Soc. Mass Spectrom. 9 (4), 275281 (1998).CrossRefGoogle Scholar
11.Lu, X. J., Zhang, L. F., Meng, L. Z. and Liu, Y. H., Polym. Bull. 59 (2), 195206 (2007).CrossRefGoogle Scholar
12.Couet, J. and Biesalski, M., Macromolecules 39 (21), 72587268 (2006).CrossRefGoogle Scholar
13.Merrifield, R. B., Federation Proceedings 21 (2), 412-& (1962).Google Scholar
14.Merrifield, R. B., J. Am. Chem. Soc. 85 (14), 2149-& (1963).CrossRefGoogle Scholar
15.Maslovskis, A., Saiani, A. and Miller, A. F., Soft Matter, advance article (2011).Google Scholar