Abstract
End-functionalization of biodegradable polymers/oligomers based on L-lactide and glycolide by cholesteryl moiety was investigated. We established the feasibility of preparing the functionalized polymers/oligomers, Chol-(LG)m+n, through ring-opening copolymerization initiated by cholesterol bearing a hydroxyl group, without adding any catalyst. The functionalized polymers/oligomers of different molecular weights were obtained by controlling the feed ratio of the initiator cholesterol to the monomers. The chemical structure of end-functionalized polymers/oligomers was confirmed by FTIR and 1H NMR. Incorporation of cholesteryl moiety into the polymer chains induces liquid crystallinity in the resultant oligomers when the molecular chains are not very long. The enzymatic degradation studies, for all the samples, were carried out using enzyme, proteinase K. Interestingly, the enzymatic degradation of cholesteryl end-functionalized polymers/oligomers resulted in a lamella-like porous structure on the sample surface, which is altogether different from the commonly reported spherical-pore structure formed during the degradation of conventional polyesters.
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References
Ignatius AA, Claes LE (1996) Biomaterials 17:831
Kricheldorf HR, Kreiser-Saunders I (1994) Polymer 35:4175
Hwang JJ, Iyer SN, Li LS, Claussen R, Harrington DA, Stupp SI (2003) PNAS 99:9662
Klok HA, Hwang JJ, Stupp SI (2002) Macromolecules 35:746
Klok HA, Hwang JJ, Hartgerink JD, Stupp SI (2002) Macromolecules 35:6101
Simons K, Ikonen E (2000) Science 290:1721
Urata K, Takaishi N (2001) Eur J Lipid Sci Technol 103:29
Koyama Y, Ito T, Kimura T, Murakami A, Yamaoka T (2001) J Control Rel 77:357
Kasperczyk J (1996) Polymer 37:201
Breitenbach A, Pistel KF, Kissel T (2000) Polymer 41:4781
Williams DF (1981) Eng Med 10:5
MacDonald RT, McCarthy SP, Gross RA (1996) Macromolecules 29:7356
Li S, Girard A, Garreau H, Vert M (2001) Polym Degrad Stabil 71:61
Li S, Tenon M, Garreau H, Braud C, Vert M (2000) Polym Degrad Stabil 67:85
McColluch I, Shalaby S (eds) (1998) Tailored polymeric materials for controlled delivery systems. ACS symposium series 709, American Chemical Society, Washington DC, p 242
Cai Q, Shi G, Bei J, Wang S (2003) Biomaterials 24:629
Acknowledgments
This research was supported by grant (20204010) from the National Natural Science Foundation of China. One of the authors, Si-Xue Cheng, is grateful to the Ministry of Education of China for the financial support under “Trans-Century Training Programme Foundation for the Talents” and Wuhan University for the grant of “Innovative Project Foundation for Young Scientists”. Special thanks are due to Ms Qing-Rong Wang for the GPC measurement.
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Zou, T., Cheng, SX. & Zhuo, RX. Synthesis and enzymatic degradation of end-functionalized biodegradable polyesters. Colloid Polym Sci 283, 1091–1099 (2005). https://doi.org/10.1007/s00396-004-1267-0
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DOI: https://doi.org/10.1007/s00396-004-1267-0