The synthesis, deprotection and properties of poly(γ-benzyl-l-glutamate)

Diethylamine, di- n -hexylamine, dicyclohexylamine and triethylamine have been used as initiators for the ring-opening polymerization of γ-benzyl- l -glutamate N -carboxyanhydride (BLG NCA) to synthesize poly(γ-benzyl- l -glutamate) (PBLG). The relationship between the molecular weight of PBLG and t...

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Bibliographic Details
Published in:Science China. Chemistry 2013-06, Vol.56 (6), p.729-738
Main Authors: Han, JinDong, Ding, JianXun, Wang, ZhiChun, Yan, ShiFeng, Zhuang, XiuLi, Chen, XueSi, Yin, JingBo
Format: Article
Language:English
Subjects:
Acetic acid
Aqueous solutions
Biocompatibility
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Degree of polymerization
Hydrobromic acid
Initiators
Molecular weight
Monomers
Polymerization
Reagents
Ring opening polymerization
Triethylamine
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Summary:Diethylamine, di- n -hexylamine, dicyclohexylamine and triethylamine have been used as initiators for the ring-opening polymerization of γ-benzyl- l -glutamate N -carboxyanhydride (BLG NCA) to synthesize poly(γ-benzyl- l -glutamate) (PBLG). The relationship between the molecular weight of PBLG and the molar ratio of monomer and initiator was studied. With dicyclohexylamine as initiator, the influence of monomer concentration, and reaction temperature and time on the polymerization of BLG NCA was examined. Three reagents were used for the deprotection of benzyl groups in PBLG, including hydrobromic acid/acetic acid (33 wt.%), NaOH aqueous solution and trimethylsilyl iodide (TMSI). Through examining the molecular weight of PLGA obtained using different deprotection methods, it was revealed that TMSI could minimize chain cleavage in the process of deprotection and retain the degree of polymerization. The biocompatibilities of PBLG obtained using different initiators were evaluated by a live/dead assay against L929 fibroblast cells. The in vitro cytotoxicities of PLGA obtained using different deprotecting agents were evaluated by a methyl thiazolyl tetrazolium assay. The results revealed that both PBLG and PLGA exhibited good biocompatibilities.
ISSN:1674-7291
1869-1870
DOI:10.1007/s11426-013-4839-3