Synthesis and characterization of bioactive molecules grafted on poly(-caprolactone) by “click” chemistry

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• 作者：Jiraphong Suksiriworapong ; Kittisak Sripha ; Varaporn Buraphacheep Junyaprasert
• 关键词：Bioactive molecules ; Poly( ; //www.sciencedirect.com/scidirimg/entities/25b.gif"" alt=""var epsilon"" title=""var epsilon"" border=""0"">-caprolactone) ; Click chemistry
• 刊名：Polymer
• 出版年：2010
• 出版时间：14 May 2010
• 年：2010
• 卷：51
• 期：11
• 页码：2286-2295
• 全文大小：919 K

文摘

A facile and efficient strategy to graft bioactive molecules (nicotinic acid, p-aminobenzoic acid, and phthaloyltryptophan) onto poly(-caprolactone) (P(CL)) was achieved by copper-catalyzed Huisgen’s 1,3-dipolar cycloaddition known as click reaction. P(αClCL), with 10, 20, and 30 % of α-chloro--caprolactone (αClCL) units were copolymerized by ring opening polymerization using CL and αClCL as starting materials in the presence of 1,4-butanediol and Sn(Oct)₂. Subsequently, the chloride pendent was converted to azide followed by cycloaddition with terminal alkyne derivatives of the aforementioned bioactive molecules. The complete addition was accomplished at all ratios. The characteristic molecular features of these copolymers were evaluated by FTIR, NMR, and GPC. Thermal analysis data indicated that the grafted compounds led to polymorphic alteration and different pattern of thermal degradation depending on the molecular structure and the size of the grafted compounds. They are the basis for further development of grafted copolymer as drug delivery carriers.