Methoxy-Poly(ethylene glycol)-block-Poly(ϵ-caprolactone) Bearing Pendant Aldehyde Groups as pH-Responsive Drug Delivery Carrier
Gejun Ma A , Deshan Li A , Ji Wang A , Xuefei Zhang A B C and Haoyu Tang A B C
+ Author Affiliations
- Author Affiliations
A College of Chemistry, Xiangtan University, Xiangtan, 411105, Hunan Province, China.
B Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, Key Laboratory of Polymeric Materials and Application Technology of Hunan Province and Universities of Hunan Province, Xiangtan, 411105, China.
C Corresponding authors. Email: zxf7515@163.com; cranetang@gmail.com
Australian Journal of Chemistry 66(12) 1576-1583 https://doi.org/10.1071/CH13297
Submitted: 10 June 2013 Accepted: 20 August 2013 Published: 16 September 2013
Abstract
A biodegradable amphiphilic block copolymer of methoxy poly(ethylene glycol)-block-poly(ϵ-caprolactone) bearing pendant aldehyde groups was synthesised by a combination of ring-opening polymerisation and thio-bromo ‘click’ chemistry. The free aldehyde groups on the copolymer were reacted with hydrophobic payloads (p-methoxylaniline as a model drug) by a benzoic–imine linker, which was responsive to pH change. NMR, FTIR, and gel permeation chromatography analysis confirmed the copolymer structures. In vitro release studies revealed that under acid stimulus, hydrolysis of the benzoic–imine bond resulted in a rapid drug release. This new amphiphilic block copolymer is expected to have promising applications in biodegradable controlled drug delivery systems.
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