Lipase-catalyzed synthesis of oxidation-responsive poly(ethylene glycol)-b-poly(β-thioether ester) amphiphilic block copolymers

A series of novel oxidation-responsive amphiphilic diblock copolymers with β-thioether ester groups were synthesized via the one-step lipase-catalyzed polycondensation of methyl 3-((2-hydroxyethyl)thio)propanoate (MHETP) with monomethoxy poly(ethylene glycol) (mPEG) using immobilized lipase B from C...

Full description

Saved in:
Bibliographic Details
Published in:RSC advances 2016, Vol.6 (14), p.11870-11879
Main Authors: Wu, Wan-Xia, Yang, Xian-Ling, Liu, Bei-Yu, Deng, Qing-Feng, Xun, Miao-Miao, Wang, Na, Yu, Xiao-Qi
Format: Article
Language:English
Subjects:
Addition polymerization
Copolymers
Drug delivery systems
Esters
Light scattering
Micelles
Nanostructure
Transmission electron microscopy
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A series of novel oxidation-responsive amphiphilic diblock copolymers with β-thioether ester groups were synthesized via the one-step lipase-catalyzed polycondensation of methyl 3-((2-hydroxyethyl)thio)propanoate (MHETP) with monomethoxy poly(ethylene glycol) (mPEG) using immobilized lipase B from Candida antarctica (CALB) as the catalyst. The amphiphilic poly(ethylene glycol)- b -poly(β-thioether ester) (mPEG- b -PTE) diblock copolymers could self-assemble to form nanosized micelles in aqueous solution with low critical micelle concentration (CMC). The micelles were able to undergo a H 2 O 2 -triggered disassembly due to the oxidizable thioether groups and degradable ester groups in the hydrophobic PTE core. The oxidation-responsive behaviour of the micelles was further investigated by dynamic light scattering (DLS) and transmission electron microscopy (TEM). Nile Red, a hydrophobic model drug, was encapsulated into the polymeric micelles and showed fast release upon the addition of H 2 O 2 . Cell cytotoxicity tests indicated that the micelles had low cytotoxicity toward HeLa cells. The oxidation-insensitive poly(ethylene glycol)- b -poly(ε-caprolactone) (mPEG- b -PCL) diblock copolymer was also prepared for comparison. All these findings demonstrated the potential of mPEG- b -PTE diblock copolymers as a promising oxidation-responsive nanocarrier for controlled drug delivery.
ISSN:2046-2069
2046-2069
DOI:10.1039/C5RA21779B