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Novel Biodegradable Polymer with Redox‐Triggered Backbone Cleavage Through Sequential 1,6‐Elimination and 1,5‐Cyclization Reactions
Author(s) -
Whang ChangHee,
Kim Kyeong Soo,
Bae Jungeun,
Chen Jun,
Jun HoWook,
Jo Seongbong
Publication year - 2017
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201700395
Subject(s) - monomer , redox , chemistry , polymer , linker , combinatorial chemistry , polymer chemistry , polymerization , copolymer , biodegradable polymer , organic chemistry , computer science , operating system
In the past decade, the self‐immolative biodegradable polymer arose as a novel paradigm for its efficient degradation mechanism and vast potential for advanced biomedical applications. This study reports successful synthesis of a novel biodegradable polymer capable of self‐immolative backbone cleavage. The monomer is designed by covalent conjugations of both pendant redox‐trigger (p‐nitrobenzyl alcohol) and self‐immolative linker (p‐hydroxybenzyl alcohol) to the cyclization spacer (n‐2‐(hydroxyethyl)ethylene diamine), which serves as the structural backbone. The polymerization of the monomer with hexamethylene diisocyanate yields a linear redox‐sensitive polymer that can systemically degrade via sequential 1,6‐elimination and 1,5‐cyclization reactions within an effective timeframe. Ultimately, the polymer's potential for biomedical application is simulated through in vitro redox‐triggered release of paclitaxel from polymeric nanoparticles.