Abstract
Inspired by the spontaneous cyclization of ornithine in peptides, polyesters containing protected ornithine (Orn) side chains along the backbone were synthesized and shown to degrade rapidly upon deprotection through intramolecular cyclization. A new ornithine-based poly(ester amide) PEA 1 and a lysine-based control PEA 2, both bearing the light-sensitive protecting group o-nitrobenzyl alcohol (ONB), were synthesized. Tert-butyl carbamate (Boc)-protected versions 1-Boc and 2-Boc were also synthesized for proof of concept. GPC confirmed that 1-Boc degrades over 40 times faster than 2-Boc following deprotection into the designed intramolecular cyclization products. Finally, TEM visualization of particles made from 1 encapsulating iron oxide nanoparticles reveals complete disruption of nanoparticles and release of payload within a day upon UV irradiation.
Original language | English (US) |
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Pages (from-to) | 3783-3790 |
Number of pages | 8 |
Journal | Journal of Polymer Science, Part A: Polymer Chemistry |
Volume | 51 |
Issue number | 18 |
DOIs | |
State | Published - Sep 15 2013 |
Keywords
- biomaterials
- controlled release
- depolymerization
- intramolecular cyclization
- photochemistry
- polyester amide
- self-immolative
- stimuli-sensitive polymers
- triggered release
ASJC Scopus subject areas
- Polymers and Plastics
- Organic Chemistry
- Materials Chemistry