Intramolecular cyclization assistance for fast degradation of ornithine-based poly(ester amide)s

Caroline De Gracia Lux, Jason Olejniczak, Nadezda Fomina, Mathieu L. Viger, Adah Almutairi

Research output: Contribution to journalArticle

16 Scopus citations

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 languageEnglish (US)
Pages (from-to)3783-3790
Number of pages8
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume51
Issue number18
DOIs
StatePublished - Sep 15 2013

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Keywords

  • biomaterials
  • controlled release
  • depolymerization
  • intramolecular cyclization
  • photochemistry
  • polyester amide
  • self-immolative
  • stimuli-sensitive polymers
  • triggered release

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics
  • Organic Chemistry

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