Well-defined poly(lactic acid)s containing poly(ethylene glycol) side chains

José A. Castillo, Dorothee E. Borchmann, Amy Y. Cheng, Yufeng Wang, Chunhua Hu, Andrés J. García, Marcus Weck

Research output: Contribution to journalArticlepeer-review

Abstract

Poly(ethylene glycol) (PEG) side-chain functionalized lactide analogues have been synthesized in four steps from commercially available l-lactide. The key step in the synthesis is the 1,3-dipolar cycloaddition between PEG-azides and a highly strained spirolactide-heptene monomer, which proceeds in high conversions. The PEG-grafted lactide analogues were polymerized via ring-opening polymerization using triazabicyclodecene as organocatalyst to give well-defined tri- and hepta(ethylene glycol)-poly(lactide)s (PLA) with molecular weights above 10 kDa and polydispersity indices between 1.6 and 2.1. PEG-poly(lactide) (PLA) with PEG chain M n 2000 was also prepared, but GPC analysis showed a bimodal profile indicating the presence of starting macromonomer. Cell adhesion assays were performed using MC3T3-E1 osteoblast-like cells demonstrating that PEG-containing PLA reduces cell adhesion significantly when compared to unfunctionalized PLA.

Original languageEnglish (US)
Pages (from-to)62-69
Number of pages8
JournalMacromolecules
Volume45
Issue number1
DOIs
StatePublished - Jan 10 2012

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

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