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 journalArticle

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

Fingerprint

Lactic acid
Polyethylene glycols
Ethylene Glycol
Ethylene glycol
Cell adhesion
Azides
Cycloaddition
poly(lactic acid)
Osteoblasts
Ring opening polymerization
Polydispersity
Assays
Monomers
Molecular weight
poly(lactide)
dilactide

ASJC Scopus subject areas

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

Cite this

Castillo, J. A., Borchmann, D. E., Cheng, A. Y., Wang, Y., Hu, C., García, A. J., & Weck, M. (2012). Well-defined poly(lactic acid)s containing poly(ethylene glycol) side chains. Macromolecules, 45(1), 62-69. https://doi.org/10.1021/ma2016387

Well-defined poly(lactic acid)s containing poly(ethylene glycol) side chains. / Castillo, José A.; Borchmann, Dorothee E.; Cheng, Amy Y.; Wang, Yufeng; Hu, Chunhua; García, Andrés J.; Weck, Marcus.

In: Macromolecules, Vol. 45, No. 1, 10.01.2012, p. 62-69.

Research output: Contribution to journalArticle

Castillo, JA, Borchmann, DE, Cheng, AY, Wang, Y, Hu, C, García, AJ & Weck, M 2012, 'Well-defined poly(lactic acid)s containing poly(ethylene glycol) side chains', Macromolecules, vol. 45, no. 1, pp. 62-69. https://doi.org/10.1021/ma2016387
Castillo JA, Borchmann DE, Cheng AY, Wang Y, Hu C, García AJ et al. Well-defined poly(lactic acid)s containing poly(ethylene glycol) side chains. Macromolecules. 2012 Jan 10;45(1):62-69. https://doi.org/10.1021/ma2016387
Castillo, José A. ; Borchmann, Dorothee E. ; Cheng, Amy Y. ; Wang, Yufeng ; Hu, Chunhua ; García, Andrés J. ; Weck, Marcus. / Well-defined poly(lactic acid)s containing poly(ethylene glycol) side chains. In: Macromolecules. 2012 ; Vol. 45, No. 1. pp. 62-69.
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