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

doi:10.1021/ma2016387

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

Chemistry

Research output: Contribution to journal › Article

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 language	English (US)
Pages (from-to)	62-69
Number of pages	8
Journal	Macromolecules
Volume	45
Issue number	1
DOIs	https://doi.org/10.1021/ma2016387
State	Published - Jan 10 2012

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ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Inorganic Chemistry
Materials 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

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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.",

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AU - Castillo, José A.

AU - Borchmann, Dorothee E.

AU - Cheng, Amy Y.

AU - Wang, Yufeng

AU - Hu, Chunhua

AU - García, Andrés J.

AU - Weck, Marcus

PY - 2012/1/10

Y1 - 2012/1/10

N2 - 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.

AB - 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.

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10.1021/ma2016387