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 | |
| State | Published - Jan 10 2012 |
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ASJC Scopus subject areas
- Organic Chemistry
- Materials Chemistry
- Polymers and Plastics
- Inorganic Chemistry
Cite this
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 journal › Article
}
TY - JOUR
T1 - Well-defined poly(lactic acid)s containing poly(ethylene glycol) side chains
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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U2 - 10.1021/ma2016387
DO - 10.1021/ma2016387
M3 - Article
VL - 45
SP - 62
EP - 69
JO - Macromolecules
JF - Macromolecules
SN - 0024-9297
IS - 1
ER -