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Hyperbranched Copolymers Based on Glycidol and Amino Glycidyl Ether: Highly Biocompatible Polyamines Sheathed in Polyglycerols
journal contribution
posted on 2016-10-14, 14:04 authored by Suhee Song, Joonhee Lee, Songa Kweon, Jaeeun Song, Kyuseok Kim, Byeong-Su KimFunctional hyperbranched polyglycerols
(PGs) have recently garnered
considerable interest due to their potential in biomedical applications.
Here, we present a one-pot synthesis of hyperbranched PGs possessing
amine functionality using a novel amino glycidyl ether monomer. A
Boc-protected butanolamine glycidyl ether (BBAG) monomer was designed
and polymerized with glycidol (G) through anionic ring-opening multibranching
polymerization to yield a series of hyperbranched P(G-co-BBAG) with controlled molecular weights (4800–16700 g/mol)
and relatively low molecular weight distributions (1.2–1.6).
The copolymerization and subsequent deprotection chemistry allow the
incorporation of an adjustable fraction of primary amine moieties
(typically, 5–20% monomer ratio) within the hyperbranched PG
backbones, thus providing potentials for varying charge densities
and functionality in PGs. The copolymerization kinetics of G and BBAG
was also evaluated using a quantitative in situ 13C NMR
spectroscopic analysis, which revealed gradient copolymerization between
the comonomers. The free amine groups within the deprotected P(G-co-BAG) copolymer were further utilized for a facile conjugation
chemistry with a model molecule in a quantitative manner. Furthermore,
the superior biocompatibility of the prepared P(G-co-BAG) polymers was demonstrated via cell viability assays, outperforming
many existing polyamines possessing relatively high cytotoxicity.
Taken together, the biocompatibility with facile conjugation chemistry
of free amine groups sheathed within the framework of hyperbranched
PGs holds the prospect of advancing biological and biomedical applications.
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13 C NMR spectroscopic analysisfunctionalityring-opening multibranching polymerizationamine groups sheathedconjugation chemistryBiocompatible Polyamines Sheathedglycidyl ether monomerhyperbranched PGscell viability assayshyperbranched PG backbonesBoc-protected butanolamine glycidyl ethercopolymerizationPolyglycerols Functional hyperbranched polyglycerolsBBAGbiocompatibilityapplicationAmino Glycidyl Ether
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