Keto-functionalized polymer scaffolds as versatile precursors to polymer side-chain conjugates

Jingquan Liu; Ronald C Li; Gregory J Sand; Volga Bulmus; Thomas Paul Davis; Heather D Maynard

doi:10.1021/ma302183g

Keto-functionalized polymer scaffolds as versatile precursors to polymer side-chain conjugates

Jingquan Liu, Ronald C Li, Gregory J Sand, Volga Bulmus, Thomas Paul Davis, Heather D Maynard

Research output: Contribution to journal › Article › Research › peer-review

50 Citations (Scopus)

Abstract

A new methacrylate monomer with a reactive ketone side chain, 2-(4-oxopentanoate)ethyl methacrylate (PAEMA), was synthesized and subsequently polymerized by reversible addition-fragmentation chain transfer (RAFT) polymerization to give a polymer with a narrow molecular weight distribution (PDI = 1.25). The polymer was chain extended with poly(ethylene glycol methyl ether methacrylate) (PEGMA) to yield a block copolymer. Aminooxy-containing small molecules and oligoethylene glycol were conjugated to the ketone functionality of the side chains in high yields. Cytotoxicity of the oxime-linked tetra(ethylene glycol) polymer to mouse fibroblast cells was investigated; the polymer was found to be noncytotoxic up to 1 mg/mL. The ease with which this polymer is functionalized suggests that it may be useful in forming tailored polymeric medicines.

Original language	English
Pages (from-to)	8 - 14
Number of pages	7
Journal	Macromolecules
Volume	46
Issue number	1
DOIs	https://doi.org/10.1021/ma302183g
Publication status	Published - 2013
Externally published	Yes

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title = "Keto-functionalized polymer scaffolds as versatile precursors to polymer side-chain conjugates",

abstract = "A new methacrylate monomer with a reactive ketone side chain, 2-(4-oxopentanoate)ethyl methacrylate (PAEMA), was synthesized and subsequently polymerized by reversible addition-fragmentation chain transfer (RAFT) polymerization to give a polymer with a narrow molecular weight distribution (PDI = 1.25). The polymer was chain extended with poly(ethylene glycol methyl ether methacrylate) (PEGMA) to yield a block copolymer. Aminooxy-containing small molecules and oligoethylene glycol were conjugated to the ketone functionality of the side chains in high yields. Cytotoxicity of the oxime-linked tetra(ethylene glycol) polymer to mouse fibroblast cells was investigated; the polymer was found to be noncytotoxic up to 1 mg/mL. The ease with which this polymer is functionalized suggests that it may be useful in forming tailored polymeric medicines.",

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doi = "10.1021/ma302183g",

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T1 - Keto-functionalized polymer scaffolds as versatile precursors to polymer side-chain conjugates

AU - Liu, Jingquan

AU - Li, Ronald C

AU - Sand, Gregory J

AU - Bulmus, Volga

AU - Davis, Thomas Paul

AU - Maynard, Heather D

PY - 2013

Y1 - 2013

N2 - A new methacrylate monomer with a reactive ketone side chain, 2-(4-oxopentanoate)ethyl methacrylate (PAEMA), was synthesized and subsequently polymerized by reversible addition-fragmentation chain transfer (RAFT) polymerization to give a polymer with a narrow molecular weight distribution (PDI = 1.25). The polymer was chain extended with poly(ethylene glycol methyl ether methacrylate) (PEGMA) to yield a block copolymer. Aminooxy-containing small molecules and oligoethylene glycol were conjugated to the ketone functionality of the side chains in high yields. Cytotoxicity of the oxime-linked tetra(ethylene glycol) polymer to mouse fibroblast cells was investigated; the polymer was found to be noncytotoxic up to 1 mg/mL. The ease with which this polymer is functionalized suggests that it may be useful in forming tailored polymeric medicines.

AB - A new methacrylate monomer with a reactive ketone side chain, 2-(4-oxopentanoate)ethyl methacrylate (PAEMA), was synthesized and subsequently polymerized by reversible addition-fragmentation chain transfer (RAFT) polymerization to give a polymer with a narrow molecular weight distribution (PDI = 1.25). The polymer was chain extended with poly(ethylene glycol methyl ether methacrylate) (PEGMA) to yield a block copolymer. Aminooxy-containing small molecules and oligoethylene glycol were conjugated to the ketone functionality of the side chains in high yields. Cytotoxicity of the oxime-linked tetra(ethylene glycol) polymer to mouse fibroblast cells was investigated; the polymer was found to be noncytotoxic up to 1 mg/mL. The ease with which this polymer is functionalized suggests that it may be useful in forming tailored polymeric medicines.

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UR - https://www.scopus.com/pages/publications/84872117267

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DO - 10.1021/ma302183g

M3 - Article

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VL - 46

SP - 8

EP - 14

JO - Macromolecules

JF - Macromolecules

IS - 1

ER -

Keto-functionalized polymer scaffolds as versatile precursors to polymer side-chain conjugates

Abstract

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