Synthesis of well-defined poly[(2-β-D-glucopyranosyloxy)ethyl acrylate] by atom transfer radical polymerization

Liang, Yu-Zeng; Li, Zi‐Chen; Chen, Guang‐Qiang; Li, Fu‐Mian

doi:10.1002/(sici)1097-0126(199909)48:9<739::aid-pi283>3.0.co;2-6

Cited by 29 publications

(8 citation statements)

References 22 publications

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“…Although atom transfer radical polymerization (ATRP) has been found to be a useful technique for the synthesis of glycopolymers, as with NMP, the majority of the syntheses have involved the use of protected glycomonomers 54–70. Narain and Armes successfully synthesized glycomonomers [Fig.…”

Section: Glycopolymer Synthesis By the Polymerization Of Carbohydratementioning

confidence: 99%

Recent advances in the synthesis of well‐defined glycopolymers

Spain

Gibson

Cameron

2007

J. Polym. Sci. A Polym. Chem.

235

208

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Glycopolymers are receiving increasing interest due to their application in areas, such as glycomics, medicine, biotechnology, sensors, and separation science. Consequently, new methods for their synthesis are constantly being developed, with an increasing emphasis on the preparation of well‐defined polymers and on the production of complex macromolecular architectures such as stars. This review covers recent developments in the synthesis of glycopolymers, with a particular emphasis on (i) the use of controlled radical polymerization to prepare well‐defined glycopolymers from unprotected monomers and (ii) postpolymerization modification strategies using reactive polymer precursors (including “click” reactions). Recent work on the production of glycosylated polypeptides, which are under investigation as mimics of naturally occurring glycoproteins, is also included. The authors offer some suggestions as to future developments and remaining challenges in this topical area of polymer chemistry. © 2007 Wiley Periodicals, Inc. J Polym Sci PartA: Polym Chem45: 2059–2072, 2007

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Section: Glycopolymer Synthesis By the Polymerization Of Carbohydratementioning

confidence: 99%

Recent advances in the synthesis of well‐defined glycopolymers

Spain

Gibson

Cameron

2007

J. Polym. Sci. A Polym. Chem.

235

208

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“…[16][17][18] The tolerance of atom transfer radical polymerization (ATRP) toward hydroxyl groups has enabled the direct synthesis of sugar-carrying polymers without protecting chemistry. 19,20 ATRP has been used for the synthesis of many sugar-carrying block 21,22 and graft 16 polymers. Controlled/"living" radical polymerization has thus proved to be a very facile approach for the well-defined and controlled synthesis of glycopolymers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Methacrylate-Type Hyperbranched Glycopolymers via Self-Condensing Atom Transfer Radical Copolymerization

2005

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We report the synthesis of hyperbranched glycopolymers by self-condensing vinyl copolymerization (SCVCP) of the methacrylic AB* inimer 2-(2-bromoisobutyryloxy)ethyl methacrylate (BIEM) with 3-O-methacryloyl-1,2:5,6-di-O-isopropylidene-R-D-glucofuranose (MAIGlc) via atom transfer radical polymerization, followed by deprotection of the isopropylidene protecting groups. Homopolymerization of MAIGlc with the (PPh3)2NiBr2 catalyst system in solution proceeds smoothly, resulting in linear poly-(MAIGlc) having controlled molecular weights and narrow molecular weight distribution. The catalyst system could be applied for SCVCP to synthesize hyperbranched poly(MAIGlc)s, as confirmed by GPC and GPC/viscosity analyses and 1 H, 13 C, and 2D NMR measurements. Depending on the comonomer ratio, γ ) [MAIGlc]0/[BIEM]0, branched poly(MAIGlc)s with number-average molecular weights between 17500 and 29800 and Mark-Houwink exponents between 0.20 and 0.34 were obtained within reasonable polymerization time (4 h), the polymerization being very much faster than that of the corresponding glycopolyacrylates. Deprotection of the isopropylidene protecting groups of the branched poly(MAIGlc)s resulted in water-soluble glycopolymers with randomly branched architectures, which were characterized by elemental analyses and 1 H NMR and FT-IR measurements.

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“…Zemplén deprotection is commonly used in the deprotection of glycopolymers with minimal degradation. [48][49][50][51][52][53] However, an in-depth study to examine the affect that this reaction can have on other polymeric esters would be of great interest.…”

Section: Chain Extension Of Macro-cta Via Automated Synthesismentioning

confidence: 99%

Glycosylated Nanoparticles Derived from RAFT Polymerization for Effective Drug Delivery to Macrophages

Rushworth

Montgomery

Cao

et al. 2020

ACS Appl. Bio Mater.

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The functional-group tolerance and simplicity of reversible addition fragmentation chain transfer (RAFT) polymerization enables its use in the preparation of a wide range of functional polymer architectures for a variety of applications, including drug delivery. Given the role of tumor-associated macrophages (TAMs) in cancer and their dependence on the tyrosine kinase receptor FMS (CSF-1R), the key aim of this work was to achieve effective delivery of an FMS inhibitor to cells using a polymer delivery system. Such a system has the potential to exploit biological features specific to macrophages and therefore provide enhanced selectivity. Building on our prior work, we have prepared RAFT polymers based on a P(BMA-co-MAA) diblock, which were extended with a hydrophilic block, cross-linker and mannose-based monomer scaffold; exploiting the abundance of macrophage mannose receptors (CD206) on the surface of macrophages. We demonstrate that the prepared polymers can be assembled into nanoparticles and are successfully internalized into macrophages, in part, via the macrophage mannose receptor (CD206). Finally, we showcase the developed nanoparticles in the delivery of an FMS inhibitor to cells, resulting in inhibition of the FMS receptor. As such, this study lays the groundwork for further drug delivery studies aimed at specifically targeting TAMs with molecularly targeted therapeutics.

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Synthesis of well-defined poly[(2-β-D-glucopyranosyloxy)ethyl acrylate] by atom transfer radical polymerization

Cited by 29 publications

References 22 publications

Recent advances in the synthesis of well‐defined glycopolymers

Recent advances in the synthesis of well‐defined glycopolymers

Synthesis and Characterization of Methacrylate-Type Hyperbranched Glycopolymers via Self-Condensing Atom Transfer Radical Copolymerization

Glycosylated Nanoparticles Derived from RAFT Polymerization for Effective Drug Delivery to Macrophages

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