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Glycopolymer Conjugates

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Bio-synthetic Polymer Conjugates

Part of the book series: Advances in Polymer Science ((POLYMER,volume 253))

Abstract

This review describes recent developments in the field of glycopolymer (polymer–carbohydrate conjugate) synthesis. The interest in this class of polymers that have a wide range of biological recognition properties has grown rapidly in the last decade due to their application in the areas of biotechnology and medicinal chemistry. Modern synthetic methodologies such as controlled radical polymerization, ionic polymerization, ring-opening polymerization (ROP), ring-opening metathesis polymerization (ROMP) and Click chemistry have recently been proven to be extremely efficient and versatile tools for building tailor-made functional polymers with different molecular architectures. The use of these synthetic methods to prepare glycopolymer conjugates is outlined and discussed in detail. The self-assembling behavior of these glycopolymer designs and their interactions with their corresponding lectins (cell surface receptor proteins) are also presented in this review.

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Abbreviations

AcGalEMA:

2-(2′,3′,4′,6′-Tetra-O-acetyl-β-d-galactosyloxy)ethyl methacrylate

AcGEA:

2-(2′,3′,4′,6′-Tetra-O-acetyl-β-d-glucopyranosyloxy)-ethyl acrylate

ACPA:

4,4′-Azobis(4-cyanopentanoic acid)

AFM:

Atomic force microscopy

ARGET:

Activators regenerated by electron transfer

ATRP:

Atom transfer radical polymerization

BLG:

Benzyl l-glutamate

BSA:

Bovine serum albumin

Con-A:

Concanavalin A

CRP:

Controlled radical polymerization

CuAAC:

Copper-catalyzed azide-alkyne cycloaddition

DEGMA:

Di(ethylene glycol) methyl ether methacrylate

DIPEA:

N,N-diisopropylethylamine

DLS:

Dynamic light scattering

ELISA:

Enzyme-linked immunosorbent assay

FRP:

Free radical polymerization

GalEMA:

2-(β-d-Galactosyloxy)ethyl methacrylate

GAMA:

2-Gluconamidoethyl methacrylate

GluEMA:

2-(β-d-Glucosyloxy)ethyl methacrylate

HEMA:

2-Hydroxyethyl methacrylate

HIA:

Hemagglutination inhibition assay

ICAR:

Initiators for continuous activator regeneration

ITC:

Isothermal titration microcalorimetry

LAMA:

2-Lactobionamidoethyl methacrylate

MAGlu:

2-Methacryloxyethyl glucoside

MAIpGlc:

3-O-methacryloyl-1,2:5,6-di-O-isopropylidene-d-glucofuranose

MALDI-TOF:

Matrix-assisted laser desorption/ionization-time of flight

MCDO:

5-Methyl-5-carboxyl-1,3-dioxan-2-one

MS:

Mass spectrometry

NCA:

N-carboxyanhydride

NHS:

N-hydroxysuccinimide

NIPAM:

N-isopropylacrylamide

NMP:

Nitroxide-mediated polymerization

PCL:

Poly(ε-caprolactone)

PDEA:

Poly[2-(diethylamino)ethyl methacrylate]

PDEGMA:

Poly(diethyleneglycol methacrylate)

PDI:

Polydispersity index

PDPA:

Poly[2-(diisopropylaminoethyl methacrylate)]

PET:

Poly(ethylene terephthalate)

PG:

Propargylglycine

PGAMA:

Poly(glucosamidoethyl methacrylate)

PGMMA:

Poly(glycerol monomethacrylate)

PLA:

Poly(lactide)

PLAMA:

Poly(2-lactobionamidoethyl methacrylate)

PLG:

Poly(l-glutamate)

PNA:

Peanut agglutinin

PNIPAM:

Poly(N-isopropylacrylamide)

PVA:

Poly(vinyl alcohol)

Pβ-BLG:

Poly(β-benzyl l-glutamate)

Pγ-BLG:

Poly(γ-benzyl l-glutamate)

RAFT:

Reversible addition–fragmentation chain transfer

RCA120 :

Ricinus communis agglutinin

ROMP:

Ring-opening metathesis polymerization

ROP:

Ring-opening polymerization

SEC:

Size exclusion chromatography

SPR:

Surface plasmon resonance

TEM:

Transmission electron microscopy

TEMPO:

2,2,6,6-Tetramethylpiperidinyloxy

TMC:

Trimethylene carbonate

VLA:

N-(p-vinylbenzyl)-[O-β-d-galactopyranosyl-(1-4)]-d-gluconamide

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Acknowledgments

We thank the Leverhulme Trust (grant no. F/00128/BO) for financial support. The P2M program from the ESF is also gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry & Biophysical Sciences Institute (BSI), Durham University, South Road, Durham, DH1 3LE, UK

    Ahmed M. Eissa & Neil R. Cameron

  2. Department of Polymers, Chemical Industries Research Division, National Research Centre (NRC), Dokki, Cairo, Egypt

    Ahmed M. Eissa

Authors
  1. Ahmed M. Eissa
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  2. Neil R. Cameron
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Correspondence to Neil R. Cameron .

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Editors and Affiliations

  1. Research Campus Golm, Department of Colloid Chemistry, Max Planck Institute of Colloids and Int, Research Campus Golm, Potsdam, 14424, Germany

    Helmut Schlaad

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Eissa, A.M., Cameron, N.R. (2012). Glycopolymer Conjugates. In: Schlaad, H. (eds) Bio-synthetic Polymer Conjugates. Advances in Polymer Science, vol 253. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2012_177

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