Synthesis of Glycopolymers by Controlled Radical Polymerization Techniques and Their Applications

Vázquez-Dorbatt, Vimary; Lee, Jun-Young; Lin, En-Wei; Maynard, Heather D.

doi:10.1002/cbic.201200480

Cited by 91 publications

(79 citation statements)

References 160 publications

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“…sugar composition, linkage, molar mass and conformation) of these bioactive polysaccharides (and any natural variation in fine structure) could lead to potential routes to modification (Inngjerdingen, et. al., 2007;, synthesis (Flitsch, 2000;Ladmiral, Melia and Haddleton, 2004;Vázquez-Dorbatt, Lee, Lin and Maynard, 2012) or fractionation (Morris and Ralet, 2012a,b) which may produce more effective carbohydrates for use in the control of diabetes or in the supplementation of functional foods (Norfezah, et al, 2011;Morris and Morris, 2012). Currently there is no research to suggest whether the biologically active component of these plants is the same in each cucurbit through the effects seem to be consistent throughout the cucurbit family.…”

Section: Discussionmentioning

confidence: 99%

The anti-diabetic potential of polysaccharides extracted from members of the cucurbit family: A review

Simpson

Morris

2014

Bioactive Carbohydrates and Dietary Fibre

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Diabetes is a growing global problem and a heavy financial burden on health care services. It is estimated that over 380 million people suffer from this condition which causes many deaths each year in addition to being associated with increased risk of other health problems.Traditional medicine is a promising area of research in diabetes therapy as it is widely accessible and it is believed that over 200 plants have anti-diabetic properties including members of the cucurbit family. Studies in animal and human models have shown that treatment with some cucurbits has hypoglycaemic effects and stimulates beta cell regeneration in addition to other anti-diabetic effects which are equal to that of commonly prescribed anti-diabetic drugs. It has also been shown that at least one of the bioactive components which stimulate these effects is a polysaccharide.

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Section: Discussionmentioning

confidence: 99%

The anti-diabetic potential of polysaccharides extracted from members of the cucurbit family: A review

Simpson

Morris

2014

Bioactive Carbohydrates and Dietary Fibre

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“…[30][31][32][33][34][35][36][37] Although structurally different from natural polysaccharides, glycopolymers incorporating key structural motifs have been shown to mimic the biological activity of their naturally occurring counterpart. 34,35 However, to the best of our knowledge, no reports have been published for the synthesis of fucoidan-mimetics by this approach.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Fucoidan-Mimetic Glycopolymers through Cyanoxyl-Mediated Free-Radical Polymerization

Tengdelius¹,

Lee²,

Grenegård

et al. 2014

Biomacromolecules

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The sulfated marine polysaccharide fucoidan has been reported to have health benefits ranging from antivirus and anticancer properties to modulation of high blood pressure. Hence, they could enhance the biological function of materials for biomedical applications. However, the incorporation of fucoidan into biomaterials has been difficult, possibly due to its complex structure and lack of suitable functional groups for covalent anchoring to biomaterials. We have developed an approach for a rapid synthesis of fucoidan-mimetic glycopolymer chains through cyanoxyl-mediated free-radical polymerization, a method suitable for chain-end functionalizing and subsequent linkage to biomaterials. The resulting sulfated and nonsulfated methacrylamido α-L-fucoside glycopolymers' fucoidan-mimetic properties were studied in HSV-1 infection and platelet activation assays. The sulfated glycopolymer showed similar properties to natural fucoidan in inducing platelet activation and inhibiting HSV-1 binding and entry to cells, thus indicating successful syntheses of fucoidan-mimetic glycopolymers.

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“…Such RAFT reagents have recently been used in a few glycopolymer preparations [5][6][7] . Compared with other glycopolymer preparation protocols, RAFT-mediated polymerizations demonstrate several advantages, including the tolerance to a variety of monomer structures and reaction conditions, potential compatibility with aqueous solutions, and low size dispersity of the desired polymeric products 8,9 . Of notable interest are protocols for preparation of RAFT-based tri-component glycopolymers, allowing control of compositions of different monomers, each of which may have distinct functions [10][11][12][13] .…”

Section: Introductionmentioning

confidence: 99%

Facile and Efficient Preparation of Tri-component Fluorescent Glycopolymers via RAFT-controlled Polymerization

Wang

Lester

Amorosa

et al. 2015

JoVE

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Synthetic glycopolymers are instrumental and versatile tools used in various biochemical and biomedical research fields. An example of a facile and efficient synthesis of well-controlled fluorescent statistical glycopolymers using reversible addition-fragmentation chain-transfer (RAFT)-based polymerization is demonstrated. The synthesis starts with the preparation of β-galactose-containing glycomonomer 2-lactobionamidoethyl methacrylamide obtained by reaction of lactobionolactone and N-(2-aminoethyl) methacrylamide (AEMA). 2-Gluconamidoethyl methacrylamide (GAEMA) is used as a structural analog lacking a terminal β-galactoside. The following RAFT-mediated copolymerization reaction involves three different monomers: N-(2-hydroxyethyl) acrylamide as spacer, AEMA as target for further fluorescence labeling, and the glycomonomers. Tolerant of aqueous systems, the RAFT agent used in the reaction is (4-cyanopentanoic acid)-4-dithiobenzoate. Low dispersities (≤1.32), predictable copolymer compositions, and high reproducibility of the polymerizations were observed among the products. Fluorescent polymers are obtained by modifying the glycopolymers with carboxyfluorescein succinimidyl ester targeting the primary amine functional groups on AEMA. Lectin-binding specificities of the resulting glycopolymers are verified by testing with corresponding agarose beads coated with specific glycoepitope recognizing lectins. Because of the ease of the synthesis, the tight control of the product compositions and the good reproducibility of the reaction, this protocol can be translated towards preparation of other RAFT-based glycopolymers with specific structures and compositions, as desired.

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Synthesis of Glycopolymers by Controlled Radical Polymerization Techniques and Their Applications

Cited by 91 publications

References 160 publications

The anti-diabetic potential of polysaccharides extracted from members of the cucurbit family: A review

The anti-diabetic potential of polysaccharides extracted from members of the cucurbit family: A review

Synthesis and Biological Evaluation of Fucoidan-Mimetic Glycopolymers through Cyanoxyl-Mediated Free-Radical Polymerization

Facile and Efficient Preparation of Tri-component Fluorescent Glycopolymers via RAFT-controlled Polymerization

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