SYNTHESIS, NMR, AND CONFORMATIONAL STUDIES OF FUCOIDAN FRAGMENTS 4: 4-MONO- AND 4,4′-DISULFATED (1→3)-α-<scp>l</scp>-FUCOBIOSIDE AND 4-SULFATED FUCOSIDE FRAGMENTS

Gerbst, Alexey G.; Ustuzhanina, Nadezhda E.; Грачев, А. А.; Zlotina, Natalya S.; Khatuntseva, Elena A.; Tsvetkov, D. E.; Shashkov, Alexander S.; Усов, А. И.; Nifantiev, Nikolay E.

doi:10.1081/car-120013500

Cited by 36 publications

(25 citation statements)

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“…18 They have presented the first PES analysis for such fragments and compare them with experimentally determined features. 19,20 In connection with our work on bioactive fucoidans, 14 …”

Section: Introductionmentioning

confidence: 98%

mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

Stortz

2004

Carbohydrate Research

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“…18 They have presented the first PES analysis for such fragments and compare them with experimentally determined features. 19,20 In connection with our work on bioactive fucoidans, 14 …”

Section: Introductionmentioning

confidence: 98%

mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

Stortz

2004

Carbohydrate Research

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“…17 The Nifantiev group has presented extensive work synthesizing di-, tri-, tetra-, hexa-, octa-, dodeca-and hexadecafucosides with various differences in branching-, sulfation-and fucosidic linkage patterns. [18][19][20][21][22][23][24][25] These fucoidan fragments were subjected to extensive conformational studies through NMR, [18][19][20][21][22][23]25 yet no biological activity studies have been published. We also noted that all the synthetic fucoidan fragments referred to were produced through saccharide formation, which is often time-consuming and results in poor yields with growing saccharide chain length.…”

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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“…The resulting pyridinium ions on the resulting O-sulfates were then exchanged for sodium ions by adding sodium bicarbonate. This method had previously been employed by the Nifantiev group in the synthesis of fucoidan-mimetic oligosaccharides [37][38][39]41]. It proved somewhat troublesome, though, as the sulfate esters turned out to be labile and purification became difficult.…”

Section: Synthetic Strategymentioning

confidence: 99%

“…Recently, this group synthesized a fragment from the brown seaweed Chordaria flagelliformis containing an α-L-fucofuranosyl unit (see Figure 1.2 D), which is unusual compared to the α-L-fucopyranosyl conformation that constitutes the vast majority of the L-fucosides found in fucoidan [43]. The conformation of all of these fucosides have been carefully studied by NMR spectroscopy, but their biological properties have remained almost entirely unpublished [35][36][37][38][39][40][41][42][43]. As an exception a recent study showed that a fully sulfated α(1→3) octa-L-fucoside displayed no or decreased antibacterial phagocytic activity compared to fucoidan of larger molecular weights from natural sources [44].…”

Section: Fucoidan-mimetic Oligosaccharidesmentioning

confidence: 99%

“…Since 2000 this group has synthesized a broad series of mono-, di-, tri-, tetra-, hexa-, octa-, dodeca-, and hexadeca-α-L-fucosides (see Figure 1.2 C) bearing various glycosidic linkage patterns, branching, and sulfation degree and patterns [35][36][37][38][39][40][41][42]. Recently, this group synthesized a fragment from the brown seaweed Chordaria flagelliformis containing an α-L-fucofuranosyl unit (see Figure 1.2 D), which is unusual compared to the α-L-fucopyranosyl conformation that constitutes the vast majority of the L-fucosides found in fucoidan [43].…”

Section: Fucoidan-mimetic Oligosaccharidesmentioning

confidence: 99%

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Fucoidan-Mimetic Glycopolymers : Synthesis and Biomedical Applications

Tengdelius¹

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Cover: 3D models of three different fucoidan-mimetic glycopolymers Linköping Studies in Science and Technology Dissertations No. 1743 Printed by LiU-Tryck, Linköping, Sweden, 2016 Till morfar som inspirerade mig att börja och Lina och Theo som inspirerar mig att fortsätta. Mattias Tengdelius Fucoidan-Mimetic Glycopolymers -Synthesis and Biomedical Applications I AbstractThe marine polysaccharide fucoidan has demonstrated several interesting biological properties, for instance being antiviral, anticoagulant, anti-inflammatory, anticancer, and platelet activating. Many of these properties are desirable for various biomedical applications. Yet, there are few reports on fucoidan being used in such applications. The reasons for this are primarily the heterogeneity and low structural reproducibility of fucoidan.This thesis describes the synthesis of polymers with pendant saccharides bearing the key structural features of fucoidan. These glycopolymers were synthesized via different radical polymerization techniques yielding polymers of different chain lengths and dispersity. These glycopolymers showed antiviral and platelet activating properties similar to those of natural fucoidan, thus making them fucoidan-mimetic glycopolymers. However, compared to fucoidan from natural sources, the fucoidan-mimetic glycopolymers had homogeneous and reproducible structures making them suitable for biomedical applications.Further studies demonstrated that platelet activation, caused by these glycopolymers, showed dose-response curves almost identical to fucoidan. The platelet activation was induced via intracellular signaling and caused platelet surface changes similar to those of fucoidan. Fucoidan-mimetic glycopolymers can therefore be used as unique biomolecular tools for studying the molecular and cellular responses of human platelets.Fucoidan-mimetic glycopolymers generally assert their antiviral activity by blocking viral entry to host cells, thus inhibiting spreading of the viral infection but not acting virucidal, i.e. not killing the viruses. Introduction of hydrophobic groups to the polymer's chain ends improved the antiviral properties significantly and is an important step towards yielding glycopolymers with virucidal properties.The fucoidan-mimetic glycopolymers were also applied as capping agents when synthesizing gold nanoparticles. These fucoidan-mimetic glycopolymer coated gold nanoparticles showed improved colloidal stability compared to uncapped gold nanoparticles. Furthermore, the nanoparticles also demonstrated selective cytotoxicity against a human colon cancer cell line over fibroblast cells. III Populärvetenskaplig SammanfattningSedan urminnes tider har människan vänt sig till naturen för att bota sjukdomar och andra krämpor. Genom extrakt från framförallt växter har bland annat feber, inflammationer och olika infektioner behandlats långt innan läkemedelskonsten utvecklades till vad den är idag. Även när den moderna läkemedelsvetenskapen, farmakologin, började utvecklas var det naturen som var den främst...

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SYNTHESIS, NMR, AND CONFORMATIONAL STUDIES OF FUCOIDAN FRAGMENTS 4: 4-MONO- AND 4,4′-DISULFATED (1→3)-α-l-FUCOBIOSIDE AND 4-SULFATED FUCOSIDE FRAGMENTS

Cited by 36 publications

References 13 publications

mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

mm3 Potential energy surfaces of α-3-linked l-fucobiose and fucotriose and their sulfated counterparts

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

Fucoidan-Mimetic Glycopolymers : Synthesis and Biomedical Applications

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