Synthesis and anticancer properties of fucoidan-mimetic glycopolymer coated gold nanoparticles

Tengdelius, Mattias; Gurav, Deepanjali D.; Konradsson, Peter; Påhlsson, Peter; Griffith, May; Oommen, Oommen P.

doi:10.1039/c5cc02387d

Cited by 44 publications

(28 citation statements)

References 18 publications

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“…1 H NMR spectrum of glycopolymer 4 (Figure a) showed successful polymerization by general broadening of the peaks, loss of peak splitting, and the upfield moves of the signals corresponding to the protons on the methacrylates. The spectrum was in accordance with our previously reported glycopolymers . Glycopolymers 5 and 6 displayed similar 1 H NMR spectra.…”

Section: Resultssupporting

confidence: 91%

“…This new protocol showed more efficient removal of residual salts and by‐products. 1 H NMR spectra of glycopolymers 7 , 8 , and 9 all showed downfield moves in shift for the protons neighboring the sulfate esters which confirmed successful O ‐sulfation in accordance with our previously described syntheses of fucoidan‐mimetic glycopolymers . The DS, i.e., the percentage conversion of hydroxyl groups to sulfate esters, was determined by comparing the carbon and sulfur contents of the sulfated glycopolymers from elemental analysis (Table ).…”

Section: Resultssupporting

confidence: 82%

“…We have previously demonstrated the synthesis of fucoidan‐mimetic glycopolymers by cyanoxyl‐mediated free‐radical polymerization and thiol‐mediated chain transfer free‐radical polymerization techniques . The latter technique yielded glycopolymer 2 from 2‐methacrylamidoethyl 2,3,4‐tri‐ O ‐acetyl‐α‐L‐fucopyranoside ( 1 ) under the conditions previously described (Scheme ) .…”

Section: Resultsmentioning

confidence: 95%

“…To furnish the fucoidan‐mimetic glycopolymers, all glycopolymers were O ‐sulfated as the sulfate esters have shown to be crucial for the fucoidan‐mimetic activity . Glycopolymer 2 was O ‐sulfated according to our previously described protocol to give sulfated glycopolymer 3 . Glycopolymers 4 , 5 , and 6 were partially O ‐sulfated by treatment with sulfur trioxide pyridine complex in N , N ‐dimethylformamide (DMF) over two nights, during which rapid precipitation of the product occurred to give sulfated glycopolymers 7 , 8 , and 9 , respectively.…”

Section: Resultsmentioning

confidence: 99%

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Fucoidan-Mimetic Glycopolymers as Tools for Studying Molecular and Cellular Responses in Human Blood Platelets

et al. 2016

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The marine sulfated polysaccharide fucoidan displays superior ability to induce platelet aggregation compared to other sulfated polysaccharides. As such, it is an attractive tool for studying molecular and cellular responses in activated platelets. The heterogeneous structure, however, poses a problem in such applications. This study describes the synthesis of sulfated α-l-fucoside-pendant poly(methacryl amides) with homogeneous structures. By using both thiol-mediated chain transfer and reversible addition-fragmentation chain transfer polymerization techniques, glycopolymers with different chain lengths are obtained. These glycopolymers show platelet aggregation response and surface changes similar to those of fucoidan, and cause platelet activation through intracellular signaling as shown by extensive protein tyrosine phosphorylation. As the platelet activating properties of the glycopolymers strongly mimic those of fucoidan, this study concludes these fucoidan-mimetic glycopolymers are unique tools for studying molecular and cellular responses in human blood platelets.

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Section: Resultssupporting

confidence: 91%

Section: Resultssupporting

confidence: 82%

Section: Resultsmentioning

confidence: 95%

Section: Resultsmentioning

confidence: 99%

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Fucoidan-Mimetic Glycopolymers as Tools for Studying Molecular and Cellular Responses in Human Blood Platelets

et al. 2016

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“…1 H NMR spectrum for glycopolymer 16 in D2O, 300 MHz (top); GPC traces for glycopolymers 16 (red) and 17 (blue) using water as eluent and dextran/pullulan standards (bottom). Adapted from [93] with permission from the Royal Society of Chemistry.…”

Section: Thiol-mediated Chain Transfer Radical Polymerizations (Papermentioning

confidence: 99%

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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Novel Organic and Inorganic Nanoparticles as a Targeted Drug Delivery Vehicle in Cancer Treatment

Muthukrishnan¹,

Anand²,

Palanisamy³

et al. 2022

Nanotechnology in the Life Sciences

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Synthesis and anticancer properties of fucoidan-mimetic glycopolymer coated gold nanoparticles

Cited by 44 publications

References 18 publications

Fucoidan-Mimetic Glycopolymers as Tools for Studying Molecular and Cellular Responses in Human Blood Platelets

Fucoidan-Mimetic Glycopolymers as Tools for Studying Molecular and Cellular Responses in Human Blood Platelets

Fucoidan-Mimetic Glycopolymers : Synthesis and Biomedical Applications

Novel Organic and Inorganic Nanoparticles as a Targeted Drug Delivery Vehicle in Cancer Treatment

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