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

Abstract

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.

Computational sensing of herpes simplex virus using a cost-effective on-chip microscope

“…The streptavidin coated coverslips can be used immediately or stored in the freezer for future use and testing. The virus solution in buffer was mixed with biotin tagged antibodies and gently mixed in a shaker for ~1–2 h. This is also in agreement with previously reported experimental protocols on labeling of HSV-1 particles, performed by antibody incubation for ~1 h 39 . The antibodies were used at a dilution of 1:20 as specified by the company.…”

The in vitro and in vivo effects of the low molecular weight fucoidan on the bone osteogenic differentiation properties

“…The intensity of biological activities of fucoidan varies with species, molecular weight, composition, structure and the route of extraction (Fitton 2011), and its non-animal origin brings particular pharmacological activities (Senni et al 2006). Fucoidan has been well studied for its antitumor (Hsu et al 2013), antiviral (Tengdelius et al 2014), anti-inflammatory (Hwang et al 2011), and anticoagulant (Irhimeh et al 2009) activities. These biological activities are closely related to fucoidan's molecular weight (Yang et al 2008) and sulfate content (Soeda et al 1992).…”

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

“…To synthesize FM--glycopolymer, we utilized our previously reported fucoside monomer (2--methacrylamidoethyl 2,3,4--tri--O-acetyl--α--ʟ--fucopyranoside) 4 1 as a suitable starting material. Monomer 1 was polymerized in dioxane through a classical free-radical chain transfer polymerization with 2--(trimethylsilyl)ethanethiol as chain transfer agent and AIBN as the radical initiator (Scheme 1).…”