Design and Synthesis of Biotin Chain-Terminated Glycopolymers for Surface Glycoengineering

Sun, Xue‐Long; Faucher, Keith M.; Houston, Michelle; Grande, Daniel; Chaikof, Elliot L.

doi:10.1021/ja025788v

Cited by 102 publications

(111 citation statements)

References 12 publications

(15 reference statements)

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“…46,[66][67][68][69][70] In the present work we aimed to modify our "click" approach to glycopolymers for the synthesis of R-mannopyranosidecontaining glycoprotein mimics suitable for probing interactions with mannose-binding lectin (MBL), a key mammalian lectin of the immune system. Mannoside structures are prevalent on the cell surfaces of many bacterial and fungal pathogens, their arrangements distinct from human mannoside glycans, thus being distinguishable from the human host.…”

Section: Introductionmentioning

confidence: 99%

Site-Directed Conjugation of “Clicked” Glycopolymers To Form Glycoprotein Mimics: Binding to Mammalian Lectin and Induction of Immunological Function

et al. 2007

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Synthesis of well-defined neoglycopolymer-protein biohybrid materials and a preliminary study focused on their ability of binding mammalian lectins and inducing immunological function is reported. Crucial intermediates for their preparation are well-defined maleimide-terminated neoglycopolymers (Mn ) 8-30 kDa; Mw/Mn ) 1.20-1.28) presenting multiple copies of mannose epitope units, obtained by combination of transition-metal-mediated living radical polymerization (TMM LRP) and Huisgen [2+3] cycloaddition. Bovine serum albumin (BSA) was employed as single thiol-containing model protein, and the resulting bioconjugates were purified following two independent protocols and characterized by circular dichroism (CD) spectroscopy, SDS PAGE, and SEC HPLC. The versatility of the synthetic strategy presented in this work was demonstrated by preparing a small library of conjugating glycopolymers that only differ from each other for their relative epitope density were prepared by coclicking of appropriate mixtures of mannopyranoside and galactopyranoside azides to the same polyalkyne scaffold intermediate. Surface plasmon resonance binding studies carried out using recombinant rat mannose-binding lectin (MBL) showed clear and dose-dependent MBL binding to glycopolymer-conjugated BSA. In addition, enzyme-linked immunosorbent assay (ELISA) revealed that the neoglycopolymer-protein materials described in this work possess significantly enhanced capacity to activate complement via the lectin pathway when compared with native unmodified BSA.

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Section: Introductionmentioning

confidence: 99%

Site-Directed Conjugation of “Clicked” Glycopolymers To Form Glycoprotein Mimics: Binding to Mammalian Lectin and Induction of Immunological Function

et al. 2007

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“…Additionally, since streptavidin is a tetramer with four binding sites, each site binding to one molecule of biotin, it has been shown that surface engineering of various other biotinylated proteins on streptavidin-bound surfaces is possible. 44,47,[49][50][51] An alkoxyamine initiator bearing biotin was synthesized for the preparation of patterned brush layers end-capped with biotin functionality for the selective attachment of streptavidin protein. Hydroxymethyl-functionalized alkoxyamine, 3, was chosen as the precursor for the functionalization scheme ( Figure 9).…”

Section: Resultsmentioning

confidence: 99%

Chain-End Functionalized Nanopatterned Polymer Brushes Grown via in Situ Nitroxide Free Radical Exchange

et al. 2008

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The patterning of biologically active materials has been accomplished by the use of imprint lithography of functional photopolymer resins to create controlled nanoscale patterns of a cross-linked photopolymer containing embedded initiator groups. Functionalized polymer brushes consisting of polystyrene and poly(N,N-dimethylacrylamide) were grown from these patterned layers by nitroxide-mediated polymerization. Chain-end functionalization of the brush layer was accomplished by nitroxide radical exchange during the polymerization. Accordingly, brush layers terminated by pyrene and biotin functional groups were obtained by exchange with the appropriate alkoxyamines. The presence of pyrene functionality at the chain ends of the brushes was confirmed by fluorescent emission measurements. Fluorescently labeled streptavidin protein was selectively attached with high selectivity to the patterned biotinylated brush layer through biotin−streptavidin interactions. The functionalized polymer grafted surfaces and nanopatterns have been successfully characterized using a fluorescence spectrophotometer, AFM, SEM, confocal microscopy, and water contact angle measurements.

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“…Chaikof et al have explored the applicability of cyanoxyl-mediated radical polymerization (CMRP) in the synthesis of well-defined glycopolymers directly from unprotected glycomonomers [76][77][78][79][80][82][83][84][85]102,103]. As first noticed by Druliner in the early 1990s and by Gnanou more recently [69][70][71], a certain degree of control can be achieved when (meth)acrylic monomers are polymerized in the presence of cyanoxyl persistent radicals.…”

Section: Alkene Monomersmentioning

confidence: 99%

“…The resulting polymers were used to fabricate a series of glycocalyx-mimetic surfaces that showed uniform carbohydrate coating on a membrane-like thin film [84,85] and to functionalize quantum dots and magnetic beads [82].…”

Section: (Meth)acrylamide Monomersmentioning

confidence: 99%

Synthesis of Glycopolymer Architectures by Reversible-Deactivation Radical Polymerization

Ghadban

Albertin

2013

Polymers

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This review summarizes the state of the art in the synthesis of well-defined glycopolymers by Reversible-Deactivation Radical Polymerization (RDRP) from its inception in 1998 until August 2012. Glycopolymers architectures have been successfully synthesized with four major RDRP techniques: Nitroxide-mediated radical polymerization (NMP), cyanoxyl-mediated radical polymerization (CMRP), atom transfer radical polymerization (ATRP) and reversible addition-fragmentation chain transfer (RAFT) polymerization. Over 140 publications were analyzed and their results summarized according to the technique used and the type of monomer(s) and carbohydrates involved. Particular emphasis was placed on the experimental conditions used, the structure obtained (comonomer distribution, topology), the degree of control achieved and the (potential) applications sought. A list of representative examples for each polymerization process can be found in tables placed at the beginning of each section covering a particular RDRP technique.

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Design and Synthesis of Biotin Chain-Terminated Glycopolymers for Surface Glycoengineering

Cited by 102 publications

References 12 publications

Site-Directed Conjugation of “Clicked” Glycopolymers To Form Glycoprotein Mimics: Binding to Mammalian Lectin and Induction of Immunological Function

Site-Directed Conjugation of “Clicked” Glycopolymers To Form Glycoprotein Mimics: Binding to Mammalian Lectin and Induction of Immunological Function

Chain-End Functionalized Nanopatterned Polymer Brushes Grown via in Situ Nitroxide Free Radical Exchange

Synthesis of Glycopolymer Architectures by Reversible-Deactivation Radical Polymerization

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