Virus–glycopolymer conjugates by copper(i) catalysis of atom transfer radical polymerization and azide–alkyne cycloaddition

Gupta, Sayam Sen; Raja, Krishnaswami; Kaltgrad, Eiton; Strable, Erica; Finn, M. G.

doi:10.1039/b502444g

Cited by 184 publications

(136 citation statements)

References 69 publications

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“…We employed these particles as reagents in the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction, using CuOTf and accelerating ligand 4 under inert atmosphere as has been previously described (61,62). The purified virus was pelleted out of solution, taken into an inert-atmosphere glovebox, and resuspended in degassed 0.1 M Tris buffer (pH 8.0) to prepare for reaction with fluorescein alkyne 3 under our standard conditions, as shown in Figure 5.…”

Section: Conjugation To Genetically Incorporated Azide and Alkyne Groupsmentioning

confidence: 99%

Unnatural Amino Acid Incorporation into Virus-Like Particles

et al. 2008

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Virus-like particles composed of hepatitis B virus (HBV) or bacteriophage Qβ capsid proteins have been labeled with azide-or alkyne-containing unnatural amino acids by expression in a methionine auxotrophic strain of E. coli. The substitution does not affect the ability of the particles to selfassemble into icosahedral structures indistinguishable from native forms. The azide and alkyne groups were addressed by Cu(I)-catalyzed [3 + 2] cycloaddition: HBV particles were decomposed by the formation of more than 120 triazole linkages per capsid in a location-dependent manner, whereas Qβ suffered no such instability. The marriage of these well-known techniques of sensecodon reassignment and bioorthogonal chemical coupling provides the capability to construct polyvalent particles displaying a wide variety of functional groups with near-perfect control of spacing.

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Section: Conjugation To Genetically Incorporated Azide and Alkyne Groupsmentioning

confidence: 99%

Unnatural Amino Acid Incorporation into Virus-Like Particles

et al. 2008

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“…Wang et al first showed that the presence of natural reactive lysine residues on the particle surface and the inherent stability of the particles to temperature, pH, and organic solvents facilitated chemical conjugation (60). This method has been expanded through the use of azide-alkyne chemistry, often called click chemistry (22,59). The ability to create infectious chimeras by insertion of residues and peptides on the capsid surface further allows the multivalent display and controlled chemical modification of the particles (13, 61).…”

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confidence: 99%

Interaction between a 54-Kilodalton Mammalian Cell Surface Protein and Cowpea Mosaic Virus

Koudelka

Rae

Gonzalez

et al. 2007

J Virol

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Cowpea mosaic virus (CPMV), a plant virus that is a member of the picornavirus superfamily, is increasingly being used for nanotechnology applications, including material science, vascular imaging, vaccine development, and targeted drug delivery. For these applications, it is critical to understand the in vivo interactions of CPMV within the mammalian system. Although the bioavailability of CPMV in the mouse has been demonstrated, the specific interactions between CPMV and mammalian cells need to be characterized further. Here we demonstrate that although the host range for replication of CPMV is confined to plants, mammalian cells nevertheless bind and internalize CPMV in significant amounts. This binding is mediated by a conserved 54-kDa protein found on the plasma membranes of both human and murine cell lines. Studies using a deficient cell line, deglycosidases, and glycosylation inhibitors showed that the CPMV binding protein (CPMV-BP) is not glycosylated. A possible 47-kDa isoform of the CPMV-BP was also detected in the organelle and nuclear subcellular fraction prepared from murine fibroblasts. Further characterization of CPMV-BP is important to understand how CPMV is trafficked through the mammalian system and may shed light on how picornaviruses may have evolved between plant and animal hosts.In the past several years, aside from understanding the natural life cycles of viruses as obligate intracellular pathogens, the power of viruses as tools for material applications has begun to be harnessed. There are several reasons why viruses are an excellent choice in this regard. First, rigid viral capsids provide natural molecular scaffolds that allow precise attachments for building nanostructures, with control over orientation and spacing that is not attainable using other materials, such as dendrimers or liposomes (14,26,29,31,46). Second, virus capsids use highly repeated structural motifs allowing for the polyvalent display of peptides (11), polysaccharides (22, 48), nucleic acids (54), or other synthetic structures (43). Selfassembly of virus capsids also ensures a lack of morphological polydispersity in the capsid size and shape, which is difficult to accomplish using synthetic materials (35,36). Third, viral genomes are generally easy to manipulate, allowing the generation of mutants that can allow specific tailoring of the particle surface (12,13,60,61). Fourth, procedures for inexpensive, efficient amplification of many such structures, e.g., plant viruses, virus-like particles, and bacteriophages, are already well defined (24,25,41,49,67).Plant viruses are especially attractive for development in material science, nanotechnology, and vaccine applications because of their ease of production and purification. In particular, cowpea mosaic virus (CPMV) has been studied increasingly as a material for these purposes. CPMV is the type member of the genus Comovirus, which is part of the Picornaviridae superfamily spanning the plant and animal kingdoms and including Poliovirus and Rhinovirus. CPMV has a singl...

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“…3. The amide-bond formations using fluoresceinamine were performed using a modified version of the procedure described by Finn et al [17].…”

Section: Technical Approachmentioning

confidence: 99%

Preparation of novel optical fibre-based Cocaine sensors using a molecular imprinted polymer approach

Wren

Nguyen

Gascoine³

et al. 2014

Sensors and Actuators B: Chemical

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Virus–glycopolymer conjugates by copper(i) catalysis of atom transfer radical polymerization and azide–alkyne cycloaddition

Abstract: The Cu(I)-catalyzed ATRP and azide-alkyne cycloaddition reactions together provide a versatile method for the synthesis of end-functionalized glycopolymers and their attachment to a suitably modified viral protein scaffold.

Cited by 184 publications

References 69 publications

Unnatural Amino Acid Incorporation into Virus-Like Particles

Unnatural Amino Acid Incorporation into Virus-Like Particles

Interaction between a 54-Kilodalton Mammalian Cell Surface Protein and Cowpea Mosaic Virus

Preparation of novel optical fibre-based Cocaine sensors using a molecular imprinted polymer approach

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