Glycopolymer Conjugates

Eissa, Ahmed M.; Cameron, Neil R.

doi:10.1007/12_2012_177

Cited by 29 publications

(25 citation statements)

References 223 publications

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“…The described avidity pattern can be mimicked by synthetic multivalent glycoconjugates. They are based on a range of carrier scaffolds [ 4 ], of which glycopolymers embrace an exceptional structural and functional variability [ 5 , 6 ]. The synthesis of glycopolymers may advantageously employ Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC)—a type of “click chemistry” [ 7 ] that couples unprotected glycans under the formation of a triazole moiety.…”

Section: Introductionmentioning

confidence: 99%

Biocompatible glyconanomaterials based on HPMA-copolymer for specific targeting of galectin-3

et al. 2018

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BackgroundGalectin-3 (Gal-3) is a promising target in cancer therapy with a high therapeutic potential due to its abundant localization within the tumor tissue and its involvement in tumor development and proliferation. Potential clinical application of Gal-3-targeted inhibitors is often complicated by their insufficient selectivity or low biocompatibility. Nanomaterials based on N-(2-hydroxypropyl)methacrylamide (HPMA) nanocarrier are attractive for in vivo application due to their good water solubility and lack of toxicity and immunogenicity. Their conjugation with tailored carbohydrate ligands can yield specific glyconanomaterials applicable for targeting biomedicinally relevant lectins like Gal-3.ResultsIn the present study we describe the synthesis and the structure-affinity relationship study of novel Gal-3-targeted glyconanomaterials, based on hydrophilic HPMA nanocarriers. HPMA nanocarriers decorated with varying amounts of Gal-3 specific epitope GalNAcβ1,4GlcNAc (LacdiNAc) were analyzed in a competitive ELISA-type assay and their binding kinetics was described by surface plasmon resonance. We showed the impact of various linker types and epitope distribution on the binding affinity to Gal-3. The synthesis of specific functionalized LacdiNAc epitopes was accomplished under the catalysis by mutant β-N-acetylhexosaminidases. The glycans were conjugated to statistic HPMA copolymer precursors through diverse linkers in a defined pattern and density using Cu(I)-catalyzed azide–alkyne cycloaddition. The resulting water-soluble and structurally flexible synthetic glyconanomaterials exhibited affinity to Gal-3 in low μM range.ConclusionsThe results of this study reveal the relation between the linker structure, glycan distribution and the affinity of the glycopolymer nanomaterial to Gal-3. They pave the way to specific biomedicinal glyconanomaterials that target Gal-3 as a therapeutic goal in cancerogenesis and other disorders.Electronic supplementary materialThe online version of this article (10.1186/s12951-018-0399-1) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Biocompatible glyconanomaterials based on HPMA-copolymer for specific targeting of galectin-3

et al. 2018

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“…Moreover, different architectures and functionalities are accessible and a large number of polymeric systems were shown to be non-toxic and biocompatible. These attributes are especially interesting for biomedical applications employing glycopolymeric drugs or drug delivery systems (44)(45)(46)(47)(48).…”

Section: Precision Glycomacromolecules As Novel Glycomimetics Naturalmentioning

confidence: 99%

Recent Advances in Solid Phase Polymer Synthesis: Polyamides from Tailor-Made Building Blocks

Wojcik

Ponader

Mosca

et al. 2014

ACS Symposium Series

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“…Especially in biological research fields, SPAAC has been viewed as one of the most successful bioorthogonal reaction candidates for preparing the bio-synthetic polymer conjugates in both in-vivo and in-vitro situations. For the formation of bio-synthetic polymer conjugates by covalently connecting synthetic polymer segments and biological entities, it is vital for the preparation of well-defined polymers end-functionalized with bioorthogonally clickable groups [25][26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Cyclopropenone-masked dibenzocyclooctyne end-functionalized polymers from reversible addition-fragmentation chain transfer polymerization

Sun

et al. 2017

Polymer

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Functional reversible addition-fragmentation chain transfer polymerization (RAFT) agent was developed to have a cyclopropenone-masked dibenzocyclooctyne end group. RAFT polymerization was then explored on three typical types of vinyl monomers in free radical polymerization such as styrene, methyl methacrylate, and tert-butyl acrylate. The living polymerization behaviors were demonstrated for all three cases, which guaranteed the production of well-defined polystyrene, poly(methyl methacrylate), and poly(tert-butyl acrylate) end-functionalized with cyclopropenone-masked dibenzocyclooctyne groups from the convenient RAFT polymerization technique. Under UV irradiation, the cyclopropenone-masked dibenzocyclooctyne end group could be quantitatively changed to dibenzocyclooctyne clickable group, which was widely used in the metal-free strain-promoted azide-alkyne cycloaddition (SPAAC) click reaction. Subsequently, using

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Glycopolymer Conjugates

Cited by 29 publications

References 223 publications

Biocompatible glyconanomaterials based on HPMA-copolymer for specific targeting of galectin-3

Biocompatible glyconanomaterials based on HPMA-copolymer for specific targeting of galectin-3

Recent Advances in Solid Phase Polymer Synthesis: Polyamides from Tailor-Made Building Blocks

Cyclopropenone-masked dibenzocyclooctyne end-functionalized polymers from reversible addition-fragmentation chain transfer polymerization

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