An Approach to the High-Throughput Fabrication of Glycopolymer Microarrays through Thiol–Ene Chemistry

Neumann, Kevin; Conde-González, Antonio; Owens, Matthew; Venturato, Andrea; Zhang, Yichuan; Geng, Jin; Bradley, Mark

doi:10.1021/acs.macromol.7b00952

Cited by 26 publications

(21 citation statements)

References 54 publications

(68 reference statements)

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“…As a result, many new functional polymers have been explored and used in interdisciplinary fields as sensors, gene/drug carriers, antibacterial surfaces, tissue engineering scaffolds, (stem)cell factories, etc. (Akinc et al., 2003, Algahtani et al., 2014, Anderson et al., 2004, Anderson et al., 2005, Anderson et al., 2006, Bosman et al., 2001, Celiz et al., 2014, Chapman et al., 2016, Goldberg et al., 2008, Gupta et al., 2010, Hook et al., 2012, Khan et al., 2010, Lynn et al., 2001, Mao et al., 2018, Mei et al., 2010, Meier et al., 2004a, Meier et al., 2004b, Neumann et al., 2017, Ting et al., 2015, Ting et al., 2016). This has opened new research directions in polymer science and expanded the application scope of polymers beyond traditional plastics and rubbers.…”

Section: Introductionmentioning

confidence: 99%

High-Throughput Preparation of Antibacterial Polymers from Natural Product Derivatives via the Hantzsch Reaction

Liu

Zhang

et al. 2020

iScience

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SummaryThe Hantzsch and free-radical polymerization reactions were combined in a one-pot high-throughput (HTP) system to simultaneously prepare 30 unique polymers in parallel. Six aldehydes derived from natural products were used as the starting materials to rapidly prepare the library of 30 poly(1,4-dihydropyridines). From this library, HTP evaluation methods led to the identification of an antibacterial polymer. Mechanistic studies revealed that the dihydropyridine group in the polymer side-chain structure plays an important role in resisting bacterial attachment to the polymer surface, thus leading to the antibacterial function of this polymer. This research demonstrates the value of multicomponent reactions (MCRs) in interdisciplinary fields by discovering functional polymers for possible practical applications. It also provides insights to further developing new functional polymers using MCRs and HTP methods with important implications in organic chemistry, polymer chemistry, and materials science.

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Section: Introductionmentioning

confidence: 99%

High-Throughput Preparation of Antibacterial Polymers from Natural Product Derivatives via the Hantzsch Reaction

Liu

Zhang

et al. 2020

iScience

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“…The glycan microarray provides a powerful platform for rapid profiling of protein interactions with surface-immobilized glycans [41]. Established initially as a way to present individual glycans [42], the array concept was later expanded to include well-defined synthetic glycoconjugates, such as neo-glycoproteins [43,44], glycodendrimers [45] or glycopolymers [39,46,47], allowing for presentation of glycans in a number of modes with control over scaffold geometry, glycan valency and spacing, and surface density of glycoconjugates. Most recently, glycan arrays prepared by immobilization of glycan mixtures within individual spots revealed that the presence of neighbouring glycans may result in higher avidity antibody binding to target epitope and that both density and structure of neighbouring glycans can effect recognition (figure 3) [48,49].…”

Section: Static Surface-supported Glycocalyx Modelsmentioning

confidence: 99%

Synthetic glycoscapes: addressing the structural and functional complexity of the glycocalyx

Purcell

Godula

2019

Interface Focus.

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One contribution of 12 to a theme issue 'Synthetic glycobiology'.The glycocalyx is an information-dense network of biomacromolecules extensively modified through glycosylation that populates the cellular boundary. The glycocalyx regulates biological events ranging from cellular protection and adhesion to signalling and differentiation. Owing to the characteristically weak interactions between individual glycans and their protein binding partners, multivalency of glycan presentation is required for the high-avidity interactions needed to trigger cellular responses. As such, biological recognition at the glycocalyx interface is determined by both the structure of glycans that are present as well as their spatial distribution. While genetic and biochemical approaches have proven powerful in controlling glycan composition, modulating the three-dimensional complexity of the cell-surface 'glycoscape' at the sub-micrometre scale remains a considerable challenge in the field. This focused review highlights recent advances in glycocalyx engineering using synthetic nanoscale glycomaterials, which allows for controlled de novo assembly of complexity with precision not accessible with traditional molecular biology tools. We discuss several exciting new studies in the field that demonstrate the power of precision glycocalyx editing in living cells in revealing and controlling the complex mechanisms by which the glycocalyx regulates biological processes.

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“…The Bradley group has reported the preparation of a glycopolymer library using a substrate and high-throughput analyses with lectins, showing the utility of the library method. 14…”

Section: Introductionmentioning

confidence: 99%

Screening of a Glycopolymer Library of GM1 Mimics Containing Hydrophobic Units Using Surface Plasmon Resonance Imaging

et al. 2019

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Effective screening methods for the development of glycopolymers as molecular recognition materials are desirable for the discovery of novel biofunctional materials. A glycopolymer library was prepared to obtain guidelines for the design of glycopolymers for the recognition of cholera toxin B subunits (CTB). Glycopolymers with varying ratios of hydrophobic and sugar units were synthesized by reversible addition fragmentation chain transfer polymerization. N-tert-Butylacrylamide, N-phenylacrylamide, and N-cyclohexylacrylamide as hydrophobic units were copolymerized in the polymer backbone, and galactose, which contributes to CTB recognition, was introduced into the side chains by “post-click” chemistry. The thiol-terminated glycopolymers were immobilized on a gold surface. The polymer immobilization substrate was analyzed in terms of interaction with galactose recognition proteins (CTB, peanut agglutinin, and Ricinus communis agglutinin I) using surface plasmon resonance imaging. The polymers with high ratios of sugar and hydrophobic units had the strongest interactions with the CTB, which was different from the trend with peanut agglutinin and Ricinus communis agglutinin I. The binding constant of the CTB with the glycopolymer with hydrophobic units was 4.1 × 106 M–1, which was approximately eight times larger than that of the polymer without hydrophobic units. A correlation was observed between the log P value and the binding constant, indicating that the hydrophobic interaction played an important role in binding. New guidelines for the design of recognition materials were obtained by our screening method.

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An Approach to the High-Throughput Fabrication of Glycopolymer Microarrays through Thiol–Ene Chemistry

Cited by 26 publications

References 54 publications

High-Throughput Preparation of Antibacterial Polymers from Natural Product Derivatives via the Hantzsch Reaction

High-Throughput Preparation of Antibacterial Polymers from Natural Product Derivatives via the Hantzsch Reaction

Synthetic glycoscapes: addressing the structural and functional complexity of the glycocalyx

Screening of a Glycopolymer Library of GM1 Mimics Containing Hydrophobic Units Using Surface Plasmon Resonance Imaging

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