Glycopolymers for Antibacterial and Antiviral Applications

Mei, Ruoyao; Heng, Xingyu; Liu, Xiaoli; Chen, Gaojian

doi:10.3390/molecules28030985

Cited by 9 publications

(4 citation statements)

References 82 publications

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“…12,14 Synthetic multivalent ligands, or polymer probes, provide an array of tunable ligand displays that have been shown to act as excellent effectors or inhibitors of biological activity through receptor clustering, chelation, and increased local concentration near target receptors. [15][16][17][18] Additionally, multivalent displays have been shown to improve binding avidity and specificity when properties such as polymer flexibility, conformation, valency, or molecular weight are manipulated. [19][20][21][22] In this work, bicyclo[4.2.0]oct-6-ene-7-carboxamide bearing mannose or fucose was allowed to react with cyclohexene or 4,7-dihydro-1,3-dioxepin via ruthenium-catalyzed AROMP.…”

Section: Introductionmentioning

confidence: 99%

Glycopolymers Prepared by Alternating Ring-Opening Metathesis Polymerization Provide Access to Distinct, Multivalent Structures for the Probing of Biological Activity

Mendez,

Boadi,

Kennedy

et al. 2024

Preprint

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A myriad of biological processes are facilitated by ligand-receptor interactions. The low affinities of these interactions are typically enhanced by multivalent engagements to promote binding. However, each biological interaction requires a unique display and orientation of ligands. Therefore, the availability and diversity of synthetic multivalent probes are invaluable to the investigation of ligand-receptor binding interactions. Here, we report glycopolymers prepared from bicyclo[4.2.0]oct-6-ene-7-carboxamide and 4,7-dihydro-1,3-dioxepin or cyclohexene. These glycopolymers, synthesized by alternating ring-opening metathesis polymerization, display precise ligand spacing as well as the option of a hydrophobic or acetal-functionalized polymer backbone. Small-angle X-ray scattering (SAXS) data analysis revealed that these [4.2.0] glycopolymers adopted distinct conformations in solution. In aqueous media, [4.2.0]-dioxepin glycopolymers formed swollen polymer chains with rod-like, flexible structures while [4.2.0]-cyclohexene glycopolymers assumed compact, globular structures. To illustrate how these glycopolymers could aid in the exploration of ligand-receptor interactions, we incorporated the [4.2.0] glycopolymers into a biological assay to assess their potential as activators of acrosomal exocytosis (AE) in mouse sperm. The results of the biological assay confirmed that the differing structures of the [4.2.0] glycopolymers would evoke distinct biological responses; [4.2.0]-cyclohexene glycopolymers induced AE in mouse sperm while [4.2.0]-dioxepin glycopolymers did not. Herein, we provide two options for glycopolymers with low to moderate molecular weight dispersities and low cytotoxicity that can be implemented into biological assays based on the desired hydrophobicity, rigidity, and structural conformation of the polymer probe.

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Section: Introductionmentioning

confidence: 99%

Glycopolymers Prepared by Alternating Ring-Opening Metathesis Polymerization Provide Access to Distinct, Multivalent Structures for the Probing of Biological Activity

Mendez,

Boadi,

Kennedy

et al. 2024

Preprint

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“…Various carbohydrate polymers exist, such as natural polysaccharides, synthetic polysaccharides, and saccharide–synthetic polymer conjugates. Glycopolymers, synthetic polymers with pendant saccharide moieties on their side chains, are functional polymers and saccharide–synthetic polymer conjugates [ 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. The most important characteristic of glycopolymers is their multivalent binding affinity, called the “glycocluster effect”, in which multiple saccharide moieties are densely packed around a polymer backbone, resulting in stronger binding to receptor biomolecules, such as lectins, viruses, and antibodies [ 23 , 24 , 25 ].…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Polymers Bearing Activated Esters for the Synthesis of Glycopolymers by Postpolymerization Modification

Tanaka

2024

Polymers

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Glycopolymers are functional polymers with saccharide moieties on their side chains and are attractive candidates for biomaterials. Postpolymerization modification can be employed for the synthesis of glycopolymers. Activated esters are useful in various fields, including polymer chemistry and biochemistry, because of their high reactivity and ease of reaction. In particular, the formation of amide bonds caused by the reaction of activated esters with amino groups is of high synthetic chemical value owing to its high selectivity. It has been employed in the synthesis of various functional polymers, including glycopolymers. This paper reviews the recent advances in polymers bearing activated esters for the synthesis of glycopolymers by postpolymerization modification. The development of polymers bearing hydrophobic and hydrophilic activated esters is described. Although water-soluble activated esters are generally unstable and hydrolyzed in water, novel polymer backbones bearing water-soluble activated esters are stable and useful for postpolymerization modification for synthesizing glycopolymers in water. Dual postpolymerization modification can be employed to modify polymer side chains using two different molecules. Thiolactone and glycine propargyl esters on the polymer backbone are described as activated esters for dual postpolymerization modification.

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“…The obtained materials proved to have good properties, which recommended them for different applications in fields like medicine, as tissue replacement or drug delivery candidates [30], agriculture, food packaging, etc. [31][32][33].…”

Section: Introductionmentioning

confidence: 99%

Study on the Biodegradation Process of D-Mannose Glycopolymers in Liquid Media and Soil

et al. 2023

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Polymers derived from natural raw materials have become of great interest due to their increased biodegradable features and possible biocompatibility. Our group has successfully synthesized and characterized polymers derived from D-mannose oligomer (M), 2-hydroxy propyl acrylate (HPA), and methacrylate (HPMA) in different weight ratios. Their biodegradation was studied in liquid media with pure Proteus mirabilis inoculum for the samples with the most sugar residue, and the results show that the methacrylate derivative M_HPMA1 lost about 50% of its weight during incubation. SEM/EDX techniques were employed to display the modifications of the samples during the biodegradation process. The glycopolymers were buried in garden soil, and the experiment proved that more than 40% of the weight of the M_HPA1 sample was lost during biodegradation, while the other samples encountered an average of about 32% weight loss. The biodegradation profile was fitted against linear and polynomial mathematical models, which enabled an estimate of about a year for the total degradation of the D-mannose glycopolymers sample in soil.

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Glycopolymers for Antibacterial and Antiviral Applications

Cited by 9 publications

References 82 publications

Glycopolymers Prepared by Alternating Ring-Opening Metathesis Polymerization Provide Access to Distinct, Multivalent Structures for the Probing of Biological Activity

Glycopolymers Prepared by Alternating Ring-Opening Metathesis Polymerization Provide Access to Distinct, Multivalent Structures for the Probing of Biological Activity

Recent Advances in Polymers Bearing Activated Esters for the Synthesis of Glycopolymers by Postpolymerization Modification

Study on the Biodegradation Process of D-Mannose Glycopolymers in Liquid Media and Soil

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