Synthesis of well-defined cyclic glycopolymers and the relationship between their physical properties and their interaction with lectins

Nagao, Masashi; Hoshino, Yu; Miura, Yoshiko

doi:10.1039/d2py00941b

Cited by 4 publications

(4 citation statements)

References 39 publications

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“…T 2 relaxation times were measured by 1 H NMR on c-PNB 25 -TEG-Man and l-PNB 28 -TEG-Man using the Carr–Purcell–Meiboom–Gill (CPMG) pulse sequence, at chemical shifts of 5.35, 3.30, and 1.38 ppm, corresponding to the alkene and CH protons of the main chain, and the gem -dimethyl group of the side chain, respectively (Figure S32 in the Supporting Information). In contrast to previous studies, − the cyclic polymer shows higher T 2 values (Table S2 in the Supporting Information). Aggregates observed with c-PNB 25 -TEG-Man in water, as shown by dynamic light scattering (DLS, Figure S33 in the Supporting Information), reduce the large-scale mobility and increase T 2 , T 2 being determined by large-scale motions including intermolecular interactions .…”

Section: Resultscontrasting

confidence: 89%

“…Specifically, we aim to determine if rigid mannose-coated polymers with a cyclic topology, denoted as c-PNB X -TEG-Man, can compete with their linear counterparts, l-PNB X -TEG-Man, possessing similar DP n . To the best of our knowledge, such a comparison has only been provided in the literature for flexible glycopolymers. ,− These polymers are obtained through CuAAc cyclization of their linear analogs, which are terminated with azide and alkyne groups. If flexible glycomacrocycles were shown to give higher affinity constant on a panel of human innate immune lectins (DC-SIGN, MBL, SP-D, dectin-2, and mincle) compared to their linear analogues, other sets of cyclic glycopolymers showed significantly weaker interactions with their model lectins (ConA and RCA120). , Thus, topological effects of polymeric scaffold on the binding affinity of specific targets remain unpredictable.…”

Section: Resultsmentioning

confidence: 99%

“…If flexible glycomacrocycles were shown to give higher affinity constant on a panel of human innate immune lectins (DC-SIGN, MBL, SP-D, dectin-2, and mincle) compared to their linear analogues, 77 other sets of cyclic glycopolymers showed significantly weaker interactions with their model lectins (ConA and RCA120). 55,76 Thus, topological effects of polymeric scaffold on the binding affinity of specific targets remain unpredictable.…”

Section: ■ Introductionmentioning

confidence: 99%

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A Versatile Cyclic Clickable Platform by Ring-Expansion Metathesis Polymerization: Cyclic Glycopolymers with Lectin-Binding Ability

Gonnot,

Scalabrini,

Roubinet

et al. 2024

Macromolecules

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A new versatile cyclic polymer platform for the design of advanced cyclic materials was prepared by combining ring-expansion metathesis polymerization (REMP) and click chemistry. Cyclic poly(norbornenyl azlactone) backbones were synthesized over an unprecedented length range with number-average degree of polymerization (DP n ) ranging from 25 to 1000. The cyclic topology was thoroughly characterized using 1H NMR, size exclusion chromatography (SEC) with multiangle light scattering (MALS) and viscometer detection. Postpolymerization modification (PPM) of these scaffolds was carried out with amino-terminated mannoses using the click aminolysis of the azlactone moiety to prepare a library of multivalent cyclic glycopolymers. The binding inhibition of the resulting cyclic glycopolymers was assessed against a panel of model and biologically relevant lectins (Bc2L-A, FimH, langerin, DC-SIGN, and ConA). The cyclic carbohydrate-functionalized polynorbornenes exhibited high lectin-binding inhibitory potency in the biochip assay, surpassing their monovalent analogues by several orders of magnitude and competing strongly with their linear polymer analogues in terms of IC50 values. Interestingly, the cyclic polymers also prevented the adhesion of Adherent-Invasive Escherichia coli implied in Crohn’s disease, to intestinal cells.

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Section: Resultscontrasting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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A Versatile Cyclic Clickable Platform by Ring-Expansion Metathesis Polymerization: Cyclic Glycopolymers with Lectin-Binding Ability

Gonnot,

Scalabrini,

Roubinet

et al. 2024

Macromolecules

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“…[35] Miura reported the synthesis of welldefined cyclic glycopolymers with functional units for biomolecular recognition and evaluated their physical properties, including their molecular mobility (Figure 8). [36] The inhibited molecular mobility of the cyclic glycopolymers weakened the interactions with the target proteins, thus demonstrating a potential effect of polymer topology on molecular recognition.…”

Section: Physical Properties and Applications Of Cyclic Polymersmentioning

confidence: 99%

Cyclic Polymers: Controlled Synthesis, Properties and Perspectives

Gao

et al. 2023

Chemistry A European J

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Recently, cyclic polymers have attracted increasing interest due to their unique topologies, properties, and functions compared to the linear analogues. This mini-review focuses on the recent advances in the synthesis and applications of cyclic polymers. First, the main synthetic methods for cyclic polymers, namely ring closure and ring expansion methods, are presented and discussed, followed by a review on the exploration of the properties and applications of synthetic cyclic polymers. Finally, a critical assessment of the preliminary studies exploring the efficient synthesis and potential applications of cyclic polymers are presented, and the remaining challenges in the field as well as ideas for solving these challenges will be discussed.

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Effects of Cyclic Glycopolymers Molecular Mobility on their Interactions with Lectins

Jin,

Nagao,

Kumon

et al. 2024

ChemPlusChem

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Cyclic polymers, which are found in the field of biopolymers, exhibit unique physical properties such as suppressed molecular mobility. Considering thermodynamics, the suppressed molecular mobility of cyclic polymers is expected to prevent unfavorable entropy loss in molecular interactions. In this study, we synthesized cyclic glycopolymers carrying galactose units and investigated the effects of their molecular mobility on the interactions with a lectin (peanut agglutinin). The synthesized cyclic glycopolymers exhibited delayed elution time on size exclusion chromatography and a short spin–spin relaxation time, indicating typical characteristics of cyclic polymers, including smaller hydrodynamic size and suppressed molecular mobility. The hemagglutination inhibition assay revealed that the cyclic glycopolymers exhibited weakened interactions with PNA compared to the linear counterparts, attributable to the suppressed molecular mobility. Although the results are contrary to our expectations, the impact of polymer topology on molecular recognition remains intriguing, particularly in the context of protein repellent activity in the biomedical field.

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Synthesis of well-defined cyclic glycopolymers and the relationship between their physical properties and their interaction with lectins

Abstract: Cyclic polymers, which have a different topology from that of linear polymers, show potential as novel nanomaterials. In this communication, we report the synthesis of well-defined cyclic glycopolymers that have...

Cited by 4 publications

References 39 publications

A Versatile Cyclic Clickable Platform by Ring-Expansion Metathesis Polymerization: Cyclic Glycopolymers with Lectin-Binding Ability

A Versatile Cyclic Clickable Platform by Ring-Expansion Metathesis Polymerization: Cyclic Glycopolymers with Lectin-Binding Ability

Cyclic Polymers: Controlled Synthesis, Properties and Perspectives

Effects of Cyclic Glycopolymers Molecular Mobility on their Interactions with Lectins

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