Hyaluronan (HA)-inspired glycopolymers as molecular tools for studying HA functions

Collis, Dominic W. P.; Yilmaz, Gökhan; Yuan, Yichen; Monaco, Alessandra; Ochbaum, Guy; Shi, Yonghui; O'Malley, Clare; Uzunova, Veselina; Napier, Richard; Bitton, Ronit; Becer, C. Remzi; Azevedo, Helena S.

doi:10.1039/d0cb00223b

Cited by 7 publications

(6 citation statements)

References 63 publications

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“…There are different molecular designs of HA copolymers: most of them are based on the grafting of synthetic polymer chains at the −COOH groups of HA, and only a few examples are reported in which HA is end-on linked (i.e., at the reducing end) to a synthetic core. These examples include diblock copolymers − and glycopolymers made of a synthetic core with short (mono-, di-, and tetrasaccharides) glycan branches. − The synthetic core can vary to control the molecular architecture of the glycopolymer, while the glycan branches determine the selectivity, specificity, and avidity in the biointeractions of these polymers. Previously, we have reported the preparation of star-like copolymers with long HA branches and a hyperbranched polyglycerol core (HPG) .…”

Section: Resultsmentioning

confidence: 99%

Hyaluronan Brush-like Copolymers Promote CD44 Declustering in Breast Cancer Cells

Carvalho

Valcárcel

Costa

et al. 2022

ACS Appl. Mater. Interfaces

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We report on the synthesis of hyaluronan (HA) brush-like copolymers and their application as antagonists of tumorigenic CD44-HA interactions. HA (4.8 kDa, ca. 24 saccharides) was grafted on 2-hydrohyethyl methacrylate (HEMA) by end-on oxime ligation. The obtained copolymers were compared with low and high molecular weight HA in terms of hydrolysis kinetics in the presence of hyaluronidase (isothermal titration calorimetry) and interactions with CD44 (surface plasmon resonance). The results evidenced that the high molecular weight HA and HA-g-HEMA have a much higher affinity to CD44 than low molecular weight HA. Additionally, slower enzymatic degradation was observed for the copolymer, making it an excellent candidate for active targeting of tumorigenic CD44-HA interactions. We, therefore, investigated the effect of the copolymer on cancer cell lines with different expression of CD44 and observed an efficient declustering of CD44 that is usually associated with reduction of metastasis and drug resistance.

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Section: Resultsmentioning

confidence: 99%

Hyaluronan Brush-like Copolymers Promote CD44 Declustering in Breast Cancer Cells

Carvalho

Valcárcel

Costa

et al. 2022

ACS Appl. Mater. Interfaces

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Section: Applicationsmentioning

confidence: 99%

“…116 Besides, glycopolymers with pendant N-acetyl glucosamine and/or glucuronic acid groups could mimic hyaluronic acid to recognize hyaluronic acid-binding proteins, such as cell surface protein cluster of differentiation 44 (CD44). 117 Other glycopolymers with complex structures and morphologies have been reported to recognize lections. For example, the spike protein (haemagglutinin (HA)) of the influenza A virus (IAV) can bind to sialyl glycan on the host cells.…”

Section: Polymer Chemistry Reviewmentioning

confidence: 99%

Glycopolymers based on carbohydrate or vinyl backbones and their biomedical applications

et al. 2023

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“…Similarly, reversible addition–fragmentation chain transfer polymerization (RAFT) has been commonly used for the preparation of many different kinds of glycopolymers. − In RAFT polymerization, a free radical initiator (typically AIBN) creates free radicals that reacts with the monomer to generate propagating species. These radical species react with a chain transfer agent (aka RAFT agent) to regulate the chain length and dispersity.…”

Section: Strategies For Glycopolymer Synthesismentioning

confidence: 99%

Hierarchy of Complex Glycomacromolecules: From Controlled Topologies to Biomedical Applications

et al. 2022

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Carbohydrates bearing a distinct complexity use a special code (Glycocode) to communicate with carbohydrate-binding proteins at a high precision to manipulate biological activities in complex biological environments. The level of complexity in carbohydrate-containing macromolecules controls the amount and specificity of information that can be stored in biomacromolecules. Therefore, a better understanding of the glycocode is crucial to open new areas of biomedical applications by controlling or manipulating the interaction between immune cells and pathogens in terms of trafficking and signaling, which would become a powerful tool to prevent infectious diseases. Even though a certain level of progress has been achieved over the past decade, synthetic glycomacromolecules are still lagging far behind naturally existing glycans in terms of complexity and precision because of insufficient and inefficient synthetic techniques. Currently, specific targeting at a cellular level using synthetic glycomacromolecules is still challenging. It is obvious that multidisciplinary collaborations are essential between different specialized disciplines to enhance the carbohydrate receptor-targeting paradigm for new biomedical applications. In this Perspective, recent developments in the synthesis of sophisticated glycomacromolecules are highlighted, and their biological and biomedical applications are also discussed in detail.

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Hyaluronan (HA)-inspired glycopolymers as molecular tools for studying HA functions

Abstract: Glycopolymers based on hyaluronan (HA) were synthesised as homopolymers and alternating copolymers and used as probes to study the interactions with known HA-binding proteins and peptides.

Cited by 7 publications

References 63 publications

Hyaluronan Brush-like Copolymers Promote CD44 Declustering in Breast Cancer Cells

Hyaluronan Brush-like Copolymers Promote CD44 Declustering in Breast Cancer Cells

Glycopolymers based on carbohydrate or vinyl backbones and their biomedical applications

Hierarchy of Complex Glycomacromolecules: From Controlled Topologies to Biomedical Applications

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