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Discrimination between sialic acid linkage modes using sialyllactose-imprinted polymers
Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, SE-20506 Malmö, Sweden.
Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, SE-20506 Malmö, Sweden.
Bioorganic and Biophysical Chemistry Laboratory, Linnaeus University Centre for Biomaterials Chemistry, Department of Chemistry and Biomedical Sciences, Linnaeus University, Kalmar, Sweden.
Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, SE-20506 Malmö, Sweden.
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2021 (Engelska)Ingår i: RSC Advances, E-ISSN 2046-2069, Vol. 11, nr 36, s. 22409-22418Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Glycosylation plays an important role in various pathological processes such as cancer. One key alteration in the glycosylation pattern correlated with cancer progression is an increased level as well as changes in the type of sialylation. Developing molecularly-imprinted polymers (MIPs) with high affinity for sialic acid able to distinguish different glycoforms such as sialic acid linkages is an important task which can help in early cancer diagnosis. Sialyllactose with α2,6′vs.α2,3′ sialic acid linkage served as a model trisaccharide template. Boronate chemistry was employed in combination with a library of imidazolium-based monomers targeting the carboxylate group of sialic acid. The influence of counterions of the cationic monomers and template on their interactions was investigated by means of1H NMR titration studies. The highest affinities were afforded using a combination of Br−and Na+counterions of the monomers and template, respectively. The boronate ester formation was confirmed by MS and1H/11B NMR, indicating 1 : 2 stoichiometries between sialyllactoses and boronic acid monomer. Polymers were synthesized in the form of microparticles using boronate and imidazolium monomers. This combinatorial approach afforded MIPs selective for the sialic acid linkages and compatible with an aqueous environment. The molecular recognition properties with respect to saccharide templates and glycosylated targets were reported.

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Royal Society of Chemistry, 2021. Vol. 11, nr 36, s. 22409-22418
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Organisk kemi Biokemi och molekylärbiologi
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URN: urn:nbn:se:umu:diva-185760DOI: 10.1039/d1ra02274aISI: 000667711300053Scopus ID: 2-s2.0-85108896879OAI: oai:DiVA.org:umu-185760DiVA, id: diva2:1577935
Forskningsfinansiär
EU, Horisont 2020, 722171, H2020-MSCA-ITN-2016Tillgänglig från: 2021-07-05 Skapad: 2021-07-05 Senast uppdaterad: 2024-07-02Bibliografiskt granskad

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Huynh, Chau MinhIrgum, Knut

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