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Combinatorial design of a sialic acid imprinted binding site exploring a dual ion receptor approach
Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.
Malmö University, Faculty of Health and Society (HS), Department of Biomedical Science (BMV). Malmö University, Biofilms Research Center for Biointerfaces.ORCID iD: 0000-0002-2392-3305
2021 (English)In: RSC Advances, E-ISSN 2046-2069, Vol. 11, no 54, article id 34329Article in journal (Refereed) Published
Abstract [en]

Aberrant sialic acid expression is one of the key indicators of pathological processes. This acidic saccharide is overexpressed in tumor cells and is a potent biomarker. Development of specific capture tools for various sialylated targets is an important step for early cancer diagnosis. However, sialic acid recognition by synthetic hosts is often complicated due to the competition for the anion binding by their counterions, such as Na+ and K+. Here we report on the design of a sialic acid receptor via simultaneous recognition of both the anion and cation of the target analyte. The polymeric receptor was produced using neutral (thio)urea and crown ether based monomers for simultaneous complexation of sialic acid's carboxylate group and its countercation. Thiourea and urea based functional monomers were tested both in solution by 1H NMR titration and in a polymer matrix system for their ability to complex the sodium salt of sialic acid alone and in the presence of crown ether. Combination of both orthogonally acting monomers resulted in higher affinities for the template in organic solvent media. The imprinted polymers displayed enhanced sialic acid recognition driven to a significant extent by the addition of the macrocyclic cation host. The effect of various counterions and solvent systems on the binding affinities is reported. Binding of K+, Na+ and NH4+ salts of sialic acid exceeded the uptake of bulky lipophilic salts. Polymers imprinted with sialic or glucuronic acids displayed a preference for their corresponding templates and showed a promising enrichment of sialylated peptides from the tryptic digest of glycoprotein bovine fetuin.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2021. Vol. 11, no 54, article id 34329
Keywords [en]
carbohydrate receptor, mlocular imprinting, crown ether, ion par recognition
National Category
Biomedical Laboratory Science/Technology
Identifiers
URN: urn:nbn:se:mau:diva-45668DOI: 10.1039/D1RA06962DISI: 000709877800001PubMedID: 35497298Scopus ID: 2-s2.0-85120525004OAI: oai:DiVA.org:mau-45668DiVA, id: diva2:1591366
Available from: 2021-09-06 Created: 2021-09-06 Last updated: 2024-02-05Bibliographically approved
In thesis
1. Moleculary imprinted micro- and nanoparticles for cancer associated glycan motifs
Open this publication in new window or tab >>Moleculary imprinted micro- and nanoparticles for cancer associated glycan motifs
2021 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Sialic acids are an important family of monosaccharides that are typically found as terminal moieties of glycans. Aberrant sialylation has been proven to correlate with various diseases including cancer. Glycosylation analysis is complex due to high diversityof the glycan isomers and their low abundance. Antibodies and lectins are commonly used in glycan purification and enrichment. However, high cost, poor availability, and limitation in storage/testing conditions hinders their application on a broader scale. This thesis is focused on the development of alternative glycan specific receptors with their potential applications in glycomics and cell imaging. The underlying technique for producing the synthetic receptors is molecular imprinting. Highly complementary binding sites are formed by fixing pre-ordered template/functional monomer complexes into a highly crosslinked polymer matrix. Fundamental investigation of this intermolecular imprinting approach in the imprinting of glycosylated targets is reported here. The core of this study focuses on the elucidation of relative contribution of orthogonally interacting functional monomers, their structural tuning and the importance of monomer, solvent and counterion choice on the imprinting. Molecularly imprinted polymers (MIPs) are developed as particles of different sizes for glycan/glycopeptide enrichment applications or combined with fluorescent reportergroups for use as glycan imaging nanolabels. Special attention is given to the improvement of sialic acid MIP selectivities toward particular structures associated with cancer biomarkers. Development of MIPs against such complex targets includes design of linkage selective MIPs with comprehensive studies of the affinities and selectivities of the final glycan specific materials.

Place, publisher, year, edition, pages
Malmö: Malmö universitet, 2021. p. 67
Series
Malmö University Health and Society Dissertations, ISSN 1653-5383 ; 2021:4
Keywords
Moleculary imprinted polymer, sialic acid, glycan recognition, synthetic receptor
National Category
Biomedical Laboratory Science/Technology
Identifiers
urn:nbn:se:mau:diva-45682 (URN)10.24834/isbn.9789178772063 (DOI)9789178772056 (ISBN)9789178772063 (ISBN)
Public defence
2021-09-24, Aulan AS:E002 Hälsa och samhälles byggnad, samt digitalt, Jan Waldenströms gata 25, Malmö, 13:15 (English)
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Supervisors
Available from: 2021-09-06 Created: 2021-09-06 Last updated: 2023-08-15Bibliographically approved

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Mavliutova, LiliiaSellergren, Börje

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