Rational Design of Highly Selective Sialyllactose-Imprinted Nanogels.

Autor: Contardi C; Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100, Pavia, Italy., Mavliutova L; Biofilms Research Center for Biointerfaces, Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, Per Albin Hanssons Väg 35, 21432, Malmö, Sweden., Serra M; Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100, Pavia, Italy., Rubes D; Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100, Pavia, Italy., Dorati R; Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100, Pavia, Italy., Vistoli G; Department of Pharmaceutical Sciences, University of Milan, Via Mangiagalli 25, 20133, Milan, Italy., Macorano A; Department of Pharmaceutical Sciences, University of Milan, Via Mangiagalli 25, 20133, Milan, Italy., Sellergren B; Biofilms Research Center for Biointerfaces, Department of Biomedical Sciences, Faculty of Health and Society, Malmö University, Per Albin Hanssons Väg 35, 21432, Malmö, Sweden., De Lorenzi E; Department of Drug Sciences, University of Pavia, Viale Taramelli 12, 27100, Pavia, Italy.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Aug 12; Vol. 30 (45), pp. e202401232. Date of Electronic Publication: 2024 Jul 25.
DOI: 10.1002/chem.202401232
Abstrakt: We describe a facile method to prepare water-compatible molecularly imprinted polymer nanogels (MIP NGs) as synthetic antibodies against target glycans. Three different phenylboronic acid (PBA) derivatives were explored as monomers for the synthesis of MIP NGs targeting either α2,6- or α2,3-sialyllactose, taken as oversimplified models of cancer-related sT and sTn antigens. Starting from commercially available 3-acrylamidophenylboronic acid, also its 2-substituted isomer and the 5-acrylamido-2-hydroxymethyl cyclic PBA monoester derivative were initially evaluated by NMR studies. Then, a small library of MIP NGs imprinted with the α2,6-linked template was synthesized and tested by mobility shift Affinity Capillary Electrophoresis (msACE), to rapidly assess an affinity ranking. Finally, the best monomer 2-acrylamido PBA was selected for the synthesis of polymers targeting both sialyllactoses. The resulting MIP NGs display an affinity constant≈10 6  M -1 and selectivity towards imprinted glycans. This general procedure could be applied to any non-modified carbohydrate template possessing a reducing end.
(© 2024 Wiley-VCH GmbH.)
Databáze: MEDLINE
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