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Three different phenylboronic acid (PBA) derivatives were explored as monomers for the synthesis of MIP NGs targeting either \u03b12,6\u2010 or \u03b12,3\u2010sialyllactose, taken as oversimplified models of cancer\u2010related sT and sTn antigens. Starting from commercially available 3\u2010acrylamidophenylboronic acid, also its 2\u2010substituted isomer and the 5\u2010acrylamido\u20102\u2010hydroxymethyl cyclic PBA monoester derivative were initially evaluated by NMR studies. Then, a small library of MIP NGs imprinted with the \u03b12,6\u2010linked template was synthesized and tested by mobility shift Affinity Capillary Electrophoresis (msACE), to rapidly assess an affinity ranking. Finally, the best monomer 2\u2010acrylamido PBA was selected for the synthesis of polymers targeting both sialyllactoses. The resulting MIP NGs display an affinity constant\u224810<jats:sup>6<\/jats:sup>\u2005M<jats:sup>\u22121<\/jats:sup> and selectivity towards imprinted glycans. This general procedure could be applied to any non\u2010modified carbohydrate template possessing a reducing end.<\/jats:p>","DOI":"10.1002\/chem.202401232","type":"journal-article","created":{"date-parts":[[2024,6,7]],"date-time":"2024-06-07T10:48:20Z","timestamp":1717757300000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Rational Design of Highly Selective Sialyllactose\u2010Imprinted Nanogels"],"prefix":"10.1002","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0459-9527","authenticated-orcid":false,"given":"Cecilia","family":"Contardi","sequence":"first","affiliation":[{"name":"Department of Drug Sciences University of Pavia  Viale Taramelli 12 27100 Pavia Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9638-340X","authenticated-orcid":false,"given":"Liliia","family":"Mavliutova","sequence":"additional","affiliation":[{"name":"Biofilms Research Center for Biointerfaces Department of Biomedical Sciences Faculty of Health and Society Malm\u00f6 University  Per Albin Hanssons V\u00e4g 35 21432 Malm\u00f6 Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6724-4355","authenticated-orcid":false,"given":"Massimo","family":"Serra","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences University of Pavia  Viale Taramelli 12 27100 Pavia Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8557-4577","authenticated-orcid":false,"given":"Davide","family":"Rubes","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences University of Pavia  Viale Taramelli 12 27100 Pavia Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5774-9547","authenticated-orcid":false,"given":"Rossella","family":"Dorati","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences University of Pavia  Viale Taramelli 12 27100 Pavia Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3939-5172","authenticated-orcid":false,"given":"Giulio","family":"Vistoli","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Sciences University of Milan  Via Mangiagalli 25 20133 Milan Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0008-2743-1827","authenticated-orcid":false,"given":"Alessio","family":"Macorano","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Sciences University of Milan  Via Mangiagalli 25 20133 Milan Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2392-3305","authenticated-orcid":false,"given":"B\u00f6rje","family":"Sellergren","sequence":"additional","affiliation":[{"name":"Biofilms Research Center for Biointerfaces Department of Biomedical Sciences Faculty of Health and Society Malm\u00f6 University  Per Albin Hanssons V\u00e4g 35 21432 Malm\u00f6 Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5450-7208","authenticated-orcid":false,"given":"Ersilia","family":"De Lorenzi","sequence":"additional","affiliation":[{"name":"Department of Drug Sciences University of Pavia  Viale Taramelli 12 27100 Pavia Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,7,25]]},"reference":[{"key":"e_1_2_8_1_1","first-page":"77","volume-title":"Essentials of Glycobiology","author":"Varki A.","year":"2015"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1093\/glycob\/cww086"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1093\/glycob\/11.12.1051"},{"key":"e_1_2_8_4_1","volume-title":"Glycans in Acquired Human Diseases","author":"Freeze H. 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