{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,24]],"date-time":"2026-01-24T15:28:54Z","timestamp":1769268534728,"version":"3.49.0"},"reference-count":56,"publisher":"Wiley","issue":"20","license":[{"start":{"date-parts":[[2004,9,10]],"date-time":"2004-09-10T00:00:00Z","timestamp":1094774400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2004,10,18]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The detection of sialic acid in living systems is of importance for the diagnosis of several types of malignancy. We have designed and synthesized two new lanthanide ion ligands (L<jats:sup>1<\/jats:sup> and L<jats:sup>2<\/jats:sup>) that are capable of molecular recognition of sialic acid residues. The basic structure of these ligands consists of a DTPA\u2010bisamide (DTPA, diethylenetriamine pentaacetic acid) whose amide moieties each bear both a boronic function for interaction with the diol groups in the side chain of sialic acid, and a functional group that is positively charged at physiologic pH values and is designed to interact with the carboxylate anion of sialic acid. The relaxometric properties of the Gd<jats:sup>3+<\/jats:sup> complexes of these two ligands were evaluated. The relaxivity of the GdL<jats:sup>1<\/jats:sup> complex has a significant second\u2010sphere contribution at pH values above the p<jats:italic>K<\/jats:italic><jats:sub>a<\/jats:sub> of its phenylboronic acid moiety. The interaction of the Gd<jats:sup>3+<\/jats:sup> complexes of L<jats:sup>1<\/jats:sup> and L<jats:sup>2<\/jats:sup> with each of several saccharides was investigated by means of a competitive fluorescent assay. The results show that both complexes recognize sialic acid with good selectivity in the presence of other sugars. The adduct formed by GdL<jats:sup>2<\/jats:sup> with sialic acid has the higher conditional formation constant (50.43\u00b14.61\u2009<jats:sc>M<\/jats:sc><jats:sup>\u22121<\/jats:sup> at pH 7.4). The ability of such complexes to recognize sialic acid was confirmed by the results of a study on the interaction of corresponding radiolabeled complexes (<jats:sup>153<\/jats:sup>SmL<jats:sup>1<\/jats:sup> and <jats:sup>153<\/jats:sup>SmL<jats:sup>2<\/jats:sup>) with C6 glioma rat cells. <jats:sup>153<\/jats:sup>SmL<jats:sup>2<\/jats:sup> in particular is retained on the cell surface in significant amounts.<\/jats:p>","DOI":"10.1002\/chem.200400369","type":"journal-article","created":{"date-parts":[[2004,9,14]],"date-time":"2004-09-14T05:44:57Z","timestamp":1095140697000},"page":"5205-5217","source":"Crossref","is-referenced-by-count":58,"title":["Towards Targeted MRI: New MRI Contrast Agents for Sialic Acid Detection"],"prefix":"10.1002","volume":"10","author":[{"given":"Luca","family":"Frullano","sequence":"first","affiliation":[]},{"given":"Jan","family":"Rohovec","sequence":"additional","affiliation":[]},{"given":"Silvio","family":"Aime","sequence":"additional","affiliation":[]},{"given":"Thomas","family":"Maschmeyer","sequence":"additional","affiliation":[]},{"given":"M. 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