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• W2036003812 endingPage "4223" @default.
• W2036003812 startingPage "4212" @default.
• W2036003812 abstract "Herein we report two new ligands, 1,4,7-tris(carboxymethyl)-10-[2-(dihydroxyboranyl)benzyl]-1,4,7,10-tetraazacyclododecane (L1) and 1,4,7-tris(carboxymethyl)-10-[3-(dihydroxyboranyl)benzyl]-1,4,7,10-tetraazacyclododecane (L2), which contain a phenylboronic acid (PBA) function and a 1,4,7,10-tetraazacyclododecane-1,4,7-triacetate cage for complexation of lanthanide ions in an aqueous solution. The pKa of the PBA function amounts to 4.6 in [Gd(L1)] and 8.9 in [Gd(L2)], with the value of the L2 analogue being very similar to that of PBA (8.8). These results are explained by the coordination of the PBA function of L1 to the GdIII ion, which results in a dramatic lowering of its pKa. As a consequence, [Gd(L1)] does not bind to saccharides at physiological pH. The nuclear magnetic relaxation dispersion profiles recorded for [Gd(L1)] and [Gd(L2)] confirm that the phenylboronate function is coordinated to the metal ion in the L1 derivative, which results in a q = 0 complex. The interaction of the [Gd(L2)] complex with 5-acetylneuraminic acid (Neu5Ac) and 2-α-O-methyl-5-acetylneuraminic acid (MeNeu5Ac) has been investigated by means of spectrophotometric titrations in an aqueous solution (pH 7.4, 0.1 M 3-(N-morpholino)propanesulfonic acid buffer). Furthermore, we have also investigated the binding of these receptors with competing monosaccharides such as d-(+)-glucose, d-fructose, d-mannose, d-galactose, methyl α-d-galactoside, and methyl α-d-mannoside. The binding constants obtained indicate an important selectivity of [Gd(L2)] for Neu5Ac (Keq = 151) over d-(+)-glucose (Keq = 12.3), d-mannose (Keq = 21.9), and d-galactose (Keq = 24.5). Furthermore, a very weak binding affinity was observed in the case of methyl α-d-galactoside and methyl α-d-mannoside. An 8-fold increase of the binding constant of [Gd(L2)] with Neu5Ac is observed when compared to that of PBA determined under the same conditions (Keq = 19). 13C NMR spectroscopy and density functional theory calculations performed at the B3LYP/6-31G(d) level show that this is due to a cooperative two-site binding of Neu5Ac through (1) ester formation by interaction on the PBA function of the receptor and (2) coordination of the carboxylate group of Neu5Ac to the GdIII ion. The emission lifetime of the 5D4 level of TbIII in [Tb(L2)] increases upon Neu5Ac binding, in line with the displacement of inner-sphere water molecules due to coordination of Neu5Ac to the metal ion." @default.
• W2036003812 created "2016-06-24" @default.
• W2036003812 creator A5030925836 @default.
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• W2036003812 date "2010-04-07" @default.
• W2036003812 modified "2023-10-17" @default.
• W2036003812 title "Molecular Recognition of Sialic Acid by Lanthanide(III) Complexes through Cooperative Two-Site Binding" @default.
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