8-Hydroxyquinoline as a building block for artificial receptors: binding preferences in the recognition of glycopyranosides.

doi:10.1039/c0ob00960a

Paper

8-Hydroxyquinoline as a building block for artificial receptors: binding preferences in the recognition of glycopyranosides.

Published Mar 16, 2011 · M. Mazik, C. Geffert

Organic & biomolecular chemistry

Q2 SJR score

39

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1

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Abstract

8-Hydroxyquinoline-based receptors 1-3, containing a trisubstituted triethylbenzene core, were prepared and their binding properties towards glycosides were evaluated. (1)H NMR and fluorescence titrations as well as binding studies in two-phase systems, such as dissolution of solid carbohydrates in apolar media and phase transfer of sugars from aqueous into organic solvents, revealed β- vs.α-anomer binding preferences in the recognition of glycosides. Compared to the previously described three-armed aminopyridine-based receptor, compounds 1 and 2 showed significantly increased affinity to β-galactoside. Receptor 2, incorporating two 8-hydroxyquinoline units, was shown to be the most effective receptor for β-galactoside. Compound 3, bearing one 8-hydroxyquinoline group, was found to be a highly effective receptor for β-glucoside and shown to be a more powerful receptor than the quinoline-based compound 4, indicating an important role of the quinoline hydroxy group in the complex formation.

In Vitro Study

Study Snapshot

8-Hydroxyquinoline-based receptors show increased affinity for -galactoside and -glucoside, with compound 2 being the most effective for -galactoside and compound 3 for -glucoside.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

8-Hydroxyquinoline as a building block for artificial receptors: binding preferences in the recognition of glycopyranosides.

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