The stoichiometry, geometry, stability, and solubility of the inclusion complexes of melatonin (MLT) with native cyclomaltooligosaccharides (α-, β- or γ-cyclodextrins, CDs) are determined experimentally by high-resolution NMR spectroscopy, calorimetric and solubility measurements, and mass spectrometry. The observed differences are discussed in terms of molecular recognition expression of the host-guest (h-g) interactions within the hydrophobic CDs cavities of different size. The 1:1 h-g stoichiometry in water solution prevails at low CD concentrations; the trend to form higher order associations is observed at increasing CD concentrations. The stability order β-CD>γ-CD>α-CD for the complexes in water solution and β-CD>α-CD>γ-CD for the protonated or alkali-cationated complexes in the gas phase are rationalized on the grounds of the structural data from NMR spectroscopy and of the thermodynamic parameters from calorimetric measurements. © 2002 Elsevier Science Ltd. All rights reserved.

Bongiorno, D., Ceraulo, L., Mele, A., Panzeri, W., Selva, A., & TURCO LIVERI, V. (2002). Structural and physicochemical characterization of the inclusion complexes of cyclomaltooligosaccharides (cyclodextrins) with melatonin. CARBOHYDRATE RESEARCH, 337(8), 743-754 [10.1016/S0008-6215(02)00049-6].

Structural and physicochemical characterization of the inclusion complexes of cyclomaltooligosaccharides (cyclodextrins) with melatonin

BONGIORNO, David;CERAULO, Leopoldo;TURCO LIVERI, Vincenzo
2002

Abstract

The stoichiometry, geometry, stability, and solubility of the inclusion complexes of melatonin (MLT) with native cyclomaltooligosaccharides (α-, β- or γ-cyclodextrins, CDs) are determined experimentally by high-resolution NMR spectroscopy, calorimetric and solubility measurements, and mass spectrometry. The observed differences are discussed in terms of molecular recognition expression of the host-guest (h-g) interactions within the hydrophobic CDs cavities of different size. The 1:1 h-g stoichiometry in water solution prevails at low CD concentrations; the trend to form higher order associations is observed at increasing CD concentrations. The stability order β-CD>γ-CD>α-CD for the complexes in water solution and β-CD>α-CD>γ-CD for the protonated or alkali-cationated complexes in the gas phase are rationalized on the grounds of the structural data from NMR spectroscopy and of the thermodynamic parameters from calorimetric measurements. © 2002 Elsevier Science Ltd. All rights reserved.
Bongiorno, D., Ceraulo, L., Mele, A., Panzeri, W., Selva, A., & TURCO LIVERI, V. (2002). Structural and physicochemical characterization of the inclusion complexes of cyclomaltooligosaccharides (cyclodextrins) with melatonin. CARBOHYDRATE RESEARCH, 337(8), 743-754 [10.1016/S0008-6215(02)00049-6].
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10447/243656
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