Binding mechanisms in cyclohexaamylose complexes

Gelb, Robert I.; Schwartz, Lowell M.; Cardelino, Beatriz H.; Fuhrman, Howard S.; Johnson, Robert F.; Laufer, Daniel A.

doi:10.1021/ja00397a027

Cited by 156 publications

(42 citation statements)

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“…Much higher upfield displacements (-3 ppm) have generally been noted for complexes in which the terminal carboxylate group is preferentially bound in the Cd cavity. 19 The maximum upfield shift of the carboxylate anion of NAP induced by @d was -1 ppm, a value very close to that observed in the wd:flurbiprofen system.20 This displacement is probably due to a diminished electronic density around the C-1 carbon atom involved in strong hydrogen bonds.…”

Section: Resultsmentioning

confidence: 64%

Carbon-13 Nuclear Magnetic Resonance Study of Naproxen Interaction with Cyciodextrins in Solution

Bettinetti

Melani

Mura

et al. 1991

Journal of Pharmaceutical Sciences

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Section: Resultsmentioning

confidence: 64%

Carbon-13 Nuclear Magnetic Resonance Study of Naproxen Interaction with Cyciodextrins in Solution

Bettinetti

Melani

Mura

et al. 1991

Journal of Pharmaceutical Sciences

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“…Inclusion complexes involving aromatic compounds have been often characterized by NMR (Bergeron et al 1978;Gelb et al 1981;McAlpine and Garcia-Garibay 1996; McAlpine and Garcia-Garibay1998). The method relies on mutual changes in chemical shifts caused by the guest and the host interaction.…”

Section: Nuclear Magnetic Resonance Assignments and Chemical Shifts Amentioning

confidence: 99%

Investigating the inclusion properties of aromatic amino acids complexing beta-cyclodextrins in model peptides

et al. 2015

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Cyclodextrins are commonly used as complexing agents in biological, pharmaceutical, and industrial applications since they have an effect on protein thermal and proteolytic stability, refolding yields, solubility, and taste masking. β-cyclodextrins (β-CD), because of their cavity size are a perfectly suited complexing agent for many common guest moieties. In the case of peptide-cyclodextrin and protein-cyclodextrin host-guest complexes the aromatic amino acids are reported to be the principal responsible of the interaction. For these reasons, we have investigated the inclusion properties of nine designed tripeptides, obtained permuting the position of two L-alanines (Ala, A) with that of one L-tryptophan (Trp, W), L-phenylalanine (Phe, F), or L-tyrosine (Tyr, Y), respectively. Interestingly, the position of the aromatic side-chain in the sequence appears to modulate the β-CD:peptide binding constants, determined via UV-Vis and NMR spectroscopy, which in turn assumes values higher than those reported for the single amino acid. The tripeptides containing a tyrosine showed the highest binding constants, with the central position in the Ac-AYA-NH2 peptide becoming the most favorite for the interaction. A combined NMR and Molecular Docking approach permitted to build detailed complex models, highlighting the stabilizing interactions of the neighboring amino acids backbone atoms with the upper rim of the β-CD.

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“…The pH of the solutions was adjusted to 7.4 by addition of a few drops of dilute aqueous reagent grade NaOH in order to simulate blood pH. Although cyclodextrins are known to include OH-ions, there is no significant reduction in free cyclodextrin concentrations at such low OH-levels (9). To account for other differences between whole blood and the aqueous glucose solutions (ionic strength, viscosity, etc.)…”

Section: Kcye Kcyementioning

confidence: 99%

Complexation of glucose by α- and β-cyclodextrins

Hirsch¹,

Müller²,

Pizer³

et al. 1995

Can. J. Chem.

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The concentration of glucose in aqueous solutions was monitored, using a blood glucose meter, as small weighed cyclodextrin portions were added. Equilibrium constants for the formation of inclusion complexes were calculated. A binding constant determined by this method has been verified by a technique involving competition of the guest with methyl orange indicator dye. AH' values for the reactions were estimated using calorimetry. These values along with AGO provided estimates of the standard entropies. The values calculated compare favorably with those from a previously determined empirical equation. The possibility of hydrogen bond formation is suggested by the large negative enthalpies as well as by molecular mechanics calculations.Key words: a-, P-cyclodextrin, glucose, binding constants.RCsumC : Utilisant un glucomktre pour le sang, on a mesure la concentration du glucose dans des solutions aqueuses alors qu'on y ajoutait des portions mesurCes de cyclodextrine. On a calculC les constantes d'equilibre pour la formation de complexes d'inclusion. Faisant appel ii une technique impliquant une compCtition de l'h6te pour I'indicateur color6 mCthylorange, on a vCrifiC une constante de fixation dCterminCe par cette methode. On a CvaluC les AH' des ces rkactions en utilisant la calorimktrie. Ces valeurs utilisCes de concert avec des AGO ont fourni des Cvaluations des entropies standard. Les valeurs calculCes se comparent avantageusement avec celles obtenues sur la base d'une equation empirique dCterminCe antkrieurement. La possibilitC de formation de liaison hydrogkne est suggtrCe par les fortes enthalpies nCgatives ainsi que par des calculs de mCcanique molCculaire.

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Binding mechanisms in cyclohexaamylose complexes

Cited by 156 publications

References 0 publications

Carbon-13 Nuclear Magnetic Resonance Study of Naproxen Interaction with Cyciodextrins in Solution

Carbon-13 Nuclear Magnetic Resonance Study of Naproxen Interaction with Cyciodextrins in Solution

Investigating the inclusion properties of aromatic amino acids complexing beta-cyclodextrins in model peptides

Complexation of glucose by α- and β-cyclodextrins

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