Host–guest inclusion complexes of α and β-cyclodextrins with α-amino acids

Roy, Mahendra Nath; Ekka, Deepak; Saha, Subhadeep; Roy, Milan Chandra

doi:10.1039/c4ra07877b

Cited by 87 publications

(62 citation statements)

References 12 publications

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“…[16][17] It is observed that γ for aqueous solution of IL show and also surrounded by water molecules. This is also in correlation with the data from density and viscosity measurements, discussing underway, undoubtedly establish that β-CD has the favourable structure for the formation of inclusion complexes with the above selected IL.…”

Section: Surface Tensionmentioning

confidence: 93%

Investigation of an inclusion complex formed by ionic liquid and β-cyclodextrin through hydrophilic and hydrophobic interactions

Roy

2015

RSC Adv.

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Investigation of inclusion behavior of a guest ionic liquid (IL) 1-methyl-3-octylimidazolium tetrafluoroborate into the host cavity of β-cylodextrin in aqueous solution has been studied on modern research gaining far reaching effect. Surface tension and Conductivity measurements results showed that 1:1 hosts-guest inclusion complexes are formed and favourable with the above system. Density, viscosity and refractivity measurements were also employed to study the same. The limiting apparent molar volume, viscosity B-coefficient, and molar refraction data have been used to characterize the solutesolvent interaction between IL and cyclodextrin in the experimental ternary solution systems.

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Section: Surface Tensionmentioning

confidence: 93%

Investigation of an inclusion complex formed by ionic liquid and β-cyclodextrin through hydrophilic and hydrophobic interactions

Roy

2015

RSC Adv.

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“…Aromatic amino acids are reported to be the principal responsible of the interaction and the formation of the host-guest complexes (Loftsson and Brewster 1996). The aim of the present work is to complement the available literature data (Kahle and Holzgrabe 2004;Rekharsky and Inoue 1998;Roy et al 2014) by detailing the interaction of β-CD with different tripeptides designed in such a way that each of them contains a different aromatic amino acid in different position in the chain.…”

Section: Introductionmentioning

confidence: 94%

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 plot also shows that there is a single discernible break in the curve, which not only points out the formation of IC but also indicates the 1:1 stoichiometric ratio for the IC formed ( Figure 7) [34,35]. The value of γ and corresponding concentrations of vitamin and β-CD at break have been listed in Table 1, which also indicate that at break point the concentration ratio of host and guest is about 1:1, establishing the formation of 1:1 IC between the studied vitamin and β-CD [8,36]. …”

Section: Surface Tension Study Elucidates the Inclusion As Well As Stmentioning

confidence: 97%

“…Formation of the host-guest IC is the dimensional suitability between the two species, which is favoured by the unique cyclodextrin molecule that provides an appropriate condition by encapsulating the apolar part of the guest molecule inside the cavity, as well as stabilizing the polar part by the polar rims [36]. The other driving force for the formation of IC is the release of the water molecules from the hydrophobic cavity into the bulk thereby increasing the entropy of the system [1,51].…”

Section: Isothermal Titration Calorimetry: Characterization Of the Comentioning

confidence: 99%

Encapsulation of Vitamin C into β‐Cyclodextrin for Advanced and Regulatory Release

Saha¹,

Roy²

2017

Vitamin C

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Host-guest inclusion complex (IC) of vitamin C with β-cyclodextrin (β-CD) in aqueous medium has been explored by spectroscopic, physicochemical and calorimetric methods as stabilizer, carrier and regulatory releaser. Job plot has been drawn by UV-visible spectroscopy to confirm the 1:1 stoichiometry of the host-guest assembly. Stereo-chemical nature of the inclusion complex has been explained by two-dimensional (2D) NMR spectroscopy. Surface tension and conductivity studies further support the inclusion process. Association constants for the vitamin C-β-CD inclusion complex have been calculated by UV-visible spectroscopy using both Benesi-Hildebrand method and nonlinear programme, while the thermodynamic parameters have been estimated with the help of van't Hoff equation. Isothermal titration calorimetric study has been performed to determine the stoichiometry, association constant and thermodynamic parameters with high accuracy.

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Host–guest inclusion complexes of α and β-cyclodextrins with α-amino acids

Cited by 87 publications

References 12 publications

Investigation of an inclusion complex formed by ionic liquid and β-cyclodextrin through hydrophilic and hydrophobic interactions

Investigation of an inclusion complex formed by ionic liquid and β-cyclodextrin through hydrophilic and hydrophobic interactions

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

Encapsulation of Vitamin C into β‐Cyclodextrin for Advanced and Regulatory Release

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