Inclusion complexes of ibuprofen and β-cyclodextrin: Supramolecular structure and stability

Pereva, Stiliyana; Nikolova, Valya; Sarafska, Tsveta; Angelova, Silvia; Spassov, Тony; Dudev, Todor

doi:10.1016/j.molstruc.2019.127575

Cited by 24 publications

(23 citation statements)

References 18 publications

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“…[ 50,51 ] However, it was recently possible to model successfully several inclusion complexes of βCD with ibuprofen using density functional theory (DFT) calculations. [ 52 ] The authors were able to select the preferable complexation mode, which was in good agreement with experimental 2D‐ROESY spectra.…”

Section: Introductionsupporting

confidence: 75%

Interaction of 5‐fluorouracil with β‐cyclodextrin: A density functional theory study with dispersion correction

Buczek

Staś

Hebenstreit

et al. 2020

Int J of Quantum Chemistry

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Detailed studies on the stability, interaction, and microstructure of host‐guest complexes in the vacuum of 5‐fluorouracil (5FU) with β‐cyclodextrin (βCD) were performed using B3LYP with the inclusion of Grimme's dispersion correction GD3 term and 6‐31+G(d,p) basis set. Among several studied 1:1 5FU‐βCD complexes, the one placing the keto tautomer of 5FU vertically in the host cavity and forming N‐H···OCD and CO···HOCD hydrogen bonds with hydroxyl groups of the smaller rim of βCD has the highest stability (Eint = −195 kJ/mol). Interestingly, there are no interactions with the inner hydrophobic part of the βCD host cavity. The strength of the intermolecular H‐bonds to the smaller rim of βCD is comparable to those in 5FU‐water and 5FU‐methanol clusters, used as model systems characterizing the noncovalent interactions. Of several studied host‐guest complexes, the inner ones are more stable than the outer systems. Our results reveal that taking dispersion interaction in DFT into account is essential for reliable modeling of the structure, interaction, and stability of 5FU‐βCD complexes. This study is crucial for understanding the interaction of 5FU with βCD in the solid state and additionally suggests the presence of equilibrium between 5FU‐βCD complex and solvated 5FU.

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Section: Introductionsupporting

confidence: 75%

Interaction of 5‐fluorouracil with β‐cyclodextrin: A density functional theory study with dispersion correction

Buczek

Staś

Hebenstreit

et al. 2020

Int J of Quantum Chemistry

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“…of theoretical and experimental NMR (2D-ROESY) studies. The theoretical calculations show that the less polar part of the ibuprofen is inserted into the cyclodextrin cavity, their results also show stability of the formed complex even if the polarity of the solvents used is changed [10].…”

Section: Pereva Et Al Studied Ibuprofen Inclusion In β Cyclodextrin By a Combinationmentioning

confidence: 96%

Gold Nanoparticles Incorporated with Cyclodextrins and Its Applications

Abdulaziz¹,

Salah²

2021

JBNB

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“…Host-guest systems have attracted much attention from researchers for decades, due to their wide range of applications in pharmacy, analytical chemistry, food, cosmetics, agriculture, textiles, etc. [1][2][3] The most frequently used strategy for investigating host-guest systems is to combine experiments with molecular simulations. [1][2][3][4] Recently, there has been a surge in pure theoretical studies that have provided new insights into the binding mode and interaction mechanism of host-guest systems.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3] The most frequently used strategy for investigating host-guest systems is to combine experiments with molecular simulations. [1][2][3][4] Recently, there has been a surge in pure theoretical studies that have provided new insights into the binding mode and interaction mechanism of host-guest systems. [5][6][7][8][9][10][11][12][13][14][15][16] b-Cyclodextrin (b-CD) is one of the most common and significant host molecules and is internally hydrophobic and externally hydrophilic, and is often used to encapsulate guest molecules containing a phenyl group.…”

Section: Introductionmentioning

confidence: 99%

How areN-methylcarbamates encapsulated by β-cyclodextrin: insight into the binding mechanism

Bao

Liu

Dou

et al. 2023

Phys. Chem. Chem. Phys.

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Inclusion complexes of ibuprofen and β-cyclodextrin: Supramolecular structure and stability

Cited by 24 publications

References 18 publications

Interaction of 5‐fluorouracil with β‐cyclodextrin: A density functional theory study with dispersion correction

Interaction of 5‐fluorouracil with β‐cyclodextrin: A density functional theory study with dispersion correction

Gold Nanoparticles Incorporated with Cyclodextrins and Its Applications

How areN-methylcarbamates encapsulated by β-cyclodextrin: insight into the binding mechanism

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