68419-51-2Relevant academic research and scientific papers
Rapid analysis of drug binding to β-cyclodextrin: Part II substituents effect on physicochemical and co-conformational stability of drug/cyclodextrin complex
Dahab, Ali Aboel
, p. 6624 - 6637 (2014)
In the pharmaceutical industry, the most common application of cyclodextrins (CyDs) is to enhance the solubility, stability, safety and bioavailability of drug molecules. Although, there have been many reports on the complexation of drugs with cyclodextrins, to date, CyDs interaction with drugs is not well understood. The purpose of this work is to show the successful applications of previous work employing a novel, versatile, compact, low-volume, routine apparatus, which consists of a pump, flask and a rotating cell holder for the simultaneous measurements of absorbance and circular dichroism (CD) that allows for the concurrent use of four different pathlengths for binding studies. To show the effect of substituents on drug/CyD binding, benzoic acid as an important precursor for the synthesis of many other organic substances and benzoic acid derivatives were used in this study. Also, an effective novel method for binding titration was employed. The pKa, binding constants, stoichiometry and structural co-conformations of benzoic acid and derivatives/β-CyD complexes were elucidated and determined with accuracy. Substituents type and location show a significant effect on the extent of binding and physicochemical properties of the binding complex. The system proved efficiency, ability to be used routinely and the analysis time was reduced significantly to less than one fourth of the total analysis time used in conventional methods, with possible automation for high-throughput analysis.
Complexation of cyclodextrins with benzoic acid in water-organic solvents: A solvation-thermodynamic approach
Alister, Diana A.,Biondi, Marco,Gamov, George A.,Giancola, Concetta,Kabirov, Dzhovidon N.,Kuranova, Natalya N.,Kushnir, Roman A.,Le, Thi My Hanh,Lindt, Dmitry A.,Nguyen, Thi Thu Ha,Panyushkin, Viktor T.,Pham, Thi Lan,Sharnin, Valentin A.,Usacheva, Tatyana R.,Volynkin, Vitaly A.
, (2021)
The aim of this research is to obtain new data about the complexation between β-cyclodextrin (β-CD) and benzoic acid (BA) as a model reaction of the complex formation of hydrophobic molecules with cyclodextrins (CDs) in various media. This research may he
Ultrasonic relaxation associated with inclusion complex of drugs and β-cyclodextrin
Nishikawa, Sadakatsu,Kondo, Minako,Kamimura, Eri,Xing, Shaoyong
, p. 694 - 698 (2007)
The dynamic interactions between β-cyclodextrin (β-CD) (host) and salicylic acid (guest) at pH ≈6 and ≈3 and between β-CD and benzoic acid (guest) at pH ≈6 were investigated in aqueous solutions in terms of ultrasonic absorption in the frequency range fro
Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies
Méndez, Santiago García,Otero Espinar, Francisco J.,Alvarez, Asteria Luzardo,Longhi, Marcela R.,Quevedo, Mario A.,Zoppi, Ariana
, p. 33 - 48 (2016)
β-Cyclodextrin (β-CD) is a well-known host molecule used to prepare inclusion complexes. Considering that the three dimensional array of these complexes depends on the inclusion mode of the guest molecule within the β-CD cavity, the development of methods
Special Features of Formation of Inclusion Complexes ofMono-Substituted β-Cyclodextrin Derivatives
Glushko, V. V.,Grachev, M. K.,Kurochkina, G. I.,Kutyasheva, N. V.
, p. 1070 - 1074 (2021/08/06)
Abstract: In an attempt to obtain inclusion compounds of a series of mono derivatives ofβ-cyclodextrin containing ester and ether bonds with certain aromatic andaliphatic carboxylic acids, unexpected guest-host inclusion compounds have been obtained, presumablydue to the preliminary inclusion of the guestinto the of β-cyclodextrin cavity. Structure and composition of the inclusioncomplexes have been confirmed by 1H and13C NMR spectroscopy. [Figure not available: see fulltext.]
Thermodynamic and nuclear magnetic resonance study of the reactions of α- and β-cyclodextrin with acids, aliphatic amines, and cyclic alcohols
Rekharsky, Mikhail V.,Mayhew, Martin P.,Goldberg, Robert N.,Ross, Philip D.,Yamashoji, Yuko,Inoue, Yoshihisa
, p. 87 - 100 (2007/10/03)
Titration calorimetry was used to determine equilibrium constants and standard molar enthalpy, Gibbs energy, and entropy changes for the reactions of a series of acids, amines, and cyclic alcohols with α- and β-cyclodextrin. The results have been examined in terms of structural features in the ligands such as the number of alkyl groups, the charge number, the presence of a double bond, branching, and the presence of methyl and methoxy groups. The values of thermodynamic quantities, in particular the standard molar Gibbs energy, correlate well with the structural features in the ligands. These structural correlations can be used for the estimation of thermodynamic quantities for related reactions. Enthalpy-entropy compensation is evident when the individual classes of substances studied herein are considered, but does not hold when these various classes of ligands are considered collectively. The NMR results indicate that the mode of accommodation of the acids and amines in the α-cyclodextrin cavity is very similar, but that the 1-methyl groups in 1-methylhexylamine and in 1-methylheptylamine and the N-methyl group in N-methylhexylamine lie outside the α-cyclodextrin cavity. This latter finding is consistent with the calorimetric results. Many of the thermodynamic and NMR results can be qualitatively understood in terms of van der Waals forces and hydrophobic effects.
