Structural Studies for Specific Binding Capacity of β‐Cyclodextrin with Ibuprofen

Liu, Wei; Zhang, Yong; Zhao, Bing

doi:10.1002/jccs.201200071

Cited by 3 publications

(3 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A formation constant of 9558 M −1 and an inclusion enthalpy of −3326 cal·mol −1 have been obtained by this global approach, which lead to high accuracy (±129 M −1 and ±13 cal·mol −1 for K β-CD-IBU and Δ H β-CD-IBU , respectively) owing to the high amount of experimental information. The stability is in agreement with the range of affinity (7000–14000 M −1 ) found in most published studies [ 22 – 27 ], even if some extreme values have also been observed [ 28 – 29 ]. The specificities of each individual experiment are described in the following.…”

Section: Resultssupporting

confidence: 91%

Improving ITC studies of cyclodextrin inclusion compounds by global analysis of conventional and non-conventional experiments

Bertaut¹,

Landy²

2014

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryThe study of 1:1 cyclodextrin inclusion compounds by isothermal titration calorimetry was explored in a theoretical and experimental point of view to compare the efficiency of conventional and non-conventional experiments. All direct and competitive protocols were described and evaluated in terms of accuracy on both binding constant and inclusion enthalpy. Significant improvement in the calorimetric characterization may be obtained by means of the global analysis of non-conventional experiments coupled to the standard titration protocol. While the titration-release approach proved to be the most accurate strategy for classical complexations, the valuable contribution of other non-conventional experiments was demonstrated for issues concerning weak stability, enthalpy, or solubility.

show abstract

Section: Resultssupporting

confidence: 91%

Improving ITC studies of cyclodextrin inclusion compounds by global analysis of conventional and non-conventional experiments

Bertaut¹,

Landy²

2014

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…The association constant of IBR/β-CD complex falls in the range of 10 3 –10 4 M −1 [47–48], while that of MB/β-CD is less than 10 3 M −1 [49–50]. According to NMR studies IBR is deeply included into the cavity [51], while MB is too large to be completely shielded by complexation. The too strong association between IBR and the cavities of CMBCD-P can be a possible reason of protection instead of catalytic decomposition in this process.…”

Section: Resultsmentioning

confidence: 99%

Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

Agócs¹,

Puskás²,

Varga³

et al. 2016

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

Advanced oxidation processes (AOPs) are considered highly competitive water treatment technologies for the removal of organic pollutants. Among AOP techniques, photocatalysis has recently been the most widely studied. Our aims were to investigate how the dispersion of nanosized titanium dioxide (nanoTiO2) applied in photodegradation-based procedures can be stabilized with cyclodextrins in order to obtain a new, more efficient photocatalyst for the purification of waters polluted by xenobiotics applying UV irradiation. During our work, on the one hand, we studied the behavior and stability of nanoTiO2 in cyclodextrin solutions. On the other hand, we used various monomer and polymer cyclodextrin derivatives, and assessed the options for nanoTiO2 stabilization in the presence of various salts and tap water on the basis of turbidity tests. The physical stability of nanoTiO2 dispersions is diminished in the presence of the salts found in tap water (and occurring also in surface waters and ground water) and they are precipitated immediately. This colloidal instability can be improved by cyclodextrin derivatives. Based on the results of our studies we have selected carboxymethyl β-cyclodextrin polymer (CMBCD-P) for stabilization of nanoTiO2 dispersions. The photocatalytic degradation of methylene blue and ibuprofen as model organic pollutants in various media (distilled water, NaCl solution and tap water) has been studied using nanoTiO2 as catalyst stabilized by CMBCD-P. CMBCD-P itself showed a catalytic effect on the UV degradation of methylene blue. In addition to enhancing the colloid stability of nanoTiO2 CMBCD-P showed also synergistic effects in catalyzing the photodecomposition process of the dye. On the other hand, ibuprofen as a model pharmaceutical, a pollutant of emerging concern (EP), was protected by CMBCD-P against the photocatalytic degradation showing that inclusion complex formation can result in opposite effects depending on the structure of the host–guest complex.

show abstract

“…The binding mode of the interactions between the guest molecules and CDs depends on the dimensions of the organic compound and CD cavity, as well as their nature, ionization state, etc. The advantage of CDs (oligomers of α-D-glucopyranose) as chiral selectors is based on their ability to form diastereomeric inclusion complexes with enantiomeric pairs due to the intrinsic chirality [10,11].…”

Section: Introductionmentioning

confidence: 99%

Chiral Recognition R- and RS- of New Antifungal: Complexation/Solubilization/Dissolution Thermodynamics and Permeability Assay

et al. 2022

View full text Add to dashboard Cite

Novel potential antifungal of 1,2,4-triazole class have been synthesized as pure enantiomer (R-98) and racemic (RS-186). The effect of 2-hydroxypropyl-β-cyclodextrin (CD) on the solubility and permeability of RS-186 and R-98 in terms of chiral recognition was investigated. Phase solubility studies were carried out at 4 temperatures in 0–0.05 M CD concentration range for pH 2.0 and pH 7.4. AL- and AL−-type phase-solubility profiles were obtained for both compounds in pH 2.0 and pH 7.4. The racemic formed more stable complexes with CD as compared to R-isomer. Disclosing of chiral discrimination was facilitated using the approach based on the complex consideration of the derived complexation/solubilization/inherent dissolution thermodynamic functions, including the differential parameters between the racemic compound and R-enantiomer. The differences in the thermodynamic parameters determined by the chirality were discussed in terms of the driving forces of the processes and the main interactions of the compounds with CD in solution. The membrane permeability of both samples in the presence of CD was accessed in order to evaluate the specificity of enantioselective transport through the lipophilic membrane. The solubility/permeability interrelation was disclosed. The investigated compounds were classified as medium permeable in pure buffers and low permeable in the presence of 0.01 M CD. The obtained results can be useful for the design of pharmaceutical products in the form of liquid formulations based on the investigated substances.

show abstract

Structural Studies for Specific Binding Capacity of β‐Cyclodextrin with Ibuprofen

Cited by 3 publications

References 15 publications

Improving ITC studies of cyclodextrin inclusion compounds by global analysis of conventional and non-conventional experiments

Improving ITC studies of cyclodextrin inclusion compounds by global analysis of conventional and non-conventional experiments

Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

Chiral Recognition R- and RS- of New Antifungal: Complexation/Solubilization/Dissolution Thermodynamics and Permeability Assay

Contact Info

Product

Resources

About