Elucidation of the mechanism of complexation between oncocalyxone A and cyclodextrins by isothermal titration calorimetry and molecular modeling

Xavier, Francisco Humberto; Tavares, C.T.; Rabello, Marcelo Montenegro; Hernandes, Marcelo Zaldini; Bezerra, Beatriz Pinheiro; Ayala, A. P.; Pessoa, Otília Deusdênia Loiola; Ximenes, Rafael Matos; Santos-Magalhães, Nereide Stela

doi:10.1016/j.molliq.2018.10.129

Cited by 20 publications

(18 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…To determine stability constants and thermodynamic parameters, a number of techniques are used [6,7], including UV-Vis [8][9][10] and fluorescence [8,9,11] spectroscopy, conductometry [12,13], isothermal calorimetry [14][15][16][17], phase solubility study with UV-Vis spectroscopy [14,18,19] or high-performance liquid chromatography [20], potentiometry [21], capillary electrophoresis [22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39], and other techniques. Capillary electrophoresis (CE) has advantages such as rapidity, high selectivity, a small value of samples, and low-cost of analysis.…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic parameters for the complexation of water-soluble betulin derivatives with (2-hydroxypropyl)-β-cyclodextrin determined by affinity capillary electrophoresis

Sursyakova

Levdansky

Rubaylo

2019

Journal of Molecular Liquids

View full text Add to dashboard Cite

The interaction between (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD) and water-soluble betulin derivatives, betulin 3,28-disulfate (DSB) and betulin 3-acetate-28-sulfate (ASB), belonging to the class of pentacyclic lupane triterpenoids, was studied using affinity capillary electrophoresis. It was found that 1:1 and 1:2 complexes were formed. The stability constants of the complexes in the temperature range of 293.15-318.15 K were determined. The values obtained are sufficiently large; log K (1:1) and log K (1:2) are 4.25-5.02 and 6.08-7.59, respectively. This phenomenon can be explained by the presence of broad hydrophobic regions in the molecules of the compound studied. The stability constants decrease with increasing temperature. The stability constants for ASB complexes are slightly higher as compared to the constants for DSB complexes. The thermodynamic parameters for the complexation were calculated from the van't Hoff plots. The complexation was found to be controlled by the enthalpy change. The obtained values of stability constants at 298 K were compared with values for the β-CD complexes of the compounds under study and for the HP-β-CD an d β-CD complexes of water-insoluble betulin derivatives. It was found that water-soluble betulin derivatives form more stable complexes with CDs as compared to water-insoluble derivatives (betulonic and betulinic acids), and the HP-β-CD complexes are more stable than the β-CD complexes.

show abstract

Section: Introductionmentioning

confidence: 99%

Thermodynamic parameters for the complexation of water-soluble betulin derivatives with (2-hydroxypropyl)-β-cyclodextrin determined by affinity capillary electrophoresis

Sursyakova

Levdansky

Rubaylo

2019

Journal of Molecular Liquids

View full text Add to dashboard Cite

show abstract

“…The hydrophobic predominant interactions have been described also for the inclusion complex of HP-β-CD and other CDs with oncocalyxone A (onco A) [28]. Onco A is a natural product, a quinone isolated from Auxemma oncocalyx tree of northeast Brazil and endowed with many biological activities [29].…”

Section: Hp-β-cd Interaction With Nutraceuticals/natural Productsmentioning

confidence: 99%

Thermodynamic properties of hydroxypropyl-β-cyclodextrin/guest interaction: a survey of recent studies

D’Aria

Pagano

Giancola

2021

J Therm Anal Calorim

View full text Add to dashboard Cite

For many years, cyclodextrins (CDs) have been the object of attention for their capability of improving the stability, solubility and bioavailability of numerous molecules of interest, including drugs and nutraceuticals. They have low toxicity and for this reason have been employed for different routes of administration, including oral, ocular, nasal and parenteral. Among them, the hydroxypropyl-β-cyclodextrin (HP-β-CD) is the least toxic. Several physicochemical methodologies have been employed for studying cyclodextrin/guest interaction, but isothermal titration calorimetry (ITC) is the only one capable of simultaneously providing the binding constant, ΔH°, ΔS°, ΔG° and the binding stoichiometry. Here, we present the state of the art of ITC studies applied to HP-β-CD/guest complexes, discussing selected publications of the last five years, highlighting the thermodynamic factors that are decisive for optimal encapsulation.

show abstract

“…Within this context, diverse analytical methods have been applied to identify the thermodynamic profile of CD-drug complexation reaction, e.g., 1 H-NMR, differential scanning calorimetry (DSC), UV spectroscopy, fluorimetry, isothermal titration calorimetry (ITC), and molecular modeling (15,16). Among these, ITC has been extensively used for the development of a complete and precise thermodynamic profile of many binding interactions, including the binding between CDs and various lipophilic drugs, where the binding energy was large enough to be measured (17)(18)(19). However, the potential of the ITC to analyze less stable binding interaction with low binding energies, e.g., CDs and watersoluble compounds, is yet to be evaluated.…”

Section: Introductionmentioning

confidence: 99%

“…Among these, ITC has been extensively used for the development of a complete and precise thermodynamic profile of many binding interactions, including the binding between CDs and various lipophilic drugs, where the binding energy was large enough to be measured ( 17 – 19 ). However, the potential of the ITC to analyze less stable binding interaction with low binding energies, e.g., CDs and water-soluble compounds, is yet to be evaluated.…”

Section: Introductionmentioning

confidence: 99%

“…Moreover, the curves produced by ITC are sometimes rather complex and cannot be easily interpreted ( 20 ). Therefore, the combination of ITC experimental techniques with theoretical perspectives, e.g., molecular modeling, is helpful to interpret ITC complex curves and for developing a three-dimensional illustration of the most stable inclusion complexes ( 19 ).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Cyclodextrin Complex Formation with Water-Soluble Drugs: Conclusions from Isothermal Titration Calorimetry and Molecular Modeling

2021

View full text Add to dashboard Cite

Cyclodextrin (CD) complexes are frequently used for enhancing the solubility or absorption of poorly water-soluble drugs. On the contrary, little is known about their complex formation with water-soluble drugs. Here, we have studied the interaction between 2-hydroxypropyl β-CD (HPβCD) and three water-soluble drugs, namely naloxone (NX), oxycodone (OC), and tramadol (TR), by isothermal titration calorimetry (ITC) combined with molecular modeling in view of the potential impact on drug release. The results showed that the complex formation of HPβCD with all three drugs occurs spontaneously. The complexes formed with NX and OC were found to be 2NX:1HPβCD and 3OC:2HPβCD, respectively. TR was found to form 2 complexes with HPβCD; of 1:2 and 1:1 complexation ratios. The binding of HPβCD to NX was greater than to OC due to the higher hydrophobicity of the structure of the former. Moreover, the binding affinity of HPβCD to TR was higher than to OC, which indicated the effect of the higher flexibility of the guest in increasing the binding affinity. In vitro drug release experiments from the various complexes revealed a significant impact of the stoichiometry of the complex on the release profiles. Accordingly, the co-administration of cyclodextrins with water-soluble drugs should be closely monitored, as it may result in unintentional complex formation that can potentially impact the drugs’ gastrointestinal absorption.

show abstract

Elucidation of the mechanism of complexation between oncocalyxone A and cyclodextrins by isothermal titration calorimetry and molecular modeling

Cited by 20 publications

References 36 publications

Thermodynamic parameters for the complexation of water-soluble betulin derivatives with (2-hydroxypropyl)-β-cyclodextrin determined by affinity capillary electrophoresis

Thermodynamic parameters for the complexation of water-soluble betulin derivatives with (2-hydroxypropyl)-β-cyclodextrin determined by affinity capillary electrophoresis

Thermodynamic properties of hydroxypropyl-β-cyclodextrin/guest interaction: a survey of recent studies

Cyclodextrin Complex Formation with Water-Soluble Drugs: Conclusions from Isothermal Titration Calorimetry and Molecular Modeling

Contact Info

Product

Resources

About