How to conduct and interpret ITC experiments accurately for cyclodextrin–guest interactions

Bouchemal, Kawthar; Mazzaferro, Silvia

doi:10.1016/j.drudis.2012.01.023

Cited by 94 publications

(63 citation statements)

References 65 publications

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“…This is in accordance with the fact that b-CD is cyclic oligosaccharides composed of seven D-(+)-glucopyranose units linked by a- (1-4) bonds. The hydroxyl group on the ring extends from the top to bottom of the cylinder, producing sites for strong hydrogen bonding [42,43]. While MTM clay is found in the form of irregular aggregates of primary stacks consisting of multiple layers of aluminosilicate sheets with individual platelets, its fundamental units are comprised of two tetrahedral sheets sandwiched with edge-shared octahedral sheet [10] and the geometry of SiO 4 tetrahedrons on the surface of the aluminosilicates is conducive to cooperative hydrogen bonding [36].…”

Section: Self-assembling Mechanism Of the B-cd Modified Mtm Nanosheetsmentioning

confidence: 99%

Dendrimer-like assemblies based on organoclays as multi-host system for sustained drug delivery

Li¹,

Sun²,

Pan³

et al. 2014

European Journal of Pharmaceutics and Biopharmaceutics

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Section: Self-assembling Mechanism Of the B-cd Modified Mtm Nanosheetsmentioning

confidence: 99%

Dendrimer-like assemblies based on organoclays as multi-host system for sustained drug delivery

Li¹,

Sun²,

Pan³

et al. 2014

European Journal of Pharmaceutics and Biopharmaceutics

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“…Molecular binding affinity is a straightforward characterizer of recognition and can be obtained experimentally by enthalpimetry such as calorimetry. 1,2 However, it is difficult to measure the binding entropy directly from experiments, and it is impossible to measure separate entropy contributions from the solvent and solute. Recent studies have revealed the importance of kinetic properties 3–5 and showed that drug efficacy is sometimes correlated with the kinetic properties better than binding affinity.…”

Section: Introductionmentioning

confidence: 99%

Binding Thermodynamics and Kinetics Calculations Using Chemical Host and Guest: A Comprehensive Picture of Molecular Recognition

Tang

Chang

2017

J. Chem. Theory Comput.

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Understanding the fine balance between changes of entropy and enthalpy and the competition between a guest and water molecules in molecular binding is crucial in fundamental studies and practical applications. Experiments provide measurements. However, illustrating the binding/unbinding processes gives a complete picture of molecular recognition not directly available from experiments, and computational methods bridge the gaps. Here, we investigated guest association/dissociation with β-cyclodextrin (β-CD) by using microsecond-time-scale molecular dynamics (MD) simulations, postanalysis and numerical calculations. We computed association and dissociation rate constants, enthalpy, and solvent and solute entropy of binding. All the computed values of kon, koff, ΔH, ΔS, and ΔG using GAFF-CD and q4MD-CD force fields for β-CD could be compared with experimental data directly and agreed reasonably with experiment findings. In addition, our study further interprets experiments. Both force fields resulted in similar computed ΔG from independently computed kinetics rates, ΔG = −RT ln(kon·C0/koff), and thermodynamics properties, ΔG = ΔH − TΔS. The water entropy calculations show that the entropy gain of desolvating water molecules are a major driving force, and both force fields have the same strength of nonpolar attractions between solutes and β-CD as well. Water molecules play a crucial role in guest binding to β-CD. However, collective water/β-CD motions could contribute to different computed kon and ΔH values by different force fields, mainly because the parameters of β-CD provide different motions of β-CD, hydrogen-bond networks of water molecules in the cavity of free β-CD, and strength of desolvation penalty. As a result, q4MD-CD suggests that guest binding is mostly driven by enthalpy, while GAFF-CD shows that gaining entropy is the major driving force of binding. The study deepens our understanding of ligand–receptor recognition and suggests strategies for force field parametrization for accurately modeling molecular systems.

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“…CDs are rigid, cone shaped with a semipolar interior cavity 24,25 and have the unique ability to form stable inclusion complexes with a variety of molecules in which guest molecules are included in the hydrophobic cavities of the CDs through 'host-guest' complexation in aqueous solution. 32 It is used for the determination of thermodynamic parameters of host-guest complexation, particularly that of weak interactions with great success. Among the three natural CDs, b-CD is the most widely used one for this purpose as its cavity size is suitable for common drug molecules with molar masses in the range 200 to 800 g mol À1 .…”

Section: Introductionmentioning

confidence: 99%

Physicochemical properties of inclusion complexes of sanguinarine with natural cyclodextrins: spectroscopy, calorimetry and NMR studies

Hazra

Kumar

2015

RSC Adv.

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The supramolecular interactions for the formation of inclusion complexes of sanguinarine with a-, b-, and g-cyclodextrins (CDs) were studied by UV-vis absorbance, fluorescence, circular dichroism and proton nuclear magnetic resonance spectroscopy, and isothermal titration calorimetry. The results revealed that sanguinarine binds with the three natural CDs in 1 : 1 stoichiometry. The binding affinity followed the order b > a > g-CDs; the affinity to b-CD was the highest compared to the other two CDs apparently due to the perfect cavity size for the inclusion of sanguinarine into the b-CD cavity. The association of sanguinarine with a-, and b-CDs is synergistically driven by a greater entropy contribution to the Gibbs energy of the association, whereas it was favoured by both enthalpy and entropy contributions for the g-CD. The NMR study indicated that encapsulation of sanguinarine in a-, and b-CDs, involves partial inclusion and to g-CD it is non-specific and complete inclusion i.e., both ends of sanguinarine, can be included into the CD cavity.

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How to conduct and interpret ITC experiments accurately for cyclodextrin–guest interactions

Cited by 94 publications

References 65 publications

Dendrimer-like assemblies based on organoclays as multi-host system for sustained drug delivery

Dendrimer-like assemblies based on organoclays as multi-host system for sustained drug delivery

Binding Thermodynamics and Kinetics Calculations Using Chemical Host and Guest: A Comprehensive Picture of Molecular Recognition

Physicochemical properties of inclusion complexes of sanguinarine with natural cyclodextrins: spectroscopy, calorimetry and NMR studies

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