Thermodynamic Studies of Interactions between Sertraline Hydrochloride and Randomly Methylated β-Cyclodextrin Molecules Supported by Circular Dichroism Spectroscopy and Molecular Docking Results
Abstract
:1. Introduction
2. Results and Discussion
2.1. Isothermal Titration Calorimetry (ITC)
2.2. Circular Dichroism Spectroscopy (CD)
2.3. Molecular Docking (MD)
3. Materials and Methods
3.1. Materials
3.2. Methods
3.2.1. Isothermal Titration Calorimetry (ITC)
- the aqueous solution of the cyclodextrin was added into the pure water placed in the measurement cell and
- the aqueous solution of sertraline hydrochloride was diluted with water injected from the syringe and the heat of the dilution for both stages were registered.
3.2.2. Circular Dichroism (CD) Spectroscopy
3.2.3. Computational Studies
Ligands and Macromolecules Preparation for Molecular Docking
Molecular Docking
- -
- entry from Figure 7 (three molecules of βCD I-II-III): a grid box size of 20 Å × 20 Å × 20 Å centered on the C47 atom (x = −5.017, y = 1.413, z = 0.074);
- -
- entry A from Figure 8 (two molecules of βCD I-II): a grid box size of 20 Å × 20 Å × 20 Å centered on the C45 atom (x = 5.849, y = 3.007, z = −5.646);
- -
- entry B from Figure 8 (two molecules of βCD II-III): a grid box size of 20 Å × 20 Å × 20 Å centered on the C23 atom (x = 4.807, y = 1.076, z = 7.878);
- -
- entry A from Figure 9 (one molecule of βCD I): a grid box size of 20 Å × 20 Å × 20 Å centered on the C45 atom (x = 5.849, y = 3.007, z = −5.646);
- -
- entry B from Figure 9 (one molecule of βCD II): a grid box size of 20 Å × 20 Å × 20 Å centered on the C43 atom (x = 5.243, y = 0.841, z = 1.262);
- -
- entry C from Figure 9 (one molecule of βCD III): a grid box size of 20 Å × 20 Å × 20 Å centered on the C43 atom (x = 4.602, y = −1.221, z = 8.714);
- -
- entry from Figure 10 (two molecules of TMβCD I-II): a grid box size of 20 Å × 20 Å × 20 Å centered on the C11 atom (x = 3.352, y = 6.710, z = 2.402);
- -
- entry A from Figure 11 (two molecules of TMβCD I): a grid box size of 20 Å × 20 Å × 20 Å centered on the C11 atom (x = 3.352, y = 6.710, z = 2.402);
- -
- entry B from Figure 11 (one molecule of TMβCD II): a grid box size of 20 Å × 20 Å × 20 Å centered on the C10 atom (x = 6.775, y = 12.684, z = 10.278);
- -
- entry from Figure 12 (one molecule of RMβCD): a grid box size of 20 Å × 20 Å × 20 Å centered on the C45 atom (x = 2.967, y = 2.155, z = −4.366);
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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n | K/M−1 | ΔH/kJ·mol−1 | TΔS/kJ·mol−1 | ΔG/kJ·mol−1 | |
---|---|---|---|---|---|
β-CD a,b | 1.20 a 1.31 b | 5820 a 4999.3 | −20.44 a −15.6 b | 1.06 a 5.5 b | −21.53 a −21.1 b |
HPβCD c | 1.23 | 6530 | −16.72 | 5.05 | −21.77 |
DMβCD a | 1.60 | 7960 | −14.20 | 7.96 | −22.19 |
RMβCD * | 1.26 ± 0.05 | 4520 ± 74 | −8.37 ± 0.07 | 12.49 ± 0.04 | −20.86 ± 0.11 |
n | K/M−1 | ΔCDmax/mdeg | Reduced χ2 | R2 |
---|---|---|---|---|
1.57 ± 0.11 | 5315 ± 500 | 6.14 ± 0.05 | 0.00197 | 0.99976 |
Representative Geometry | Crystal Structure Name (Refcode from CSD) | Free Energy of Binding kcal∙mol−1 (kJ∙mol−1) |
---|---|---|
Figure 7 | 648855 | −9.2 (−38) |
(three molecules of βCD I-II-III) | ||
A | 648855 | −8.6 (−36) |
Figure 8 | (two molecules of βCD I-II) | |
B | 648855 | −8.0 (−33) |
Figure 8 | (two molecules of βCD II-III) | |
A | 648855 | −5.7 (−24) |
Figure 9 | (one molecule of βCD I) | |
B | 648855 | −5.7 (−24) |
Figure 9 | (one molecule of βCD II) | |
C | 648855 | −6.0 (−25) |
Figure 9 | (one molecule of βCD III) | |
ALIGAE | −7.4 (−31) | |
Figure 10 | (two molecules of TMβCD I-II) | |
A | ALIGAE | −6.5 (−27) |
Figure 11 | (one molecule of TMβCD I) | |
B | ALIGAE | −5.8 (−24) |
Figure 11 | (one molecule of TMβCD II) | |
JOSWOD | −6.3 (−26) | |
Figure 12 | (one molecule of RMβCD) |
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Belica-Pacha, S.; Daśko, M.; Buko, V.; Zavodnik, I.; Miłowska, K.; Bryszewska, M. Thermodynamic Studies of Interactions between Sertraline Hydrochloride and Randomly Methylated β-Cyclodextrin Molecules Supported by Circular Dichroism Spectroscopy and Molecular Docking Results. Int. J. Mol. Sci. 2021, 22, 12357. https://doi.org/10.3390/ijms222212357
Belica-Pacha S, Daśko M, Buko V, Zavodnik I, Miłowska K, Bryszewska M. Thermodynamic Studies of Interactions between Sertraline Hydrochloride and Randomly Methylated β-Cyclodextrin Molecules Supported by Circular Dichroism Spectroscopy and Molecular Docking Results. International Journal of Molecular Sciences. 2021; 22(22):12357. https://doi.org/10.3390/ijms222212357
Chicago/Turabian StyleBelica-Pacha, Sylwia, Mateusz Daśko, Vyacheslav Buko, Ilya Zavodnik, Katarzyna Miłowska, and Maria Bryszewska. 2021. "Thermodynamic Studies of Interactions between Sertraline Hydrochloride and Randomly Methylated β-Cyclodextrin Molecules Supported by Circular Dichroism Spectroscopy and Molecular Docking Results" International Journal of Molecular Sciences 22, no. 22: 12357. https://doi.org/10.3390/ijms222212357