Inclusion Complexes of Naringenin in Dimethylated and Permethylated β-Cyclodextrins: Crystal Structures and Molecular Dynamics Studies
Abstract
:1. Introduction
2. Results
2.1. Crystal Structures Description
2.1.1. Naringenin/DM-β-CD Inclusion Complex
2.1.2. Naringenin/TM-β-CD Inclusion Complex
2.2. Molecular Dynamics Studies
3. Materials and Methods
3.1. X-ray Crystallography
3.1.1. Sample Preparation
3.1.2. Data Collection and Reduction
3.1.3. Crystal Structure Determination
3.1.4. Crystallographic Analysis and Coordinates Deposition
3.2. Molecular Dynamics
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Naringenin/DM-β-CD | Naringenin/TM-β-CD | |
---|---|---|
Enthalpic Term | ||
ΔEvdW | −33.50 ± 2.77 | −23.40 ± 4.63 |
ΔEele | −8.07 ± 2.46 | −13.09 ± 3.25 |
ΔEGB | 21.95 ± 2.11 | 24.58 ± 3.24 |
ΔEsurf | −3.31 ± 0.16 | −2.79 ± 0.29 |
ΔGgas | −41.58 ± 3.9 | −36.49 ± 6.02 |
ΔGsolv | 18.64 ± 2.07 | 21.79 ± 3.18 |
a ΔG(GB) | −22.93 ± 2.75 | −14.69 ± 3.94 |
Entropic Term | ||
(TΔS) | −18.19 ± 1.16 | −17.69 ± 1.71 |
Binding Energy | ||
b (ΔGbind) | −4.74 ± 2.98 | 3.0 ± 4.29 |
Crystal Data | Naringenin/DM-β-CD | Naringenin/TM-β-CD |
---|---|---|
Chemical formula | C56H98O35·C15H12O5·4.6(H2O) | C63H112O35·C15H12O5 |
Mr | 1687 | 1701.76 |
Crystal system, space group | Orthorhombic, P212121 | Monoclinic, P21 |
Temperature (K) | 100(2) | 100(2) |
Unit cell parameters a, b, c (Å) | 15.531(1), 17.810(1), 30.149(2) | 15.758(3), 12.913(2), 22.273(3) β = 109.936 (1) (°) |
V (Å3) | 8340.1 (10) | 4260.6 (13) |
Z | 4 | 2 |
Radiation type | Cu Ka | Cu Ka |
μ (mm−1) | 0.96 | 0.90 |
Crystal size (mm3) | 0.5 × 0.1 × 0.1 | 0.45 × 0.3 × 0.2 |
Data collection | ||
Diffractometer | Bruker APEX-II | Bruker APEX-II |
Absorption correction | Multi-scan SADABS2014/5—Bruker AXS area detector scaling and absorption correction | Multi-scan SADABS2014/5 - Bruker AXS area detector scaling and absorption correction |
Tmin, Tmax | 0.583, 0.752 | 0.496, 0.753 |
No. of measured, independent, and observed [I > 2σ(I)] reflections | 65,321, 11,718, 10,457 | 65,916, 15,008, 14,866 |
Rint | 0.056 | 0.046 |
(sin θ/λ)max (Å-1) | 0.556 | 0.596 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.127, 1.05 | 0.043, 0.110, 1.06 |
No. of reflections | 11,718 | 15,008 |
No. of parameters | 959 | 1050 |
No. of restraints | 80 | 147 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.51, −0.43 | 0.38, −0.35 |
Absolute structure | Flack x determined using 4169 quotients [(I+) − (I−)]/[(I+) + (I−)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249–259). | Flack x determined using 6895 quotients [(I+) − (I−)]/[(I+) + (I−)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249–259). |
Absolute structure parameter | −0.04 (6) | 0.07 (3) |
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Papaioannou, A.; Christoforides, E.; Bethanis, K. Inclusion Complexes of Naringenin in Dimethylated and Permethylated β-Cyclodextrins: Crystal Structures and Molecular Dynamics Studies. Crystals 2020, 10, 10. https://doi.org/10.3390/cryst10010010
Papaioannou A, Christoforides E, Bethanis K. Inclusion Complexes of Naringenin in Dimethylated and Permethylated β-Cyclodextrins: Crystal Structures and Molecular Dynamics Studies. Crystals. 2020; 10(1):10. https://doi.org/10.3390/cryst10010010
Chicago/Turabian StylePapaioannou, Andreas, Elias Christoforides, and Kostas Bethanis. 2020. "Inclusion Complexes of Naringenin in Dimethylated and Permethylated β-Cyclodextrins: Crystal Structures and Molecular Dynamics Studies" Crystals 10, no. 1: 10. https://doi.org/10.3390/cryst10010010