Selective Binding of Cyclodextrins with Leflunomide and Its Pharmacologically Active Metabolite Teriflunomide
The selectivity of encapsulation of leflunomide and teriflunomide by native α-, β- and γ-cyclodextrins was investigated through <sup>1</sup>H NMR and molecular modeling. Thermodynamic analysis revealed the main driving forces involved in the binding. For α-cyclodextrin, the partial encap...
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2020-11-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/21/23/9102 |
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doaj-c4ab4616044e417da988d19a940405db2020-12-01T00:01:01ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672020-11-01219102910210.3390/ijms21239102Selective Binding of Cyclodextrins with Leflunomide and Its Pharmacologically Active Metabolite TeriflunomideIrina Terekhova0Iliya Kritskiy1Mikhail Agafonov2Roman Kumeev3Carlos Cortes-Martínez4Horacio Pérez-Sánchez5G.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, RussiaG.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, RussiaG.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, RussiaG.A. Krestov Institute of Solution Chemistry of Russian Academy of Sciences, 153045 Ivanovo, RussiaStructural Bioinformatics and High Performance Computing Research Group (BIO-HPC), Universidad Católica de Murcia (UCAM), 30107 Guadalupe, SpainStructural Bioinformatics and High Performance Computing Research Group (BIO-HPC), Universidad Católica de Murcia (UCAM), 30107 Guadalupe, SpainThe selectivity of encapsulation of leflunomide and teriflunomide by native α-, β- and γ-cyclodextrins was investigated through <sup>1</sup>H NMR and molecular modeling. Thermodynamic analysis revealed the main driving forces involved in the binding. For α-cyclodextrin, the partial encapsulation was obtained while deep penetration was characterized for the other two cyclodextrins, where the remaining polar fragment of the molecule is located outside the macrocyclic cavity. The interactions via hydrogen bonding are responsible for high negative enthalpy and entropy changes accompanying the complexation of cyclodextrins with teriflunomide. These results were in agreement with the molecular modeling calculations, which provide a clearer picture of the involved interactions at the atomic level.https://www.mdpi.com/1422-0067/21/23/9102cyclodextrinleflunomideteriflunomidecomplex formationmolecular modelingselectivity |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Irina Terekhova Iliya Kritskiy Mikhail Agafonov Roman Kumeev Carlos Cortes-Martínez Horacio Pérez-Sánchez |
| spellingShingle |
Irina Terekhova Iliya Kritskiy Mikhail Agafonov Roman Kumeev Carlos Cortes-Martínez Horacio Pérez-Sánchez Selective Binding of Cyclodextrins with Leflunomide and Its Pharmacologically Active Metabolite Teriflunomide International Journal of Molecular Sciences cyclodextrin leflunomide teriflunomide complex formation molecular modeling selectivity |
| author_facet |
Irina Terekhova Iliya Kritskiy Mikhail Agafonov Roman Kumeev Carlos Cortes-Martínez Horacio Pérez-Sánchez |
| author_sort |
Irina Terekhova |
| title |
Selective Binding of Cyclodextrins with Leflunomide and Its Pharmacologically Active Metabolite Teriflunomide |
| title_short |
Selective Binding of Cyclodextrins with Leflunomide and Its Pharmacologically Active Metabolite Teriflunomide |
| title_full |
Selective Binding of Cyclodextrins with Leflunomide and Its Pharmacologically Active Metabolite Teriflunomide |
| title_fullStr |
Selective Binding of Cyclodextrins with Leflunomide and Its Pharmacologically Active Metabolite Teriflunomide |
| title_full_unstemmed |
Selective Binding of Cyclodextrins with Leflunomide and Its Pharmacologically Active Metabolite Teriflunomide |
| title_sort |
selective binding of cyclodextrins with leflunomide and its pharmacologically active metabolite teriflunomide |
| publisher |
MDPI AG |
| series |
International Journal of Molecular Sciences |
| issn |
1661-6596 1422-0067 |
| publishDate |
2020-11-01 |
| description |
The selectivity of encapsulation of leflunomide and teriflunomide by native α-, β- and γ-cyclodextrins was investigated through <sup>1</sup>H NMR and molecular modeling. Thermodynamic analysis revealed the main driving forces involved in the binding. For α-cyclodextrin, the partial encapsulation was obtained while deep penetration was characterized for the other two cyclodextrins, where the remaining polar fragment of the molecule is located outside the macrocyclic cavity. The interactions via hydrogen bonding are responsible for high negative enthalpy and entropy changes accompanying the complexation of cyclodextrins with teriflunomide. These results were in agreement with the molecular modeling calculations, which provide a clearer picture of the involved interactions at the atomic level. |
| topic |
cyclodextrin leflunomide teriflunomide complex formation molecular modeling selectivity |
| url |
https://www.mdpi.com/1422-0067/21/23/9102 |
| work_keys_str_mv |
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