Guest-Mediated Reversal of the Tumbling Process in Phosphorus-Dendritic Compounds Containing β-Cyclodextrin Units: An NMR Study
| Autor: | Javier Illescas, Fabián Cuétara-Guadarrama, Israel González-Méndez, X. X. Zhu, Mireille Vonlanthen, Kendra Sorroza-Martínez, Ernesto Rivera |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
phosphorus dendritic compounds
Pharmaceutical Science chemistry.chemical_element 010402 general chemistry 01 natural sciences Article Pharmacy and materia medica host-guest interaction Dendritic Compounds Drug Discovery Spectroscopy chemistry.chemical_classification Aqueous solution Cyclodextrin 010405 organic chemistry Phosphorus Limiting 0104 chemical sciences 1-adamantanecarboxylic acid RS1-441 Crystallography tumbling process chemistry β-cyclodextrin Molecular Medicine Medicine Titration Two-dimensional nuclear magnetic resonance spectroscopy |
| Zdroj: | Pharmaceuticals Volume 14 Issue 6 Pharmaceuticals, Vol 14, Iss 556, p 556 (2021) |
| ISSN: | 1424-8247 |
| DOI: | 10.3390/ph14060556 |
| Popis: | The conformational study of dendritic platforms containing multiple β-cyclodextrin (βCD) units in the periphery is relevant to determine the availability of βCD cavities for the formation of inclusion complexes in aqueous biological systems. In this work, we performed a detailed conformational analysis in D2O, via 1D and 2D NMR spectroscopy of a novel class of phosphorus dendritic compounds of the type P3N3-[O-C6H4-O-(CH2)n-βCD]6 (where n = 3 or 4). We unambiguously demonstrated that a functionalized glucopyranose unit of at least one βCD unit undergoes a 360° tumbling process, resulting in a deep inclusion of the spacer that binds the cyclodextrin to the phosphorus core inside the cavity, consequently limiting the availability of the inner cavities. In addition, we confirmed through NMR titrations that this tumbling phenomenon can be reversed for all βCD host units using a high-affinity guest, namely 1-adamantanecarboxylic acid (AdCOOH). Our findings have demonstrated that it is possible to create a wide variety of multi-functional dendritic platforms. |
| Databáze: | OpenAIRE |
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