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Article

Guest-Mediated Reversal of the Tumbling Process in Phosphorus-Dendritic Compounds Containing β-Cyclodextrin Units: An NMR Study

1
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México City CP 04510, Mexico
2
Tecnológico Nacional de México/Instituto Tecnológico de Toluca, Avenida Tecnológico S/N Col. Agrícola Bellavista, Metepec CP 52140, Mexico
3
Département de Chimie, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montreal, QC H3C 3J7, Canada
*
Authors to whom correspondence should be addressed.
Academic Editors: Laura Catenacci, Milena Sorrenti and Maria Cristina Bonferoni
Pharmaceuticals 2021, 14(6), 556; https://0-doi-org.brum.beds.ac.uk/10.3390/ph14060556
Received: 21 May 2021 / Revised: 1 June 2021 / Accepted: 1 June 2021 / Published: 11 June 2021
(This article belongs to the Special Issue New Frontiers in Cyclodextrin Technologies)
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. View Full-Text
Keywords: phosphorus dendritic compounds; β-cyclodextrin; tumbling process; host-guest interaction; 1-adamantanecarboxylic acid phosphorus dendritic compounds; β-cyclodextrin; tumbling process; host-guest interaction; 1-adamantanecarboxylic acid
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MDPI and ACS Style

Sorroza-Martínez, K.; González-Méndez, I.; Vonlanthen, M.; Cuétara-Guadarrama, F.; Illescas, J.; Zhu, X.X.; Rivera, E. Guest-Mediated Reversal of the Tumbling Process in Phosphorus-Dendritic Compounds Containing β-Cyclodextrin Units: An NMR Study. Pharmaceuticals 2021, 14, 556. https://0-doi-org.brum.beds.ac.uk/10.3390/ph14060556

AMA Style

Sorroza-Martínez K, González-Méndez I, Vonlanthen M, Cuétara-Guadarrama F, Illescas J, Zhu XX, Rivera E. Guest-Mediated Reversal of the Tumbling Process in Phosphorus-Dendritic Compounds Containing β-Cyclodextrin Units: An NMR Study. Pharmaceuticals. 2021; 14(6):556. https://0-doi-org.brum.beds.ac.uk/10.3390/ph14060556

Chicago/Turabian Style

Sorroza-Martínez, Kendra, Israel González-Méndez, Mireille Vonlanthen, Fabián Cuétara-Guadarrama, Javier Illescas, Xiao X. Zhu, and Ernesto Rivera. 2021. "Guest-Mediated Reversal of the Tumbling Process in Phosphorus-Dendritic Compounds Containing β-Cyclodextrin Units: An NMR Study" Pharmaceuticals 14, no. 6: 556. https://0-doi-org.brum.beds.ac.uk/10.3390/ph14060556

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