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

Pharmaceuticals

Xiao Xia Zhu¹  Kendra Sorroza-Martínez²  Israel González-Méndez²  Fabián Cuétara-Guadarrama²  Mireille Vonlanthen²  Ernesto Rivera²  Javier Illescas³ 

[1] Département de Chimie, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montreal, QC H3C 3J7, Canada;Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México City CP 04510, Mexico;Tecnológico Nacional de México/Instituto Tecnológico de Toluca, Avenida Tecnológico S/N Col. Agrícola Bellavista, Metepec CP 52140, Mexico;

关键词: phosphorus dendritic compounds;    β-cyclodextrin;    tumbling process;    host-guest interaction;    1-adamantanecarboxylic acid;   

DOI  :  10.3390/ph14060556

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown