First Class of Phosphorus Dendritic Compounds Containing β-Cyclodextrin Units in the Periphery Prepared by CuAAC

Kendra Sorroza-Martínez (1) , Israel González-Méndez (1) , Mireille Vonlanthen (1) , Kathleen Moineau-Chane Ching (2) , Anne-Marie Caminade (2) , Javier Illescas (3) , Ernesto Rivera (1)

1 Instituto de Investigaciones en Materiales (Mexico, Mexico)
2 LCC - Laboratoire de chimie de coordination
3 TecNM - Tecnológico Nacional de México

A new class of phosphorus dendritic compounds (PDCs) having a cyclotriphosphazene (P 3 N 3) core and decorated with six β-cyclodextrin (βCD) units, named P 3 N 3-[O-C 6 H 4-O-(CH 2) n-βCD] 6 , where n = 3 or 4 was designed, and the synthesis was performed using copper (I) catalyzed alkyne-azide cycloaddition (CuAAC). To obtain the complete substitution of the P 3 N 3 , two linkers consisting of an aromatic ring and an aliphatic chain of two different lengths were assessed. We found that, with both linkers, the total modification of the periphery was achieved. The two new obtained dendritic compounds presented a considerably high water solubility (>1 g/mL). The compounds comprised in this new class of PDCs are potential drug carrier candidates, since the conjugation of the βCD units to the P 3 N 3 core through the primary face will not only serve as surface cover but, also, provide them the faculty to encapsulate various drugs inside the βCDs cavities.

Mots clés: Phosphorus dendritic compounds; β-cyclodextrin; CuAAC reaction

Domaines: Chimie de coordination

Kendra Sorroza-Martínez, Israel González-Méndez, Mireille Vonlanthen, Kathleen Moineau-Chane Ching, Anne-Marie Caminade, et al.. First Class of Phosphorus Dendritic Compounds Containing β-Cyclodextrin Units in the Periphery Prepared by CuAAC. Molecules, 2020, 25 (18), pp.4034. ⟨10.3390/molecules25184034⟩. ⟨hal-02930049⟩