Synthesis of a poly(ester) dendritic β-cyclodextrin derivative by "click" chemistry: Combining the best of two worlds for complexation enhancement.

Autor: López-Méndez LJ; Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Mexico City, 04510, Mexico. Electronic address: udgwid_l@hotmail.com., González-Méndez I; Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Mexico City, 04510, Mexico. Electronic address: israel__025@hotmail.com., Aguayo-Ortiz R; Facultad de Química, Departamento de Fisicoquímica, Universidad Nacional Autónoma de México, Mexico City, 04510, Mexico. Electronic address: rodaguayo@comunidad.unam.mx., Dominguez L; Facultad de Química, Departamento de Fisicoquímica, Universidad Nacional Autónoma de México, Mexico City, 04510, Mexico. Electronic address: lauraok@gmail.com., Alcaraz-Estrada SL; División de Medicina Genómica, Centro Médico Nacional '20 de Noviembre'-ISSSTE, Mexico City, 03100, Mexico. Electronic address: sofializeth@gmail.com., Rojas-Aguirre Y; Facultad de Química, Departamento de Farmacia, Universidad Nacional Autónoma de México, Mexico City, 04510, Mexico. Electronic address: yareli.rojas@iim.unam.mx., Guadarrama P; Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Mexico City, 04510, Mexico. Electronic address: patriciagua@iim.unam.mx.
Jazyk: angličtina
Zdroj: Carbohydrate polymers [Carbohydr Polym] 2018 Mar 15; Vol. 184, pp. 20-29. Date of Electronic Publication: 2017 Dec 20.
DOI: 10.1016/j.carbpol.2017.12.049
Abstrakt: In spite of the progress in the cyclodextrins chemistry, the synthesis of monodisperse derivatives with a defined degree of substitution is still a challenge. In this work we present a novel dendritic material produced by combining βCD and second generation poly(ester) dendrons. The selective attachment of dendrons in the seven positions of the βCD-primary face was performed through a CuAAC click reaction, which along with a very simple work-up, allowed obtaining the monodisperse material in very high yields. The product showed a great aqueous solubility and an in vitro non-toxic profile. The enhanced complexation potential of the product was evidenced through the formation of an inclusion complex with albendazole, which presented a K c  = 29636.17 M -1 . In this system, albendazole was 45 times more water-soluble in comparison to the complex albendazole-native βCD. All these features make the dendritic material very attractive for further applications in the formulation and drug delivery fields.
(Copyright © 2017 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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