Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Mexico City, 04510, Mexico.
Facultad de Química, Departamento de Fisicoquímica, Universidad Nacional Autónoma de México, Mexico City, 04510, Mexico.
Carbohydr Polym. 2018 Mar 15;184:20-29. doi: 10.1016/j.carbpol.2017.12.049. Epub 2017 Dec 20.
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 = 29636.17 M. 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.
尽管环糊精化学取得了进展，但合成具有确定取代度的单分散衍生物仍然是一个挑战。在这项工作中，我们展示了一种通过结合β-CD 和第二代聚酯树枝状大分子制备的新型树枝状材料。通过 CuAAC 点击反应选择性地将树枝状大分子连接到β-CD-伯面的七个位置上，该反应与非常简单的后处理相结合，可获得非常高产率的单分散材料。该产物具有出色的水溶性和体外无毒特性。通过与阿苯达唑形成包合物证明了产物的增强的络合潜力，其络合常数为 29636.17 M。在该体系中，与阿苯达唑-天然β-CD 复合物相比，阿苯达唑的水溶性提高了 45 倍。所有这些特性使得树枝状材料非常有吸引力，可进一步应用于制剂和药物输送领域。
