Dal Bó Alexandre G, Soldi Valdir, Giacomelli Fernando C, Travelet Christophe, Borsali Redouane, Fort Sébastien
Univ. Grenoble Alpes, CERMAV, F-38000 Grenoble, France; CNRS, CERMAV, F-38000 Grenoble, France; Post-Graduate Program of Science and Materials Engineering, Universidade do Extremo Sul Catrinense UNESC, 88806-000 Criciúma, SC, Brazil.
Departamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis, SC, Brazil.
Carbohydr Res. 2014 Oct 9;397:31-6. doi: 10.1016/j.carres.2014.07.021. Epub 2014 Aug 5.
Here we report the preparation and physico-chemical characterization of carbohydrate-decorated micelles and their interaction with lectins. A library of biosourced amphiphiles was prepared by copper-catalyzed azide-alkyne cycloaddition (CuAAC) between alkynyl sugars (lactose, N-acetyl-D-glucosamine) and azido-functionalized poly(ethylene glycol) esters (N3-PEG900-decanoate (C10) and -dodecanoate (C12)). In water, these glycoconjugates self-assemble into micelles of homogeneous nanometric size (11 nm) as evidenced by scattering techniques (DLS for light, and SAXS for X-ray). A comparative study with previously synthesized octadecanoate counterparts pointed out that that nature of the fatty acid has no significant influence on the particle size but only affects their compactness. These findings are in favor of a possible bulk preparation from lipid mixtures such as those encountered in renewable vegetable oils. The presence of the carbohydrate epitopes on the surface of the micelles and their bioavailability for lectin targeting were also evidenced by light scattering measurements using wheat germ agglutinin (WGA) and peanut (Arachis hypogaea) (PNA) lectins, supporting possible application as targeted drug nanocarriers.
在此，我们报告了碳水化合物修饰的胶束的制备、物理化学表征及其与凝集素的相互作用。通过炔基糖（乳糖、N-乙酰-D-葡萄糖胺）与叠氮基官能化的聚乙二醇酯（N3-PEG900-癸酸酯（C10）和-十二酸酯（C12））之间的铜催化叠氮-炔环加成反应（CuAAC），制备了一系列生物源两亲物。在水中，这些糖缀合物自组装成均一纳米尺寸（11纳米）的胶束，散射技术（光散射用动态光散射，X射线用小角X射线散射）证明了这一点。与先前合成的十八烷酸对应物的比较研究指出，脂肪酸的性质对粒径没有显著影响，但仅影响其紧密程度。这些发现有利于从脂质混合物（如可再生植物油中遇到的那些）进行可能的大规模制备。使用麦胚凝集素（WGA）和花生（落花生）（PNA）凝集素的光散射测量也证明了胶束表面碳水化合物表位的存在及其对凝集素靶向的生物利用度，支持了作为靶向药物纳米载体的可能应用。
