Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University of Jena, Humboldtstr 10, 07743 Jena, Germany.
Department of Hematology and Medical Oncology, Jena University Hospital, Am Klinikum 1, 07747 Jena, Germany.
Molecules. 2021 Jul 1;26(13):4026. doi: 10.3390/molecules26134026.
Polysaccharide (PS) based nanoparticles (NP) are of great interest for biomedical applications. A key challenge in this regard is the functionalization of these nanomaterials. The aim of the present work was the development of reactive PS-NP that can be coupled with an amino group containing compounds under mild aqueous conditions. A series of cellulose phenyl carbonates (CPC) and xylan phenyl carbonates (XPC) with variable degrees of substitution (DS) was obtained by homogeneous synthesis. The preparation of PS-NP by self-assembling of these hydrophobic derivatives was studied comprehensively. While CPC mostly formed macroscopic aggregates, XPC formed well-defined spherical NP with diameters around 100 to 200 nm that showed a pronounced long-term stability in water against both particle aggregation as well as cleavage of phenyl carbonate moieties. Using an amino group functionalized dye it was demonstrated that the novel XPC-NP are reactive towards amines. A simple coupling procedure was established that enables direct functionalization of the reactive NP in an aqueous dispersion. Finally, it was demonstrated that dye functionalized XPC-NP are non-cytotoxic and can be employed in advanced biomedical applications.
多糖（PS）基纳米粒子（NP）在生物医学应用中具有重要的意义。在这方面的一个关键挑战是这些纳米材料的功能化。本工作的目的是开发可在温和的水相条件下与含氨基化合物偶联的反应性 PS-NP。通过均相合成得到了一系列具有不同取代度（DS）的纤维素苯碳酸酯（CPC）和木聚糖苯碳酸酯（XPC）。通过这些疏水性衍生物的自组装研究了 PS-NP 的制备。虽然 CPC 主要形成宏观聚集物，但 XPC 形成了直径约为 100 至 200nm 的定义良好的球形 NP，在水中具有明显的长期稳定性，既可以防止颗粒聚集，也可以防止苯碳酸酯部分的断裂。使用氨基功能化染料证明了新型 XPC-NP 对胺具有反应性。建立了一种简单的偶联程序，可在水分散体中直接对反应性 NP 进行功能化。最后，证明了染料功能化的 XPC-NP 无细胞毒性，可用于先进的生物医学应用。
