Institute of Physical Chemistry, University of Hamburg , Grindelallee 117, 20146 Hamburg, Germany.
Langmuir. 2013 Oct 8;29(40):12593-600. doi: 10.1021/la402826f. Epub 2013 Sep 26.
Herein, we present a strategy for the glycoconjugation of nanoparticles (NPs), with a special focus on fluorescent quantum dots (QDs), recently described by us as "preassembly" approach. Therein, prior to the encapsulation of diverse nanoparticles by an amphiphilic poly(isoprene)-b-poly(ethylene glycol) diblock copolymer (PI-b-PEG), the terminal PEG appendage was modified by covalently attaching a carbohydrate moiety using Huisgen-type click-chemistry. Successful functionalization was proven by NMR spectroscopy. The terminally glycoconjugated polymers were subsequently used for the encapsulation of QDs in a phase transfer process, which fully preserved fluorescence properties. Binding of these nanoconstructs to the lectin Concanavalin A (Con A) was studied via surface plasmon resonance (SPR). Depending on the carbohydrate moiety, namely, D-manno-heptulose, D-glucose, D-galactose, 2-deoxy-2-{[methylamino)carbonyl]amino}-D-glucopyranose ("des(nitroso)-streptozotocin"), or D-maltose, the glycoconjugated QDs showed enhanced affinity constants due to multivalent binding effects. None of the constructs showed toxicity from 0.001 to 1 μM (particle concentration) using standard WST and LDH assays on A549 cells.
在此，我们提出了一种纳米粒子（NPs）糖基化的策略，特别关注我们最近描述的“预组装”方法的荧光量子点（QDs）。在此方法中，在通过两亲性聚异戊二烯-b-聚乙二醇二嵌段共聚物（PI-b-PEG）将各种纳米粒子封装之前，通过使用Huisgen 型点击化学将末端 PEG 侧链通过共价键连接修饰碳水化合物部分。通过 NMR 光谱证明了成功的功能化。随后，将末端糖基化聚合物用于在相转移过程中封装 QD，该过程完全保留了荧光特性。通过表面等离子体共振（SPR）研究了这些纳米结构与凝集素伴刀豆球蛋白 A（Con A）的结合。根据碳水化合物部分，即 D-甘露庚酮糖、D-葡萄糖、D-半乳糖、2-脱氧-2-[[甲基氨基）羰基]氨基]-D-吡喃葡萄糖（“去（亚硝基）-链脲佐菌素”）或 D-麦芽糖，由于多价结合效应，糖基化的 QD 显示出增强的亲和常数。在使用 A549 细胞的标准 WST 和 LDH 测定法中，从 0.001 到 1 μM（颗粒浓度）的浓度范围内，没有一种构建物显示出毒性。
