Graduate Institute of Biomedical Engineering, National Chung Hsing University, Taichung, 40227, Taiwan.
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung, 80708, Taiwan.
Chem Asian J. 2021 Nov 2;16(21):3462-3468. doi: 10.1002/asia.202100865. Epub 2021 Sep 14.
The purpose of this study was to develop a colorimetric assay for detecting hydrogen peroxide (H O ) through a combination of using an aryl boronate (AB) derivative and gold nanoparticles (AuNPs). The unique optical property of AuNPs is applied to design a detection probe. The aggregation of AuNPs could be directly observed as a color change by the naked eye. A mannoside-boronate-sulfide (MBS) ligand was designed that contains an arylboronate (AB), a mannoside, and a thiol group. The thiol group bonds covalently with the surface of AuNPs to obtain MBS@AuNPs. The mannoside moiety recognizes concanavalin A (Con A), a lectin with four carbohydrate recognition sites that can specifically recognize the non-reducing end of an α-D-mannoside or α-D-glucoside structure. The AB structure on MBS first reacts with H O and then inserts an oxygen atom in the B-H bond, which triggers intramolecular electron rearrangement to cleave the covalent bond, resulting in a MBSt mixture. The MBS or MBSt is then modified to citrate-coated AuNPs (c-AuNPs) to have MBS@AuNPs or MBSt@AuNPs. When the MBS@AuNPs are incubated with Con A, the Con A recognizes multiple mannosides on the surface of the MBS@AuNPs. Subsequently, the MBS@AuNPs aggregate and the solution's color changes from red to purple, but this color change does not occur in the case of MBSt@AuNPs. The phenomenon can be observed by the naked eye.
本研究旨在开发一种通过芳基硼酸（AB）衍生物和金纳米粒子（AuNPs）结合检测过氧化氢（H2O2）的比色法。AuNPs 的独特光学性质被应用于设计检测探针。AuNPs 的聚集可以通过肉眼直接观察到颜色变化。设计了一种含有芳基硼酸（AB）、甘露糖苷和巯基的甘露糖苷-硼酸-硫醚（MBS）配体。巯基与 AuNPs 表面共价键合，得到 MBS@AuNPs。甘露糖苷部分识别伴刀豆球蛋白 A（Con A），Con A 是一种凝集素，具有四个碳水化合物识别位点，能够特异性识别α-D-甘露糖苷或α-D-葡萄糖苷结构的非还原端。MBS 上的 AB 结构首先与 H2O2 反应，然后在 B-H 键中插入一个氧原子，引发分子内电子重排，使共价键断裂，形成 MBSt 混合物。然后将 MBS 或 MBSt 修饰为柠檬酸涂层的 AuNPs（c-AuNPs），得到 MBS@AuNPs 或 MBSt@AuNPs。当 MBS@AuNPs 与 Con A 孵育时，Con A 识别 MBS@AuNPs 表面上的多个甘露糖苷。随后，MBS@AuNPs 聚集，溶液颜色从红色变为紫色，但在 MBSt@AuNPs 的情况下不会发生这种颜色变化。可以通过肉眼观察到这种现象。
