文献：

FITC-labeled D-glucose analog is suitable as a probe for detecting insulin dependent glucose uptake

文献链接：

https://pubmed.ncbi.nlm.nih.gov/30293953/#:~:text=The%20detection%20of%20the%20insulin-dependent%20glucose%20uptake%20is,by%20the%20reaction%20of%20commercially%20available%20

作者：

Lin Sua , Rui Wua , Xinrou Chen, Wei Hou, Benfang Helen Ruan

原文摘要：

The detection of the insulin-dependent glucose uptake is a vital part in the research of diabetes. To establish a sensitive assay for measuring glucose uptake in living cells, we synthesized a FITC linked D-glucosamine 2 as a probe. 2 was obtained by the reaction of commercially available D-glucosamine hydrochloride and FITC and was determined as a single anomeric form by 1 H NMR and 13C NMR. 2 exhibited good water solubility and stability. An uptake assay in HepG2 cells with or without insulin demonstrated that FITC showed strong cellular uptake, whereas uptake of 2 is much less but is insulin dependent. This suggests that 2 is specifically transported into cells through a receptor that is regulated by insulin and has potential application in screening of compounds or genes that regulate the insulin-dependence in cell-based assays.

荧光素及其衍生物是一类具有高消光系数和水中光致发光量子效率的荧光染料。其具有良好的生物相容性，使其作为敏感的荧光探针被应用于生物医学研究。荧光素异硫氰酸酯（FITC）引入了一种官能团，在温和的条件下容易与氨基反应，因C-6位置的修饰会抑制葡萄糖的磷酸化，C-2位置的修饰则不会抑制葡萄糖的磷酸化。因此，合成化合物FITC-葡萄糖衍生物作为检测葡萄糖摄取的荧光探针。

图：FITC-葡萄糖衍生物

基于该荧光探针，以FITC和盐酸葡萄糖胺作为起始材料，选择了DMF作为反应溶剂。当FITC而C-2位置被和D-Glucosamine Hydrochloride以1： 1.2和1.2的比例反应时，化合物FITC-葡萄糖衍生物的分离收率为36%。将FITC和D-Glucosamine Hydrochloride的比率逆转为1.2： 1后，产量略有提高。条件总结为：FITC和D-Glucosamine Hydrochloride=1.2：1。

图：FITC和d-葡萄糖胺盐酸盐反应获得FITC 连接的 d-葡萄糖胺

结论：d-葡萄糖胺探针几乎不溶于二氯甲烷、乙酸乙酯等疏水溶剂，且在DMSO、DMF、MeOH等亲水溶剂中具有良好的溶解度。重要的是，它在水中的溶解度高达150 μg/mL，表现出良好的水溶性和稳定性。