Shi Wen-Jing, Lo Pui-Chi, Zhao Shirui, Wong Roy C H, Wang Qiong, Fong Wing-Ping, Ng Dennis K P
Department of Chemistry, The Chinese University of Hong Kong, Shatin, N.T., Hong Kong, China.
Dalton Trans. 2016 Nov 28;45(44):17798-17806. doi: 10.1039/c6dt03141b. Epub 2016 Oct 24.
An efficient ferrocenyl BODIPY based dark quencher has been developed and employed to construct a FRET-based fluorescent probe that contains a biotin moiety as a potential directing ligand for cancer cells and a glutathione-cleavable disulfide linker connecting the quencher and a distyryl BODIPY fluorophore. This molecular probe is deactivated in the native form through FRET followed by intramolecular charge transfer due to the ferrocenyl unit. However, upon interaction with glutathione in phosphate buffered saline and inside cancer cells, the fluorescence emission is significantly increased due to detachment of the fluorophore from the quencher. As shown by flow cytometry, this probe also exhibits preferential uptake by the biotin-receptor-expressing A549 human lung adenocarcinoma epithelial cells over the Chinese hamster ovary CHO-K1 cells used as the negative control. On the basis that both biotin receptor and GSH level are often overexpressed or elevated in cancer cells, this dual functional fluorescent probe serves as a promising agent for cancer imaging.
一种基于二茂铁基BODIPY的高效暗猝灭剂已被开发出来，并用于构建一种基于荧光共振能量转移（FRET）的荧光探针。该探针含有生物素部分作为癌细胞的潜在导向配体，以及一个可被谷胱甘肽裂解的二硫键连接子，用于连接猝灭剂和二苯乙烯基BODIPY荧光团。这种分子探针在天然形式下通过FRET失活，随后由于二茂铁单元发生分子内电荷转移。然而，在磷酸盐缓冲盐溶液中以及癌细胞内与谷胱甘肽相互作用时，由于荧光团与猝灭剂分离，荧光发射显著增加。流式细胞术结果表明，与用作阴性对照的中国仓鼠卵巢CHO-K1细胞相比，该探针在表达生物素受体的A549人肺腺癌上皮细胞中表现出优先摄取。基于生物素受体和谷胱甘肽水平在癌细胞中通常过表达或升高，这种双功能荧光探针有望成为一种癌症成像剂。
