Organic and Polymer Synthesis Laboratory, Department of Chemistry, National Institute of Technology, Tiruchirappalli - 620 015, India.
Org Biomol Chem. 2019 Apr 3;17(14):3538-3544. doi: 10.1039/c9ob00143c.
Fluorescence imaging is a dynamic tool for monitoring the functions of biomolecules in living systems. Probes with emission in the far-red to near-infrared range have been found to demonstrate great application prospects in bioimaging due to their deep tissue penetration, low background fluorescence, minimum photodamage to the tissue and high sensitivity. The present study aimed to construct a far-red to near-infrared emitting probe (PI) bearing dicyanoisophorone coupled with a phenothiazine moiety. The probe exhibits an instant response towards HOCl with a colour change from red to yellow with a 100 fold fluorescence enhancement at 620 nm with a low detection limit (42 nM). The electron-rich sulfur atom can be oxidised by HOCl; this endows the probe with distinct selectivity over other anions as well as other reactive oxygen species. The probe demonstrates great cell permeability with low toxicity to the cell. Therefore, the probe can be effectively applied in biological systems to monitor the endogenous level of HOCl produced by PMA in living systems and in the fluorescence imaging of endogenous HOCl in zebrafish and the RAW 264.7 cell line.
荧光成像是一种用于监测生物分子在活系统中功能的动态工具。发远红到近红外光的探针由于其具有深组织穿透性、低背景荧光、对组织最小的光损伤和高灵敏度，已被发现具有巨大的生物成像应用前景。本研究旨在构建一种带有二氰异戊烯基偶联吩噻嗪部分的远红到近红外发射探针 (PI)。该探针对 HOCl 具有即时响应，颜色从红色变为黄色，在 620nm 处荧光增强 100 倍，检测限低至 42 nM。富电子的硫原子可被 HOCl 氧化；这使探针对其他阴离子以及其他活性氧物种具有明显的选择性。该探针具有良好的细胞通透性，对细胞的毒性低。因此，该探针可有效应用于生物系统，以监测活系统中 PMA 产生的内源性 HOCl 的水平，并对斑马鱼和 RAW 264.7 细胞系中的内源性 HOCl 进行荧光成像。
