Design and Synthesis of Reactive Perylene Tetracarboxylic Diimide Derivatives for Rapid Cell Imaging.

A new water-soluble reactive perylene tetracarboxylic diimide derivative (PDI-pfp) is designed and synthesized that can realize fast imaging of the endoplasmic reticulum in living cells. The PDI-pfp comprises three functional moieties: perylene tetracarboxylic diimide as fluorescent backbone, poly(ethylene glycol) for providing good water disperse ability, and pentafluorophenol active ester as the reactive group under physiological condition. On the basis of covalent reaction between the active ester group of PDI-pfp and amine groups on cytomembrane, PDI-pfp can rapidly interact with cytomembrane, followed by uptake by living MCF-7 cells within 1 min and also exhibit low cell cytotoxicity. Furthermore, it is proved that PDI-pfp acts as a universal imaging agent for other types of cells. This fluorescent probe is of great potential for the application in the rapid imaging of organelles in cells.