A Novel BODIPY Quaternary Ammonium Salt-Based Fluorescent Probe: Synthesis, Physical Properties, and Live-Cell Imaging

Abstract

The development of biological fluorescent probes is of great significance to the field of cancer bio-imaging. However, most current probes within the bulky hydrophobic group have limited application in aqueous medium and restricted imaging under physiological conditions. Herein, we proposed two efficient molecules to study their physical properties and imaging work, and the absorption and fluorescence intensity were collected with varying ions attending in aqueous medium. We enhance the water solubility through the quaternization reaction and form a balance between hydrophilic and hydrophobicity with dipyrrome-theneboron difluoride (BODIPY) fluorophore. We introduced pyridine and dimethylaminopyridine (DMAP) by quaternization and connected the BODIPY fluorophore by ethylenediamine. The final synthesized probes have achieved ideal affinity with HeLa cells (human cervical carcinoma cell line) in live-cell imaging which could be observed by Confocal Microscope. The probes also have a good affinity with subcutaneous tumor cells in mice in in vivo imaging, which may make them candidates as oncology imaging probes.

A chemical probe inhibitor targeting STAT1 restricts cancer stem cell traits and angiogenesis in colorectal cancer

“…Among these molecules, BODIPY has been considered fluorescent molecule used in applications ranging from fundamental biological research to clinical diagnostics and theranostics over the past decade due to its excellent photostable and photophysical properties as well as its relative insensitivity in the physiological pH range [ 66 ]. In particular, the properties of BODIPYs can be easily turned by chemical modification on the dipyrromethene core, providing a versatile platform for further functionalization of all aspects of desirable photophysical and theranostic properties [ 67 ]. In this study, we first designed and synthesized the chemical probe inhibitor BODIPY-THIF to target STAT1.…”

Bodipy-carbohydrate systems: synthesis and bio-applications

“…Among the various important characteristics that a good small fluorescent probe must possess, the solubility is one indispensable requirement for its application in the biological field. 38,39 Therefore, the lipophilic skeleton of BODIPY, that guarantees a certain cellular membrane permeability, has been opportunely modified with hydrophilic functionalities, such as carboxylic acid 40 or ammonium group, 41 or grafted to water-soluble carbohydrates 42 or polyethylene glycol, 43 or further linked to targeting groups, to penetrate the cellular membrane and visualize biomolecules in the cytosol and in specific organelles of cells. 44 In particular, the conjugation of a carbohydrate moiety to the BODIPY significantly improves the selectivity of the imaging probe towards a specific biological target.…”

A fluorescently labelled quaternary ammonium compound (NBD-DDA) to study mode-of-action and resistance mechanisms in bacteria

“…This is in accordance with the assumption that the cell membrane is the primary target of BAC 2,3 . Thus, NBD-DDA could be leveraged in live cell imaging applications of mammalian and bacterial cells to label cell membranes 21 .…”