BODIPY‐Based Nanomicelles as Near‐Infrared Fluorescent “Turn‐On” Sensors for Biogenic Thiols

Abstract We report novel, aqueous, soluble, distyryl boron dipyrromethene (BODIPY)‐containing nanomicelles as biogenic thiol sensors with near‐infrared (NIR) “turn‐on” properties. The average hydrodynamic diameter of these nanomicelles is 30 nm. They show good photostability, are selective towards biogenic thiols, and function within a broad pH window (pH 3–10). Near‐infrared‐emitting distyryl‐BODIPY was chemically linked to fluorescence quencher group of 2,4‐dinitrobenzenesulfonyl (DNBS) and was then water solubilized and formed into nanomicelles via polylactic acid‐polyethylene glycol (PLA‐PEG) encapsulation. When thiols react with the DNBS moiety, we observe subsequent recovery of distyryl‐BODIPY fluorescence both in vitro and in living cells. This work provides a simple and general method to construct intracellular nanoprobes for biogenic thiols and may pave the way to the development other fluorescence‐dye‐based sensors.