A BODIPY-picolinium-cation conjugate as a blue-light-responsive caged group

Caged compounds protected with photolabile protecting groups (PPGs) are useful for controlling various biological events with high spatiotemporal resolution. Most of the commonly used PPGs are controlled by ultraviolet light irradiation, but it is desirable to have PPGs controlled by visible light irradiation in order to minimize tissue damage. Here, we describe a boron-dipyrromethene (BODIPY)-picolinium conjugate (BPc group) that functions as a blue-light-controllable PPG. ESR experiments indicate that the photolysis mechanism is based on intramolecular photoinduced electron transfer. We illustrate the applicability of the BPc group to biologically active compounds by employing it firstly to photocontrol release of histamine, and secondly to photocontrol release of a soluble guanylyl cyclase (sGC) activator, GSK2181236A, which induces photovasodilation. The BPc group is expected to be a useful PPG for controlling various biological events with blue light irradiation. A new blue-light-controlled protecting group based on photoinduced electron transfer has been developed, enabling photo-release of histamine and a vasodilator.

Automated summary

We report a boron-dipyrromethene (BODIPY)-picolinium conjugate (BPc group), which functions as a blue-light-controllable protecting group for controlling the release of biologically active compounds. The BPc group is based on intramolecular photoinduced electron transfer and has been applied to the photocontrol release of histamine and a vasodilator. This new blue-light-controlled protecting group shows promise in controlling various biological events.