Organelle‐Targeted BODIPY Photocages: Visible‐Light‐Mediated Subcellular Photorelease

Abstract

Photocaging facilitates non‐invasive and precise spatio‐temporal control over the release of biologically relevant small‐ and macro‐molecules using light. However, sub‐cellular organelles are dispersed in cells in a manner that renders selective light‐irradiation of a complete organelle impractical. Organelle‐specific photocages could provide a powerful method for releasing bioactive molecules in sub‐cellular locations. Herein, we report a general post‐synthetic method for the chemical functionalization and further conjugation of meso ‐methyl BODIPY photocages and the synthesis of endoplasmic reticulum (ER)‐, lysosome‐, and mitochondria‐targeted derivatives. We also demonstrate that 2,4‐dinitrophenol, a mitochondrial uncoupler, and puromycin, a protein biosynthesis inhibitor, can be selectively photoreleased in mitochondria and ER, respectively, in live cells by using visible light. Additionally, photocaging is shown to lead to higher efficacy of the released molecules, probably owing to a localized and abrupt release.

Photoresponsive molecular tools for emerging applications of light in medicine

“…The authors showed that by adding triphenylphosphonium to the BODIPY high accumulation was found in the mitochondria. 107 Besides structural changes to help improve the solubility, another important point to keep in mind during the design of a photoswitchable bioactive system is that both isomers need to be soluble in aqueous solutions to prevent aggregation, 108 which can lead to results that are difficult to interpret and highly depend on the type of medium, its ionic strength, co-solvents added, etc. However, change in solubility can also be taken advantage of.…”

A facile way to obtain near-infrared room-temperature phosphorescent soft materials based on Bodipy dyes

“…Boron dipyrromethene (Bodipy) has long been a widely used chromophore with a large molar absorption coefficient, high uorescence quantum yield and good photostability. [39][40][41][42] Since traditional Bodipy dyes generally suffer from small Stokes shi which restricts their applications in biomedical areas because of the disturbance of background uorescence, it would be promising to study the phosphorescence emission of Bodipy dyes with larger Stokes shi. In the last few years, the heavy atom effect has been utilized to promote the intersystem crossing (ISC) efficiency of Bodipy by enhancing spin-orbital coupling and NIR RTP has been achieved at low temperature.…”

Light‐Activated Carbon Monoxide Prodrugs Based on Bipyridyl Dicarbonyl Ruthenium(II) Complexes

“…In this way, it could be shown that [Ru(CO) 3 Cl(glycinate)] (CORM‐3) was efficiently taken up by the cells and CO was released. Very recently it has been shown that a relatively simple modification of the BODIPY framework leads to organelle‐specific targeting . However, the processes that determine the targeting are not well understood.…”