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

Dnyaneshwar Kand, Lorena Pizarro, Inbar Angel, Adi Avni, Dinorah Friedmann-Morvinski, Roy Weinstain*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)4659-4663
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number14
DOIs
StatePublished - 26 Mar 2019

Keywords

  • BODIPY
  • mitochondria
  • organelles
  • photo-release
  • photocages

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