Boron dipyrromethene as a fluorescent caging group for single-photon uncaging with long-wavelength visible light

Nobuhiro Umeda, Hironori Takahashi, Mako Kamiya, Tasuku Ueno, Toru Komatsu, Takuya Terai, Kenjiro Hanaoka, Tetsuo Nagano, Yasuteru Urano

Research output: Contribution to journalArticlepeer-review

60 Citations (Scopus)

Abstract

Caged compounds are useful tools for precise spatiotemporal modulation of cell functions, but in most cases uncaging requires ultraviolet (UV) light, which is cytotoxic and has limited tissue penetration. Therefore, caged compounds that can be activated by longer-wavelength light are required. Here we describe a novel photoelimination reaction of 4-aryloxy boron dipyrromethene (BODIPY) derivatives and show that BODIPY can function as a caging group for phenol groups. We developed a novel BODIPY-caged histamine compound, which is photoactivatable with blue-green visible light to stimulate cultured HeLa cells in a spatiotemporally well-controlled manner. This caging strategy is expected to be widely applicable to develop tools for probing various cellular functions. (Chemical Equation Presented).

Original languageEnglish
Pages (from-to)2242-2246
Number of pages5
JournalACS chemical biology
Volume9
Issue number10
DOIs
Publication statusPublished - 2014 Oct 17
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine

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