Mitochondrial Specific H2S n Fluorogenic Probe for Live Cell Imaging by Rational Utilization of a Dual-Functional-Photocage Group

ACS Sens. 2018 Sep 28;3(9):1622-1626. doi: 10.1021/acssensors.8b00456. Epub 2018 Aug 30.

Abstract

Reactive sulfur species play a very important role in modulating neural signal transmission. Hydrogen polysulfides (H2S n, n > 1) are recently suggested to be the actual signaling molecules. There are still few spatiotemporal controllable-based probes to detect H2S n. In this work, for the first time, we proposed the photocleavage product of the common photoremovable protecting group (2-nitrophenyl moiety) capable of trapping H2S n. Taking advantage of this, we constructed the probe H1 containing a photocontrollable group, a mitochondrial directing unit and a signal reporter fluorescein dye. H1 exhibited excellent fluorescence enhancement (50-fold) in response to H2S n under the aqueous buffer only after UV irradiation. H1 also showed high selectivity and sensitivity for H2S n over other reactive sulfur species, reactive oxygen species, and other analytes, especially biothoils including hydrogen sulfide, cysteine, homocysteine, and glutathione. We showed the utility of H1 to image H2S n in living cells with high spatiotemporal resolution.

Keywords: fluorogenic probe; hydrogen polysulfide; light control; live cell imaging; mitochondria; photocontrollable group.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Fluoresceins / chemical synthesis
  • Fluoresceins / chemistry
  • Fluoresceins / radiation effects
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / radiation effects
  • Hep G2 Cells
  • Humans
  • Limit of Detection
  • Microscopy, Confocal / methods
  • Microscopy, Fluorescence / methods
  • Mitochondria / metabolism*
  • Nitrobenzoates / chemical synthesis
  • Nitrobenzoates / chemistry
  • Nitrobenzoates / radiation effects
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Organophosphorus Compounds / radiation effects
  • Sulfides / analysis*
  • Sulfides / metabolism
  • Ultraviolet Rays

Substances

  • Fluoresceins
  • Fluorescent Dyes
  • Nitrobenzoates
  • Organophosphorus Compounds
  • Sulfides
  • polysulfide