4.5 Article

A red-emitting naphthofluorescein-based fluorescent probe for selective detection of hydrogen peroxide in living cells

Journal

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 18, Issue 22, Pages 5948-5950

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2008.08.035

Keywords

Fluorescent probe; Hydrogen peroxide; Naphthofluorescein; Flow cytometry; Near infrared

Funding

  1. Beckman, Packard, and Sloan Foundations
  2. NIH [GM 79465, T32 GM066698]
  3. ACS Organic Division
  4. UC Berkeley
  5. Stauffer fellowship

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We report the synthesis, properties, and cellular application of Naphtho-Peroxyfluor-1 (NPF1), a new fluorescent indicator for hydrogen peroxide based on a red-emitting naphthofluorescein platform. Owing to its boronate cages, NPF1 features high selectivity for hydrogen peroxide over a panel of biologically relevant reactive oxygen species (ROS), including superoxide and nitric oxide, as well as excitation and emission profiles in the far-red region of the visible spectrum (>600 nm). Flow cytometry experiments in RAW264.7 macrophages establish that NPF1 can report changes in peroxide levels in living cells. (C) 2008 Elsevier Ltd. All rights reserved.

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