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PMID: 16305254 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't

Boronate-based fluorescent probes for imaging cellular hydrogen peroxide.

Journal of the American Chemical Society ·Vol. 127 ·No. 47 ·2005-11-30 ·Pages 16652-9

Miller EW, Albers AE, Pralle A, Isacoff EY, Chang CJ

Abstract

The syntheses, properties, and biological applications of the Peroxysensor family, a new class of fluorescent probes for hydrogen peroxide, are presented. These reagents utilize a boronate deprotection mechanism to provide high selectivity and optical dynamic range for detecting H2O2 in aqueous solution over similar reactive oxygen species (ROS) including superoxide, nitric oxide, tert-butyl hydroperoxide, hypochlorite, singlet oxygen, ozone, and hydroxyl radical. Peroxyresorufin-1 (PR1), Peroxyfluor-1 (PF1), and Peroxyxanthone-1 (PX1) are first-generation probes that respond to H2O2 by an increase in red, green, and blue fluorescence, respectively. The boronate dyes are cell-permeable and can detect micromolar changes in H2O2 concentrations in living cells, including hippocampal neurons, using confocal microscopy and two-photon microscopy. The unique combination of ROS selectivity, membrane permeability, and a range of available excitation/emission colors establishes the potential value of PR1, PF1, PX1, and related probes for interrogating the physiology and pathology of cellular H2O2.

MeSH Terms
Boron Compounds/chemistry Cell Line Cells/chemistry Fluorescent Dyes/chemical synthesis,chemistry Hydrogen Peroxide/analysis,chemistry,metabolism Microscopy, Confocal Microscopy, Fluorescence Molecular Structure Photons Solutions/chemistry Water/chemistry
Chemicals
Boron Compounds Fluorescent Dyes Solutions Water Hydrogen Peroxide
Authors & Affiliations
5 authors, click to expand affiliations / ORCID
Miller Evan W
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Albers Aaron E
Pralle Arnd
Isacoff Ehud Y
Chang Christopher J
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Article Info
Journal
Journal of the American Chemical Society
Abbr.
J Am Chem Soc
ISSN
0002-7863
DOI
10.1021/ja054474f
Published
2005-11-30
Pages
16652-9
Language
English
Region
United States
NLM ID
7503056
PMCID
PMC1447675
Subset
IM
Grants
NINDS NIH HHS · R01 NS050833 · United States
NIGMS NIH HHS · T32 GM066698 · United States
External Links
PubMed source DOI: 10.1021/ja054474f PMC Full Text View journal details
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