Journal
CHEMBIOCHEM
Volume 14, Issue 5, Pages 593-598Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201200724
Keywords
fluorescent probes; hydrogen peroxide; oxidative stress; reactive oxygen species
Funding
- National Institutes of Health [R01 GM098435, R01A112075, 5T32K007233-34, P30 NS047101]
- AHA [12GRNT12040467]
- UCSD Skaggs School of Pharmacy and Pharmaceutical Sciences
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Hydrogen peroxide is a major component of oxygen metabolism in biological systems that, when present in high concentrations, can lead to oxidative stress in cells. Noninvasive molecular imaging of H2O2 using fluorogenic systems represents an effective way to detect and measure the accumulation of this metabolite. Herein, we detail the development of robust H2O2-sensitive fluorescent probes using a boronic ester trigger appended to the fluorophore through a benzyl ether linkage. A major advantage of the probes presented here is their synthetic accessibility, with only one step needed to generate the probes on the gram scale. The sensitivity of the probes was evaluated in simulated physiological conditions, showing micromolar sensitivity to H2O2. The probes were tested in biological model systems, demonstrating effective imaging of unstimulated, endogenous H2O2 levels in RAW 264.7 cells and murine brain tissue.
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