A unique paradigm for a turn-ON near-infrared cyanine-based probe: Noninvasive intravital optical imaging of hydrogen peroxide

Naama Karton-Lifshin, Ehud Segal, Liora Omer, Moshe Portnoy, Ronit Satchi-Fainaro*, Doron Shabat

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

The development of highly sensitive fluorescent probes in combination with innovative optical techniques is a promising strategy for intravital noninvasive quantitative imaging. Cyanine fluorochromes belong to a superfamily of dyes that have attracted substantial attention in probe design for molecular imaging. We have developed a novel paradigm to introduce a Turn-ON mechanism in cyanine molecules, based on a distinctive change in their π-electrons system. Our new cyanine fluorochrome is synthesized through a simple two-step procedure and has an unprecedented high fluorescence quantum yield of 16% and large extinction coefficient of 52 000 M-1cm-1. The synthetic strategy allows one to prepare probes for various analytes by introducing a specific triggering group on the probe molecule. The probe was equipped with a corresponding trigger and demonstrated efficient imaging of endogenous hydrogen peroxide, produced in an acute lipopolysaccharide-induced inflammation model in mice. This approach provides, for the first time, an available methodology to prepare modular molecular Turn-ON probes that can release an active cyanine fluorophore upon reaction with specific analyte.

Original languageEnglish
Pages (from-to)10960-10965
Number of pages6
JournalJournal of the American Chemical Society
Volume133
Issue number28
DOIs
StatePublished - 20 Jul 2011

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