A Unique Paradigm for a Turn-ON Near-Infrared Cyanine-Based Probe: Noninvasive Intravital Optical Imaging of Hydrogen Peroxide
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(-1)cm(-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.
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Cyanine dyes, particularly heptamethine cyanines and their derivatives such as Cy7 and HCy dyes, represent one of the most prominent classes of NIR fluorophores.
“Cyanine dyes, particularly heptamethine cyanines and their derivatives (e.g., Cy7 and HCy dyes), represent one of the most prominent classes of near-infrared (NIR) fluorophores77,78.”
From Organic small-molecule NIR-II fluorophores for tumor phototheranostics (2026) · cites this paper as [77]
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“Cyanine dyes, particularly heptamethine cyanines and their derivatives (e.g., Cy7 and HCy dyes), represent one of the most prominent classes of near-infrared (NIR) fl uorophores 77,78 .”
- Authors
- Karton-Lifshin, N., Segal, E., Omer, L., Portnoy, M., Satchi-Fainaro, R., & Shabat, D.
- Affiliations
- Tel Aviv University (IL)
- School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences and ‡Department of Physiology and Pharmacology, Sackler School of Medicine, Tel Aviv University, Tel Aviv 69978, Israel
- Corresponding author
- Shabat, Doron
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-06-22
- Volume
- 133
- Issue
- 28
- Pages
- 10960-10965
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2002134534
- Cited by
- 366
- References
- 31
- Citations by year
- 2026: 11 · 2025: 12 · 2024: 14 · 2023: 15 · 2022: 20 · 2021: 15 · 2020: 25 · 2019: 32 · 2018: 33 · 2017: 31 · 2016: 42 · 2015: 32 · 2014: 28 · 2013: 29 · 2012: 21
- FWCI
- 12.18
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biophysics › Advanced Fluorescence Microscopy Techniques
- Keywords
- fluorogenic probes, near-infrared fluorescence, lipopolysaccharide-induced inflammation, molecular imaging, fluorescence quantum yield, reactive oxygen species
- MeSH terms
- Animals, Carbocyanines, Fluorescent Dyes, Hydrogen Peroxide, Infrared Rays, Mice, Optical Phenomena, Molecular Imaging
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