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T-00227: Benzofurazan Disulfide Derivatives as Fluorogenic Agents


Thiol groups play a significant role in various cellular functions. Cellular thiol concentrations can be affected by various physiological or pathological factors. A fluorescence imaging agent that can effectively and specifically image and quantify thiols in live cells through fluorescence microscopy is desirable for live cell thiol monitoring.


This technology provides benzofurazan compounds, including benzofurazans that are fluorogenic agents, benzofurazans that are fluorescent agents, and benzofurazan thiol conjugates. The benzofurazans can be, for example, benzofurazan thioethers. The benzofurazans can be benzofurazan sulfide compounds that are "thiol-specific" fluorogenic agents. This invention describes the design, synthesis and determination of specificity, sensitivity and stability of novel thiol-specific Benzofurazan fluorogenic and fluorescent agents.


There is high demand for a thiol specific fluorogenic agent as a research tool or a potential diagnostic tool. There are only a few thiol specific agents which can be used to determine thiols through fluorescence microscopy in live cells; none of these can quickly and completely determine thiols and be used for thiol quantification in live cells. Our compound can specifically, instantaneously and completely react with a thiol to form a strong fluorescent adduct. Our compound can also be used to image and quantify thiols in live cells through fluorescence microscopy. Quantification of thiols in live cells can provide extremely valuable information on thiol-related cellular functions in real-time. It also reduces the experimental time, as well as potential artifacts associated with thiol sample isolation and processing. Our compounds can also be potentially used for determination of thiols on cell surface or in subcellular organelles.

United States provisional patent application 61/649,167

Li Y, et al., “Benzofurazan Sulfides for Thiol Imaging and Quantification in Live Cells through Fluorescence Microscopy”, Anal Chem. 2012 Aug 7;84(15):6877-83. Epub 2012 Jul 26.