Rational Design of a Dual‐Reactivity‐Based Fluorescent Probe for Visualizing Intracellular HSNO

Thionitrous acid (HSNO), the smallest S‐nitrosothiol, is emerging as a potential key intermediate in cellular redox regulation linking two signaling molecules H2S and NO. However, the chemical biology of HSNO remains poorly understood. A major hurdle is the lack of methods for selective detection of...

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Published inAngewandte Chemie International Edition Vol. 58; no. 45; pp. 16067 - 16070
Main Authors Chen, Wei, Matsunaga, Tetsuro, Neill, Deshka L., Yang, Chun‐tao, Akaike, Takaaki, Xian, Ming
Format Journal Article
LanguageEnglish
Published Germany Wiley Subscription Services, Inc 04.11.2019
EditionInternational ed. in English
Subjects
Aqueous solutions
Biology
biosensors
Fluorescent indicators
fluorescent probes
Hydrogen sulfide
imaging agents
Organic chemistry
S-nitrosothiols
Selectivity
biosensors
S-nitrosothiols
imaging agents
hydrogen sulfide
fluorescent probes
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Summary:Thionitrous acid (HSNO), the smallest S‐nitrosothiol, is emerging as a potential key intermediate in cellular redox regulation linking two signaling molecules H2S and NO. However, the chemical biology of HSNO remains poorly understood. A major hurdle is the lack of methods for selective detection of HSNO in biological systems. Herein, we report the rational design, synthesis, and evaluation of the first fluorescent probe TAP‐1 for HSNO detection. TAP‐1 showed high selectivity and sensitivity to HSNO in aqueous media and cells, providing a useful tool for understanding the functions of HSNO in biology. Light‐up intracellular HSNO: A unique dual‐reactivity‐based fluorescent probe for HSNO was developed. The probe exhibited high selectivity and sensitivity to HSNO in aqueous media and cells, providing a useful tool for understanding the functions of HSNO in biology.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201908950