An increasing number of physiological processes are recognized to be signaled or regulated by hydrogen sulfide (H2S). Fluorescent small molecule probes making use of the reduction potential of H2S are being developed to better understand the different biological roles of H2S. Many recently-developed probes rely on the H2S-mediated reduction of an azide to function and are limited by the photosensitivity of the azide functional group. In response to this limitation, we present the design, synthesis, and characterization of two ChemiLuminescent Sulfide Sensors (CLSS-1 and CLSS-2) for H2S detection. Despite the structural similarities of the two sensors, the selectivity of CLSS-2 for H2S over biologically relevant reactive sulfur, oxygen, and nitrogen species is significantly higher than that of CLSS-1. By using a combination of structural analysis, solution thermodynamic measurements from 1H NMR data, and computational modeling, we attribute the different reactivity profiles of CLSS-1 and CLSS-2 to substrate hydrogen bonding interactions. We demonstrate the efficacy of CLSS-2 to detect enzymatically produced H2S by using both isolated and purified cystathionine-?-lyase (CSE) enzyme as well as lysates from CSE expressing C6 cells. Furthermore, use of CLSS-2 allows for differentiation between normal H2S biosynthesis and biosynthesis inhibited by �-cyanoalanine (BCA). The cell-based studies, taken in combination with the high selectivity of CLSS-2 for H2S over other reactive species, demonstrates the viability of using CLSS-2 as a platform for biological H2S detection.

Chemiluminescent detection and quantification of hydrogen sulfide (H<sub>2</sub>S)

248th National Meeting (2014)

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Chemiluminescent detection and quantification of hydrogen sulfide (H2S)

Chemiluminescent detection and quantification of hydrogen sulfide (H₂S)