Low-Cytotoxicity Fluorescent Probes Based on Anthracene Derivatives for Hydrogen Sulfide Detection.
Front Chem, 2018;6:202.
Shang X[1], Li J[1], Feng Y[2], Chen H[3], Guo W[1], Zhang J[2], Wang T[4], Xu X[5]
Affiliations
PMID: 29988478DOI: 10.3389/fchem.2018.00202
Impact factor: 5.545
Abstract
Owing to the role of H2S in various biochemical processes and diseases, its accurate detection is a major research goal. Three artificial fluorescent probes based on 9-anthracenecarboxaldehyde derivatives were designed and synthesized. Their anion binding capacity was assessed by UV-Vis titration, fluorescence spectroscopy, HRMS, 1HNMR titration, and theoretical investigations. Although the anion-binding ability of compound 1 was insignificant, two compounds 2 and 3, containing benzene rings, were highly sensitive fluorescent probes for HS- among the various anions studied (HS-, F-, Cl-, Br-, I-, AcO-, H2PO4- , SO32- , Cys, GSH, and Hcy). This may be explained by the nucleophilic reaction between HS- and the electron-poor C=C double bond. Due to the presence of a nitro group, compound 3, with a nitrobenzene ring, showed stronger anion binding ability than that of compound 2. In addition, compound 1 had a proliferative effect on cells, and compounds 2 and 3 showed low cytotoxicity against MCF-7 cells in the concentration range of 0-150 μg·mL-1. Thus, compounds 2 and 3 can be used as biosensors for the detection of H2S in vivo and may be valuable for future applications.
Keywords: 9-anthracenecarboxaldehyde; cytotoxicity; fluorescent probe; hydrogen sulfide; nucleophilic substitution
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