Low-Cytotoxicity Fluorescent Probes Based on Anthracene Derivatives for Hydrogen Sulfide Detection.

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 ?g·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.

SUBMITTER: Shang X 

PROVIDER: S-EPMC6024568 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature