2,4-dinitrophenyl ether-containing chemodosimeters for the selective and sensitive ‘in vitro’ and ‘in vivo’ detection of hydrogen sulfide

Four probes (i.e. D1–D4) for the selective and sensitive fluorogenic detection of HS− have been prepared and characterised. HEPES (10 mM, pH 7.4)–DMSO 99:1 v/v solutions of D1–D4 are essentially non-fluorescent. Changes in the emission using D1–D4 in the presence of anions (F− , Cl− , Br− , I− , , CN− , SCN− , AcO− , , , , HS− and OH− ), biothiols (GSH, Cys, Hcy, Me–Cys and lipoic acid), reducing agents ( and ) and oxidants (H2O2) demonstrated that only HS− is able to induce the appearance of intense emission bands in the 400–520 nm range in the four probes. The selectivity observed was ascribed to a unique hydrogen sulfide-induced hydrolysis of the 2,4-dinitrophenyl ether moiety that yielded the corresponding free highly fluorescent alcohols. The potential detection of intracellular HS− was also studied.