Azide and sulfonylazide functionalized fluorophores for the selective and sensitive detection of hydrogen sulfide

作者：Elsayed Sameh; de la Torre Cristina; Santos Figueroa Luis E; Marin Hernandez Cristina; Martinez Manez Ramon^*; Sancenon Felix; Costero Ana M; Gil Salvador; Parra Margarita

来源：Sensors and Actuators B: Chemical , 2015, 207: 987-994.

DOI：10.1016/j.snd.2014.04.047

• Hydrogen sulfide
• Fluorescence
• Azide
• Sulfonylazide
• In vivo detection

Three fluorescent probes (1-3) for the selective and sensitive detection of hydrogen sulfide have been synthesized and characterized. Probe 1 is a coumarin derivative functionalized with an azide moiety whereas 2 contain the azide reactive group into a naphthalene fluorophore backbone. Probe 3 is composed also by a naphthalene fluorophore but, in this case, functionalized with a sulfonylazide reactive moiety. Probes 1 and 3 are non-fluorescent whereas 2 is weakly emissive in HEPES (10 mM, pH 7.4)-DMS0 99:1 (v/v). The emission behavior of the three probes was tested against selected anions, bio-thiols and oxidant molecules. Of all the chemical species tested, only HS- is able to induce an enhancement in the emission intensity (50, 11 and 20-fold for 1,2 and 3, respectively). The observed emission in the presence of hydrogen sulfide is ascribed, in the case of probes 1 and 2, to an azide-amine reduction induced by HS- anion, whereas for probe 3 the sensing mechanism is related with a sulfonylazide-sulfonamide conversion. The three probes are very sensitive to HS- anion with limits of detection of 0.17, 0.20 and 0.40 mM for 1,2 and 3 respectively. Cell viability studies demonstrated that 1-3 probes are essentially non-toxic at concentrations 10-50 mu M and are well suited for in vivo studies. Finally, probe 1 was used for the detection on intracellular HS- anion in HeLa cells by means of confocal microscopy.

• 出版日期2015-2