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

SENSORS AND ACTUATORS B-CHEMICAL

卷:207

Article

Elsayed, Sameh^1,2,3,4  de la Torre, Cristina^1,2,3,4  Santos-Figueroa, Luis E.^1,2,3,4  Marin-Hernandez, Cristina^1,2,3,4  Martinez-Manez, Ramon^1,2,3,4  Sancenon, Felix^1,2,3,4  Costero, Ana M.^1,2,5  Gil, Salvador^1,2,5  Parra, Margarita^1,2,5 

[1] Univ Politecn Valencia, Ctr Mixto, Ctr Reconocimiento Mol & Desarrollo Tecnol IDM, Valencia 46022, Spain

[2] Univ Valencia, E-46003 Valencia, Spain

[3] Univ Politecn Valencia, Dept Quim, Valencia 46022, Spain

[4] CIBER Bioingn Biomat & Nanotecnol CIBER BNN, Barcelona, Spain

[5] Univ Valencia, Fac Ciencias Quim, Dept Quim Organ, E-46100 Valencia, Spain

关键词: Hydrogen sulfide;    Fluorescence;    Azide;    Sulfonylazide;    In vivo detection;   

DOI  :  10.1016/j.snb.2014.04.047

来源: Elsevier

【 摘 要 】

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. (C) 2014 Elsevier B.V. All rights reserved.

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