Curcumin-Based "Enhanced SNAr" Promoted Ultrafast Fluorescent Probe for Thiophenols Detection in Aqueous Solution and in Living Cells.
We report herein a highly selective and sensitive turn-on fluorescent probe (compound 1) with a fast response time (less than 2 min) for thiophenol detection based on an "enhanced SNAr" reaction between thiophenols and a sulfonyl-ester moiety covalently attach to curcumin. Reaction of 1 in Hepes-MeOH (1:1, v/v, pH 7.4) in the presence of 4-methylthiophenol (MTP) resulted in a remarkable enhancement of the fluorescence. A linear response in the presence of MTP of the relative fluorescent intensity (F - F0) of 1 at 536 nm in the 0-40 μM MTP concentration range was found. A limit of detection (LOD) for the detection of MTP of 26 nM, based on the definition by IUPAC (CDL= 3 Sb/m), was calculated. Probe 1 was applied to monitor and imaging exogenous MTP in live cells and to the detection of MTP in real water samples.
Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Key Laboratory of Materials for Energy Conversion and Storage of Shanxi Province, Institute of Molecular Science, Shanxi University , Taiyuan 030-006, China.
Yongkang
Y
Yue
Research Institute of Applied Chemistry, Shanxi University , Taiyuan 030-006, China.
Fangjun
F
Huo
Research Institute of Applied Chemistry, Shanxi University , Taiyuan 030-006, China.
Yongbin
Y
Zhang
Research Institute of Applied Chemistry, Shanxi University , Taiyuan 030-006, China.
Jianbin
J
Chao
Instituto Interuniversitario de Investigación de Reconocimiento Molecular y Desarrollo Tecnológico, (IDM), Universitat Politécnica de València, Universitat de València . Camino de Vera s/n, 46022, Valencia, Spain.|CIBER de Bioingeniería, Biomateriales y Nanotecnología (CIBER-BBN) , 28029 Madrid, Spain.
Ramón
R
Martínez-Máñez
Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Key Laboratory of Materials for Energy Conversion and Storage of Shanxi Province, Institute of Molecular Science, Shanxi University , Taiyuan 030-006, China.
Caixia
C
Yin
D003474:Curcumin / Q000031:analogs & derivatives*; D005456:Fluorescent Dyes / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D060106:Lakes / Q000032:analysis; D057230:Limit of Detection; D061848:Optical Imaging / Q000379:methods; D010636:Phenols / Q000032:analysis*; D013050:Spectrometry, Fluorescence / Q000379:methods; D013438:Sulfhydryl Compounds / Q000032:analysis*
D005456:Fluorescent Dyes; D010636:Phenols; D013438:Sulfhydryl Compounds; C042983:thiophenol; D003474:Curcumin