A simple fluorescent probe for sensing cysteine over homocysteine and glutathione based on PET.
A big challenge is the discrimination of sulfhydryl-containing amino acids due to their structural similarity. We designed and synthesized a simple fluorescent probe 3 for specific detection of cysteine based on photo-induced electron transfer (PET). The acrylate and BODIPY moieties in probe 3 act as a reaction site and reporter group, respectively. So the synergistic effect of the substituent groups endows probe 3 very strong green fluorescence at 525nm (λex=500nm). The cleavage reaction induced by cysteine leads to acrylate hydrolysis, and thereby triggers PET on, which effectively quench the fluorescence of 3. Probe 3 exhibited a rapid response towards cysteine over homocysteine and glutathione. Probe 3 is successfully applied for sensing and imaging cysteine in vitro or in vivo cells with low cytotoxicity.
Key Laboratory of Chemical Sensing & Analysis in Universities of Shandong (University of Jinan), Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
Wenlong
W
Fan
Key Laboratory of Chemical Sensing & Analysis in Universities of Shandong (University of Jinan), Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
Ximing
X
Huang
Key Laboratory of Chemical Sensing & Analysis in Universities of Shandong (University of Jinan), Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
Xiaomin
X
Shi
College of Science, Beijing University of Chemical Technology, Beijing 100029, China.
Zhuo
Z
Wang
Key Laboratory of Chemical Sensing & Analysis in Universities of Shandong (University of Jinan), Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China. Electronic address: zhengliang.lu@yahoo.com.
Zhengliang
Z
Lu
Key Laboratory of Chemical Sensing & Analysis in Universities of Shandong (University of Jinan), Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
Chunhua
C
Fan
Key Laboratory of Chemical Sensing & Analysis in Universities of Shandong (University of Jinan), Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.
Qibing
Q
Bo
D000179:Acrylates / Q000737:chemistry / Q000494:pharmacology; D001896:Boron Compounds / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D005456:Fluorescent Dyes / Q000737:chemistry / Q000494:pharmacology; D005978:Glutathione / Q000378:metabolism*; D006710:Homocysteine / Q000378:metabolism*; D006801:Humans; D008856:Microscopy, Fluorescence
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D000179:Acrylates; D001896:Boron Compounds; D005456:Fluorescent Dyes; D006710:Homocysteine; D005978:Glutathione; C036658:acrylic acid
Bioimaging; Cysteine; Fluorescence; Probe; Selectivity