Constructing a fluorescent probe for specific detection of cysteine over homocysteine and glutathione based on a novel cysteine-binding group but-3-yn-2-one
| Autor: | Yuan-Qiang Sun, Song Zhang, Yawei Liu, Jing Liu, Xin Lv, Wei Guo |
|---|---|
| Rok vydání: | 2014 |
| Předmět: |
Photochemistry
Biochemistry Photoinduced electron transfer Analytical Chemistry chemistry.chemical_compound Cascade reaction Coumarins Cell Line Tumor Electrochemistry Humans Environmental Chemistry Cysteine Carcinoma Renal Cell Homocysteine Spectroscopy Fluorescent Dyes Microscopy Confocal Chemistry Optical Imaging Glutathione Fluorescence Spectrometry Fluorescence Intramolecular force Michael reaction Isomerization |
| Zdroj: | The Analyst. 139:4081-4087 |
| ISSN: | 1364-5528 0003-2654 |
| DOI: | 10.1039/c4an00639a |
| Popis: | A but-3-yn-2-one-based 7-diethylaminocoumarin dye was exploited as a fluorescent probe to specifically detect Cys over Hcy/GSH in pure PBS buffer. The probe itself is nonfluorescent due to the donor-excited photoinduced electron transfer (d-PET) process. The Cys-induced Michael addition-rearrangement cascade reaction leads to an amino-substituted product with strong fluorescence due to inhibiting C[double bond, length as m-dash]C isomerization induced fluorescence quenching by a produced intramolecular N-HO hydrogen bond. The Hcy (or GSH)-induced Michael addition reaction leads to a thiol-substituted product (or ), which lacks any intramolecular hydrogen-bonding interaction, and thus displays very poor fluorescence due to the efficient C[double bond, length as m-dash]C isomerization induced fluorescence quenching. Even in the presence of Hcy (or GSH), the probe could also detect Cys with the obvious fluorescence enhancement. Assisted by using a laser scanning confocal microscope, we demonstrated that the probe could selectively image Cys in the human renal cell carcinoma 786-0 cells. |
| Databáze: | OpenAIRE |
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