A turn on ESIPT probe for rapid and ratiometric fluorogenic detection of homocysteine and cysteine in water with live cell-imaging

作者：Goswami Shyamaprosad^*; Manna Abhishek; Paul Sima; Das Avijit K; Nandi Prasanta K; Maity Anup Kumar; Saha Partha

来源：Tetrahedron Letters, 2014, 55(2): 490-494.

DOI：10.1016/j.tetlet.2013.11.055

• Ratiometric sensor
• Homocysteine and cysteine sensor
• ESIPT
• Cell-imaging
• Resonance assisted hydrogen bond

5(Benzothiazol-2-yl)-4-hydroxyisophthalaldehyde (BHI), an intense ESIPT containing molecule in mixed media loses its properties due to resonance-assisted H-bond (RAHB) in absolute water. Due to resonance-assisted H-bond the o-aldehyde is more reactive than the other one. With addition of cysteine/homocysteine into this solution the o-aldehyde group gets transformed into thiazolidine/thiazine ring, respectively, and the phenolic proton becomes free enough for transfer to nitrogen of the benzothiazole ring in excited state, that is, the ESIPT of BHI is turned on. Thus we can detect cysteine/homocysteine in water as well as in live cells.

• 出版日期2014-1-8