Journal
TETRAHEDRON LETTERS
Volume 55, Issue 2, Pages 490-494Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.11.055
Keywords
Ratiometric sensor; Homocysteine and cysteine sensor; ESIPT; Cell-imaging; Resonance assisted hydrogen bond
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Funding
- D.S.T.
- CSIR (Govt. of India)
- CSIR
- UGC
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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. (C) 2013 Elsevier Ltd. All rights reserved.
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