Coumarin Based Highly Selective ‘Turn-On’ Fluorescent Probe for Ascorbic Acid: Single Crystal X-Ray Structure and Cell Staining Properties

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International Journal of Research and Scientific Innovation (IJRSI) | Volume IV, Issue X, October 2017 | ISSN 2321–2705

Coumarin Based Highly Selective ‘Turn-On’ Fluorescent Probe for Ascorbic Acid: Single Crystal X-Ray Structure and Cell Staining Properties

Dr. Subarna Guha
Faculty of Chemistry, Central Institute of Plastic Engineering and Technology, Haldia, West Bengal, India

Abstract:- A vanillin-coumarin hybrid molecule, 6E)-6-(4- hydroxy-3-methoxybenzylideneamino)-2H-chromen-2-one (VC) has been found to interact with ascorbic acid (AA) very selectively via intermolecular H-bond formation resulting a 8 fold enhancement of its fluorescence intensity. Interaction has been monitored by different spectroscopic techniques like 1H NMR, QTOF–MS ES+ and FTIR analysis. Structure of VC has been confirmed by single crystal X-ray structure analysis. In DMSO/water (1:4, v/v) at pH 7.4, the method is linear up to 14 µM of AA and can detect as low as 0.5 µM AA. Interference from common cations, anions and some common pharmaceutical compounds with close structural resemblance is negligible. VC can detect intracellular AA in living cells very efficiently.

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Keywords: Turn-on fluorescence, ascorbic acid, coumarin, living cell imaging.


Use of fluorescence technique for trace level detection1-2 of analyte has become very popular and the volume of research work in this field is exponentially rising. L-Ascorbic acid (AA), a water-soluble vitamin C, is widely distributed in fruits and vegetables, and plays an important role in human metabolism as a free-radical scavenger.5 Radical induced disease6 such as cancer and Parkinson’s disease is prevented by it. Deficiency of this acid causes scurvy disease. It also plays many important biological roles7-8 e.g. a vital role in disease prevention. It also used some commercial soft drink beverages, pharmaceutical formulations, and cosmetic applications.9 Due to the above importance of AA, its determination in solutions is very important. Recently, AA has attracted considerable attention for its use in modern cancer therapy.10-11 A wide variety of analytical techniques is available for the determination of AA, including as titrimetric analysis, spectroscopy, chromatography, and electroanalysis.12-13 So far, various AA analytical procedures have been reported, including HPLC,14 spectrometric,15 chemiluminescence,16-18 capillaryelectrophoresis,19 modified electrodes,20-22 electrochemical methods23 chemiluminescence,24 atomic absorption spectrometry,25 luminescent26 and so on. Although, very few AA selective fluorescence sensors have so far been reported, 27-30 and the majority of them require a tedious synthetic methodology.