A Sensitive Ratiometric Long-Wavelength Fluorescent Probe for Selective Determination of Cysteine/Homocysteine

The development of sensitive fluorescence probes to detect biothiols such as cysteine and homocysteine has attracted great attention in recent times. Herein, we described the design and synthesis of coumarin based long-wavelength fluorescence probe, Bromo-2-benzothiazolyl-3-cyano-7-hydroxy coumarin...

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Bibliographic Details
Published in:Journal of fluorescence 2016-07, Vol.26 (4), p.1489-1495
Main Authors: Manibalan, Kesavan, Chen, Sin-Ming, Mani, Veerappan, Huang, Tsung-Tao, Huang, Sheng-Tung
Format: Article
Language:English
Subjects:
Analytical Chemistry
Animals
Biochemistry
Biological and Medical Physics
Biomedical and Life Sciences
Biomedicine
Biophysics
Biotechnology
Cattle
Coumarins - chemistry
Cysteine - analysis
Cysteine - chemistry
Cysteine - urine
Fluorescent Dyes - chemistry
Homocysteine - analysis
Homocysteine - chemistry
Homocysteine - urine
Humans
Limit of Detection
Original Article
Serum Albumin, Bovine - chemistry
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Summary:The development of sensitive fluorescence probes to detect biothiols such as cysteine and homocysteine has attracted great attention in recent times. Herein, we described the design and synthesis of coumarin based long-wavelength fluorescence probe, Bromo-2-benzothiazolyl-3-cyano-7-hydroxy coumarin (BBCH, 2) for selective detections of cysteine and homocysteine. The probe is rationally designed in such a way that both sulfhydryl and adjacent amino groups of thiols are involved in sensing process. Only cysteine/homocysteine able to react with BBCH to release fluorescence reporter ( BCH, 1 ); while, glutathione and other amino acids unable to react with BBCH due to the absence of adjacent amino groups. In presence of cysteine, the color of BBCH is turns from colorless to red and thus BBCH is a naked eye fluorescence indicator for cysteine. Besides, BBCH can discriminate cysteine and homocysteine based on color changes and different reaction rates. The described sensing platform showed good sensing performances to detect cysteine and homocysteine with detection limits of 0.87 and 0.19 μM, respectively. Practical applicability was verified in biological and pharmaceutical samples.
ISSN:1053-0509
1573-4994
DOI:10.1007/s10895-016-1844-x