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

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Abstract

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.

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Acknowledgments

This work was supported by the Ministry of Science and Technology, Taiwan (NSC 103-2811-M-027-002, 102-2113-M-027-002-MY3, and MOST 104-2622-M-027-001-CC3).

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Authors and Affiliations

  1. Department of Chemical Engineering and Biotechnology, National Taipei University of Technology, Taipei, 10608, Taiwan, Republic of China

    Kesavan Manibalan, Sin-Ming Chen, Veerappan Mani & Sheng-Tung Huang

  2. Institue of Biochemical and Biomedical Engineering, National Taipei University of Technology, Taipei, 10608, Taiwan, Republic of China

    Tsung-Tao Huang & Sheng-Tung Huang

  3. Biomedical Instrument Technology Division, Instrument Technology Research Center, National Applied Research Laboratories, 20, R&D Rd. VI, Hsinchu Science Park, Hsinchu, Taiwan, Republic of China

    Tsung-Tao Huang

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  1. Kesavan Manibalan
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Correspondence to Sheng-Tung Huang.

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Manibalan, K., Chen, SM., Mani, V. et al. A Sensitive Ratiometric Long-Wavelength Fluorescent Probe for Selective Determination of Cysteine/Homocysteine. J Fluoresc 26, 1489–1495 (2016). https://doi.org/10.1007/s10895-016-1844-x

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  • DOI: https://doi.org/10.1007/s10895-016-1844-x

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