A Highly Selective and Sensitive Ratiometric Fluorescent Probe for Hypochlorite and Its Application

Abstract

A novel water-soluble hybrid fluorescein-coumarin dye(FLNC) fluorescence ratiometric probe to recognize OCl⁻ was designed and synthesized. The most prominent feature of the probe is that the molecular structure contains two different fluorophores, and the fluorescein moiety was connected to coumarin moiety by diacylhydrazine linker. When OCl⁻ was added, the two fluorophores in the FLNC probe could have a rapid respond simultaneously, with high selectivity and sensitivity towards OCl^– among other reactive oxygen species/reactive nitrogen species(ROS/RNS) and anions, and the detection limit was measured to be 0.30 μmol/L. In addition, the color changes of the solution could be observed by the naked eye and have a short response time(completed within 1 min), which suggestes that the probe FLNC has the potential to be used for real-time detection.

Keywords

Fluorescent probe / Dual-fluorophore / Ratiometric / Hypochlorite

References

[1] Zhao Y., Li H. Y., Xue Y. Y., Ren Y. H., Han T. H. Sens. Actuators B: Chem., 2017, 241: 335.

[2] Eryılmaz M., Palabıyık I. M. Trop. J. Pharm. Res., 2013, 12: 123.

[3] Long L. L., Zhang D. D., Li X. F., Zhang J. F., Zhang C., Zhou L. P. Anal. Chim. Acta, 2013, 775: 100.

[4] Hu Z. Q., Zhu J. H., Gu Y. Y., Hu W. Z., Li M., Jiang Y. Microchim. Acta, 2014, 181: 1401.

[5] Khatib S., Musaa R., Vaya J. Bioorg. Med. Chem., 2007, 15: 3661.

[6] Jasin H. E. Inflammation, 1993, 17: 167.

[7] Chen X., Lee K., Ren X. T., Ryu J., Kim G., Lee W., Yoon J. Nat. Protoc., 2016, 11: 1219.

[8] Chen X., Tian X., Shin I., Yoon J. Chem. Soc. Rev., 2011, 40: 4783.

[9] Zhu H., Fan J. L., Wang J. Y., Mu H. Y., Peng X. J. J. Am. Chem. Soc., 2014, 136: 12820.

[10] Du J., Hu M., Fan J., Peng X. Chem. Soc. Rev., 2012, 41: 4511.

[11] Cheng G. H., Fan J. L., Sun W., Cao J. F., Hu C., Peng X. J. Chem. Commun., 2014, 50: 1018.

[12] Liu S., Wu S. Org. Lett., 2013, 15: 878.

[13] Venkatesan P., Wu S. Analyst, 2015, 140: 1349.

[14] Hu J., Wong N., Gu Q., Bai X., Ye S., Yang D. Org. Lett., 2014, 16: 3544.

[15] Cheng G. H., Fan J. L., Sun W., Sui K., Jin X., Wang J. Y. Analyst, 2013, 138: 6091.

[16] Reja S. I., Bhalla V., Sharma A., Kaurb G., Kumar M. Chem. Commun., 2014, 50: 11911.

[17] Yue Y. K., Yin C. X., Huo F. J., Chao J. B., Zhang Y. B. Sens. Actuators B: Chem., 2014, 202: 551.

[18] Chen S. M., Lu J. X., Sun C. D., Ma H. M. Analyst, 2010, 135: 577.

[19] Wang Q., Liu C., Chang J. J., Lu Y., He S., Zhao L. C., Zeng X. S. Dyes Pigm., 2013, 99: 733.

[20] Zhu B. C., Xu Y. H., Liu W. Q., Shao C. X., Wu H. F., Jiang H. L. Sens. Actuators B: Chem., 2014, 191: 473.

[21] Komatsu K., Urano Y., Kojima H., Nagano T. J. Am. Chem. Soc., 2007, 129: 13447.

[22] Srikun D., Miller E. W., Domaille D. W., Chang C. J. J. Am. Chem. Soc., 2008, 130: 4596.

[23] Wen Y., Liu K. Y., Yang H. R., Li Y., Lan H. C., Liu Y. Anal. Chem., 2014, 86: 9970.

[24] Kang J., Huo F. J., Yue Y. K., Wen Y., Chao J. B., Zhang Y. B., Yin C. X. Dyes and Pigm., 2017, 136: 852.

[25] Mello J. V., Finney N. S. Chem. Int. Ed., 2001, 40: 1536.

[26] Chen G. W., Song F. L., Wang J. Y., Yang Z. Y., Sun S. G., Fan J. L., Qiang X. X., Wang X., Dou B. R., Peng X. J. Chem. Commun., 2012, 48: 2949.

[27] Lin W. Y., Long L. L., Chen B. B., Tan W. Chem Eur J., 2009, 15: 2305.

[28] Yuan L., Lin W. J., Xie Y. A., Chen B., Song J. Z. Chem. Eur. J., 2012, 18: 2700.

[29] Chen X., Li Z., Xiang Y., Tong A. Tetrahedron Lett., 2008, 9: 4697.

[30] Long L. L., Wu Y. J., Wang L., Gong A. H., Hu F. L., Zhang C. Chem. Commun., 2015, 51: 10435.

[31] Chen X. C., Wang X. C., Wang S. J., Shi W., Wang K., Ma H. M. Chem. Eur. J., 2008, 14: 4719.