Abstract
A near-infrared (NIR) and water-soluble probe was synthesized and studied for the detection of Cys/Hcy in aqueous solution, living cells and mice. The probe was composed of cyanine derivative as the NIR fluorescent reporting unit and pyrimidiny-thioether moiety as the Cys/Hcy responsive unit. Treatment with Cys/Hcy induced the formation of sulfur-substituted products, then intramolecular rearrangement reaction would occur to produce amino-substituted products and resulting in enhanced red fluorescence emissions. It could be applied to sense Cys/Hcy both in solution with the detection limit of 0.17 μM (or 0.32 μM) and in living cells. Cell imaging experiments proved that such a probe exhibited good cell penetration. In addition, the probe could detect Cys/Hcy in live mice with strong turn-on fluorescent response.
Similar content being viewed by others
References
H. Tapiero, D. M. Townsend, and K. D. Tew, Biomed. Pharmacother., 2003, 57, 134.
S. Seshadri, A. Beiser, J. Selhub, P. F. Jacques, I. H. Rosenberg, R. B. D’Agostino, P. W. F. Wilson, and P. A. Wolf, N. Engl. J. Med., 2002, 346, 476.
H. Refsum, P. M. Ueland, O. Nygard, and S. E. Vollset, Annu. Rev. Med., 1998, 49, 31.
S. Shahrokhian, Anal. Chem., 2001, 73, 5972.
Z. A. Wood, E. Schröder, H. J. Robin, and L. B. Poole, Trends Biochem Sci., 2003, 28, 32.
R. O. Ball, G. Courtney-Martin, and P. B. Pencharz, J. Nutr., 2006, 136, 16825.
D. P. Jones, Y. M. Go, C. L. Anderson, T. R. Ziegler, J. J. Kinkade, and W. G. Kirlin, FASEB J., 2004, 18, 1246.
X. Q. Jiang, J. W. Chen, A. Bajic, C. W. Zhang, X. Z. Song, S. L. Carroll, Z. L. Cai, M. L. Tang, M. S. Xue, N. H. Cheng, C. P. Schaaf, F. Li, K. R. MacKenzie, A. C. M. Ferreon, F. Xia, M. C. Wang, M. M. Maletic-Savatic, and J. Wang, Nat. Commun., 2017, 8, 16163.
Y. W. Sun, S. G. Guo, C. Hu, J. L. Fan, and X. J. Peng, Chem. Rev., 2016, 116, 7768.
H. S. Jung, X. Q. Chen, J. S. Kim, and J. Yoon, Chem. Soc. Rev., 2013, 42, 6019.
L. Y. Niu, Y. Z. Chen, H. R. Zhang, L. Z. Wu, C. H. Tung, and Q. Z. Yang, Chem. Soc. Rev., 2015, 44, 6143.
X. H. Li, X. H. Gao, W. Shi, and H. M. Ma, Chem. Rev., 2014, 114, 590.
Z. Q. Guo, S. Park, J. Yoon, and I. Shin, Chem. Soc. Rev., 2014, 43, 16.
W. Xu, X. Li, J. Yin, W. Liu, Y. Yang, and W. Li, Anal. Sci., 2019, 35, 1341.
H. Wu, X. Yang, J. Men, H. Zhang, and J. Zhou, Anal. Sci., 2019, 35, 1305.
Y. Wang, L. W. Zhang, S. Z. Zhang, Z. Liu, and L. X. Chen, Anal. Chem., 2019, 91, 7812.
H. Y. Li, X. H. Li, W. Shi, Y. H. Xu, and H. M. Ma, Angew. Chem., Int. Ed., 2018, 57, 12830.
D. D. Li, S. F. Wang, Z. H. Lei, C. X. Sun, A. M. El-Toni, M. S. Alhoshan, Y. Fan, and F. Zhang, Anal. Chem., 2019, 91, 4771.
X. Wang, P. Li, Q. Ding, C. C. Wu, W. Zhang, and B. Tang, Angew. Chem., Int. Ed., 2019, 58, 4674.
Y.-B. Hao, D. Yuan, Y.-X. Chang, W.-J. Song, and H.-S. Wang, Anal. Sci., 2018, 34, 1379.
S. C. Lee and C. Kim, Anal. Sci., 2019, 35, 1189.
F. P. Qi, Y. Zhang, B. H. Wang, W. Q. Chen, L. Yang, Z. G. Yang, and X. Z. Song, Sens. Actuators, B, 2019, 296, 126533.
J. Zhang, X. Ji, J. L. Zhou, Z. J. Chen, X. C. Dong, and W. L. Zhao, Sens. Actuators, B, 2018, 257, 1076.
N. N. Wang, M. Chen, J. H. Gao, X. Ji, J. L. He, J. Zhang, and W. L. Zhao, Talanta, 2019, 195, 281.
X. F. Hou, Z. S. Li, B. L. Li, C. H. Liu, and Z. H. Xu, Sens. Actuators, B, 2018, 260, 295.
J. Zhang, X. Ji, H. Ren, J. L. Zhou, Z. J. Chen, X. C. Dong, and W. L. Zhao, Sens. Actuators, B, 2018, 260, 861.
X. L. Xie, M. M. Li, F. Y. Tang, Y. Li, L. L. Zhang, X. Y. Jiao, X. Wang, and B. Tang, Anal. Chem., 2017, 89, 3015.
J. Xu, H. Yu, Y. Hu, M. Z. Chen, and S. J. Shao, Biosens. Bioelectron., 2016, 75, 1.
L. W. He, X. L. Yang, K. X. Xu, X. Q. Kong, and W. Y. Lin, Chem. Sci., 2017, 8, 6257.
A. C. Sedgwick, J. E. Gardiner, G. Kim, M. Yevglevskis, M. D. Lloyd, T. A. Jenkins, S. D. Bull, J. Yoon, and T. D. James, Chem. Commun., 2018, 54, 4786.
H. S. Jung, J. H. Han, T. Pradhan, S. Kim, S. W. Lee, J. L. Sessler, T. W. Kim, C. Kang, and J. S. Kim, Biomaterials, 2017, 33, 945.
M. Zhang, M. X. Fu, F. Y. Li, M. W. Zhu, M. Y. Li, Y. H. Gao, L. Li, Z. Q. Liu, J. P. Zhang, D. Q. Zhang, T. Yi, and C. H. Huang, J. Am. Chem. Soc., 2007, 129, 10322.
F. Y. Wang, L. Zhou, C. C. Zhao, R. Wang, Q. Fei, S. H. Luo, Z. Q. Guo, H. Tian, and W. H. Zhu, Chem. Sci., 2015, 6, 2584.
X. Yang and Y. Qian, New J. Chem., 2019, 43, 3725.
H. Zhu, C. Liu, H. Zhang, P. Jia, Z. Li, X. Zhang, Y. Yu, W. Sheng, and B. Zhu, Anal. Sci., 2020, 36, 255.
W. Zhou, J. W. Shultz, N. Murphy, E. M. Hawkins, L. Bernad, T. Good, L. Moothart, S. Frackman, D. H. Klaubert, R. F. Bulleitb, and K. V. Wood, Chem. Commun., 2006, 4620.
M. Hemmi, Y. Ikeda, Y. Shindo, T. Nakajima, S. Nishiyama, K. Oka, M. Sato, Y. Hiruta, D. Citterio, and K. Suzuki, Chem. Asian J., 2018, 13, 648.
N. Nomura, R. Nishihara, T. Nakajima, S. B. Kim, N. Iwasawa, Y. Hiruta, S. Nishiyama, M. Sato, D. Citterio, and K. Suzuki, Anal. Chem., 2019, 91, 9546.
X. Li, Y. F. Tang, J. Li, X. M. Hu, C. Yin, Z. Yang, Q. Wang, Z. Z. Wu, X. M. Lu, W. J. Wang, W. Huang, and Q. L. Fan, Chem. Commun., 2019, 55, 5934.
J. P. Wang, Y. Wen, F. J. Huo, and C. X. Yin, Sens. Actuators, B, 2019, 297, 126773.
Y. Huang, N. He, Y. D. Wang, L. W. Zhang, Q. Kang, Y. Q. Wang, D. Z. Shen, J. Choo, and L.X. Chen, J. Mater. Chem. B, 2019, 7, 2557.
D. Lee, K. Jeong, X. Luo, G. Kim, Y. J. Yang, X. Q. Chen, S. Kim, and J. Yoon, J. Mater. Chem. B, 2018, 6, 2541.
X. Q. Chen, D. Lee, S. Yu, G. Kim, S. Lee, Y. Cho, H. Jeong, K. T. Nam, and J. Yoon, Biomaterials, 2017, 122, 130.
R. Wang, F. B. Yu, L. X. Chen, H. Chen, L. J. Wang, and W. W. Zhang, Chem. Commun., 2012, 48, 11757.
X. Y. Han, F. B. Yu, X. Y. Song, and L. X. Chen, Chem. Sci., 2016, 7, 5098.
X. Q. Chen, Y. Zhou, X. J. Peng, and J. Y. Yoon, Chem. Soc. Rev., 2010, 39, 2120.
Y. Zhou and J. Y. Yoon, Chem. Soc. Rev., 2012, 41, 52.
Y. M. Yang, Q. Zhao, W. Feng, and F. Y. Li, Chem. Rev., 2013, 113, 192.
J. H. Gao, Y. F. Tao, J. Zhang, N. N. Wang, X. Ji, J. L. He, Y. B. Si, and W. L. Zhao, Chem.—Eur. J., 2019, 25, 11246.
J. Zhang, N. N. Wang, X. Ji, Y. F. Tao, J. M. Wang, and W. L. Zhao, Chem.—Eur. J., 2020, 26, 4172.
J. M. Wang, L. Q. Niu, J. Huang, Z. J. Yan, and J. H. Wang, Spectrochim. Acta, Part A, 2018, 192, 52.
Acknowledgments
This work was supported by the Key Scientific Research Program of the Higher Education Institution of Henan Province (18A150003).
Author information
Authors and Affiliations
Corresponding authors
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Men, Y., Zhou, X., Yan, Z. et al. A Water-soluble Near-infrared Fluorescent Probe for Cysteine/ Homocysteine and Its Application in Live Cells and Mice. ANAL. SCI. 36, 1053–1057 (2020). https://doi.org/10.2116/analsci.20P016
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2116/analsci.20P016