Abstract
Cysteine (Cys), as one of the important amino acids, plays a vital role in various physiological and pathological processes. Hence, it is meaningful to develop a convenient and sensitive detection method. Herein, a novel BODIPY-based fluorescent probe (BDP-DM) was developed, which had a higher selectivity for Cys than other amino acids, including homocysteine (Hcy) and glutathione (GSH). Ultimately, we concluded that the BDP-DM probe could be used to successfully detected intracellular Cys in living HeLa cells.
Similar content being viewed by others
References
Z.A. Wood, E. Schroder, J.R. Harris, L.B. Poole, Trends Biochem. Sci., 2003, 28, 32.
H. Refsum, P.M. Ueland, O. Nygard, S.E. Vollset, Annu. Rev. Med., 1998, 49, 31.
R.O. Ball, G. Courtney-Martin, P.B. Pencharz, J. Nutr., 2006, 136, 16825.
S. Shahrokhian, Anal. Chem., 2001, 73, 5972.
S. Seshadri, A. Beiser, J. Selhub, P.F. Jacques, I.H. Rosenberg, R.B. D'Agostino, P.W.F. Wilson, P.A. Wolf, New Engl. J. Med., 2002, 346, 476.
J.M. Estrela, A. Ortega, E. Obrador, Crit. Rev. Clin. Lab. Sci., 2006, 43, 143.
H. Tapiero, D. Townsend, K. Tew, Biomed. Pharmacother., 2003, 57, 134.
H.S.J. James, S. Melnyk, S. Jernigan, M.A. Cleves, C.H. Halsted, D.H. Wong, P. Cutler, K. Bock, M. Boris, J.J. Bradstreet, Am. J. Med. Genet. Part B, 2006, 141, 947.
N.S. Mohammad, P.S. Shruti, V. Bharathi, C.K. Prasad, T. Hussain, S.A. Alrokayan, U. Naik, A.R.R. Devi, Psychiatr. Genet., 2016, 26, 281.
O. Nekrassova, Talanta, 2003, 60, 1085.
Y.V. Tcherkas and A.D. Denisenko, J. Chromatogr., A, 2001, 913, 309.
Z. Huang, Y. Yang, Y. Long, H. Zheng, Anal. Method, 2018, 10, 2676.
G.L. Ellman, Arch. Biochem. Biophys., 1959, 82, 70.
C. Zhao, J. Zhang, J. Song, Anal. Biochem., 2001, 297, 170.
D. Jia, F. Li, L. Sheng, Q. Ren, S. Dong, S. Xu, Y. Mu, Y. Miao, Electrochem. Commun., 2011, 13, 1119.
W. Xu, X. Li, J. Yin, W. Liu, Y. Yang, W. Li, Anal. Sci., 2019, 35, 1341.
J. Yin, Y. Kwon, D. Kim, D. Lee, G. Kim, Y. Hu, J.H. Ryu, J. Yoon, Nat. Protoc., 2015, 10, 1742.
C. Zhao, J. Shang, H. Li, C. Yang, Z. Li, J. Ning, Chin. Anal. Sci., 2020, 36, 329.
X. Chen, Y. Zhou, X. Peng, J. Yoon, Chem. Soc. Rev., 2010, 39, 2120.
X. Lv, J. Liu, Y. Liu, Y. Zhao, Y.Q. Sun, P. Wang, W. Guo, Chem. Commun., 2011, 47, 12843.
Y. Zhou and J. Yoon, Chem. Soc. Rev., 2012, 41, 52.
L.Y. Niu, Y.S. Guan, Y.Z. Chen, L.Z. Wu, C.H. Tung, Q.Z. Yang, J. Am. Chem. Soc., 2012, 134, 18928.
H.S. Jung, X. Chen, J.S. Kim, J. Yoon, Chem. Soc. Rev., 2013, 42, 6019.
Y. Yang, Q. Zhao, W. Feng, F. Li, Chem. Rev., 2013, 113, 192.
J. Wang, X. Shao, J. Wang, S. Shao, Chem. Lett., 2017, 46, 442.
J. Wang, L. Niu, J. Huang, Z. Yan, J. Wang, Spectrochim. Acta, Part A, 2018, 192, 52.
L.Y. Niu, Y.Z. Chen, H.R. Zheng, L.Z. Wu, C.H. Tung, Q.Z. Yang, Chem. Soc. Rev., 2015, 44, 6143.
J. Zhang, X. Bao, J. Zhou, F. Peng, H. Ren, X. Dong, W. Zhao, Biosens. Bioelectron., 2016, 85, 164.
H. Zhu, C. Liu, H. Zhang, P. Jia, Z. Li, X. Zhang, Y. Yu, W. Sheng, B. Zhu, Anal. Sci., 2020, 36, 255.
C.X. Yin, K.M. Xiong, F.J. Huo, J.C. Salamanca, R.M. Strongin, Angew. Chem., Int. Edit., 2017, 43, 13368.
Y. Yue, F. Huo, P. Ning, Y. Zhang, J. Chao, X. Meng, C. Yin, J. Am. Chem. Soc., 2017, 139, 3181.
Y. Men, X. Zhou, Z. Yan, L. Niu, Y. Luo, J. Wang, J. Wang, Anal. Sci., 2020, 36, 1053.
J. Wang, L. Niu, J. Huang, Z. Yan, X. Zhou, J. Wang, Dyes Pigm., 2018, 158, 151.
X. Shao, R. Kang, Y. Zhang, Z. Huang, F. Peng, J. Zhang, Y. Wang, F. Pan, W. Zhang, W. Zhao, Anal. Chem., 2015, 87, 399.
X. Lu, W. Wang, Q. Dong, X. Bao, X. Lin, W. Zhang, X. Dong, W. Zhao, Chem. Commun., 2015, 51, 1498.
Y. Zhang, X. Shao, Y. Wang, F. Pan, R. Kang, F. Peng, Z. Huang, W. Zhang, W. Zhao, Chem. Commun., 2015, 51, 4245.
J. Zhang, J. Zhou, X. Dong, X. Zheng, W. Zhao, RSC Adv., 2016, 6, 51304.
J. Zhang, X. Ji, J. Zhou, Z. Chen, X. Dong, W. Zhao, Sens. Actuators, B, 2018, 257, 1076.
J. Zhang, X. Ji, H. Ren, J. Zhou, Z. Chen, X. Dong, W. Zhao, Sens. Actuators, B, 2018, 260, 861.
J. Gao, Y. Tao, N. Wang, J. He, J. Zhang, W. Zhao, Spectrochim. Acta, Part A, 2018, 203, 77.
N. Wang, M. Chen, J. Gao, X. Ji, J. He, J. Zhang, W. Zhao, Talanta, 2019, 195, 281.
J. Gao, Y. Tao, J. Zhang, N. Wang, X. Ji, J. He, Y. Si, W. Zhao, Chem.—Eur. J., 2019, 25, 11246.
J. Zhang, N. Wang, X. Ji, Y. Tao, J. Wang, W. Zhao, Chem.—Eur. J., 2020, 26, 4172.
B.W. Michel, A.R. Lippert, C.J. Chang, J. Am. Chem. Soc., 2012, 134, 15668.
R. Hu, C.F. Gomez-Duran, J.W. Lam, J.L. Belmonte-Vazquez, C. Deng, S. Chen, R. Ye, E. Pena-Cabrera, Y. Zhong, K.S. Wong, B.Z. Tang, Chem. Commun., 2012, 48, 10099.
C.H. Lee, H.J. Yoon, J.S. Shim, W.D. Jang, Chem.— Eur. J., 2012, 18, 4513.
R. Ziessel, G. Ulrich, J.H. Olivier, T. Bura, A. Sutter, Chem. Commun., 2010, 46, 7978.
H. Chen, X. He, M. Su, W. Zhai, H. Zhang, C. Li, J. Am. Chem. Soc., 2017, 139, 10157.
A. Loudet and K. Burgess, Chem. Rev., 2007, 107, 4891.
Z. Chen, B. Lu, Z. Ding, K. Gao, N. Yoshikai, Org. Lett., 2013, 15, 1966.
S. Li, Y. Fu, C. Li, Y. Li, L. Yi, J. Yang, Anal. Chim. Acta, 2017, 994, 73.
L. Wang, M. Ren, Z. Li, L. Dai, W. Lin, Anal. Methods, 2019, 11, 4323.
Y. Bai, M. Wu, Q. Ma, C. Wang, J. Sun, M. Tian, J. Li, New J. Chem., 2019, 43, 14763.
Acknowledgments
This research was supported by the National Natural Science Foundation of China (No. 21702046), project funded by the China postdoctoral Science Foundation (2018M632757), Postdoctoral research grant in Henan Province (001803025) and Innovation Scientists and Technicians Troop Construction Projects of Henan Province (No. 20IRTSTHN020).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Rights and permissions
About this article
Cite this article
Wang, N., Ji, X., Wang, H. et al. BODIPY-based Fluorescent Probe for the Detection of Cysteine in Living Cells. ANAL. SCI. 36, 1317–1321 (2020). https://doi.org/10.2116/analsci.20P134
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2116/analsci.20P134