Abstract
A novel near-infrared fluorescent probe SWJT-5 based on dicyanoisophorone was synthesized. It achieved the rapid (within 40 s) and discriminative detection of Cys over Hcy and GSH with a large Stokes shift (205 nm). It showed high selectivity and sensitivity for Cys, and had an obvious enhancement of fluorescence emission. The detection limit was 0.43 μM. This probe also had low background interference and little damage to biological samples. Therefore, SWJT-5 had been applied to bioimaging in living cells successfully.
Similar content being viewed by others
Availability of Data and Material
All data generated or analysed during this study are included in this article.
References
He L, Yang X, Xu K, Kong X, Lin W (2017) Chem Sci 8:6257–6265
Wang P, Wang Y, Li N, Huang J, Wang Q, Gu Y (2017) Sens Actuators B 245:297–304
Niu L-Y, Chen Y-Z, Zheng H-R, Wu L-Z, Tung C-H, Yang Q-Z (2015) Chem Soc Rev 44:6143–6160
Zhang H, Feng W, Feng G (2017) Dyes Pigm 139:73–78
Niu L-Y, Guan Y-S, Chen Y-Z, Wu L-Z, Tung C-H, Yang Q-Z (2012) J Am Chem Soc 134:18928–18931
Zhang J, Wang J, Liu J, Ning L, Zhu X, Yu B, Liu X, Yao X, Zhang H (2015) Anal Chem 87:4856–4863
Liu Y, Yu D, Ding S, Xiao Q, Guo J, Feng G (2014) ACS Appl Mater Interfaces 6:17543–17550
Lee S, Li J, Zhou X, Yin J, Yoon J (2018) Coord Chem Rev 366:29–68
Jung HS, Chen X, Kim JS, Yoon J (2013) Chem Soc Rev 42:6019–6031
Hernandez LE, Sobrino-Plata J, Montero-Palmero MB, Carrasco-Gil S, Flores-Caceres ML, Ortega-Villasante C, Escobar C (2015) J Exp Bot 66:2901–2911
Mao G-J, Liang Z-Z, Bi J, Zhang H, Meng H-M, Su L, Gong Y-J, Feng S, Zhang G (2019) Anal Chim Acta 1048:143–153
Mao G-J, Gao G-Q, Liang Z-Z, Wang Y-Y, Su L, Wang Z-X, Zhang H, Ma Q-J, Zhang G (2019) Anal Chim Acta 1081:184–192
Mao G-J, Liang Z-Z, Gao G-Q, Wang Y-Y, Guo X-Y, Su L, Zhang H, Ma Q-J, Zhang G (2019) Anal Chim Acta 1092:117–125
Mao G-J, Gao G-Q, Dong W-P, Wang Q-Q, Wang Y-Y, Li Y, Su L, Zhang G (2021) Talanta 221:121607–121613
Mao G-J, Wang Y-Y, Dong W-P, Meng H-M, Wang Q-Q, Luo X-F, Li Y, Zhang G (2021) Spectrochim Acta A 249:119326–119333
Maeda H, Matsuno H, Ushida M, Katayama K, Saeki K, Itoh N (2005) Angew Chem Int Ed 44:2922–2925
Shao J, Guo H, Ji S, Zhao J (2011) Biosens Bioelectron 26:3012–3017
Fan L, Zhang W, Wang X, Dong W, Tong Y, Dong C, Shuang S (2019) Analyst 144:439–447
Li M, Wu X, Wang Y, Li Y, Zhu W, James TD (2014) Chem Commun 50:1751–1753
Kim T-K, Lee D-N, Kim H-J (2008) Tetrahedron Lett 49:4879–4881
Kong F, Liu R, Chu R, Wang X, Xu K, Tang B (2013) Chem Commun 49:9176–9178
Li Y (2017) Luminescence 32:1385–1390
Feng S, Fang Y, Feng W, Xia Q, Feng G (2017) Dyes Pigm 146:103–111
Manna S, Karmakar P, Ali SS, Guria UN, Samanta SK, Sarkar R, Datta P, Mahapatra AK (2019) Anal Methods 11:1199–1207
Qi Y, Huang Y, Li B, Zeng F, Wu S (2018) Anal Chem 90:1014–1020
Zhou J, Yu C, Li Z, Peng P, Zhang D, Han X, Tang H, Wu Q, Li L, Huang W (2019) Anal Methods 11:1312–1316
Xu H, Wu S-L, Lin N-J, Lu Y, Xiao J, Wang Y-W, Peng Y (2021) Sens Actuators B 346:130484–130489
Liu H-B, Xu H, Guo X, Xiao J, Cai Z-H, Wang Y-W, Peng Y (2021) Org Biomol Chem 19:873–877
Fu Z-H, Han X, Shao Y, Fang J, Zhang Z-H, Wang Y-W, Peng Y (2017) Anal Chem 89:1937–1944
Wang B-J, Liu R-J, Fang J, Wang Y-W, Peng Y (2019) Chem Commun 55:11762–11765
Yang Y-L, Zhang F-M, Wang Y-W, Zhang B-X, Fang R, Fang JG, Peng Y (2015) Chem-Asian J 10:422–426
Du W, Liu R-J, Fang J, Gao H, Wang Y-W, Peng Y (2019) Tetrahedron 75:130477–130481
Zhu M, Fan F, Zhao Z, Wu X, Wang L, Na R, Wang Y (2019) J Mol Liq 296:111832–111841
Zacuto MJ (2019) J Org Chem 84:6465–6474
Lee S-C, Lee C-L, Heo J, Jeong C-U, Lee G-H, Kim S, Yoon W, Yun H, Park SO, Kwak SK, Park S-H, Kwon O-P (2018) Chem-Eur J 24:2888–2897
Wang J, Li B, Zhao W, Zhang X, Luo X, Corkins ME, Cole SL, Wang C, Xiao Y, Bi X, Pang Y, McElroy CA, Bird AJ, Dong Y (2016) ACS Sens 1:882–887
Tamima U, Song CW, Santra M, Reo YJ, Banna H, Islam MR, Ahn KH (2020) Sens Actuators B 322:128588–128597
Guo Z, Nam S, Park S, Yoon J (2012) Chem Sci 3:2760–2765
Zhang X, Zhang L, Ma WW, Zhou Y, Lu ZN, Xu S (2019) Front Chem 7:00032–00039
Zhang H, Yan C, Li H, Shi L, Wang R, Guo Z, Zhu W-H (2020) ACS Appl Bio Mater 4:2001–2008
Niu W, Guo L, Li Y, Shuang S, Dong C, Wong MS (2016) Anal Chem 88:1908–1914
Lee C, Yang W, Parr RG (1988) Phys Rev B Condens Matter 37:785–789
Yellaturu CR, Bhanoori M, Neeli I, Rao GN (2002) J Biol Chem 277:40148–40155
Acknowledgements
We would like to thank Analytical and Testing Center of Southwest Jiaotong University for the laser confocal microscope test.
Funding
This work was supported by the National Natural Science Foundation of China (No. 22071200), and the Fundamental Research Funds for the Central Universities (Nos. 2682020CX55, 2682021ZTPY011 and XJ2021KJZK004) by MoE of China. We also thank Science and Technology Department of Sichuan Province (2020JDRC0021), and Key Research Project of Sichuan Province Science and Technology Plan (2020YFS0489).
Author information
Authors and Affiliations
Contributions
Yan-Ya Wang: conceived the work and performed most of the experiments. Xue-Shuang Yu, Xin-Jie Li, and Hong-Bo Liu carried out the bioimaging. Yan-Ya Wang, Xue-Shuang Yu, Xin-Jie Li, Hong-Bo Liu, Xi Zhu,Ya-Wen Wang, and Yu Peng analyzed the data and wrote the manuscript. Yu Peng supervised the project and conceived the style of the manuscript.
Corresponding author
Ethics declarations
Ethics Approval
Not applicable.
Consent to Participate
Informed consent was obtained from all individual participants included in the study.
Consent for Publication
The participant has consented to the submission of this work to the journal.
Competing Interest
The authors declare that they have no known competing financial interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Wang, YY., Yu, XS., Li, XJ. et al. A Rapid Near-Infrared Fluorescent Probe for Cysteine Based on Isophorone and its Application in B16 Cell Imaging. J Fluoresc 32, 1661–1667 (2022). https://doi.org/10.1007/s10895-022-02964-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-022-02964-9