A Nitroolefin Based Thiol Fluorescent Probe: Synthesis and Application in Bioimaging

doi:10.6023/cjoc201911015

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1239-1245.DOI: 10.6023/cjoc201911015 Previous Articles Next Articles

一种基于硝基烯烃的硫醇荧光探针的合成及生物成像研究

郭振波, 郑雪阳, 李雪艳, 贾清菲, 张平竹, 魏超, 李小六

河北大学化学与环境科学学院药物化学与分子诊断教育部重点实验室河北省化学生物学重点实验室河北保定 071002

收稿日期:2019-11-08 修回日期:2019-12-04 发布日期:2020-01-03
通讯作者: 魏超, 李小六 E-mail:weichao@hbu.edu.cn;lixl@hbu.edu.cn
基金资助:
国家自然科学基金（No.21572044）、河北省自然科学基金（No.B2018201234）和河北省高等学校科学技术研究（No.QN2017015）资助项目.

A Nitroolefin Based Thiol Fluorescent Probe: Synthesis and Application in Bioimaging

Guo Zhenbo, Zheng Xueyang, Li Xueyan, Jia Qingfei, Zhang Pingzhu, Wei Chao, Li Xiaoliu

Key Laboratory of Chemical Biology of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Environmental Science, Hebei University, Baoding, Hebei 071002

Received:2019-11-08 Revised:2019-12-04 Published:2020-01-03
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572044), the Natural Science Foundation of Hebei Province (No. B2018201234) and the Colleges and Universities Science Technology Research Project of Hebei Province (No. QN2017015).

1. 201239S.pdf(1050KB)

Abstract

Intracellular small-molecule thiols, such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play pivotal roles in several physiological and pathological processes. A bodipy-nitroolefin-conjugated fluorescent probe based on photoinduced electron transfer (PET) mechanism was designed and successfully constructed. The probe selectively responds to biothiols by Michael addition reaction of the sulfhydryl group to the double bond activated by Nitroolefin moiety and gives an off-on fluorescent response. The fluorescence detection limit for GSH was calculated to be 11×10^-9 mol/L. The results of fluorescence confocal imaging indicated that the probe has appreciable cell permeability and can serve as a fluorescent probe for detecting biothiols in living cells and zebrafish.

Key words: thiol, nitroolefin, fluorescent probe, bioimaging

Cite this article

Guo Zhenbo, Zheng Xueyang, Li Xueyan, Jia Qingfei, Zhang Pingzhu, Wei Chao, Li Xiaoliu. A Nitroolefin Based Thiol Fluorescent Probe: Synthesis and Application in Bioimaging[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1239-1245.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Wood, Z. A.; Schröder, E.; Robin Harris, J.; Poole, L. B. Trends Biochem. Sci. 2003, 28, 32.
[2] Townsend, D. M.; Tew, K. D.; Tapiero, H. Biomed. Pharmacother. 2003, 57, 145.
[3] Reddie, K. G.; Carroll, K. S. Curr. Opin. Chem. Biol. 2008, 12, 746.
[4] Rusin, O.; St Luce, N. N.; Agbaria, R. A.; Escobedo, J. O.; Jiang, S.; Warner, I. M.; Dawan, F. B.; Lian, K.; Strongin, R. M. J. Am. Chem. Soc. 2004, 126, 438.
[5] Paulsen, C. E.; Carroll, K. S. Chem. Rev. 2013, 113, 4633.
[6] Seshadri, S.; Beiser, A.; Selhub, J.; Jacques, P. F.; Rosenberg, I. H.; D'Agostino, R. B.; Wilson, P. W. F.; Wolf, P. A. New Engl. J. Med. 2002, 346, 476.
[7] Kaluzna-Czaplinska, J.; Zurawicz, E.; Michalska, M.; Rynkowski, J. Acta Biochim. Pol. 2013, 60, 137.
[8] Estrela, J. M.; Ortega, A.; Obrador, E. Crit. Rev. Clin. Lab. Sci. 2006, 43, 143.
[9] Holmström, K. M.; Finkel, T. Nat. Rev. Mol. Cell Biol. 2014, 15, 411.
[10] Sippel, T. O. J. Histochem. Cytochem. 1981, 29, 314.
[11] Jung, H. S.; Chen, X.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2013, 42, 6019.
[12] Wang, S. Q.; Shen, S. L.; Zhang, Y. R.; Dai, X.; Zhao, B. X. Chin. J. Org. Chem. 2014, 34, 1717(in Chinese). (王胜清, 申世立, 张延如, 戴溪, 赵宝祥, 有机化学, 2014, 34, 1717.)
[13] Niu, L.-Y.; Chen, Y.-Z.; Zheng, H.-R.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Chem. Soc. Rev. 2015, 44, 6143.
[14] Yan, P. P.; Wang, T.; Zhang, D.; Ma, X. X. Chin. J. Org. Chem. 2019, 39, 916(in Chinese). (闫沛沛, 王婷, 张丹, 马晓雪, 有机化学, 2019, 37, 916.)
[15] Hui, X. P.; Yin, C.; Ma, J.; Xu, P. F. Synth. Commun. 2009, 39, 676.
[16] Sun, Y.-Q.; Chen, M.; Liu, J.; Lv, X.; Li, J.-F.; Guo, W. Chem. Commun. 2011, 47, 11029.
[17] Zhang, M.; Wu, Y.; Zhang, S.; Zhu, H.; Wu, Q.; Jiao, L.; Hao, E. Chem. Commun. 2012, 48, 8925.
[18] Kang, J.; Huo, F.; Chao, J.; Yin, C. Spectrochim. Acta A 2018, 195, 16.
[19] Wang, L. Y.; Chen, X. G.; Cao, D. R. Sens. Actuators, B 2017, 244, 531.
[20] Jung, H. S.; Ko, K. C.; Kim, G. H.; Lee, A. R.; Na, Y. C.; Kang, C.; Lee, J. Y.; Kim, J. S. Org. Lett. 2011, 13, 1498.
[21] Ma, C.; Wei, C.; Li, X.; Zheng, X.; Chen, B.; Wang, M.; Zhang, P.; Li, X. Dyes Pigm. 2019, 162, 624.
[22] Matsumoto, T.; Urano, Y.; Takahashi, Y.; Mori, Y.; Terai, T.; Nagano, T. J. Org. Chem. 2011, 76, 3616.
[23] Kálai, T.; Hideg, K. Tetrahedron 2006, 62, 10352.

一种基于硝基烯烃的硫醇荧光探针的合成及生物成像研究

A Nitroolefin Based Thiol Fluorescent Probe: Synthesis and Application in Bioimaging

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yingzhen Zhang, Dandan Jiang, Juanhua Li, Jingjing Wang, Kunming Liu, Jinbiao Liu. Construction Strategy and Imaging of Highly Selective Selenocysteine Fluorescent Probes [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 41-53.
[2]	Haoruo Shangguan, Ping Huang, Zhenya Dai, Ping Wang. Synthesis and Application of β-Thiolated Amino Acids [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3089-3097.
[3]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[4]	Binghui Ding, Shaohui Han, Haiqing Xiong, Benhua Wang, Bojun Zuo, Xiangzhi Song. A Highly Selective Ratiometric Fluorescent Probe for the Detection of Hypochlorite in Acute Lung Injury [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2878-2884.
[5]	Yijun Shi, Xinyue Sun, Han Cao, Fusheng Bie, Jie Ma, Zhe Liu, Xingshun Cong. Thioesterification of Esters with Primary Aliphatic Thiols at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2499-2505.
[6]	Feiran Liu, Jing Jing, Xiaoling Zhang. Research Progress of Fluorescent Probes for Cysteine Targeting Cellular Organelles [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2053-2067.
[7]	Tiantian Liu, Hongpeng Zhang, Xiaomeng Jiao, Yinjuan Bai. Research Progress of Multi-signal Fluorescent Probes for Simultaneous Detection of Biothiols [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2081-2095.
[8]	Yifang Li, Yao Wang, Huawei Niu, Xiujin Chen, Zhaozhou Li, Yongguo Wang. Research Progress of Sulfur Dioxide Fluorescent Probe Targeting Mitochondria [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1952-1962.
[9]	Yasir Mumtaz, Jie Liu, Xin Huang. Copper-Promoted Trifluoromethylthiolation of Anilines with CF₃SO₂Na [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 679-685.
[10]	Zhihua Chen, Yan Hu, Lili Ma, Ziyi Zhang, Chuanxiang Liu. Rational Design of ortho-Vinylhydropyridine-Assisted Amino-fluorophore as Hypochlorite Fluorescent Probe [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 718-724.
[11]	Hongwei Tang, Chao Wang, Keli Zhong, Shuhua Hou, Lijun Tang, Yanjiang Bian. A Naked-Eye and Fluorescent Dual-Channel Probe for Rapid Detection of Hg²⁺ and Its Multiple Applications [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 712-717.
[12]	Xuehui Hou, Yihui Li, Qingling Zhang, Juntao Liu, Yajing Chen. Research and Application of Pyridinium 1,4-Zwitterionic Thiolates in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3844-3860.
[13]	Yanhui Ma, Yuqian Wu, Xiaoxu Wang, Gui Gao, Xin Zhou. Research Progress of Near-Infrared Fluorescent Probes Based on 1,3-Dichloro-7-hydroxy-9,9-dimethyl-2(9H)-acridone (DDAO) [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 94-111.
[14]	Yaxin Yang, Lin Chen, Xiaoling Hu, Keli Zhong, Shidi Li, Xiaomei Yan, Jinglin Zhang, Lijun Tang. Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 308-312.
[15]	Siyi Zhou, Xu Ding, Yongmei Zhao, Jinghua Li, Wen Luo. A Flavone-Based Long-Wavelength Fluorescent Probe to Detect Biothiols in vitro and in vivo [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 178-185.