Chinese Journal of Organic Chemistry >
Synthesis of Multifunctional Long-Wavelength-Emitting Fluorescent Probe Based on Hydrazine Dihydrazone and Its Copper Complex for Detection of H2S
Received date: 2018-02-08
Revised date: 2018-03-16
Online published: 2018-04-04
Supported by
Project supported by the Natural Science Foundation of Liaoning Province (No. 20170540019), the National Natural Science Foundation of China (Nos. 21304009, 21476029, U1608222) and the Doctoral Scientific Research Foundation of Liaoning Province (No. 20170520416).
A novel fluorescent probe L with long wavelength emission and large Stokes shift was designed and synthesized based on 1,4-diethyl-7-hydroxytetrahydroquinoxaline-6-carboxaldehyde. The color of L was changed from yellow to pink and colorless upon addition of Cu2+ and Co2+ respectively in dimethylsulfoxide (DMSO), which illustrated that probe L could recognize Cu2+ and Co2+ by naked eyes. The complex L-Cu2+ could recognize H2S with fluorescence "OFF-ON" in DMSO/H2O (V:V=7:3, HEPES, 1×10-2 mol/L, pH=7.4). The test strip assay showed that the L-Cu2+ pretreated test strip showed obvious color changes toward different concentrations of H2S, which indicated that H2S could be rapidly detected by naked eyes and fluorescent double channel. In addition, the molecular target of compound L can be searched by utilizing the reverse docking method in Discovery Studio (DS) software. Then, docking analysis was performed using CDOCKER module of DS, and it was found that molecule L has a good combination to 2x0v protein (P53_human). Therefore, it is expected to be applied in the medicine field.
Key words： long wavelength emission; fluorescent probe; H2S; recognization; molecular docking
Zhong Keli , Zhao Jie , Li Qiuying , Hou Shuhua , Tang Yiwei , Bian Yanjiang , Tang Lijun . Synthesis of Multifunctional Long-Wavelength-Emitting Fluorescent Probe Based on Hydrazine Dihydrazone and Its Copper Complex for Detection of H2S[J]. Chinese Journal of Organic Chemistry, 2018 , 38(7) : 1786 -1791 . DOI: 10.6023/cjoc201802014
[1] Liu, K.; Liu, C.; Shang, H.; Ren, M.; Lin, W. Sens. Actuators, B 2018, 256, 342.
[2] Gadalla, M. M.; Snyder, S. H. J. Neurochem. 2010, 113, 14.
[3] Li, L.; Rose, P.; Moore, P. K. Annu. Rev. Pharmacol. Toxicol. 2011, 51, 169.
[4] Yan, H.; Du, J.; Tang, C. Biochem. Biophys. Res. Commun. 2004, 313, 22.
[5] Geng, B.; Yang, J.; Qi, Y.; Zhao, J.; Pang, Y.; Du, J.; Tang, C. Biochem. Biophys. Res. Commun. 2004, 313, 362.
[6] Liu, H.; Weng, L.; Yang, C. Microchim. Acta 2017, 184, 1267.
[7] Furne, J.; Saeed, A.; Levitt, M. D. Am. J. Physiol.:Regul., Integr. Comp. Physiol. 2008, 295, R1479.
[8] Searcy, D. G.; Peterson, M. A. Anal. Biochem. 2004, 324, 269.
[9] Pandey, S. K.; Kim, K.-H. Environ. Sci. Technol. 2009, 43, 3020.
[10] Gao, M.; Yu, F.; Chen, L. Prog. Chem. 2014, 26, 1065 (in Chinese).
(高敏, 于法标, 陈令新, 化学进展, 2014, 26, 1065.)
[11] Yang, L.; Su, Y.; Sha, Z.; Geng, Y.; Qi, F.; Song, X. Org. Biomol. Chem. 2018.
[12] Chan, J.; Dodani, S. C.; Chang, C. J. Nat. Chem. 2012, 4, 973.
[13] Kumar, N.; Bhalla, V.; Kumar, M. Coord. Chem. Rev. 2013, 257, 2335.
[14] Zhou, C.; Qiu, B.; Zeng, Y.; Chen, J.; Yu, T.; Li, Y. Chin. J. Org. Chem. 2017, 37, 92 (in Chinese).
(周婵, 邱波, 曾毅, 陈金平, 于天君, 李嫕, 有机化学, 2017, 37, 92.)
[15] Yu, H.; Li, H.; Zhang, X.; Xiao, Y.; Fang, P.; Lü, C.; Hou, W. Acta Chim. Sinica. 2015, 73, 450 (in Chinese).
(于海波, 李红玲, 张新富, 肖义, 方沛菊, 吕春娇, 侯伟, 化学学报, 2015, 73, 450.)
[16] He, P.; Tang, L.; Zhong, K.; Hou, S.; Yan, X. Chin. J. Org. Chem. 2017, 37, 423 (in Chinese).
(何平, 汤立军, 钟克利, 侯淑华, 燕小梅, 有机化学, 2017, 37, 423.)
[17] Ding, S.; Feng, W.; Feng, G. Sens. Actuators, B 2017, 238, 619.
[18] Bae, S. K.; Heo, C. H.; Choi, D. J.; Sen, D.; Joe, E.-H.; Cho, B. R.; Kim, H. M. J. Am. Chem. Soc. 2013, 135, 9915.
[19] Henthorn, H. A.; Pluth, M. D. J. Am. Chem. Soc. 2015, 137, 15330.
[20] Xuan, W.; Sheng, C.; Cao, Y.; He, W.; Wang, W. Angew. Chem., Int. Ed. 2012, 51, 2282.
[21] Fan, F.; Jing, J.; Chen, X. Chin. J. Org. Chem. 2014, 34, 2178 (in Chinese).
(范方禄, 靖金球, 陈雪梅, 有机化学, 2014, 34, 2178.)
[22] Lin, V. S.; Chen, W.; Xian, M.; Chang, C. J. Chem. Soc. Rev. 2015, 44, 4596.
[23] Lin, V. S.; Chang, C. J. Curr. Opin. Chem. Biol. 2012, 16, 595.
[24] Yu, F.; Han, X.; Chen, L. Chem. Commun. 2014, 50, 12234.
[25] Kaushik, R.; Ghosh, A.; Jose, D. A. Coord. Chem. Rev. 2017, 347, 141.
[26] Huang, B.; Chen, Y.; Guo, Z.; He, W. Chin. J. Inorg. Chem. 2014, 34, 2283 (in Chinese).
(黄彬, 陈韵聪, 郭子建, 何卫江, 无机化学学报, 2013, 34, 2283.)
[27] Liu, T.; Xu, Z.; Spring, D. R.; Cui, J. Org. Lett. 2013, 15, 2310.
[28] Ji, Y.; Xia, L.-J.; Chen, L.; Guo, X.-F.; Wang, H.; Zhang, H.-J. Talanta 2018, 181, 104.
[29] Gu, B.; Su, W.; Huang, L.; Wu, C.; Duan, X.; Li, Y.; Xu, H.; Huang, Z.; Li, H.; Yao, S. Sens. Actuators, B 2018, 255, 2347.
[30] Wang, B.; Li, P.; Yu, F.; Chen, J.; Qu, Z.; Han, K. Chem. Commun. 2013, 49, 5790.
[31] Lou, Z.; Li, P.; Pan, Q.; Han, K. Chem. Commun. 2013, 49, 2445.
[32] Jagtap, A. R.; Satam, V. S.; Rajule, R. N.; Kanetkar, V. R. Dyes Pigm. 2009, 82, 84.
[33] Liu, X.; Qi, F.; Su, Y.; Chen, W.; Yang, L.; Song, X. J. Mater. Chem. C 2016, 4, 4320.
[34] Hou, P.; Chen, S.; Wang, H.; Wang, J.; Voitchovsky, K.; Song, X. Chem. Commun. 2014, 50, 320.
[35] Tang, L.; Cai, M.; Huang, Z.; Zhong, K.; Hou, S.; Bian, Y.; Nandhakumar, R. Sens. Actuators, B 2013, 185, 188.
[36] Tang, L.; Zheng, Z.; Zhong, K.; Bian, Y. Tetrahedron Lett. 2016, 57, 1361.
[37] Wang, M.; Sun, G.-B.; Du, Y.-Y.; Tian, Y.; Liao, P.; Liu, X.-S.; Ye, J.-X.; Sun, X.-B. Front. Pharmacol. 2017, 8, 353.
[38] Zhang, J.-Q.; Luo, Y.-J.; Xiong, Y.-S.; Yu, Y.; Tu, Z.-C.; Long, Z.-J.; Lai, X.-J.; Chen, H.-X.; Luo, Y.; Weng, J. J. Med. Chem. 2016, 59, 7268.
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