肼二腙类多功能长波发射荧光探针的合成及其铜配合物对H2S的识别
收稿日期: 2018-02-08
修回日期: 2018-03-16
网络出版日期: 2018-04-04
基金资助
辽宁省自然科学基金（No.20170540019）、国家自然科学基金（Nos.21304009，21476029，U1608222）和辽宁省博士科研启动基金（No.20170520416）资助项目.
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).
以1，4-二乙基-7-羟基四氢喹喔啉-6-甲醛为基础，设计合成了一种具有长波长发射、较大斯托克斯位移的新型肼二腙类荧光探针L.在探针L的二甲基亚砜（DMSO）溶液中加入Cu2+和Co2+后，溶液颜色由黄色分别变为粉色和无色，可裸眼识别Cu2+和Co2+.利用L与Cu2+形成的配合物，在DMSO/H2O（V∶V=7∶3，HEPES，1×10-2 mol/L，pH=7.4）缓冲溶液中可荧光“OFF-ON”识别H2S.试纸条实验表明，L-Cu2+对不同浓度H2S显色明显，可以通过裸眼和荧光双通道快速检测H2S.此外，利用Discovery Studio分子模拟软件，通过分子L结构反向找靶，并用CDOCKER程序进行分子对接，发现分子L对2x0v蛋白（来自人类的P53蛋白）有很好的结合作用，有望在医药领域得到应用.
钟克利 , 赵杰 , 李秋莹 , 侯淑华 , 汤轶伟 , 边延江 , 汤立军 . 肼二腙类多功能长波发射荧光探针的合成及其铜配合物对H2S的识别[J]. 有机化学, 2018 , 38(7) : 1786 -1791 . DOI: 10.6023/cjoc201802014
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
[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.
/
| 〈 |
|
〉 |
