Chinese Journal of Organic Chemistry >
Synthesis of Reversible Fluorescence Quenched Probe for Cu2+ and Imaging in PK-15 cells
Received date: 2015-12-23
Revised date: 2016-01-15
Online published: 2016-02-24
Supported by
Project supported by the Natural Science Foundation of Gansu Province (No. 2014GS03265 ).
A new pyrazoline derivative 1-(2-hydroxyphenyl)-4-(9-anthryl)-3-benzothiazole pyrazolin (P1) was designed and synthesized. The recognition properties of the target compound P1 with metal ions had been investigated by UV absorption and fluorescence spectrophotometry. The probe exhibits several favorable features, including instantaneous, reversible recognition, high sensitivity and selectivity to copper ions. Cytotoxicity test and fluorescent immunoassay results show that compound P1 has good biocompatibility and low toxicity with its IC50 value of 376.558 μmol/L.
Key words： pyrazoline; fluorescent probe; copper ions; recognition; PK-15 living cells
Zhang Yingpeng , You Caixia , Yang Yunshang , Liu Xiaoyu , Guo Huichen , Dong Yuying . Synthesis of Reversible Fluorescence Quenched Probe for Cu2+ and Imaging in PK-15 cells[J]. Chinese Journal of Organic Chemistry, 2016 , 36(6) : 1401 -1406 . DOI: 10.6023/cjoc201512033
[1] De Silva, A. P.; Gunaratne, H. N.; Gunnlaugsson, T.; Huxley, A. J.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
[2] Sun, H, Z.; Chen, R.; Zhi, Z, M. Prog. Chem. 2002, 14, 257 (in Chinese). (孙红哲, 陈嵘, 支志明, 化学进展, 2002, 14, 257.)
[3] Andrews, N. C. Curr. Opin. Chem. Biol. 2002, 6, 181.
[4] Waggoner, D. J.; Bartnikas, T. B.; Gitlin, J. D. Neurobiol. Dis. 1999, 6, 221.
[5] Finkel, T.; Serrano, M.; Blasco, M. A. Nature 2007, 448, 767.
[6] Waggoner, D. J.; Bartnikas, T. B.; Gitlin, J. D. Neurobiol. Dis. 1999, 6, 221.
[7] Camakaris, J.; Voskoboinik, I.; Mercer, J. F. Biochem. Biophys. Res. Commun. 1999, 261, 225.
[8] Bruijn, L. I.; Miller, T. M.; Cleveland, D. W. Annu. Rev. Neurosci. 2004, 27, 723.
[9] Hung, Y. H.; Bush, A. I.; Cherny, R. A. J. Biol. Inorg. Chem. 2010, 15, 61.
[10] Brown, D. R.; Kozlowski, H. Dalton Trans. 2004, 13, 1907.
[11] Fan, J. L.; Xu, Q. L.; Zhu, H.; Peng, X. J. Chin. J. Org. Chem. 2014, 34, 1623 (in Chinese). (樊江莉, 徐群利, 朱浩, 彭孝军, 有机化学, 2014, 34, 1623.)
[12] Du, J. J. Ph.D. Dissertation, Dalian University of Technology, Dalian, 2009 (in Chinese). (杜建军, 博士论文, 大连理工大学, 大连, 2009.)
[13] Ma, W. H.; Xia, W.; Han, H. Y.; Song, B.; Sun, L. W.; Liang, C. H. Acta Chim. Sinica 2012, 70, 917 (in Chinese). (马文辉, 夏威, 徐群, 韩宏彦, 宋波, 孙丽微, 梁春花, 化学学报, 2012, 70, 917.)
[14] Chen, K.; Guo, Y.; Lu, Z.; Yang, B.; Shi, Z. Chin. J. Chem. 2010, 28, 55.
[15] Pan, M.; Lin, X. M.; Li, G. B.; Su, C. Y. Coord. Chem. Rev. 2011, 255, 1921.
[16] Guerchais, V.; Fillaut, J. L. Coord. Chem. Rev. 2011, 255, 2448.
[17] Wen, Z. C.; Yang, R.; He, H.; Jiang, Y. B. Chem. Commun. 2006, 42, 106.
[18] Aksuner, N.; Henden, E.; Yilmaz, I.; Cukurovali, A. Dyes Pigm. 2009, 83, 211.
[19] Liu, Z.; Zhang, C.; Wang, X.; He, W.; Guo, Z. D. Org Lett. 2012, 14, 4378.
[20] Chen, X.; Tong, A. Dyes Pigm. 2012, 95, 776.
[21] Wang, S. Q.; Liu, S. Y.; Wang, H. Y.; Zheng, X. X.; Yuan, X.; Liu, Y. Z.; Zhao, B. X. J. Fluoresc. 2014, 24, 657.
[22] Kim, S. H.; Kim, J. S.; Park, S. M.; Chang, S. K. Org Lett. 2006, 8, 371.
[23] Mu, H.; Gong, R.; Ma, Q.; Sun, Y.; Fu, E. Tetrahedron Lett. 2007, 48, 5525.
[24] Zou, M.; Lu, J. R.; Xin, C. W.; Bao, X. R.; Yang, B.; Zhu, S. S. Chin. J. Org. Chem. 2010, 30, 1201 (in Chinese). (邹敏, 卢俊瑞, 辛春伟, 鲍秀荣, 杨波, 朱姗姗, 有机化学, 2010, 30, 1201.)
[25] Luo, Z. G.; Liu, Z. Y.; Zhang, G. L.; Ye, J. X.; Yang, Z. H. Chin. J. Org. Chem. 2014, 34, 392 (in Chinese). (罗志刚, 刘正勇, 张广龙, 叶杰欣, 杨卓鸿, 有机化学, 2014, 34, 392.)
[26] Zhang, S. Q.; Wang, L.; Wang, Z. Y. Chem. Res. Appl. 2014, 26, 777 (in Chinese). (张思琪, 王路, 王振宇, 化学研究与应用, 2014, 26, 777.)
[27] Zhu, W. Q.; Wu, Y. Z.; Zhen, X. Y. Spectrosc. Spectral Anal. 2005, 25, 509 (in Chinese). (朱文清, 吴有智, 郑新友, 光谱学与光谱分析, 2005, 25, 509.)
[28] Lei, G. D.; Lu, Z. Y.; Xie, M. G. Chem. Res. Appl. 2006, 18, 240 (in Chinese). (雷广东, 卢志云, 谢明贵, 化学研究与应用, 2006, 18, 240.)
[29] Chen, Y.; Cai, D. H.; Fan, Y. M. Chem. Technol. Mark. 2005, 28, 24 (in Chinese). (程艺, 蔡定汉, 范约明, 化工科技市场, 2005, 28, 24.)
[30] Wang, M.; Zhang, J.; Liu, J.; Xu, C.; Ju, H. J. Lumin. 2002, 99, 79.
[31] Li, M. M.; Huang, S. Y.; Ye, H.; Ge, F.; Miao, J. Y.; Zhao, B. X. J. Fluoresc. 2013, 23, 799.
[32] Zhang, Z.; Wang, F. W.; Wang, S. Q.; Ge, F.; Zhao, B. X.; Miao, J. Y. Org. Biomol. Chem. 2012, 10, 8640.
[33] Gong, Z. L.; Ge, F.; Zhao, B. X. Sens. Actuators, B 2011, 159, 148.
[34]
[34] Shen, J, S.; Sun, D, D.; Fu, L, C. Spectrosc. Spectral Anal. 2005, 25, 232 (in Chinese). (沈景山, 孙丹丹, 付连春, 光谱学与光谱分析, 2005, 25, 232.)
[35] Sheng, Z, H.; Zhu, Y, L.; Kan, Y, H. Chem Reag. 2006, 28, 16 (in Chinese). (盛振环, 朱玉兰, 阚玉和, 化学试剂, 2006, 28, 16.)
[36] Shi, H. B.; Ji, S. J.; Bian, B. Dyes Pigm. 2007, 73, 394.
[37] Bian, B.; Ji, S. J.; Shi, H. B. Dyes Pigm. 2008, 76, 348.
[38] Hu, S, L.; Zhang, S, S.; Hu, Y.; Tao, Q.; Wu, A, X. Dyes Pigm. 2013, 96, 509.
[39] Zhang, Z.; Wang, F. W.; Wang, S. Q.; Ge, F.; Zhao, B. X. Org. Biomol. Chem. 2012, 10, 8640.
[40] Gong, Z. L.; Ge, F.; Zhao, B. X. Sens. Actuators, B 2011, 159, 148.
[41] Li, M. M.; Zhao, W. B.; Zhang, T. T.; Fan, W. L.; Xu, Y.; Xiao, Y.; Zhao, B. X. J. Fluoresc. 2013, 23, 1263.
[42] Li, M. M.; Huang, S. Y.; Ye, H.; Ge, F.; Miao, J. Y.; Zhao, B. X. J. Fluoresc. 2013, 23, 799.
[43] Wang, S. Q.; Gao, Y.; Wang, H. Y.; Zheng, X. X.; Shen, S. L.; Zhang, Y. R.; Zhao, B. X. Spectrochim. Acta, Part A 2013, 106, 110.
[44] Zhang, T. T.; Wang, F. W.; Li, M. M.; Liu, J. T.; Miao, J. Y.; Zhao, B. X. Sens. Actuators, B 2013, 186, 755.
[45] Wang, S. Q.; Liu, S. Y.; Wang, H. Y.; Zheng, X. X.; Liu, Y. Z.; Zhao, B. X. J. Fluoresc. 2014, 24, 657.
[46] Zhang, T. T.; Chen, X. P.; Liu, J. T.; Zhang, L. Z.; Chu, J. M.; Su, L.; Zhao, B. X. RSC Adv. 2014, 4, 16973.
[47] Li, M. M.; Wang, F. W.; Wang, X. Y.; Zhang, T. T.; Xu, Y.; Xiao, Y.; Zhao, B. X. Anal. Chim. Acta 2014, 826, 77.
[48] Yin, D. D.; Wu, J.; Xie, C. B.; Cao, Z. P.; Lv, Q.; Zhang, R. Q. Spectrosc. Spectral Anal. 2013, 33, 3263 (in Chinese). (尹丹丹, 吴静, 谢超波, 曹知平, 吕清, 张仁权, 光谱学与光谱分析, 2013, 33, 3263.)
[49] Chen, G. F. Ph.D. Dissertation, Tianjin University of Technology, Tianjin, 2008 (in Chinese). (陈国锋, 博士论文, 天津大学, 天津, 2008.)
[50] Zhang, Y.; Niu, C. G.; Zeng, G.. M.; Qin, P. Z.; Li, H. X.; Peng, B. Chin. J. Anal. Lab. 2009, 28, 28 (in Chinese). (张妍, 牛承岗, 曾光明, 秦品珠, 李慧霞, 彭博, 分析实验室, 2009, 28, 28.)
[51] Li, J. P.; Lin, Z. P.; Zhang, X. H. Beilstein J. Org. Chem. 2007, 3, 13.
[52] Zhou, T, H.; Wang, E, K.; Lu, W, Z. Handbook of Analytical Chemistry, Chemical Industry Press, Beijing, 1999, p. 178 (in Chinese). (周同惠, 汪尔康, 陆婉珍, 分析化学手册, 化学工业出版社, 1999, 178.)
[53] Sashidhara, K. V.; Avula, S. R.; Doharey, P. K.; Singh, L. R.; Balaramnavar, V. M.; Gupta, J.; Saxena, J. K. Eur. J. Med. Chem. 2015, 103, 418.
[54] Dong, B.; Wang, M.; Xu, C. Luminescence 2013, 28, 628.
[55] Wei, Y. J.; Li, N.; Qin, S. J. Spectrosc. Spectral Anal. 2004, 24, 647 (in Chinese). (魏永巨, 李娜, 秦身钧, 光谱学与光谱分析, 2004, 24, 647.)
[56] Zhang, Y. P.; Tan, W.; Yang, Y. S.; Sun, S. Q.; Guo, H. C. Chin. J. Org. Chem. 2015, 35, 1985 (in Chinese). (张应鹏, 谭伟, 杨云裳, 孙世琪, 郭慧琛, 有机化学, 2015, 35, 1985.)
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