Chinese Journal of Organic Chemistry >
Synthesis and Live Cell Imaging of Tetraphenylethene-Based Fluorescent Nanoprobes
Received date: 2018-03-19
Revised date: 2018-05-18
Online published: 2018-06-06
Supported by
Project supported by the National Natural Science Foundation of China (No. 81671749).
In recent years, designing and synthesizing fluorescent nanoprobes with good biocompatibility, stable optical properties and low cytotoxicity are research hotspots in the biomedical field. The novel tetraphenylethene-based fluorescent probe (TPE-Rho) was synthesized by reaction of 1,1,2-triphenyl-2-(4-formylphenyl)ethene with 2-(4-oxo-3-phenyl-1,3-thia-zol-2-ylidene)malononitrile. After the aggregation-induced emission (AIE) characteristics of TPE-Rho were investigated, TPE-Rho dots with uniform particle size distribution were obtained through a modified nanoprecipitation method by using Pluronic F-127 (amphiphilic surfactant) as the encapsulation. TPE-Rho dots have excellent optical property such as strong yellow fluorescence, good stability and long Stokes shift (ca. 200 nm), and have little effect on cell growth activity. Then, TPE-Rho dots were utilized to stain live SK-Hep1 cells and LoVo cells, the staining region and fluorescent intensity were analyzed. The experimental results show that TPE-Rho dots have no significant effect on cell viability, and can stain live cells and selectively act on the cytoplasm. Thus, it can be confirmed that TPE-Rho dots has good biocompatibility, low cytotoxicity, high cell membrane permeability, and good stability, therefore it can be used as a viable cell staining agent.
Key words: tetraphenylethene; aggregation-induced emission; nanoprobes; cell imaging
Xia Qi , Chen Zikang , Zhang Zhide , Liu Ruiyuan . Synthesis and Live Cell Imaging of Tetraphenylethene-Based Fluorescent Nanoprobes[J]. Chinese Journal of Organic Chemistry, 2018 , 38(10) : 2700 -2705 . DOI: 10.6023/cjoc201803029
[1] Yan, L.; Zhang, Y.; Xu, B.; Tian, W. Nanoscale 2016, 8, 2471.
[2] Su, S.; Ma, Y.; Tian, L.; Wang, Z. Sci. Sin. Chim. 2017, 47, 1075(in Chinese) (苏姗, 马宇帆, 田立枚, 王卓, 中国科学:化学2017, 47, 1075.)
[3] Chen, X.; Ko, S. K.; Kim, M. J.; Shin, I.; Yoon, J. Chem. Commun. 2010, 46, 2751.
[4] Yuan, L.; Lin, W.; Zheng, K.; Zhu, S. Acc. Chem. Res. 2013, 46, 1462.
[5] Gao, M.; Hu, Q.; Feng, G.; Tang, B. Z.; Liu, B. J. Mater. Chem. B 2014, 2, 3438.
[6] Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z. Chem. Rev. 2015, 115, 11718.
[7] Ma, X.; Sun, R.; Cheng, J.; Liu, J.; Gou, F.; Xiang, H.; Zhou, X. J. Chem. Educ. 2015, 93, 345.
[8] Shi, C.; Guo, Z.; Yan, Y.; Zhu, S.; Xie, Y.; Zhao, Y. S.; Zhu, W.; Tian, H. ACS Appl. Mater. Interfaces 2013, 5, 192.
[9] Luo, J.; Xie, Z.; Lam, J. W. Y.; Cheng, L.; Tang, B. Z.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D. Chem. Commun. 2001, 1740.
[10] Shi, H.; Kwok, R. T.; Liu, J.; Xing, B.; Tang, B. Z.; Liu, B. J. Am. Chem. Soc. 2012, 134, 17972.
[11] Zhan, C.; You, X.; Zhang, G.; Zhang, D. Chem. Rec. 2016, 16, 2142.
[12] Liang, J.; Kwok, R. T.; Shi, H.; Tang, B. Z.; Liu, B. ACS Appl. Mater. Interfaces 2013, 5, 8784.
[13] Chatterjee, A.; Khandare, D. G.; Saini, P.; Chattopadhyay, A.; Majik, M. S.; Banerjee, M. RSC Adv. 2015, 5, 31479.
[14] Chen, Q.; Bian, N.; Cao, C.; Qiu, X. L.; Qi, A. D.; Han, B. H. Chem. Commun. 2010, 46, 4067.
[15] Li, P. F.; Liu, Y. Y.; Zhang, W. J.; Zhao, N. ChemistrySelect 2017, 2, 3788.
[16] Wu, J.; Sun, S.; Feng, X.; Shi, J.; Hu, X. Y.; Wang, L. Chem. Commun. 2014, 50, 9122.
[17] Dong, Y.; Lam, J. W. Y.; Qin, A.; Liu, J.; Li, Z.; Tang, B. Z.; Sun, J.; Kwok, H. S. Appl. Phys. Lett. 2007, 91, 1404.
[18] Hu, R.; Lager, E.; Aguilaraguilar, A.; Liu, J.; Lam, J. W. Y.; Sung, H. H. Y.; Williams, I. D.; Zhong, Y.; Wong, K. S.; Peñacabrera, E. J. Phys. Chem. C 2009, 113, 15845.
[19] Cai, Y.; Li, L.; Wang, Z.; Sun, J. Z.; Qin, A.; Tang, B. Z. Chem. Commun. 2014, 50, 8892.
[20] Huang, Y.; Lei, L.; Zheng, C.; Wei, B.; Zhao, Z.; Qin, A.; Hu, R.; Tang, B. Z. Acta Chim. Sinica 2016, 74, 885(in Chinese). (黄玉章, 雷洛奇, 郑超, 危博, 赵祖金, 秦安军, 胡蓉蓉, 唐本忠, 化学学报, 2016, 74, 885.)
[21] Lou, X.; Zhuang, Y.; Zuo, X.; Jia, Y.; Hong, Y.; Min, X.; Zhang, Z.; Xu, X.; Liu, N.; Xia, F.; Tang, B. Z. Anal. Chem. 2015, 87, 6822.
[22] Zhuang, Y.; Huang, F.; Xu, Q.; Zhang, M.; Lou, X.; Xia, F. Anal. Chem. 2016, 88, 3289.
[23] Ji, G.; Yan, L.; Wang, H.; Ma, L.; Xu, B.; Tian, W. Acta Chim. Sinica 2016, 74, 917(in Chinese). (纪光, 闫路林, 王慧, 马莲, 徐斌, 田文晶, 化学学报, 2016, 74, 917.)
[24] Leung, C. W. T.; Hong, Y.; Chen, S.; Zhao, E.; Lam, J. W. Y.; Tang, B. Z. J. Am. Chem. Soc. 2013, 135, 62.
[25] Hu, F.; Huang, Y.; Zhang, G.; Zhao, R.; Yang, H.; Zhang, D. Anal. Chem. 2014, 86, 7987.
[26] Xiong, L.; Guo, Y.; Zhang, Y.; Cao, F. J. Mater. Chem. B 2015, 4, 202.
[27] Wu, W. C.; Chen, C. Y.; Tian, Y.; Jang, S. H.; Hong, Y.; Liu, Y.; Hu, R.; Tang, B. Z.; Lee, Y. T.; Chen, C. T. Adv. Funct. Mater. 2010, 20, 1413.
[28] Zhang, X.; Liu, M.; Yang, B.; Zhang, X.; Chi, Z.; Liu, S.; Xu, J.; Wei, Y. Polym. Chem. 2013, 4, 5060.
[29] Zhang, X.; Liu, M.; Yang, B.; Zhang, X.; Wei, Y. Colloids Surf., B 2013, 112, 81.
[30] Zhang, F.; Di, Y.; Li, Y.; Qi, Q.; Qian, J.; Fu, X.; Xu, B.; Tian, W. Dyes Pigm. 2017, 142, 491.
[31] Zhang, J.; Li, C.; Zhang, X.; Huo, S.; Jin, S.; An, F. F.; Wang, X.; Xue, X.; Okeke, C. I.; Duan, G.; Guo, F.; Zhang, X.; Hao, J.; Wang, P. C.; Zhang, J.; Liang, X. J. Biomaterials 2015, 42, 103.
[32] An, F.-F.; Yang, Y.-L.; Liu, J.; Ye, J.; Zhang, J.-F.; Zhou, M.-J.; Zhang, X.-J.; Zheng, C.-J.; Liang, X.-J.; Zhang, X.-H. RSC Adv. 2014, 4, 6120.
[33] Liu, J.; Li, K.; Liu, B. Adv. Sci. (Weineim, Ger.) 2015, 2, 1500008.
[34] Rossetti, R.; Nakahara, S.; Brus, L. E. J. Chem. Phys. 1998, 79, 1086.
[35] Yuan, F.; Li, S.; Fan, Z.; Meng, X.; Fan, L.; Yang, S. Nano Today 2016, 11, 565.
[36] Yuan, X.; Luo, Z.; Yu, Y.; Yao, Q.; Xie, J. Chem. Asian J. 2013, 8, 858.
[37] Niu, X.; Chen, H.; Wang, Y.; Wang, W.; Sun, X.; Chen, L. ACS Appl. Mater. Interfaces 2014, 6, 5152.
[38] Leung, C. W. T.; Yuning, H.; Sijie, C.; Engui, Z.; Lam, J. W. Y.; Ben Zhong, T. J. Am. Chem. Soc. 2013, 135, 62.
[39] Reddy, E. R.; Yellanki, S.; Medishetty, R.; Konada, L.; Alamuru, N. P.; Haldar, D.; Parsa, K. V. L.; Kulkarni, P.; Rajadurai, M. ChemNanoMat 2016, 1, 567.
[40] Zhang, X.; Zhang, X.; Wang, S.; Liu, M.; Tao, L.; Wei, Y. Nanoscale 2013, 5, 147.
/
〈 |
|
〉 |