Advances in Fluorescent Probes Based on the Small Molecules for Zn2+
Received date: 2013-01-08
Revised date: 2013-02-22
Online published: 2013-03-07
Supported by
Project supported by the National Natural Science Foundation of China (No. 30900377, 81271634), the National Science Foundation for Distinguished Young Scholars of Hunan Province (No. 12JJ1012), the Education for New Century Excellent Talents (No. NCET-10-0800) and the Research Fund for the Doctoral Program of Higher Education (No.20120162110070).
Zinc ion (Zn2+) plays an essential role in many physiological processes of the organism, such as brain activities, gene transcription and immune function, as well as some pathological processes and so on, therefore selective recognition and detection of Zn2+ are of important biological significance. Fluorescence technology has unique advantages such as high selectivity, sensitivity, low cost, real-time and in situ monitoring, thus it has become one of the most important sensing technology for zinc ion and a hot topic area in recent years to imaging Zn2+ in cells. Herein, the latest progresses in the last 10 years of fluorescent molecular probes based on the small molecules for Zn2+ are reviewed. These important fluorescent probes are classified according to three different mechanisms action (PET, ICT and FRET). The design of molecular structure, sensing mechanism and biological applications of these probes are introduced. In addition, the structure and property relationships are elucidated. Finally, the problems and the developing trends in this field are also discussed.
Key words： zinc ions; fluorescence; molecular probe; small molecule
Liu Min , Tan Huilong , Liu Zhiguo , Wang Wei , Zeng Wenbin . Advances in Fluorescent Probes Based on the Small Molecules for Zn2+[J]. Chinese Journal of Organic Chemistry, 0 , (0) : 0 -0 . DOI: 10.6023/cjoc201301015
[1] Vallee, B. L.; Falchuk, K. H. Phys. Rev. 1993, 73, 79.
[2] Frederickson, C. J.; Koh, J. Y.; Bush, A. I. Nat. Rev. Neurosci. 2005, 6, 449.
[3] Bush, A. I.; Pettingell, W. H.; Multhaup, G.; Paradis, M. D.; Vonsattel, J. P.; Gusella, J. F.; Beyreuther, K.; Masters, C. L.; Tanzi, R. E. Science 1994, 265, 1464.
[4] Kikuchi, K.; Komatsu, K.; Nagano, T. Curr. Opin. Chem. Biol. 2004, 8, 182.
[5] Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3.
[6] Frederickson, C. J.; Kasarskis, E. J.; Ringo, D.; Frederickson, R. E. J. Neurosci. Meth. 1987, 20, 91.
[7] Fahrni, C. J.; O’Halloran, T. V.; J. Am. Chem. Soc. 1999, 121, 11448.
[8] Pearce, D. A.; Jotterand, N.; Carrico, I. S.; Imperial, B. J. Am. Chem. Soc. 2001, 123, 5160.
[9] Mikata, Y.; Wakamatsu, M.; Yano, S. Dalton Trans. 2005, 545.
[10] Royzen, M.; Durandin, A.; Young, V. G.; Geacintov, N. E.; Canary, J. W. J. Am. Chem. Soc. 2006, 128, 3854.
[11] Zhang, Y.; Guo, X. F.; Jia, L. H.; Qian, X. H. Prog. Chem. 2008, 20, 1945 (in Chinese).(张宇, 郭祥峰, 贾丽华, 钱旭红, 化学进展, 2008, 20, 1945.)
[12] Wang, H. H.; Gan, Q.; Wang, X. J.; Xue, L.; Liu, S. H.; Jiang, H. Org. Lett. 2007, 9, 4995.
[13] Zhang, C. L.; Zhang, Y. M.; Chen, Y. C.; Xie, Z. J.; Liu, Z. P.; Dong, X. D.; He, W. J.; Shen, C.; Guo, Z. J. Inorg. Chem. Commun.2011, 14, 304.
[14] You, Q. H.; Chan, P. S.; Chan, W. H.; Hau, S. C. K.; Lee, A. W. M.; Mark, N. K.; Mark, T. C. W.; Wong, R. N. S. RSC Adv. 2012, 2, 11078.
[15] Hirano, T.; Kikuchi, K.; Urano, Y.; Higuchi, T.; Nagano, T. J. Am. Chem. Soc.2000, 122, 12399.
[16] Burdette, S. C.; Walkup, G. K.; Spingler, B.; Tsien, R. Y.; Lippard, S. J. Am. Chem. Soc. 2001, 123, 7831.
[17] Nolan, E. M.; Burdette, S. C.; Harvey, J. H.; Hilderbrand, S. A.; Lippard, S. J. Inorg. Chem. 2004, 43, 2624.
[18] Chang, C. J.; Nolan, E. M.; Jaworski, J.; Okamoto, K. I.; Hayashi, Y.; Sheng, M.; Lippard, S. J. Inorg. Chem. 2004, 43, 6774.
[19] Nolan, E. M.; Lippard, S. J. Inorg. Chem. 2004, 43, 8310.
[20] Nolan, E. M.; Ryu, J. W.; Jaworski, J.; Feazell, R. P.; Sheng, M.; Lippard, S. J. J. Am. Chem. Soc. 2006, 128, 15517.
[21] Nolan, E. M.; Jaworski, J.; Okamoto, K. I., Hayashi, Y.; Sheng, M.; Lippard, S. J. J. Am. Chem. Soc. 2005, 127, 16812.
[22] Zhang, X. A.; Hayes, D.; Smith, S. J.; Friedle, S.; Lippard, S. J. J. Am. Chem. Soc. 2008, 130, 15788.
[23] Buccella, D.; Horowitz, J. A.; Lippard, S. J. J. Am. Chem. Soc. 2011, 133, 4101.
[24] Lim, N. C.; Yao, L.; Freake, H. C.; Bruckner, C. Bioorg. Med. Chem. Lett. 2003, 13, 2251.
[25] Lim, N. C.; Schuster, J. V.; Porto, M. C.; Tanudra, M. A.; Yao. L.; Freake, H. C.; Bruckner, C. Inorg. Chem. 2005, 44, 2018.
[26] Su, Z.; Chen, K. Y.; Guo, Y.; Qi, H. P.; Yang, X. F.; Zhao, M. L. J. Fluoresc. 2010, 20, 851.
[27] Koutaka, H.; Kosuge, J. I.; Fukasaku, N.; Hirano, T.; Kikuchi, K.; Urano, Y.; Kojima, H.; Nagano, T. Chem. Pharm. Bull. 2004, 52, 700.
[28] Wu, Y. K.; Peng, X. J.; Guo, B. C.; Fan, J. L.; Zhang, Z. C.; Wang, J. Y.; Cui, A. J.; Gao, Y. L. Org. Biomol. Chem. 2005, 3, 1387.
[29] Wang, J. B.; Xiao, Y.; Zhang, Z. C.; Qian, X. H.; Yang, Y. Y.; Qin, X. J. Mater. Chem. 2005, 15, 2836.
[30] Xu, Z. C.; Baek, K. H.; Kim, H. N.; Cui, J. N.; Qian, X. H.; Spring, D. R.; Shin, I.; Yoon, J. J. Am. Chem. Soc. 2010, 132, 601.
[31] Jiang, W.; Fu, Q.; Fan, H.; Wang, W. Chem. Commun. 2008, 259.
[32] Majzoub, A. E.; Cadiou, C.; Olivier, I. D.; Tinant, B.; Chuburu, F. Inorg. Chem. 2011, 50, 4029.
[33] Kwon, J. E.; Lee, S.; You, Y. M.; Baek, K. H.; Ohkubo, K.; Cho, J.; Fukuzumi, S.; Shin, I.; Park, S. Y.; Nam, W. Inorg. Chem. 2012, 51, 8760.
[34] Gee, K. R.; Zhou, Z. L.; That, D. T.; Sensi, S. L.; Weiss, J. H. Cell Calcium 2002, 31, 245.
[35] Sensi, S. L.; That, D. T.; Weiss, J. H.; Rothe, A.; Gee, K. R. Cell Calcium 2003, 34, 281.
[36] Gee, K. R.; Zhou, Z. L.; Qian, W. J.; Kennedy, R. J. Am. Chem. Soc. 2002, 124, 776.
[37] Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Biomol. Chem. 2003, 1, 3265.
[38] Roussakis, E.; Voutsadaki, S.; Pinakoulaki, E.; Sideris, D. P.; Tokatlidis, K.; Katerinopoulos, H. E. Cell Calcium 2008, 44, 270.
[39] Tang, Y. Y.; Luo, C. H.; Wu, C. Y.; Shen, G. L.; Yu, R. Q.; Acta Chim. Sinica 2007, 65, 1229 (in Chinese). (唐友云, 罗春花, 吴朝阳, 沈国励, 俞汝勤, 化学学报, 2007, 65, 1229.)
[40] Tang, B.; Huang, H.; Xu, K. H.; Tong, L.; Yang, G. W.; Liu, X.; An, L. G.; Chem. Commun.2006, 3609.
[41] Kiyose, K.; Kojima, H.; Urano, Y.; Nagano, T.; J. Am. Chem. Soc. 2006, 128, 6548.
[42] Guo, Z. Q.; Kim, G. H.; Shin, I.; Yoon, J. Biomaterials2012, 33, 7818.
[43] Yang, X. B.; Yang, B. X.; Ge, J. F.; Xu, Y. J.; Xu, Q. F.; Liang, J.; Lu, J. M. Org. Lett. 2011, 13, 2710.
[44] Zhang, Q. Q.; Yang, B. Y.; Sun, R.; Ge, J. F.; Xu, Y. J.; Li, N. J.; Lu, J. M. Sensors Act. B 2012, 171-172, 1001.
[45] Maruyama, S.; Kikuchi, K.; Hirano, T.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2002, 124, 10650.
[46] Lim, N. C.; Bruckner, C. Chem. Commun. 2004, 1094.
[47] Komatsu, K.; Urano, Y.; Kojima, H.; Nagano. T. J. Am. Chem. Soc. 2007, 129, 13447.
[48] Atilgan, S.; Ozdemir, T.; Akkaya, E. U. Org. Lett. 2008, 10, 4065.
[49] Lu, C. L.; Xu, Z. C.; Cui, J. N.; Zhang, R.; Qian, X. H. J. Org. Chem. 2007, 72, 3554.
[50] Hanaoka, K.; Muramatsu, Y.; Urano, Y.; Terai, T.; Nagano, T. Chem. Eur. J. 2010, 16, 568.
[51] Zhang, Y.; Guo, X. F.; Si, W. X.; Jia, L. H.; Qian, X. H. Org. Lett. 2008, 10, 473.
[52] Du, J. J.; Fan, J. L.; Peng, X. J.; Li, H. L.; Sun, S. G.; Sensenor Act. B 2010, 144, 337.
[53] Meng, X. M.; Wang, S. X.; Li, Y. M.; Zhu, M. Z.; Guo, Q. X. Chem. Commun. 2012, 48, 4196.
[54] Xie, G. Q.; Shi, Y. J.; Hou, F. P.; Liu, H. Y.; Huang, L.; Xi, P. X.; Chen, F. J.; Zeng, Z. Z. Eur. J. Inorg. Chem. 2012, 327.
[55] Sahoo, H. J. Photoch. Photobio. C. 2011, 12, 20.
[56] Han, Z. X.; Zhang, X. B.; Li, Z.; Gong, Y. J.; Wu, X. Y.; Jin, Z.; He, C. M.; Jian, L. X.; Zhang, J.; Shen, G. L.; Yu, R. Q. Anal. Chem. 2010, 82, 3108.
[57] Xu, Z.; Kim, G. H.; Han, S. J.; Jou, M. J.; Lee, C.; Shin, I.; Yoon, J. Tetrahedron 2009, 65, 2307.
[58] Qian, F.; Zhang, C.; Zhang, Y.; He, W.; Gao, X.; Hu, P.; Guo, Z. J. Am. Chem. Soc. 2009, 131, 1460.
[59] Zhao, C. C.; Zhang, Y. L.; Feng, P.; Cao, J. Dalton Trans. 2012, 41, 831.
[60] Woo, H; You, Y. M.; Kim, T. H.; Jhon, G. J.; Nam, W. W. J. Mater. Chem. 2012, 22, 17100.
[61] Xu, Y. Q.; Pang, Y. Dalton Trans. 2011, 40, 1503.
[62] Taki, M.; Wolford, J. L.; O’Halloran, T. V. J. Am. Chem. Soc. 2004, 126, 712.
[63] Fahrni, C. J.; Henary, M. M.; J. Phys. Chem. A. 2002, 106, 5210.
[64] Jia, J.; Tang, Q.; He, Y. F.; Zhang, M. Y.; Xing, G. W. Chin. J. Org. Chem. 2012, 32, 1803 (in Chinese)(郏佳, 唐茜, 何颖芳, 张梦雨, 刑国文, 有机化学, 2012, 32, 1803.)
[65] Xu, Z. C.; Yoon, J. Y.; Spring, D. R. Chem. Soc. Rev. 2010, 39, 1996.
/
| 〈 |
|
〉 |
