Reviews

Recent Progress in Fluorescent Probes for Zn2+/Cd2+ Based on Small Organic Molecules

  • Jia Jia ,
  • Tang Xi ,
  • He Yingfang ,
  • Zhang Mengyu ,
  • Xing Guowen
Expand
  • College of Chemistry, Beijing Normal University, Beijing 100875

Received date: 2012-03-10

  Revised date: 2012-05-08

  Online published: 2012-05-22

Supported by

Project supported by the the National Natural Science Foundation of China (Nos. 21272027, 20772013), the Beijing Natural Science Foundation (No. 2122031) and the Beijing Municipal Commission of Education.

Abstract

The recent progress in Zn2+/Cd2+ fluorescent probes based on small organic molecules is reviewed. The review summarizes the effects of receptors (R) structures on detecting Zn2+/Cd2+, and highlights the principles and applications of one fluorescent probe molecule for detecting both Zn2+and Cd2+. The future developing prospects of Zn2+/Cd2+ fluorescent probes are also discussed.

Cite this article

Jia Jia , Tang Xi , He Yingfang , Zhang Mengyu , Xing Guowen . Recent Progress in Fluorescent Probes for Zn2+/Cd2+ Based on Small Organic Molecules[J]. Chinese Journal of Organic Chemistry, 2012 , 32(10) : 1803 -1811 . DOI: 10.6023/cjoc1203103

References

[1] Frausto da Silva, J. J.; Williams, R. J. P. The Bioloical Chemistry of the Elements, Clarendon Press, Oxford, 1991, p. 302.

[2] Epner, D. E.; Herschman, H. R. J. Cell Physiol. 1991, 148, 68.

[3] Cousins, R. J.; Lee-Ambrose, L. M. J. Nutr. 1992, 122, 56.

[4] Zalewski, P. D.; Forbes, I. J.; Mazdai, G.; Giannakis, C. Biochem. Int. 1991, 24, 1093.

[5] Martin, S. J.; Mazdai, G.; Strain, J. J.; Cotter, T. G.; Hannigan, B. M. Clin. Exp. Immunol. 1991, 83, 338.

[6] Xie, X. M.; Smart, T. G. Nature 1991, 349, 521.

[7] Frederickson, C. J. Int. Rev. Neurobiol. 1989, 31, 145.

[8] Canzoniero, L. M. T.; Sensi, S. L.; Choi, D. W. Neurobiol. Dis. 1997, 4, 275.

[9] Grummt, F.; Wienmann-Dorsch, C.; Schneider-Schaulies, J.; Lux, A. Exp. Cell Res. 1986, 163, 191.

[10] Harrison, N. L.; Gibbons, S. J. Neuropharmacology 1994, 33, 935.

[11] Nordberg, G. F.; Herber, R. F. M.; Alessio, L. Cadmium in the Human Environment: Toxicity and Carcinogenicity, Oxford University Press, Oxford, 1992.

[12] Wang, Y. G.; Liu Y. The Application of Chemical Marker and Probe Technology in Molecular Biology, The Chemical Industry Press, Beijing, 2007 (in Chinese).

(王彦广, 刘洋, 化学标记与探针技术在分子生物学中的应用, 化学工业出版社, 北京, 2007.)

[13] Kawabata, E.; Kikuchi, K.; Urano, Y.; Kojima, H.; Odani, A.; Nagano, T. J. Am. Chem. Soc. 2005, 127, 818.

[14] (a) Kikuchi, K.; Komatsu, K.; Nagano, T. Curr. Opin. Chem. Biol. 2004, 8, 182.

(b) Xu, Z. C.; Yoon, J.; Spring, D. R. Chem. Soc. Rev. 2010, 39, 1996.

[15] (a) 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.)

(b) Fan, J.-L.; Peng, X.-J.; Wu, Y.-K.; Gao S. Chem. Res. Appl. 2005, 17, 137 (in Chinese).

(樊江莉, 彭孝军, 吴云扣, 高尚, 化学研究与应用, 2005, 17, 137.)

[16] Mizukami, S.; Okada, S.; Kimura, S.; Kikuchi, K. Inorg. Chem. 2009, 48, 7630.

[17] Komatsu, K.; Urano, Y.; Kojima, H.; Nagano, T. J. Am. Chem. Soc. 2007, 129, 13447.

[18] Koutaka, H.; Kosuge, J.-I.; Fukasaku, N.; Hirano, T.; Kikuchi, K.; Urano, Y.; Kojima, H.; Nagano, T. Chem. Pharm. Bull. 2004, 52, 700.

[19] Kim, S. Y.; Hong, J.-I. Tetrahedron Lett. 2009, 50, 2822.

[20] Chen, X.-Y.; Shi, J.; Li, Y.-M.; Wang, F.-L.; Wu, X.; Guo, Q.-X.; Liu, L. Org. Lett. 2009, 11, 4426.

[21] Jia, J.; Gu, Z.-Y.; Li, R.-C.; Huang, M.-H.; Xu, C.-S.; Wang, Y.-F.; Xing, G.-W.; Huang, Y.-S. Eur. J. Org. Chem. 2011, 4609.

[22] Qian, F.; Zhang, C.-L.; Zhang, Y.-M.; He, W.-J.; Gao, X.; Hu, P.; Guo, Z.-J. J. Am. Chem. Soc. 2009, 131, 1460.

[23] Jiang, W.; Fu, Q. Q.; Fan, H. Y.; Wang, W. Chem. Commun. 2008, 259.

[24] Kim, H. M.; Seo, M. S.; An, M. J.; Hong, J. H.; Tian, Y. S.; Choi, J. H.; Kwon, O.; Lee, K. J.; Cho, B. R. Angew. Chem., Int. Ed. 2008, 47, 5167.

[25] Hirano T.; Kikuchi, K.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2002, 124, 6555.

[26] Kiyose, K.; Kojima, H.; Urano, Y.; Nagano, T. J. Am. Chem. Soc. 2006, 128, 6548.

[27] Lee, A. E.; Grace, M. R.; Meyer, A. G.; Tuck, K. L. Tetrahedron Lett. 2010, 51, 1161.

[28] Fan, J.-L.; Peng, X.-J.; Wu, Y.-K.; Lu, E.-H.; Hou, J.; Zhang, H.-B.; Zhang, R.; Fu, X.-M. J. Lumin. 2005, 114, 125.

[29] Choi, M.; Kim, M.; Lee, K. D.; Han, K.-N.; Yoon, I.-A.; Chung, H.-J.; Yoon, J. Org. Lett. 2001, 3, 3455.

[30] Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Org. Lett. 2003, 5, 4065.

[31] Cheng, T.-Y.; Xu, Y.-F.; Zhang, S.-Y.; Zhu W.-P.; Qian, X.-H.; Duan, L.-P. J. Am. Chem. Soc. 2008, 130, 16160.

[32] Yang, Y.-Y.; Cheng, T.-Y.; Zhu, W.-P.; Xu, Y.-F.; Qian, X.-H. Org. Lett. 2011, 13, 264.

[33] Huston, M. E.; Engleman, C.; Czarnik, A. W. J. Am. Chem. Soc. 1990, 112, 7054.

[34] Prodi, L.; Montalti, M.; Zaccheroni, N.; Bradshaw, J. S.; Izatt, R. M.; Savage, P. B. Tetrahedron Lett. 2001, 42, 2941.

[35] Peng, X.; Du, J.; Fan, J.; Wang, J.; Wu, Y.; Zhao, J.; Sun, S.; Xu, T. J. Am. Chem. Soc. 2007, 129, 1500.

[36] Taki, M.; Desaki, M.; Ojida, A.; Iyoshi, S.; Hirayama, T.; Hamachi, I.; Yamamoto, Y. J. Am. Chem. Soc. 2008, 130, 12564.

[37] Liu, Z. P.; Zhang, C. L.; He, W. J.; Yang, Z. H.; Gao, X.; Guo, Z. J. Chem. Commun. 2010, 46, 6138.

[38] Taki, M.; Watanabe, Y.; Yamamoto, Y. Tetrahedron Lett. 2009, 50, 1345.

[39] Zhu, J.-F.; Yuan, H.; Chan, W.-H.; Lee, A. W. M. Tetrahedron Lett. 2010, 51, 3550.

[40] Liu, Y.; Zhang, N.; Chen, Y.; Wang, L.-H. Org. Lett. 2007, 9, 315.

[41] Chen, H. L.; Wu, Y. B.; Cheng, Y. F.; Yang, H.; Li, F. Y.; Yang, P.; Huang, C. H. Inorg. Chem. Commun. 2007, 10, 1413.

[42] Tang, X.-L.; Peng, X.-H.; Dou, W.; Mao, J.; Zheng, J.-R.; Qin, W.-W.; Liu, W.-S.; Chang, J.; Yao, X.-J. Org. Lett. 2008, 10, 3653.

[43] Xue, L.; Li, G.; Liu, Q.; Wang, H.; Liu, C.; Ding, X.; He, S.; Jiang, H. Inorg. Chem. 2011, 50, 3680.

[44] Hosseini, M.; Vaezi, Z.; Ganjali, M. R.; Faridbod, F.; Abkenar, S. D.; Alizadeh, K.; Salavati-Niasari, M. Spectrochim. Acta, Part A 2010, 75, 978.

[45] Zhou, Y.; Kim, H. N.; Yoon, J. Bioorg. Med. Chem. Lett. 2010, 20, 125.

[46] Wang, L. N.; Qin, W. W.; Liu, W. S. Inorg. Chem. Commun. 2010, 13, 1122.

[47] Lee, D. Y.; Singh, N.; Kim, M. J.; Jang, D. O. Tetrahedron 2010, 66, 7965.

[48] Wu, Z. K.; Chen, Q. Q.; Yang, G. Q.; Xiao, C. B,; Liu, J. G.; Yang, S. Y.; Ma, J. S. Sens. Actuator, B 2004, 99, 511.

[49] Lu, C. L.; Xu, Z. C.; Cui, J. N.; Zhang, R.; Qian, X. H. J. Org. Chem. 2007, 72, 3554.

[50] Xue, L.; Liu, C.; Jiang, H. Org. Lett. 2009, 11, 3454.

[51] Xue, L.; Liu, C.; Jiang, H. Org. Lett. 2009, 11, 1655.

[52] 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.

[53] Zhang, G.-Q.; Yang, G.-Q.; Zhu, L.-N.; Chen, Q.-Q.; Ma, J.-S. Sens. Actuator, B 2006, 114, 995.

[54] Zhang, J. F.; Bhuniya, S.; Lee, Y. H.; Bae, C.; Lee, J. H.; Kim, J. S. Tetrahedron Lett. 2010, 51, 3719.

[55] Helal, A.; Kim, S. H.; Kim, H.-S. Tetrahedron 2010, 66, 9925. Liu, W. M.; Xu, L. W.; Sheng, R. L.; Wang, P. F.; Li, H. P.; Wu, S. K. Org. Lett. 2007, 9, 3829.

Outlines

/