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2012 , Vol. 32 >Issue 04: 686 - 695

DOI: https://doi.org/10.6023/cjoc1107133

综述与进展

环糊精-卟啉超分子体系的构筑及应用进展

  • 陈韶云 ,
  • 周贤太 ,
  • 纪红兵
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  • 中山大学化学与化学工程学院 广州 510275

收稿日期: 2011-07-13

  修回日期: 2011-09-22

  网络出版日期: 2012-04-24

基金资助

国家自然科学基金(Nos. 21036009, 20976203, 21176268)、2010 年广东省高等学校高层次人才项目、中央高校基本科研业务费专项资金资助项目.

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Advance in the Construction and Application of Cyclodextrin- Porphyrin Supramolecular System

  • Chen Shaoyun ,
  • Zhou Xiantai ,
  • Ji Hongbing
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  • School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275

Received date: 2011-07-13

  Revised date: 2011-09-22

  Online published: 2012-04-24

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21036009, 20976203, 21176268), the Higher-Level Talent Project for Guangdong Provincial Universities (2010) and the Fundamental Research Funds for the Central Universities.

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摘要

环糊精具有分子识别和选择包结客体分子的独特性质, 而卟啉具有模拟酶催化、电子转移和光能转移等功能,本工作通过对环糊精-卟啉超分子体系构筑方式的介绍, 详细综述了环糊精-卟啉超分子体系在模拟酶催化、生命科学、药物控释、电子转移过程等方面的应用, 认为环糊精-卟啉超分子体系具有卟啉和环糊精双重性质的优点, 而以键联环糊精-卟啉为主体分子构筑的超分子体系能更有效地模拟生物酶, 表现出优异的区域和立体选择性, 在仿生催化方面将具有更广泛的应用前景.

关键词： 环糊精; 卟啉; 超分子化合物; 构筑

本文引用格式

陈韶云 , 周贤太 , 纪红兵 . 环糊精-卟啉超分子体系的构筑及应用进展[J]. 有机化学, 2012 , 32(04) : 686 -695 . DOI: 10.6023/cjoc1107133

Abstract

Molecular recognition and selective guest molecular inclusion are the unique performances of cyclodextrin, and porphyrin owns the behavior of biomimetic catalysis, electron transfer and light energy transfer. Based on the introduction of construction ways, the applications of cyclodextrin-porphyrins supramolecular system in biomimetic catalysis, life science, drug delivery and electron transfer were well reviewed. The cyclodextrin-porphyrins supramolecular system endowed with the advantages that concentrated the dual nature of porphyrins and cyclodextrin. The supramolecular system constructed by using the binding cyclodextrin-porphyrins as host molecular could more effectively mimic the behavior of enzymes, showing excellent regional and stereoselectivity. And it will be widely used in biomimetic catalysis.

Key words： cyclodextrin; porphyrin; supramolecular compound; construction

参考文献

[1] Meunier, B. Biomimetic Oxidations Mediated by Metal Complexes, Imperial College Press, London, 2000.

[2] Lovell, J. F.; Liu, T. W. B.; Chen, J.; Zheng, G. Chem. Rev. 2010, 110, 2839.  

[3] Haas, K. L.; Franz, K. J. Chem. Rev. 2009, 109, 4921.  

[4] Villalonga, R.; Cao, R.; Fragoso, A. Chem. Rev. 2007, 107, 3088.  

[5] Chen, H. Y.; Ji, H. B. AIChE. J. 2010, 56, 466.  

[6] Zhan, H. Y.; Liu, H. Y.; Hu, J.; Jiang, H. F. Sci. China, Ser. B 2009, 39, 253 (in Chinese). (詹海莺, 刘海洋, 胡军, 江焕峰, 中国科学B辑: 化学, 2009, 39, 253.)

[7] Huang, J.; Ren, L. Y.; Fan, H. L.; Chen, Y. M. Sci. China, Ser. B 2011, 39, 301 (in Chinese). (黄进, 任丽霞, 范红蕾, 陈永明, 中国科学B辑: 化学, 2009, 39, 301.)

[8] Breslow, R.; Zhang, X. J.; Xu, R.; Maletic, M.; Merger, R. J. Am. Chem. Soc. 1996, 118, 11678.  

[9] Breslow, R.; Huang, Y.; Zhang, X. J.; Yang, J. Proc. Natl. Acad. Sci. U.S. A. 1997, 94, 11156.

[10] Yu, S. J.; Huang, X.; Miao, L.; Zhu, J. Y.; Yin, Y. Z.; Luo, Q.; Xu, J. Y.; Shen, J. C.; Liu, J. Q. Bioorg. Chem. 2010, 38, 159.  

[11] Guo, Y. J.; Zhang, P.; Chao, J. B.; Shuang, S. M.; Dong, C. Spectrochim. Acta A 2008, 71, 946.  

[12] Manka, J. S.; Lawrence, D. S. J. Am. Chem. Soc. 1990, 112, 2440.  

[13] EL-Hachemi, Z.; Farrera, J. A.; Garcia-Ortega, H.; Ramirez- Gutierrez, O.; Ribo, J. M. J. Porphyrins Phthalocyanines 2001, 5, 465.  

[14] Mosinger, J.; Slavetinska, L.; Lang, K.; Coufal, P.; Kubat, P. Org. Biomol. Chem. 2009, 7, 3797.  

[15] Hamai, S.; Koshiyama, T. Spectrochim. Acta A 2001, 57, 985.  

[16] Kano, K. Colloid Polym. Sci. 2008, 286, 79.  

[17] Guo, Y. J.; Guo, L.; Pan, J. H. Phys. Chem. Liq. 2007, 45, 261.  

[18] Zhang, H. F.; Pan, J. H.; Gao, Y. L.; Guo, Y. J. Chin. J. Anal. Chem. 2006, 34, 1541 (in Chinese). (张红芬, 潘景浩, 高莜玲, 郭玉晶, 分析化学, 2006, 34, 1541.)

[19] Schneider, H. J. Angew. Chem., Int. Ed. 2009, 48, 3924.  

[20] Liu, J.; Xu, D. H.; Mei, W. J.; Pu, H. L.; Huang, J. W.; Ji, L. N.Chem. J. Chin. Univ. 2001, 22, 1446 (in Chinese). (刘杰, 许东晖, 梅文杰, 蒲含林, 黄锦汪, 计亮年, 高等学校化 学学报, 2001, 22, 1446.)

[21] Hamai, S. J. Inclusion Phenom. Macrocyclic Chem. 2007, 58, 241.  

[22] Qiu, W. G.; Li, Z. F.; Bai, G. M.; Meng, S. N.; Dai, H. X.; He, H. Spectrochim. Acta A 2007, 66, 1189.  

[23] Kong, L. H.; Guo, Y. J.; Li, X. X.; Pan, J. H. Chin. J. Anal. Chem. 2007, 35, 537 (in Chinese). (孔令宏, 郭玉晶, 李小香, 潘景浩, 分析化学, 2007, 35, 537.)

[24] Li, X. X.; Wang, J. W.; Guo, Y. J.; Kong, L. H.; Pan, J. H. J. Inclusion Phenom. Macrocyclic Chem. 2007, 58, 307.  

[25] Li, X. X.; Guo, Y. J.; Wang, J. W.; Kong, L. H.; Pan, J. H. Supramol. Chem. 2008, 20, 243.  

[26] Guo, Y. J.; Zhang, P.; Chao, J. B.; Shuang, S. M.; Dong, C. Spectrochim. Acta A 2008, 71, 946.  

[27] Kong, L. H.; Guo, Y. J.; Li, X. X.; Pan, J. H. Spectrochim. Acta A 2007, 66, 594.  

[28] Hu, Y.; Zhao, H. B.; Ning, J. H.; Ning, M. X.; Xu, Y. J.; Qiu, S. J.; Liao, J. X. Acta Chim. Sinica 2008, 66, 2391 (in Chinese). (胡羽, 赵鸿斌, 宁静恒, 宁满霞, 徐勇军, 仇诗军, 廖俊旭, 化 学学报, 2008, 66, 2391.)

[29] Wang, W. L.; Zhao, H. B.; Ning, J. H.; Hu, Y.; Zhang, H.; Lu, X. J.; Ye, L. Y. Chin. J. Inorg. Chem. 2010, 26, 2025 (in Chinese). (王武林, 赵鸿斌, 宁静恒, 胡羽, 张辉, 陆旭甲, 叶领云, 无机 化学学报, 2010, 26, 2025.)

[30] Carofiglio, T.; Fornasler, R.; Lucchini, V.; Simonato, L.; Tonellato, U. J. Org. Chem. 2000, 65, 9013.  

[31] Kano, K.; Nishiyabu, R.; Yamazaki, T.; Yamazaki, I. J. Am. Chem. Soc. 2003, 125, 10625.  

[32] Sasaki, K.; Nakagawa, H.; Zhang, X. Y.; Sakurai, S.; Kano, K.; Kuroda, Y. Chem. Commun. 2004, 104, 408.

[33] Fathalla, M.; Neuberger, A.; Li, S. C.; Schmehl, R.; Diebold, U.; Jayawickramarajah, J. J. Am. Chem. Soc. 2010, 132, 9966.  

[34] Yu, M.; Chen, Y.; Zhang, N.; Liu, Y. Org. Biomol. Chem. 2010, 8, 4148.  

[35] Gu, Z. Y.; Guo, D. S.; Sun, M.; Liu, Y. J. Org. Chem. 2010, 75, 3600.  

[36] Yu, S. J.; Huang, X.; Miao, L.; Zhu, J. Y.; Yin, Y. Z.; Luo, Q.; Xu, J. Y.; Shen, J. C.; Liu, J. Q. Bioorg. Chem. 2010, 38, 159.  

[37] Kiba, T.; Suzuki, H.; Hosokawa, K.; Kobayashi, H.; Baba, S.; Kakuchi, T.; Sato, S. J. Phys. Chem. B 2009, 113, 11560.  

[38] Mazzaglia, A.; Valerio, A.; Micali, N.; Villari, V.; Quaglia, F.; Castriciano, M. A.; Scolaro, L. M.; Giuffrè, M.; Siracusano, G.; Sciortino, M. T. Chem. Commun. 2011, 47, 9140.  

[39] Ribo, J. M.; Farrera, J. A.; Valero, M. L.; Virgili, A. Tetrahedron 1995, 51, 3705.  

[40] Breslow, R.; Gabriele, B.; Yang, J. Tetrahedron Lett. 1998, 39, 2887.  

[41] Yang, J.; Gabriele, B; Belvedere, S.; Huang, Y.; Breslow, R. J. Org. Chem. 2002, 67, 5057.  

[42] Kuroda, Y.; Hiroshige, T.; Sera, T.; Shiroiwa, Y.; Tanaka, H.; Ogoshi, H. J. Am. Chem. Soc. 1989, 111, 1912.  

[43] Kuroda, Y.; Hiroshige, T.; Sera, T.; Ogoshi, H. Carbohydr. Res. 1989, 192, 347.  

[44] Kuroda, Y.; Sera, T.; Ogoshi, H. J. Am. Chem. Soc. 1991, 113, 2793.  

[45] Weber, L.; Imiolczyk, I.; Haufe, G.; Rehorek, D.; Hennig, H. J. Chem. Soc., Chem. Commun. 1992, 301.

[46] French, R. R.; Holzer, P.; Leuenberger, M.; Nold, M. C.; Woggon, W. D. J. Inorg. Biochem. 2002, 88, 295.  

[47] French, R. R.; Wirz, J.; Woggon, W. D. Helv. Chim. Acta 1998, 81, 1521.  

[48] French, R. R.; Holzer, P.; Leuenberger, M. G.; Woggon W. D. Angew. Chem., Int. Ed. 2000, 39, 1267.  

[49] Lee, J. B.; Hunt, J. A.; Grove, J. T. J. Am. Chem. Soc. 1998, 120, 7493.  

[50] Li, Z. Y.; Li, J. F.; Li, C. Chin. J. Chem. 2002, 20, 399.

[51] Li, Z. Y.; Li, C.; Wu, X. Y.; Zhang, Y. N. Chin. Chem. Lett. 2000, 11, 493.

[52] Kralova, J.; Kejik, Z.; Briza, T.; Pouckova, P.; Kral, A.; Martasek, P.; Kral, V. J. Med. Chem. 2010, 53, 128.  

[53] Chen, W. H.; Yan, J. M.; Tagashira, Y.; Yamaguchi, M.; Fujita, K. Tetrahedron Lett. 1999, 40, 891.  
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