English
新闻公告
More
化学进展 2008, Vol. 20 Issue (12): 2034-2044 前一篇   后一篇

• 综述与评论 •

光敏开关及其在化学生物学中的应用*

孟祥明1,2 陈孝云1 傅尧1** 郭庆祥1**   

  1. (1. 中国科学技术大学化学系 合肥 230026; 2. 安徽大学化学系 合肥 230039)

  • 收稿日期:2008-03-04 修回日期:2008-08-28 出版日期:2008-12-24 发布日期:2008-12-25
  • 通讯作者: 傅尧;郭庆祥

Photolysis of Caged Compounds and Its Applications to Chemical Biology

Meng Xiangming1,2; Chen Xiaoyun1; Fu Yao1**; Guo Qingxiang1**   

  1. (1. Department of Chemistry, University of Science and Technology of China, Hefei 230026, China; 2. Department of Chemistry, Anhui University, Hefei 230039, China)
  • Received:2008-03-04 Revised:2008-08-28 Online:2008-12-24 Published:2008-12-25
  • Contact: Fu Yao; Guo Qingxiang
近年来随着生物医学技术的发展,人们需要越来越细致地在分子水平上研究各种生命过程。为了能够实现实时原位地观察活细胞或组织中的生命化学过程,需要使用以物理方法来选择性激活的分子探针。以共聚焦激光技术为基础的光敏开关能很好地解决这一问题。迄今,发展和用于光敏开关的光敏剂已成为化学生物学研究的重要方向。本文重点总结了各种可应用于共聚焦激光系统的单、双光子光敏基团(单光子的光敏基团主要有:硝基苯类、香豆素类等;双光子光敏基团主要有:香豆素类、喹啉类及吲哚衍生物类)以及这几类光敏基团在化学生物学中的应用。
The recent development in biomedicine demands more accurate understanding of biological processes at the molecular level. In order to observe the chemical processes of living cells or tissues in a real-time fashion with high space resolution, it is necessary to develop methods to selectively activate molecular probes. Confocal laser technology provides a very efficient method for activation of the molecular probes without any injury to tissues. Based on this technology, a series of photon switch which have biological applications have been realized. By now, the development of caging groups for photon switch has become an interesting research area. In this paper, we summarize the popular one-photon and two-photon photo-removable groups including nitrobenzene, coumarin, quinolines, indole derivatives, etc. The mechanism of these caging groups using as photon switch is surveyed. The application and the prospects of these groups in chemical biology are also discussed.

中图分类号: 

()

[1 ] Denk W, Strickler J H. Webb W W. Science , 1990 , 248 : 73 —76
[2 ] Kaplan J H , Forbush III B , Hoffman J F. Biochemistry , 1978 ,17 : 1929 —1935
[3 ] Mayer G, Heckel A. Angew. Chem. Int . Ed. , 2006 , 45 :4900 —4921
[4 ] Hug D H , ONDonnell P S , Hunter J K. Photochem. Photobiol .1980 , 32 : 841 —848
[5 ] Ellis-Davies C R. Nature Methods , 2007 , 4 (8) : 619 —628
[6 ] Giepmans B N G, Adams S R , Ellisman M H , Tsien R Y.Science , 2006 , 312 : 217 —224
[7 ] Wang Y H , Zhu M Z, Ding X Y, Ye J P , Liu L , Guo Q X. J .Phys. Chem. B , 2003 , 107 : 14087 —14093
[8 ] Helmchen F , Denk W. Nature Methods , 2005 , 2 (12) : 932 —940
[9 ] Banerjee A , Grewer C , Ramakrishnan L , J? ger J , Gameiro A ,Breitinger H GA , Gee K R , Carpenter B K, Hess G P. J . Org.Chem. , 2003 , 68 : 8361 —8367
[10] Epel D , Hemela K, Shick M, Patton C. Am. Zool . , 1999 , 39 :271 —278
[11] Barltrop J A , Schofield P. Tetrahedron Lett . , 1962 : 697 —699.
[12] Patchornik A , Amit B , Woodward R B. J . Am. Chem. Soc. ,1970 , 92 : 6333 —6335
[13] McCray J A , Herbette L , Kihara T, Trentham D R. Proc. Natl .Acad. Sci . USA , 1980 , 77 : 7237 —7241
[14] Milburn T, Matsubara N , Billington A P , Udgaokar J B , Walker J W, Carpenter B K, Webb W W, Marque J , Denk W, McCray J A , Hess G P. Biochemistry , 1989 , 28 : 49 —55
[15] Liu L , Bennett C S , Wong C H , Chem. Commun. , 2006 , 21 —33
[16] Canepari M, Nelson L , Papageorgiou G, Corrie J E T, Ogden D.J . Neurosci . Methods , 2001 , 112 : 29 —42
[17] Barltrop J A , Plant P J , Schofield P J . Chem. Soc. Chem.Commun. , 1966 , 22 : 822 —823
[18] Adams S R , Ram V R , Tsien R Y. Chemistry &Biology , 1997 ,4 (11) : 867 —878
[19] Grewer C , J? ger J , Carpenter B K, Hess G P. Biochem. , 2000 ,39 : 2063 —2070
[20] Hagen V , Dzeja C , Frings S , Bendig J , Krause E , Kaupp U B.Biochemistry , 1996 , 35 : 7762 —7771
[21] Amit B , Zehavi U , Patchornik A. Isr. J . Chem. , 1974 , 12 :103 —113
[22] Schupp H , Wong W K, Schnabel W. J . Photochem. , 1987 , 36 :85 —97
[23] Zhu Q Q , Schnabel W, Schupp H. J . Photochem. , 1987 , 39 :317 —332
[24] Pan P , Bayley H. FEBS Letters , 1997 , 405 : 81 —85
[25] Marriott G, Heidecker M. Biochemistry , 1996 , 35 : 3170 —3174
[26] Chang C Y, Niblack B , Walker B , Bayley H. Chem. Biol . ,1995 , 2 : 391 —400
[27] Wieboldt R , Gee K, Ramesh D , Carpenter B K, Hess G P.Proc. Natl . Acad. Sci . USA , 1994 , 91 : 8752 —8756
[28] Gee K R , Wieboldt R , Hess G P. J . Am. Chem. Soc. , 1994 ,116 : 8366 —8367
[29] Niu L , Gee K R , Schaper K, Hess G P. Biochemistry , 1996 ,35 : 2030 —2036
[30] Hess G P , Grewer C. Methods Enzymol . , 1998 , 291 : 443 —473
[31] Aujard I , Benbrahim C , Gouget M, Ruel O , Baudin J B , Neveu P , Jullien L. Chem. Eur. J . , 2006 , 12 : 6865 —6879
[32] Wang L , Corrie J T, Wootton J F. J . Org. Chem. , 2002 , 67 :3474 —3478
[33] Thirlwell H , Corrie J E , Reid G P , et al . Biophys. J . , 1994 ,67 : 2436 —2447
[34] Geibel S , Barth A , Amslinger S , et al . Biophys. J . , 2000 , 79 :1346 —1357
[35] Kantevari S , Egger M, Hoing C , Niggli E , Ellis2Davies G C R.ChemBioChem , 2006 , 7 : 174 —180
[36] Adams S R , Kao J P Y J , Tsien R Y. J . Am. Chem. Soc. ,1989 , 111 : 7957 —7968
[37] Wilcox M, Viola R M, Johnson KW, Billington A P , Carpenter B K, McCray J A , Guzikowski A P , Hess G P. J . Org. Chem. ,1990 , 55 : 1585 —1589
[38] Ellis-Davies G C R , Kaplan J H , Barsotti R J . Biophys. J . ,1996 , 70 : 1006 —1016
[39] Ellis-Davies G C R , Kaplan J H. Proc. Nat . Acad. Sci . USA ,1994 , 91 : 187 —191
[40] Walbert S , Pfleiderer W, Steiner U E. Helv. Chim. Acta. ,2001 , 84 : 1601 —1611
[41] Furuta T, Hirayama Y, Iwamura M. Org. Lett . , 2001 , 3 (12) :1809 —1812
[42] Min S , Wang G Y, Shuai W. J . Photochem. Photobio. A:Chem. , 2007 , 185 : 140 —143
[43] Chen Y, Steinmetz M G. Org. Lett . , 2005 , 7 : 3729 —3732
[44] Suzuki A Z, Watanabe T, Kawamoto M, Nishiyama K,Yamashita H , Ishii M, Iwamura M, Furuta T. Org. Lett . , 2003 , 5 (25) :4867 —4870
[45] Furuta T, Torigai H , Sugimoto M, Iwamura M. J . Org. Chem. ,1995 , 60 (13) : 3953 —3956
[46] Eckardt T, Hagen V , Schade B , Schmidt R , Schweitzer C ,Bendig J . J . Org. Chem. , 2002 , 67 : 703 —710
[47] Schade B , Hagen V , Schmidt R , Herbrich R , Krause E , Eckardt T, Bendig J . J . Org. Chem. , 1999 , 64 : 9109 —9117
[48] Geissler D , Antonenko Y N , Schmidt R , Keller S , Krylova O O ,Wiesner B , Bendig J , Pohl P , Hagen V. Angew. Chem. Int .Ed. , 2005 , 44 : 1195 —1198
[49] Hagen V , Bendig J , Frings S , Eckardt T, Helm S , Reuter D ,Kaupp U B. Angew. Chem. Int . Ed. , 2001 , 40 (6) : 1046 —1048
[50] Hagen V , Frings S , Bendig J , Lorenz D , Wiesner B , Kaupp U B. Angew. Chem. Int . Ed. , 2002 , 41 : 3625 —3628
[51] Hagen V , Dekowski B , Nache V , Schmidt R , Geiβler D , Lorenz D , Eichhorst J , Keller S , Kaneko H , Benndorf K, Wiesner B.Angew. Chem. Int . Ed. , 2005 , 44 : 7887 —7891
[52] Furuta T, Momotake A , Sugimoto M, Hatayama M, Torigai H ,Iwamura M. Biochem. Biophys. Res. Commun. , 1996 , 228 :193 —198
[53] Furuta T, Iwamura M. Methods Enzymol . , 1998 , 291 : 50 —63
[54] Givens R S , Jung A , Park C H , Weber J , Bartlett W. J . Am.Chem. Soc. , 1997 , 119 : 8369 —8370
[55] Song K S , Liu L , Li X S , Guo Q X. Res. Chem. Interm. ,2000 , 26 : 319 —325
[56] Furuta T, Wang S S H , Dantzker J L , et al . Proc. Natl . Acad.Sci . USA , 1999 , 96 : 1193 —1200
[57] Albota M, Beljonne D , Bredas J L , et al . Science , 1998 , 281 :1653 —1656
[58] Birge R R. Acc. Chem. Res. , 1986 , 19 : 138 —146
[59] Xu C , Webb W W. J . Opt . Soc. Am. B , 1996 , 13 : 481 —491
[60] Rumi M, Ehrlich J E , Heikal A A , et al . J . Am. Chem. Soc. ,2000 , 122 : 9500 —9510
[61] Sumalekshmy S , Henary M M, Siegel N , Lawson P D V , Wu Y G, Schmidt K, Bródas J L , Perry J W, Fahrni C J . J . Am.Chem. Soc. , 2007 , 129 : 11888 —11889
[62] Lee W H , Cho M, Jeon S J , Cho B R. J . Phys. Chem. A ,2000 , 104 : 11033 —11040
[63] Pond S J K, Rumi M, Levin MD , Parker T C , Beljonne D , Day M W, Bródas J L , Marder S R , Perry J W. J . Phys. Chem. A ,2002 , 106 : 11470 —11480
[64] Givens R S , Matuszewski J . J . Am. Chem. Soc. , 1984 , 106 :6860 —6861
[65] Schmidt R , Geissler D , Hagen V , Bendig J . J . Phys. Chem. A ,2007 , 111 : 5768 —5774
[66] Lin W, Lawrence D S. J . Org. Chem. , 2002 , 67 : 2723 —2726
[67] Lu M, Fedoryak O D , Moister B R , Dore T M. Org. Lett . ,2003 , 5 (12) : 2119 —2122
[68] Blanc A , Bochet C G. J . Org. Chem. , 2003 , 68 : 1138 —1141
[69] Furuta T, Takeuchi H , Isozaki M, Takahashi Y, Kanehara M,Sugimoto M, Watanabe T, Noguchi K, Dore T M, Kurahashi T,wamura M, Tsien R Y. ChemBioChem. , 2004 , 5 : 1119 —1128
[70] Geiβler D , Kresse K, Wiesner B , Bendig J , Kettenmann H ,Hagen V. ChemBioChem , 2003 , 4 : 162 —170
[71] Hagen V , Frings S , Wiesner B , Helm S , Kaupp U B , Bendig J .ChemBioChem. , 2003 , 4 : 434 —442
[72] Senda N , Momotake A , Nishimura Y, Arai T. Bull . Chem. Soc.Jap. , 2006 , 15 : 1753 —1757
[73] Fedoryak O D , Dore T M. Org. Lett . , 2002 , 4 (20) : 3419 —3422
[74] Zhu Y, Pavlos C M, Toscano J P , Dore T M. J . Am. Chem.Soc. , 2006 , 128 : 4267 —4276
[75] Papageorgiou G, Ogden D C , Barth A , Corrie J E T. J . Am.Chem. Soc. , 1999 , 121 : 6503 —6504
[76] Huang Y H , Sinha S R , Fedoryak O D , Ellis-Davies G C R ,Bergles D E. Biochemistry , 2005 , 44 : 3316 —3326
[77] Fedoryak O D , Sul J Y, Haydon P G, Ellis-Davies G C R.Chem. Commun. , 2005 , 3664 —3666
[78] Momotake A , Lindegger N , Niggli E , Barssotti R J , Ellis-Davies G C R. Nature Methods , 2006 , 3 (1) : 35 —40
[79] Walker J W. J . Gen. Physiol . , 1999 , 114 (1) : 2A —2A
[80] Ando H , Furuta T, Tsien R Y, Okamoto H. Nat . Genet . , 2001 ,28 : 317 —325
[81] Matsuzaki M, Ellis-Davies G C R , Nemoto T, Miyashita Y, Iino M, Kasai H. Nat . Neurosci . , 2001 , 4 (11) : 1086 —1092
[82] Matsuzaki M, Honkura N , Ellis-Davies G C R , Kasai H. Nature ,2004 , 429 (6993) : 761 —766
[83] Ellis-Davies G C R. Cell Calcium , 2006 , 39 (6) : 471 —473
[84] Noguchi J , Matsuzaki M, Ellis-Davies G C R , Kasai H. Neuron ,2005 , 46 (4) : 609 —622

[1] 郭玲香, 李菊平, 刘志洋, 李全. 聚集诱导发光型光敏剂用于线粒体靶向光动力治疗[J]. 化学进展, 2022, 34(11): 2489-2502.
[2] 胡安东, 周顺桂, 叶捷. 生物杂化体介导的半人工光合作用:机理、进展及展望[J]. 化学进展, 2021, 33(11): 2103-2115.
[3] 赖欣宜, 王志勇, 郑永太, 陈永明. 纳米金属有机框架材料在药物递送领域的应用[J]. 化学进展, 2019, 31(6): 783-790.
[4] 郑秉得, 赵园园, 李洪才, 郑碧远, 柯美荣, 黄剑东*. 可激活抗癌光敏剂[J]. 化学进展, 2018, 30(9): 1403-1414.
[5] 刘湘梅, 田康, 薛乘风, 韩艺蕃, 刘淑娟, 赵强*. X射线激发发光体在光动力治疗中的应用[J]. 化学进展, 2017, 29(12): 1488-1498.
[6] 李红茹,谢亭,胡女丹,杨刘峰,张胜涛,高放. 双光子诱导产生单重态氧的三重态光敏剂的研究*[J]. 化学进展, 2009, 21(0708): 1398-1407.
[7] 黄蕾,赵福群,黄新,张复实. 光免疫偶联物的研究进展*[J]. 化学进展, 2007, 19(04): 527-534.
[8] 闫芳,马金石,成昊,张驿. 新型绿色农药--光活化农药[J]. 化学进展, 1999, 11(04): 341-.
[9] 邱勇,董润安,宋心琦. 卟啉类化合物对生物分子的光敏化氧化[J]. 化学进展, 1998, 10(01): 45-.