中文
Announcement
More
Progress in Chemistry 2010, Vol. 22 Issue (08): 1633-1640 Previous Articles   Next Articles

• Review •

Biologically Environment-Sensitive Fluorescent Probes

Wang Ke  Ma Huimin**   

  1. (Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China)
  • Received: Revised: Online: Published:
  • Contact: Ma Huimin E-mail:mahm@iccas.ac.cn
PDF ( 2743 ) Cited
Export

EndNote

Ris

BibTeX

The alterations of locally environmental parameters (e.g., polarity, pH, viscosity and temperature) in biosystems correlate closely with some physiological function disorders. Therefore, the precise measurements of these parameters are of great importance for the explanation of complicated biological processes and diagnoses of some related diseases. Because of their high spatial and temporal resolution capability, many environment-sensitive fluorescent probes have been developed and used in life sciences. In this paper, a brief review is given on the progress and applications of various biologically environment-sensitive fluorescent probes, including some of the related results from our laboratory.

Contents 
1 Introduction 
2 Polarity-sensitive fluorescent probes 
2.1 Nile red and its derivates
2.2 Acrylodan
2.3 Aladan 
2.4 Pyrene and its derivates
2.5 Neutral red and its derivates
2.6 Others
3 pH-sensitive fluorescent probes 
4 Viscosity-sensitive fluorescent probes
5 Temperature-sensitive fluorescent probes 
6 Prospects

[1 ] 马会民(Ma H M). 生物大分子的定位光学标记与区域结构
分析( 第36 章) ,生命分析化学( 汪尔康主编) ( Site-
Specific Spectroscopic Labeling and Locally Structural Analysis of
Biomacromolecules,Chapter 36,In Analytical Chemistry for Life
Sciences,( Ed. Wang E K) . 北京: 科学出版社( Beijing:
Science Press) ,2006. 974—995
[2 ] Russell D A, Pottier R H, Valenzeno D P. Photochem.
Photobiol. ,1994,59(3) : 309—313
[3 ] Haidekker M A,Theodorakis E A. Org. Biomol. Chem. ,2007,
5(11) : 1669—1678
[4 ] Monti M, Brandt L, Ikomi-Kumm J, et al. Scand. J.
Haematol. ,1986,36(4) : 353—357
[5 ] Karnebogen M,Singer D,Kallerhoff M,et al. Thermochim.
Acta,1993,229: 147—155
[6 ] Goncalves M S T. Chem. Rev. ,2009,109(1) : 190—212
[7 ] Haugland R P. The Handbook: A Guide to Fluorescent Probes
and Labeling Technologies (10th ed) . Invitrogen Corp. ,USA,
2005
[8 ] 许金钩( Xu J G ) , 王尊本( Wang Z B ) . 荧光分析法
( Fluorescence Analytical Approach ) . 北京: 科学出版社
( Beijing: Science Press) ,2006
[9 ] Ioffe V M,Gorbenko G P,Domanov Y A,et al. J. Fluoresc. ,
2006,16(1) : 47—52
[10] 吕凤婷( Lv F T) ,高莉宁(Gao L N) ,房喻( Fang Y) . 化学进展( Progress in Chemistry) ,2005,17(5) : 773—779
[11] Zheng G R,Wang Z X,Tang L,et al. Sens. Actuators B,
2007,122(2) : 389—394
[12] Qian J H,Xu Y F,Qian X H,et al. J. Photochem. Photobiol.
A,2009,207(2 /3) : 181—189
[13] Jacobson A,Petric A,Hogenkamp D. J. Am. Chem. Soc. ,
1996,118(24) : 5572—5579
[14] Uchiyama S,Kawai M,de Silva A P,et al. J. Am. Chem.
Soc. ,2004,126(10) : 3032—3033
[15] Valeur B. Molecular Fluorescence, Weinheim: Wiley-VCH,
2002
[16] Golini C M,Williams B W,Foresman J B. J. Fluoresc. ,1998,
8(4) : 395—404,and references therein
[17] Sackett D,Wolff J. Anal. Biochem. ,1987,167 ( 2 ) : 228—
234
[18] Kim S Y,Semyonov A N,Twieg R J,et al. J. Phys. Chem. B,
2005,109(51) : 24517—24525
[19] Hungerford G,Rei A,Ferreira M I C. FEBS J. ,2005,272
(23) : 6161—6169
[20] Chen S M,Li X H,Ma H M. ChemBioChem,2009,10 ( 7 ) :
1200—1207
[21] Tricerri M A,Agree A K B,Sanchez S A,et al. Biochemistry,
2000,39(47) : 14682—14691
[22] Kamal J K A,Zhao L,Zewail A H. Proc. Natl. Acad. Sci.
USA,2004,101(37) : 13411—13416
[23] Buzády A,Savolainen J,Erostyák J,et al. J. Phys. Chem. B,
2003,107(5) : 1208—1214
[24] Cohen B E,McAnaney T B,Park E S,et al. Science,2002,
296(5573) : 1700—1703
[25] Abbyad P,Shi X H,Childs W,et al. J. Phys. Chem. B,
2007,111(28) : 8269—8276
[26] Harikumar K G. ,Pinon D I,Miller L J. J. Biol. Chem. ,
2006,281(37) : 27072—27080
[27] Sang D Y,Tian J,Ji G Z. Chin. J. Chem. ,2006,24 ( 9 ) :
1109—1116
[28] Glushko V, Thaler M S R, Karp C D. Arch. Biochem.
Biophys. ,1981,210(1) : 33—42
[29] Brahma A,Mandal C,Bhattacharyya D. Biochim. Biophys.
Acta,2005,1751(2) : 159—169
[30] 陈凯( Chen K) ,翟春熙( Zhai C X) ,李文( Li W) 等. 高等
学校化学学报( Chemical Journal of Chinese Universities ) ,
2004,25(10) : 1905—1908
[31] Singh M K, Pal H, Bhasikuttan A C, et al. Photochem.
Photobiol. ,1998,68(1) : 32—38
[32] Singh M K, Pal H, Bhasikuttan A C, et al. Photochem.
Photobiol. ,1999,69(5) : 529—535
[33] Okada D J. Neurosci. Methods,2000,101(1) : 85—92
[34] Dong S Y,Ma H M,Duan X J,et al. J. Proteome Res. ,2005,
4(1) : 161—166
[35] Dong S Y,Zhao Z W,Ma H M. J. Proteome Res. ,2006,5
(1) : 26—31
[36] Wang X C,Guo L H,Ma H M. Spectrochim. Acta Part A,
2009,73(5) : 875—878
[37] Wang X C,Wang S J,Ma H M. Analyst,2008,133 ( 4 ) :
478—484
[38] Wang S J,Chen S M,Ma H M. Sci. China Ser. B-Chem. ,
2009,52(6) : 809—814
[39] Wang S J,Wang X C,Shi W,et al. Biochim. Biophys. Acta,
2008,1784(2) : 415—422
[40] Shannigrahi M,Bagchi S. Spectrochim. Acta Part A,2005,61
(9) : 2131—2138
[41] Ju W G,Long P,Zhang X H,et al. Colloids Surf. A,2006,
279(1 /3) : 233—237
[42] Gao F,Li H R,Li X M,et al. Colloids Surf. A,2007,304(1 /
3) : 31—35
[43] Okamoto A,Tainaka K,Unzai T,et al. Tetrahedron,2007,63
(17) : 3465—3470
[44] Yushchenko D A, Bilokin M D, Pyvovarenko O V, et al.
Tetrahedron Lett. ,2006,47(6) : 905—908
[45] Uchiyama S, Takehira K, Yoshihara T, et al. Org. Lett. ,
2006,8(25) : 5869—5872
[46] Han F,Chi L N,Wu W T,et al. J. Photochem. Photobiol. A,
2008,196(1) : 10—23
[47] Liu J X,Diwu Z J,Leunga W Y. Bioorg. Med. Chem. Lett. ,
2001,11(22) : 2903—2905,and references therein
[48] 苏美红( Su M H) ,聂丽华(Nie L H) ,马会民(Ma H M) .
分析科学学报( Journal of Analytical Science) ,2005,21 (2 ) :
210—214
[49] Orlien V,Happe A K,Stapelfeldt H,et al. Food Biophysics,
2008,(3) : 94—99
[50] Pal R,Parker D. Chem. Commun. ,2007,474—476
[51] Bradley M, Alexander L, Duncan K, et al. Bioorg. Med.
Chem. Lett. ,2008,18(1) : 313—317
[52] Ge F Y,Chen L G. J. Fluoresc. ,2008,18(3 /4) : 741—747
[53] Su M H,Liu H,Ma H M,et al. Chem. Commun. ,2001,
960—961
[54] Dong S Y,Ma H M,Li X H,et al. Anal. Lett. ,2004,37
(14) : 2937—2948
[55] Tang B,Liu X,Xu K H, et al. Chem. Commun. ,2007,
3726—3728
[56] Tang B,Yu F B,Li P,et al. J. Am. Chem. Soc. ,2009,131
(8) : 3016—3023
[57] Baruah M,Qin W W,Basaric'N,et al. J. Org. Chem. ,2005,
70(10) : 4152—4157
[58] 王艳玮(Wang Y W) ,李敏( Li M) ,沈珍( Shen Z) ,等. 无
机化学学报( Chinese Journal of Inorganic Chemistry) ,2008,
24(8) : 1247—1252
[59] Tian M Z,Peng X J,Feng F,et al. Dyes Pigments,2009,81
(1) : 58—62
[60] Jin S Y,Xu Z C,Chen J P,et al. Anal. Chim. Acta,2004,
523(1) : 117—123
[61] Bagar T,Altenbach K,Read N D, et al. Eukaryotic Cell,
2009,8(5) : 703—712
[62] De Silva A P,de Silva S S K,Goonesekera N C W,et al. J.Am. Chem. Soc. ,2007,129(11) : 3050—3051
[63] Kung C E,Reed J K. Biochemistry,1989,28 ( 16 ) : 6678—
6686
[64] Belletete M,Sarpal R S,Durocher G. Chem. Phys. Lett. ,
1993,201(1 /4) : 145—152
[65] 朱爱平( Zhu A P) ,吴世康(Wu S K) . 物理化学学报(Acta
Physico-Chimica Sinica) ,1998,14(6) : 552—556
[66] Arye P P,Strashnikova N,Likhtenshtein G I. J. Biochem.
Biophys. Methods,2002,51(1) : 1—15
[67] Law K Y,Loutfy R O. Macromolecules,1981,14 ( 3 ) : 587—
591
[68] Law K Y,Loutfy R O. Polymer,1983,24(4) : 439—442
[69] Loutfy R O. Macromolecules,1981,14(2) : 270—275
[70] Loutfy R O. Pure Appl. Chem. ,1986,58(9) : 1239—1248
[71] Kung C E,Reed J K. Biochemistry,1986,25 ( 20 ) : 6114—
6121
[72] Sawada S,Iio T,Hayashi Y,et al. Anal. Biochem. ,1992,204
(1) : 110—117
[73] Iio T,Takahashi S,Sawada S. J. Biochem. ,1993,113 ( 2 ) :
196—199
[74] Haidekker M A,Brady T P,Lichlyter D,et al. Bioorg. Chem. ,
2005,33(6) : 415—425
[75] Haidekker M A,Brady T P,Chalian S H,et al. Bioorg. Chem. ,
2004,32(4) : 274—289
[76] Haidekker M A,Ling T T,Anglo M,et al. Chem. Biol. ,
2001,8(2) : 123—131
[77] Haidekker M A,Brady T P,Lichlyter D,et al. J. Am. Chem.
Soc. ,2006,128(2) : 398—399
[78] Wandelt B, Mielniczak A, Turkewitsch P, et al. Biosens.
Bioelectron. ,2003,18(4) : 465—471
[79] Wandelt B, Mielniczak A, Turkewitsch P, et al. Biosens.
Bioelectron. ,2005,20(9) : 1728—1736
[80] Kee H L,Kirmaier C,Yu L,et al. J. Phys. Chem. B,2005,
109(43) : 20433—20443
[81] Alamiry M A H,Benniston A C,Copley G, et al. Chem.
Mater. ,2008,20(12) : 4024—4032
[82] Kuimova M K,Yahioglu G,Levitt J A,et al. J. Am. Chem.
Soc. ,2008,130(21) : 6672—6673
[83] Wang K,Shi W,Jia J,et al. Talanta,2009,77 (5 ) : 1795—
1799
[84] Kuimova M K, Botchway S W, Parker A W, et al. Nat.
Chemistry,2009,1(1) : 69—73
[85] Inoue Y,Jiang P Y,Tsukada E,et al. J. Am. Chem. Soc. ,
2002,124(24) : 6942—6949
[86] Yasuhara K,Sasaki1 Y,Kikuchi J. Colloids Surf. B,2008,
67: 145—149
[87] 梁丽芳( Liang L F) ,邢达(Xing D) ,陈同生( Chen T S) 等.
光谱学与光谱分析( Spectroscopy and Spectral Analysis ) ,
2009,29(2) : 459—462
[88] Lou J F,Hatton T A,Laibinis P E. Anal. Chem. ,1997,69
(6) : 1262—1264
[89] Figueroa I D,El Baraka M,Quiňones E,et al. Anal. Chem. ,
1998,70(18) : 3974—3977
[90] Chapman C F,Liu Y,Sonek G J,et al. Photochem. Photobiol,
1995,62(3) : 416—425
[91] Uchiyama S,Matsumura Y,de Silva A P,et al. Anal. Chem. ,
2004,76(6) : 1793—1798
[92] Engeser M,Fabbrizzi L,Licchelli M,et al. Chem. Commun. ,
1999,1191—1192
[93] Schrum K F,Williams A M, Haerther S A, et al. Anal.
Chem. ,1994,66(17) : 2788—2790
[94] De Silva A P,Gunaratne H Q N,Jayasekera K R,et al. Chem.
Lett. ,1995,24(2) : 123—124
[95] Wang Z,Zhang D Q,Zhu D B. Tetrahedron Lett. ,2005,46
(27) : 4609—4612
[96] Shiraishi Y,Miyamoto R,Zhang X,et al. Org. Lett. ,2007,9
(20) : 3921—3924
[97] Shiraishi Y,Miyamoto R,Hirai T. Langmuir,2008,24 ( 8 ) :
4273—4279
[98] Uchiyama S,Matsumura Y,de Silva A P,et al. Anal. Chem. ,
2003,75(1) : 5926—5935
[99] Gota C,Uchiyama S,Ohwada T. Analyst,2007,132 ( 2 ) :
121—126
[100] Gota C,Uchiyama S,Yoshihara T,et al. J. Phys. Chem. B,
2008,112(10) : 2829—2836
[101] Gota C,Okabe K,Funatsu T,et al. J. Am. Chem. Soc. ,
2009,131(8) : 2766—2767
[102] Tang L,Jin J K,Qin A J,et al. Chem. Comm. ,2009,4974—
4976
[103] Filevich O,Etchenique R. Anal. Chem. ,2006,78 ( 21 ) :
7499—7503
[104] Tsuda A,Sakamoto S,Yamaguchi K,et al. J. Am. Chem.
Soc. ,2003,125(51) : 15722—15723
[105] Shiraishi Y,Miyamoto R,Hirai T. Org. Lett. ,2009,11 ( 7 ) :
1571—1574

[1] Bingguo Zhao, Yadi Liu, Haoran Hu, Yangjun Zhang, Zezhi Zeng. Electrophoretic Deposition in the Preparation of Electrolyte Thin Films for Solid Oxide Fuel Cells [J]. Progress in Chemistry, 2023, 35(5): 794-806.
[2] Yixue Xu, Shishi Li, Xiaoshuang Ma, Xiaojin Liu, Jianjun Ding, Yuqiao Wang. Surface/Interface Modulation Enhanced Photogenerated Carrier Separation and Transfer of Bismuth-Based Catalysts [J]. Progress in Chemistry, 2023, 35(4): 509-518.
[3] Dandan Wang, Zhaoxin Lin, Huijie Gu, Yunhui Li, Hongji Li, Jing Shao. Modification and Application of Bi2MoO6 in Photocatalytic Technology [J]. Progress in Chemistry, 2023, 35(4): 606-619.
[4] Liu Yvfei, Zhang Mi, Lu Meng, Lan Yaqian. Covalent Organic Frameworks for Photocatalytic CO2 Reduction [J]. Progress in Chemistry, 2023, 35(3): 349-359.
[5] Wang Long, Zhou Qingping, Wu Zhaofeng, Zhang Yanming, Ye Xiaowo, Chen Changxin. Photovoltaic Cells Based on Carbon Nanotubes [J]. Progress in Chemistry, 2023, 35(3): 421-432.
[6] Jiang Haoyang, Xiong Feng, Qin Mulin, Gao Song, He Liuruyi, Zou Ruqiang. Conductive Phase Change Materials (PCMs) for Electro-to-Thermal Energy Conversion, Storage and Utilization [J]. Progress in Chemistry, 2023, 35(3): 360-374.
[7] Qiyao Guo, Jialong Duan, Yuanyuan Zhao, Qingwei Zhou, Qunwei Tang. Hybrid Energy Harvesting Solar Cells―From Principles to Applications [J]. Progress in Chemistry, 2023, 35(2): 318-329.
[8] Zixuan Liao, Yuhui Wang, Jianping Zheng. Research Advance of Carbon-Dots Based Hydrophilic Room Temperature Phosphorescent Composites [J]. Progress in Chemistry, 2023, 35(2): 263-373.
[9] Feng Li, Qingyun He, Fang Li, Xiaolong Tang, Changlin Yu. Materials for Hydrogen Peroxide Production via Photocatalysis [J]. Progress in Chemistry, 2023, 35(2): 330-349.
[10] Xiaojun Liu, Lang Qin, Yanlei Yu. Light-Driven Handedness Inversion of Cholesteric Liquid Crystals [J]. Progress in Chemistry, 2023, 35(2): 247-262.
[11] Yong Zhang, Hui Zhang, Yi Zhang, Lei Gao, Jianchen Lu, Jinming Cai. Surface Synthesis of Heteroatoms-Doped Graphene Nanoribbons [J]. Progress in Chemistry, 2023, 35(1): 105-118.
[12] Xiaozhu Zhao, Wen Li, Xuerui Zhao, Naipu He, Chao Li, Xuehui Zhang. Controlled Growth of MOFs in Emulsion [J]. Progress in Chemistry, 2023, 35(1): 157-167.
[13] Jing Li, Weigang Zhu, Wenping Hu. Organic Complex Materials and Devices for Near and Shortwave Infrared Photodetection [J]. Progress in Chemistry, 2023, 35(1): 119-134.
[14] Chao Ji, Tuo Li, Xiaofeng Zou, Lu Zhang, Chunjun Liang. Two-Dimensional Perovskite Photovoltaic Devices [J]. Progress in Chemistry, 2022, 34(9): 2063-2080.
[15] Shuai Huang, Yu Tao, Yinliang Huang. Photodeformable Composite Materials Based on Liquid Crystalline Polymers [J]. Progress in Chemistry, 2022, 34(9): 2012-2023.