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DOI: 10.1055/s-0031-1290426
Fluorescein
Publication History
Publication Date:
13 June 2012 (online)
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Frank Thielbeer was born in Magdeburg, Germany, and studied chemistry at the University of Leipzig (Germany) and Monash University in Melbourne (Australia) receiving his M.Sc. degree in 2008. In the following year he started his PhD with Prof. Mark Bradley at the University of Edinburgh. His research interests focus on polymer particles and their modifications for applications in chemical biology.
Introduction
In 1871 fluorescein (1) was firstly synthesized by A. von Baeyer via a Friedel–Crafts acylation of phthalic anhydride (2) and resorcinol (3).[ 1 ] Fluorescein is a dark red powder which when dissolved displays excellent fluorescent properties (λex = 494 nm and λem = 521 nm in water) making it widely used in applications ranging from molecular sensing to labeling. It has a high quantum yield, is water soluble, can be excited with the readily available argon ion laser, is prepared in a short synthetic route and is non-toxic [LD50 = 6.7 g/kg (rat)].[ 2 ] A large number of fluorescein derivatives are commercially available while the properties can be modified to tune its fluorescent properties and widen its range of applications.
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Abstracts
(A) Metal Sensor:
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(B) pH Sensor:
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(C) Reactive Oxygen Species (ROS) Sensor:
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(D) Small Molecule Sensor:
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(E) Enzyme Activity:
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(F) Protein Labeling:
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(G) Polymerizable Fluorescein Derivatives:
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References
- 1 Baeyer A. Ber. Dtsch. Chem. Ges. 1871; 4: 555
- 2a Chen X, Pradhan T, Wang F, Kim JS, Yoon J. Chem. Rev. 2012; 112: 1910
- 2b Sjöback R, Nygren J, Kubista M. Spectrochim. Acta A 1995; 51: L7
- 2c Yankell SL, Loux JJ. J. Periodontol. 1977; 48: 228
- 3 Seo S, Lee HY, Park M, Lim JM, Kang D, Yoon J, Jung JH. Eur. J. Inorg. Chem. 2010; 843
- 4 Unciti-Broceta A, Yusop MR, Richardson PR, Walton JG. A, Bradley M. Tetrahedron Lett. 2009; 50: 3713
- 5 Miller EW, Bian SX, Chang CJ. J. Am. Chem. Soc. 2007; 129: 3458
- 6 Terai T, Urano Y, Izumi S, Kojima H, Nagano T. Chem. Commun. 2012; 48: 2840
- 7 Tanaka K, Kitamura N, Chujo Y. Macromolecules 2010; 43: 6180
- 8 Li N, Lim RK. V, Edwardraja S, Lin Q. J. Am. Chem. Soc. 2011; 133: 15316
- 9 Thielbeer F, Chankeshwara SV, Bradley M. Biomacromolecules 2011; 12: 4386
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References
- 1 Baeyer A. Ber. Dtsch. Chem. Ges. 1871; 4: 555
- 2a Chen X, Pradhan T, Wang F, Kim JS, Yoon J. Chem. Rev. 2012; 112: 1910
- 2b Sjöback R, Nygren J, Kubista M. Spectrochim. Acta A 1995; 51: L7
- 2c Yankell SL, Loux JJ. J. Periodontol. 1977; 48: 228
- 3 Seo S, Lee HY, Park M, Lim JM, Kang D, Yoon J, Jung JH. Eur. J. Inorg. Chem. 2010; 843
- 4 Unciti-Broceta A, Yusop MR, Richardson PR, Walton JG. A, Bradley M. Tetrahedron Lett. 2009; 50: 3713
- 5 Miller EW, Bian SX, Chang CJ. J. Am. Chem. Soc. 2007; 129: 3458
- 6 Terai T, Urano Y, Izumi S, Kojima H, Nagano T. Chem. Commun. 2012; 48: 2840
- 7 Tanaka K, Kitamura N, Chujo Y. Macromolecules 2010; 43: 6180
- 8 Li N, Lim RK. V, Edwardraja S, Lin Q. J. Am. Chem. Soc. 2011; 133: 15316
- 9 Thielbeer F, Chankeshwara SV, Bradley M. Biomacromolecules 2011; 12: 4386
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