Fluorescein Arsenical Helix Binder
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| General | |||||||||||||
| Surname | Fluorescein Arsenical Helix Binder | ||||||||||||
| other names |
4 ′, 5′-bis (1,3,2-dithioarsolan-2-yl) fluorescein |
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| Molecular formula | C 24 H 18 As 2 O 5 S 4 | ||||||||||||
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| properties | |||||||||||||
| Molar mass | 664.50 g · mol -1 | ||||||||||||
| Physical state |
firmly |
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| solubility |
slightly soluble in water |
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| safety instructions | |||||||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||
Fluorescein arsenical helix binder , short FlAsH EDT 2 , is a from the fluorescent dye fluorescein -derived arsenic chemical compound , which in peptides and proteins (. So-called selective to certain structures Tetracysteinsequenzen can bind). After binding to its target structure and excitation with short-wave light, FlAsH shows fluorescence . FlAsH-EDT 2 is therefore suitable as a protein tag for the selective marking and identification of proteins. This dye is also used as a fluorophore for Förster resonance energy transfer (FRET). FlAsH-EDT 2 can be classified in the group of triphenylmethane dyes as well as xanthene dyes .
biochemistry
The preferred binding structure for FlAsH-EDT 2 is a tetracysteine sequence, which is made up of four cysteine units and a spacer consisting of two amino acids in the form CCXXCC . FlAsH-EDT 2 also binds to other structures with a lower affinity , e.g. B. CXXC .
synthesis
FlAsH-EDT 2 can be synthesized from 4 ', 5'-bis (acetoxymercuri) fluorescein in a two-step synthesis . For this purpose, 4 ', 5'-bis (acetoxymercuri) fluorescein with a molar excess of arsenic (III) chloride and diisopropylethylamine in N -methylpyrrolidone under palladium acetate - catalysis implemented. The reaction product is then converted into FlAsH-EDT 2 with an excess of 1,2-ethanedithiol .
Individual evidence
- ↑ a b Material Safety Data Sheet ( Memento of the original from March 17, 2013 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. .
- ↑ Entry on arsenic compounds in the GESTIS substance database of the IFA , accessed on February 1, 2016 (JavaScript required)
- ↑ Not explicitly listed in Regulation (EC) No. 1272/2008 (CLP) , but with the specified labeling it falls under the group entry arsenic compounds, with the exception of those named in this appendix in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA) on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ^ A b B. Albert Griffin, Stephen R. Adams, Roger Y. Tsien (1998): Specific covalent labeling of recombinant protein molecules inside live cells. In: Science . Vol. 281, pp. 269-272. PMID 9657724 doi : 10.1126 / science.281.5374.269 .
- ↑ Katarina Stroffekova, Catherine Proenza, Kurt G. Beam (2001): The protein-labeling reagent FLASH-EDT 2 binds not only to CCXXCC motifs but also non-specifically to endogenous cysteine-rich proteins. In: Pflügers Arch . Vol. 442, pp. 859-866. PMID 11680618 doi : 10.1007 / s004240100619 .
