FlAsH-EDT2

FlAsH-EDT2 is an organoarsenic compound with molecular formula C24H18As2O5S4. Its structure is based around a fluorescein core with two 1,3,2-dithiarsolane substituents. It is used in bioanalytical research as a fluorescent label for visualising proteins in living cells. FlAsH-EDT2 is an abbreviation for fluorescin arsenical hairpin binder-ethanedithiol, and is a pale yellow or pinkish fluorogenic solid. It has a semi-structural formula (C2H4AsS2)2-(C13H5O3)-C6H4COOH, representing the dithiarsolane substituents bound to the hydroxyxanthone core, attached to an o-substituted molecule of benzoic acid.

FlAsH-EDT2
Names
Other names
Fluorescein Arsenical Hairpin Binder; Lumio green
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C24H18As2O5S4/c27-17-7-5-15-19(13-3-1-2-4-14(13)24(29)30)16-6-8-18(28)21(26-34-11-12-35-26)23(16)31-22(15)20(17)25-32-9-10-33-25/h1-8,27H,9-12H2,(H,29,30)
    Key: KCPRYVGBEBFLIG-UHFFFAOYSA-N
  • c1ccc(c(c1)c2c3ccc(c(c3oc-4c(c(=O)ccc24)[As]5SCCS5)[As]6SCCS6)O)C(=O)O
  • OC(=O)C1=C(C=CC=C1)C1=C2C=CC(=O)C([As]3SCCS3)=C2OC2=C([As]3SCCS3)C(O)=CC=C12
Properties
C24H18As2O5S4
Molar mass 664.49 g·mol−1
Appearance Solid
Melting point 169 to 172 °C (336 to 342 °F; 442 to 445 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

FlAsH-EDT2 is used for site-specific labelling, selectively binding to proteins containing the tetracysteine (TC) motif Cys-Cys-Xxx-Xxx-Cys-Cys and becoming fluorescent when bound. It displays non-specific binding to endogenous cysteine-rich proteins, meaning it binds to sites other than the one of interest (CCXXCC). Further optimization of the TC motif has revealed improved FlAsH binding affinity for a CCPGCC motif, and higher quantum yield when the tetracysteine motif is flanked with specific residues (HRWCCPGCCKTF or FLNCCPGCCMEP).

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