4',5'-bis(1,3,2-dithiarsolan-2-yl)-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one

• ChemBase ID: 168917
• Molecular Formular: C24H18As2O5S4
• Molecular Mass: 664.49992
• Monoisotopic Mass: 663.84689968
• SMILES: c1(ccc2c(c1[As]1SCCS1)Oc1c(ccc(c1[As]1SCCS1)O)C12OC(=O)c2c1cccc2)O
• Canonical SMILES: O=C1OC2(c3c1cccc3)c1ccc(c(c1Oc1c2ccc(c1[As]1SCCS1)O)[As]1SCCS1)O
• InChI: InChI=1S/C24H18As2O5S4/c27-17-7-5-15-21(19(17)25-32-9-10-33-25)30-22-16(6-8-18(28)20(22)26-34-11-12-35-26)24(15)14-4-2-1-3-13(14)23(29)31-24/h1-8,27-28H,9-12H2
• InChIKey: AJNUQUGWNQHQDJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4',5'-bis(1,3,2-dithiarsolan-2-yl)-3',6'-dihydroxy-3H-spiro[2-benzofuran-1,9'-xanthene]-3-one
• IUPAC Traditional name: 4',5'-bis(1,3,2-dithiarsolan-2-yl)-3',6'-dihydroxyspiro[2-benzofuran-1,9'-xanthene]-3-one
• Synonyms: 4',5'-Bis(1,3,2-dithiarsolan-2-yl)-3',6'-dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one; FlAsH; Fluorescein Arsenical Helix Binder; Lumio Green; FlAsH-EDT2

Database IDs

• CAS Number: 212118-77-9
• PubChem SID: 162263049
• PubChem CID: 9831137

CALCULATED PROPERTIES

• Acid pKa: 8.444204
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.575608
• LogD (pH = 7.4): 4.5378366
• Log P: 4.5761
• Molar Refractivity: 140.7395 cm^3
• Polarizability: 60.452873 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Orange Solid
• Melting Point: 169-172°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F335200

The Fluorescein Arsenical Hairpin Binder (FlAsH) method is presented for fluorescence labeling of proteins in living cells. Labeling proteins with the membrane-permeant fluorogenic biarsenical dye fluorescein arsenical hairpin binder-ethanedithiol (FlAsH-

REFERENCES

• Gaietta, G., et al.: Science, 296, 503 (2002)
• Hoffmann, C., et al.: Nature Methods, 2, 171 (2002)
• Dyachok, O., et al.: Nature, 439, 349 (2002)
• Gautier, A., et al.: Chem. Biol., 15, 128 (2002)