Dichlorofluorescein

Dichlorofluorescein (DCF) is an organic dye of the fluorescein family, being substituted at the 2 and 7 positions by chloride.

Dichlorofluorescein
Names
Preferred IUPAC name
2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[[2]benzofuran-1,9′-xanthen]-3-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.881
UNII
  • InChI=1S/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H checkY
    Key: VFNKZQNIXUFLBC-UHFFFAOYSA-N checkY
  • InChI=1/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H
    Key: VFNKZQNIXUFLBC-UHFFFAOYAO
  • InChI=1S/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H
    Key: VFNKZQNIXUFLBC-UHFFFAOYSA-N
  • Clc5cc4c(Oc1cc(O)c(Cl)cc1C34OC(=O)c2c3cccc2)cc5O
Properties
C20H10Cl2O5
Molar mass 401.20 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

It is used as an indicator for argentometry by Fajans method.[1][2]

When used as an indicator, upon reaching the equivalence point of a titration reaction the color shifts from colorless towards a faint pink.

It is also used in the cellular antioxidant activity (CAA) assay. Dichlorofluorescin (DCFH) is a probe that is trapped within cells and is easily oxidized to fluorescent dichlorofluorescein (DCF). The method measures the ability of compounds to prevent the formation of DCF by 2,2'-Azobis(2-amidinopropane) dihydrochloride (ABAP)-generated peroxyl radicals in human hepatocarcinoma HepG2 cells.[3] By itself, dichlorofluorescin (DCFH) also quantifies intracellular hydrogen peroxide as well as cellular oxidative stress.[4]

References
  1. Kolthoff, I. M.; Lauer, W. M.; Sunde, C. J. (1929). "The Use of Dichlorofluorescein as an Adsorption Indicator for the Argentometric Titration of Chlorides". Journal of the American Chemical Society. 51 (11): 3273. doi:10.1021/ja01386a014.
  2. Bambach, Karl; Rider, T. H. (1935). "Volumetric Determinations of Halides: Use of Dichlorofluorescein as an Adsorption Indicator". Industrial & Engineering Chemistry Analytical Edition. 7 (3): 165. doi:10.1021/ac50095a012.
  3. Wolfe, K. L.; Liu, R. H. (2007). "Cellular Antioxidant Activity (CAA) Assay for Assessing Antioxidants, Foods, and Dietary Supplements". Journal of Agricultural and Food Chemistry. 55 (22): 8896–8907. doi:10.1021/jf0715166. PMID 17902627.
  4. LeBel, C. P.; Ischiropoulos, Harry; Bondy, S. C. (1992). "Evaluation of the probe 2',7'-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress" (PDF). Chem. Res. Toxicol. 5 (2): 227–231. doi:10.1021/tx00026a012. PMID 1322737.
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