Dichlorofluorescein

Dichlorofluorescein
Names
	Preferred IUPAC name 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[[2]benzofuran-1,9′-xanthen]-3-one
Identifiers
CAS Number	76-54-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:51596 ;
ChEMBL	ChEMBL1908059 ;
ChemSpider	58471 ;
ECHA InfoCard	100.000.881
PubChem CID	64944;
UNII	56NQM5UZT1 ;
CompTox Dashboard (EPA)	DTXSID8058798 ;
	InChI 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 ; 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;
	SMILES Clc5cc4c(Oc1cc(O)c(Cl)cc1C34OC(=O)c2c3cccc2)cc5O;
Properties
Chemical formula	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). verify (what is ?) Infobox references

The printable version is no longer supported and may have rendering errors. Please update your browser bookmarks and please use the default browser print function instead.

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

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

^ 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.
^ 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.
^ 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.
^ 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.

[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.

[1]

[2]

[3]

[4]