Dichlorofluorescein

Dichlorofluorescein
Names
	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).
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	Infobox references

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.

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[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.