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Sigma-Aldrich

2′,7′-Dichlorofluorescein

BioReagent, suitable for fluorescence, ≥90% (T)

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Synonym(s):
DCF, Dichlorofluorescein
Empirical Formula (Hill Notation):
C20H10Cl2O5
CAS Number:
76-54-0
Molecular Weight:
401.20
Beilstein:
58009
EC Number:
200-968-6
MDL number:
MFCD00005047
PubChem Substance ID:
57649439
NACRES:
NA.32

product line

BioReagent

Quality Level

100

Assay

≥90% (T)

form

solid

mp

280 °C (dec.) (lit.)

fluorescence

λex 504 nm; λem 529 nm in 0.1 M Tris pH 8.0

suitability

suitable for fluorescence

SMILES string

Oc1cc2Oc3cc(O)c(Cl)cc3C4(OC(=O)c5ccccc45)c2cc1Cl

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

InChI key

VFNKZQNIXUFLBC-UHFFFAOYSA-N

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General description

2′,7′-Dichlorofluorescein, also known as DCF is a fluorescent dye. The DCF fluorescence excitation is at 498nm with emission at 522nm. The lipophilic non-fluorescent Dcfh-DA readily crosses the cell membrane through passive diffusion followed by deacetylation. The deacylated product is an oxidant sensitive 2′,7′-dichlorofluorescein (DCHF). DCHF is oxidized later to form highly fluorescent DCF, which is measured.

Application

2′,7′-Dichlorofluorescein is used as fluorescent probe to measure ROS (Reactive Oxygen Species) for biological studies. It may also be used as a dip reagent for the fluorometric determination of vicinal diols, glycosides, and phenols.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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  5. What can be used to make a solution of 2´,7´-dichlorofluorescein?

    2´,7´-Dichlorofluorescein is soluble at 25 mg/mL absolute ethanol with heating. 2´,7´-Dichlorofluorescein is also soluble in water at 0.1 mg/mL.

  6. In what types of applications can 2´,7´-Dichlorofluorescein be used?

    Some applications for use of 2´,7´-Dichlorofluorescein are listed below. This product can be used for the determination of carbohydrates by fluorescence densitometry after TLC.  See G. Gübitz et al., J. Chromatogr., 117, 337, (1976). 2´,7´-Dichlorofluorescein as also been used in the determination of H2O2 by chemiluminescence. See the following references by H. Watanabe et al. Anal. Sci. 2, 461, (1986) and T. Segawa et al. Anal. Sci. 6, 763, (1990). This product has also been used as a  fluorescent additive used in indirect fluorimetric detection in OTC-HPLC. See W.D. Pfeffer and E.S. Yeung, J. Chromatogr., 506, 401, (1990).

  7. What excitation /emission wavelengths are best for fluorescence detection of 2´,7´-Dichlorofluorescein?

    2´,7´-Dichlorofluorescein can be detected at an excitation wavelength at 504 nm and emission wavelength at 529 nm in 0.1 M Tris pH 8.0.

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W.D. Pfeffer et al.
Journal of Chromatography A, 506, 401-401 (1990)
C Rota et al.
Free radical biology & medicine, 27(7-8), 873-881 (1999-10-09)
The oxidation of 2'-7'-dichlorofluorescin (DCFH) to the fluorescent 2'-7'-dichlorofluorescein (DCF) by horseradish peroxidase (HRP) was investigated by fluorescence, absorption, and electron spin resonance spectroscopy (ESR). As has been previously reported, HRP/H2O2 oxidized DCFH to the highly fluorescent DCF. However, DCF
Masahito Miura et al.
Journal of molecular and cellular cardiology, 56, 97-105 (2012-12-26)
Ca(2+) waves are initiated not only by Ca(2+) leak from the sarcoplasmic reticulum (SR), but also by Ca(2+) dissociation from the myofilaments in the myocardium with nonuniform contraction. We investigated whether contractile properties and the production of reactive oxygen species
Xiuping Chen et al.
Free radical research, 44(6), 587-604 (2010-04-08)
Reactive oxygen species (ROS) are critically important chemical intermediates in biological studies, due to their multiple physiologically essential functions and their often pathologically deleterious effects. Consequently, it is vital that their presence in biological samples has to be quantifiable. However
T. Segawa et al.
Analytical Sciences, 6, 763-763 (1990)
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