2′,7′-Dichlorodihydrofluorescein Diacetate Chemical Properties

Melting point:

209-210 °C(lit.)

Boiling point:

593.5±50.0 °C(Predicted)

Density 

1.463±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMF: soluble

form 

Crystalline solid

pka

3.79±0.36(Predicted)

color 

White to off-white

Appearance

colorless solid

BRN 

4610273

Stability:

Light Sensitive

InChI

InChI=1S/C24H16Cl2O7/c1-11(27)31-21-9-19-15(7-17(21)25)23(13-5-3-4-6-14(13)24(29)30)16-8-18(26)22(32-12(2)28)10-20(16)33-19/h3-10,23H,1-2H3,(H,29,30)

InChIKey

PXEZTIWVRVSYOK-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=CC=C1C1C2=C(C=C(OC(C)=O)C(Cl)=C2)OC2=C1C=C(Cl)C(OC(C)=O)=C2

EPA Substance Registry System

2',7'-Dichlorohydrofluorescein diacetate (4091-99-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-26

WGK Germany 

3

F 

10-21

HS Code 

29329990

2′,7′-Dichlorodihydrofluorescein Diacetate Usage And Synthesis

Description

DCFH (commonly known as dichlorofluorescin) is used as an indicator of peroxynitrite formation. DCFH is supplied as the diacetate ester. Following enzymatic or base-catalyzed cleavage of the diacetate groups, it is readily oxidized to the highly fluorescent product dichlorofluorescein (DHF). Peroxynitrite is an efficient mediator of this oxidation and neither NO, superoxide, nor hydrogen peroxide alone appear to oxidize DCFH. Formation of DHF can be monitored by fluorescence spectroscopy using excitation and emission wavelengths of 502 and 523 nm, respectively, or by absorbance spectroscopy at 500 nm (ε = 59,500 M⁻¹cm⁻¹).

Chemical Properties

white to yellow-beige or pale pink powder

Uses

Cell-permeable fluorogenic probe used to measure reactive oxygen species (ROS) within cells by detection of enzymatically formed hydrogen peroxide.

Uses

2',7'-Dichlorodihydrofluorescein as a cell-permeable non-fluorescent probe. It is de-esterified intracellularly and turns to highly fluorescent 2’7’dichlorofluorescein upon oxidation.

Uses

2′,7′-Dichlorofluorescin diacetate is a cell-permeable non-fluorescent probe. 2′,7′-Dichlorofluorescin diacetate is de-esterified intracellularly and turns to highly fluorescent 2′,7′-dichlorofluorescein upon oxidation.
Applications include sensitive and rapid quantitation of oxygen-reactive species in response to oxidative metabolism; microplate assay for detecting oxidative products in phagocytic cells, and quantitative multiwell myeloid differentiation assay.

General Description

Cell-permeable fluorogenic probe that is useful for the detection of reactive oxygen species (ROS) and nitric oxide (?NO) and for the determination of the degree of overall oxidative stress.

Biochem/physiol Actions

Cell permeable: yes

storage

Store at -20°C

References

[1] N W KOOY  H I  J A Royall. Oxidation of 2’,7’-dichlorofluorescin by peroxynitrite.[J]. Free Radical Research, 1997, 27 3: 245-254. DOI: 10.3109/10715769709065763
[2] TARABOVá B, LUKE? P, HAMMER M U, et al. Fluorescence measurements of peroxynitrite/peroxynitrous acid in cold air plasma treated aqueous solutions[J]. Physical Chemistry Chemical Physics, 2019, 17: 8883-8896. DOI: 10.1039/c9cp00871c
[3] HYEJIN PARK. Oridonin Enhances Radiation-Induced Cell Death by Promoting DNA Damage in Non-Small Cell Lung Cancer Cells.[J]. International Journal of Molecular Sciences, 2018, 19 8. DOI: 10.3390/ijms19082378
[4] THAMIZHINIYAN VENKATESAN  Young K K  Young Woong Choi. Effect of an extraction solvent on the antioxidant quality of Pinus densiflora needle extract[J]. Journal of Pharmaceutical Analysis, 2019, 9 3: Pages 193-200. DOI: 10.1016/j.jpha.2019.03.005
[5] LINA DU. Probenecid and N-Acetylcysteine Prevent Loss of Intracellular Glutathione and Inhibit Neuronal Death after Mechanical Stretch Injury In Vitro.[J]. Journal of neurotrauma, 2016, 33 20 1: 1913-1917. DOI: 10.1089/neu.2015.4342
[6] JIN-YI YANG  Wei Y Y. Spatiotemporally controlled initiation of Parkin-mediated mitophagy within single cells.[J]. Autophagy, 2011: 1230-1238. DOI: 10.4161/auto.7.10.16626

Abs/Em Maxima

511/533 nm

Excitation / Emission Maximum

492 nm/515 nm

Fluoresene quantum yield

0.76

Extinction Coefficient

118626

CF260

0.17

CF280

0.14

2′,7′-Dichlorodihydrofluorescein Diacetate(4091-99-0)Related Product Information

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• 5-(AND-6)-CARBOXY-2',7'-DICHLOROFLUORESCEIN DIACETATE
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• 2',7'-DICHLORODIHYDROFLUORESCEIN DIACETATE, SUCCINIMIDYL ESTER