DIHYDRORHODAMINE 123 Chemical Properties

Melting point:

163–165℃

Boiling point:

526.9±50.0 °C(Predicted)

Density 

1.313±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: >5mg/mL

form 

powder

pka

4.70 ± 0.40, most basic, temperature: 25 °C

color 

Light red or pinkish-white

λmax

289 nm

BRN 

5989965

Biological Applications

Generating,detecting & measuring reactive oxygen species; generating,detecting & measuring reactive nitrogen species; detecting phosphates,peroxynitrile; measuring respiratory burst; chronic granulomatous disease DHR assay; screening

InChI

InChI=1S/C21H18N2O3/c1-25-21(24)15-5-3-2-4-14(15)20-16-8-6-12(22)10-18(16)26-19-11-13(23)7-9-17(19)20/h2-11,20H,22-23H2,1H3

InChIKey

FNEZBBILNYNQGC-UHFFFAOYSA-N

SMILES

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

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

10-23

MSDS

• Language:English Provider:SigmaAldrich

DIHYDRORHODAMINE 123 Usage And Synthesis

Description

DHR is a cell-permeable fluorogenic probe that is used as an indicator of intracellular peroxynitrite formation. It is oxidized by peroxynitrite to the highly fluorescent product rhodamine in vitro. Neither nitric oxide, superoxide, nor hydrogen peroxide alone appear to oxidize DHR. Formation of rhodamine can be monitored by fluorescence spectroscopy using excitation and emission wavelengths of 500 and 536 nm, respectively, or by absorbance spectroscopy at 500 nm (ε = 78,800 M⁻¹cm⁻¹). DHR has been used to investigate reactive oxygen intermediates produced by endothelial cells, eosinophils, and reactive microglia.

Uses

Dihydrorhodamine 123 is the uncharged and nonfluorescent reduction product of the mitochondrion-selective dye rhodamine 123 used for investigation of reacitve oxygen intermediates.

Uses

Dihydrorhodamine 123 (DHR) has been used for the detection of free intracellular radicals or ROS (reactive oxygen species) in head kidney-derived macrophages. It has also been used in DHR assay in red blood cells and in oxidative burst assay in neutrophils.

General Description

Cell-permeable fluorogenic probe that is useful for the detection of reactive oxygen species (ROS) such as peroxide and peroxynitrite. Dihydrorhodamine is not fluorescent unless it is converted to rhodamine 123.

Biochem/physiol Actions

Cell permeable: yes

References

[1] CROW J P. Dichlorodihydrofluorescein and Dihydrorhodamine 123 Are Sensitive Indicators of Peroxynitritein Vitro:Implications for Intracellular Measurement of Reactive Nitrogen and Oxygen Species[J]. Nitric oxide?: biology and chemistry, 1997, 1 2: Pages 145-157. DOI: 10.1006/niox.1996.0113
[2] K BRIVIBA. Attenuation of oxidation and nitration reactions of peroxynitrite by selenomethionine, selenocystine and ebselen.[J]. Biochemical Journal, 1996, 319 ( Pt 1): 13-15. DOI: 10.1042/bj3190013
[3] H SIES. Glutathione peroxidase protects against peroxynitrite-mediated oxidations. A new function for selenoproteins as peroxynitrite reductase.[J]. The Journal of Biological Chemistry, 1997, 272 44: 27812-27817. DOI: 10.1074/jbc.272.44.27812
[4] OSAMU HANDA  Gediminas C  Jancy Stephen. Role of endothelial nitric oxide synthase-derived nitric oxide in activation and dysfunction of cerebrovascular endothelial cells during early onsets of sepsis.[J]. American journal of physiology. Heart and circulatory physiology, 2008, 295 4: H1712-9. DOI: 10.1152/ajpheart.00476.2008
[5] PAIGE LACY. Divergence of mechanisms regulating respiratory burst in blood and sputum eosinophils and neutrophils from atopic subjects.[J]. Journal of immunology, 2003, 170 5: 2670-2679. DOI: 10.4049/jimmunol.170.5.2670
[6] JIANRONG LI. Peroxynitrite generated by inducible nitric oxide synthase and NADPH oxidase mediates microglial toxicity to oligodendrocytes.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2005, 102 28: 9936-9941. DOI: 10.1073/pnas.0502552102

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