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Dihydrorhodamine 123

Cayman Chemical Item Number 85100

DHR (CAS 109244-58-8)

Dihydrorhodamine 123 (CAS 109244-58-8)

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Description

DHR is a cell-permeable fluorogenic probe that is used as an indicator of intracellular peroxynitrite formation.1 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.1 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).2,3,1 DHR has been used to investigate reactive oxygen intermediates produced by endothelial cells, eosinophils, and reactive microglia.4,5,6

1 Crow, J.P. Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: Implications for intracellular measurement of reactive nitrogen and oxygen species. Nitric Oxide 1 145-157 (1997).

2 Briviba, K., Roussyn, I., Sharov, V.S., et al. Attenuation of oxidation and nitration reactions of peroxynitrite by selenomethionine, selenocystine and ebselen. Biochem J 319 13-15 (1996).

3 Sies, H., Sharov, V.S., Klotz, L., et al. Glutathione peroxidase protects against peroxynitrite-mediated oxidations. A new function for selenoproteins as peroxynitrite reductase. J Biol Chem 272 27812-27817 (1997).

4 Handa, O., Stephen, J., and Cepinskas, G. Role of endothelial nitric oxide synthase-derived nitric oxide in activation and dysfunction of cerebrovascular endothelial cells during early onsets of sepsis. Am J Physiol Heart Circ Physiol 295 H1712-9 (2008).

5 Lacy, P., Latif, D.A., Steward, M., et al. Divergence of mechanisms regulating respiratory burst in blood and sputum eosinophils and neutophils from atopic subjects. J Immunol 170 2670-9 (2003).

6 Li, J., Baud, O., Volpe, J.J., et al. Peroxynitrite generated by inducible nitric oxide synthase and NADPH oxidase mediates microglial toxicity to oligodendrocytes. Proc Natl Acad Sci USA 102(28) 9936-9941 (2005).

Synonyms
  • DHR
Formal Name 2-​(3,​6-​diamino-​9H-​xanthen-​9-​yl)-​benzoic acid,​ methyl ester
CAS Number 109244-58-8
Molecular Formula C21H18N2O3
Formula Weight 346.4
Formulation A crystalline solid
Purity ≥98%
λmax 223, 289 nm
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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COC(=O)​c1ccccc1C1c2ccc(N)​cc2Oc2cc(N)​ccc12

Background Reading

Briviba, K., Roussyn, I., Sharov, V.S., et al. Attenuation of oxidation and nitration reactions of peroxynitrite by selenomethionine, selenocystine and ebselen. Biochem J 319 13-15 (1996).

Crow, J.P. Dichlorodihydrofluorescein and dihydrorhodamine 123 are sensitive indicators of peroxynitrite in vitro: Implications for intracellular measurement of reactive nitrogen and oxygen species. Nitric Oxide 1 145-157 (1997).

Sies, H., Sharov, V.S., Klotz, L., et al. Glutathione peroxidase protects against peroxynitrite-mediated oxidations. A new function for selenoproteins as peroxynitrite reductase. J Biol Chem 272 27812-27817 (1997).
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Related Products

2,7-Dichlorodihydrofluorescein diacetate
DAN-1 EE (hydrochloride)
Diphenyl-1-pyrenylphosphine
Peroxynitrite
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