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309800

Sigma-Aldrich

Dihydroethidium

A cell-permeable, chemically-reduced ethidium derivative.

Sinônimo(s):

Dihydroethidium, 2,7-Diamino-10-ethyl-9-phenyl-9,10-dihydrophenanthridine, DHE

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About This Item

Fórmula empírica (Notação de Hill):
C21H21N3
Número CAS:
38483-26-0
Peso molecular:
315.41
Número MDL:
MFCD00077335
Código UNSPSC:
12161505
NACRES:
NA.25
Preço e disponibilidade não estão disponíveis no momento.

Nível de qualidade

100

descrição

RTECS - SF7935000

Ensaio

≥95% (HPLC)

Formulário

solid

fabricante/nome comercial

Calbiochem®

condição de armazenamento

OK to freeze
protect from light

cor

pink

solubilidade

DMSO: 20 mg/mL
DMF: soluble

Condições de expedição

ambient

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

Nc1c2c(cnc1)c3c(cc(cc3)N)C(C2CC)c4ccccc4

InChI

1S/C21H21N3/c1-2-15-20(13-6-4-3-5-7-13)17-10-14(22)8-9-16(17)18-11-24-12-19(23)21(15)18/h3-12,15,20H,2,22-23H2,1H3

chave InChI

ZDWPSSBKIMIPMY-UHFFFAOYSA-N

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Descrição geral

A cell-permeable, chemically reduced ethidium derivative that can be used as a fluorogenic probe for the detection of reactive oxygen species (ROS). It undergoes significant oxidation in resting leukocytes, possibly through the uncoupling of mitochondrial oxidative phosphorylation. Cytosolic dihydroethidium displays blue fluorescence, however, following oxidation to ethidium and subsequent intercalation to DNA, a bright red fluorescence is achieved. Often used to determine the level of superoxide anion in cells by flow cytometry.
A cell-permeable, chemically-reduced ethidium derivative. Commonly used to analyze respiratory burst in phagocytes. Useful fluorogenic probe for the detection of reactive oxygen species (ROS). It undergoes significant oxidation in resting leukocytes, possibly through the uncoupling of mitochondrial oxidative phosphorylation. Cytosolic dihydroethidium displays blue fluorescence, whereas after oxidation of this probe to ethidium, it intercalates cell’s DNA, staining the nucleus with a bright red fluorescence.

Ações bioquímicas/fisiológicas

Cell permeable: yes
Primary Target
Useful fluorogenic probe for the detection of reactive oxygen species (ROS)
Product does not compete with ATP.
Reversible: no

Embalagem

Packaged under inert gas

Advertência

Toxicity: Irritant (B)

Reconstituição

Following reconstitution, aliquot, flush with an inert gas, and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Outras notas

Haugen, T.S., et al. 1999. Eur. Respir. J.14, 1100.
Mancini, M., et al. 1997. J. Cell Biol.138, 449.
Carter, W.O., et al. 1994. J. Leukoc. Biol.55, 253.
Cinco, M., et al. 1994. FEMS Microbiol. Lett. 122, 187.
Perticarari, S., et al. 1994. J. Immunol. Methods 170, 117.
Perticarari, S., et al. 1991. Cytometry 12, 687.
Bucana, C.D., et al. 1990. Exp. Cell Res.190, 69.
Rothe, G., and Valet, G. 1990. J. Leukoc. Biol.47, 440.

Informações legais

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

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Questions

  1. I noticed that a compound from your catalogue is described as chemically reduced. I was wondering what the reducing agent used for this is?

    1 answer

    1. The reduction reagent used for this compound was sodium borohydride. The exact protocol used is proprietary to the lab and has not been disclosed, but the following publication may be of interest as a reference: Thomas G, Roques B., FEBS Lett. 1972; 26:169–175. The publication describes the process as follows: ...under nitrogen, in the dark and at 0°C, 500 mg of EB in 10 ml absolute methanol were added to 220 mg NaBH4. After 24 hr stirring, methanol was removed by evaporation in vacuum and 15 ml of 3% sodium hydroxide solution were added. After several extractions with ether, the phases were washed with water and dried over anhydrous sodium sulfate. Solvent was evaporated. The precipitate was recrystallized in ether to yield a light brown powder.

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