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309800

Sigma-Aldrich

Dihydroethidium

A cell-permeable, chemically-reduced ethidium derivative.

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C21H21N3
Numéro CAS:
38483-26-0
Poids moléculaire :
315.41
Numéro MDL:
MFCD00077335
Code UNSPSC :
12161505
Nomenclature NACRES :
NA.25
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

100

Description

RTECS - SF7935000

Essai

≥95% (HPLC)

Forme

solid

Fabricant/nom de marque

Calbiochem®

Conditions de stockage

OK to freeze
protect from light

Couleur

pink

Solubilité

DMSO: 20 mg/mL
DMF: soluble

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne 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

Clé InChI

ZDWPSSBKIMIPMY-UHFFFAOYSA-N

Catégories apparentées

Description générale

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.

Actions biochimiques/physiologiques

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

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Irritant (B)

Reconstitution

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

Autres remarques

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.

Informations légales

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (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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