Dihydroethidium

Name: Dihydroethidium
Brand: MM
Price: 2720 SEK

A cell-permeable, chemically-reduced ethidium derivative.

Synonym(s):

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

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25 MG

2 720,00 kr

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₂₁N₃

CAS Number:

104821-25-2

Molecular Weight:

315.41

MDL number:

MFCD00077335

UNSPSC Code:

12161505

NACRES:

NA.25

Key Documents

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Quality Level

100

description

RTECS - SF7935000

Assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze
protect from light

color

pink

solubility

DMSO: 20 mg/mL
DMF: soluble

shipped in

ambient

storage temp.

−20°C

SMILES string

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

InChI key

ZDWPSSBKIMIPMY-UHFFFAOYSA-N

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Detection Substrates & Enzymes

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1 of 4

This Item	37291	D7008	309825
Sigma-Aldrich 309800 Dihydroethidium	Sigma-Aldrich 37291 Dihydroethidium	Sigma-Aldrich D7008 Dihydroethidium	Sigma-Aldrich 309825 Dihydrorhodamine 123
color pink	color -	color pink to very dark red	color pink-white
form solid	form solid	form powder	form solid
solubility DMSO: 20 mg/mL, DMF: soluble	solubility acetonitrile: soluble, methanol: soluble	solubility chloroform: 20 mg/mL	solubility DMSO: 5 mg/mL
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
assay ≥95% (HPLC)	assay ≥95% (HPCE)	assay ≥95%	assay ≥95% (HPLC)

General description

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.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Useful fluorogenic probe for the detection of reactive oxygen species (ROS)

Product does not compete with ATP.

Reversible: no

Packaging

Packaged under inert gas

Preparation Note

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

Other Notes

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.

Legal Information

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

Disclaimer

Toxicity: Irritant (B)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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Questions

Anonymous

a year ago

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. Technical Support
  
  a year ago
  
  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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