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E8751

Sigma-Aldrich

Ethidium bromide

~95% (HPLC)

Synonym(s):

3,8-Diamino-5-ethyl-6-phenylphenanthridinium bromide, EtBr, Homidium bromide

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About This Item

Empirical Formula (Hill Notation):
C21H20BrN3
CAS Number:
1239-45-8
Molecular Weight:
394.31
Beilstein:
3642536
EC Number:
214-984-6
MDL number:
MFCD00011724
UNSPSC Code:
41105322
PubChem Substance ID:
24894683
NACRES:
NB.22

Assay

~95% (HPLC)

Quality Level

200

mp

260-262 °C (dec.) (lit.)

SMILES string

[Br-].CC[n+]1c(-c2ccccc2)c3cc(N)ccc3c4ccc(N)cc14

InChI

1S/C21H19N3.BrH/c1-2-24-20-13-16(23)9-11-18(20)17-10-8-15(22)12-19(17)21(24)14-6-4-3-5-7-14;/h3-13,23H,2,22H2,1H3;1H

InChI key

ZMMJGEGLRURXTF-UHFFFAOYSA-N

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Application

Ethidium bromide (EtBr) is the most commonly used nucleic acid stain for PAGE or agarose gel electrophoresis. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA and 25-fold on binding double-stranded DNA so that destaining the background is not necessary with a low stain concentration (10 μg/ml). Ethidium bromide has been used in a number of fluorimetric assays for nucleic acids. It has been shown to bind to single-stranded DNA (although not as strongly) and triple-stranded DNA. Because of its ability to bind to DNA, EtBr is an inhibitor of DNA polymerase.

Frameshift mutagen which intercalates double-stranded DNA and RNA.

Biochem/physiol Actions

Ethidium bromide intercalates double-stranded DNA and RNA and acts as a frameshift mutagen. It can also be used in conjunction with acridine orange to differentiate between viable, apoptotic and necrotic cells.

Reconstitution

For staining a gel after electrophoresis, dilute a sample of the stock solution to 0.5 μg/ml with water and incubate the gel for 15-30 min. Destaining is usually not needed but can be carried out in water for 15 min if decreased background is necessary. The DNA bands can then be detected on a UV light box (254 nm wavelength). Ethidium bromide can also be incorporated into the gel and running buffer at 0.5 μg/ml and visualized immediately after electrophoresis.

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Product No.
Description
Pricing

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H302,H330,H341

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 4 Oral - Muta. 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR4830
SHBQ7920
SHBQ5224
MKCM8424
MKCJ7007

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