160539
Ethidium bromide
95%
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:
Molecular Weight:
394.31
EC Number:
214-984-6
UNSPSC Code:
12171500
MDL number:
Beilstein/REAXYS Number:
3642536
assay
95%
mp
260-262 °C (dec.) (lit.)
λmax
506 nm
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
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.
Frameshift mutagen which intercalates double-stranded DNA and RNA.
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.
Preparation Note
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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Binding of ethidium bromide to double-stranded ribonucleic acid.
R J Douthart et al.
Biochemistry, 12(2), 214-220 (1973-01-16)
A fluorescent complex between ethidium bromide and nucleic acids. Physical-chemical characterization.
J B LePecq et al.
Journal of molecular biology, 27(1), 87-106 (1967-07-14)
Jaqueline Bianchi et al.
Ecotoxicology and environmental safety, 120, 174-183 (2015-06-16)
The insecticide imidacloprid and the herbicide sulfentrazone are two different classes of pesticides that are used for pest control in sugarcane agriculture. To evaluate the genotoxic potential of low concentrations of these two pesticides alone and in mixture, the comet