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Ethidium bromide information


Ethidium bromide
Names
Preferred IUPAC name
3,8-Diamino-5-ethyl-6-phenylphenanthridin-5-ium bromide
Other names
  • 2,7-Diamino-10-ethyl-6-phenylphenanthridinium bromide
  • 2,7-Diamino-10-ethyl-9-phenylphenanthridinium bromide
  • 3,8-Diamino-1-ethyl-6-phenylphenantridinium bromide
  • 5-Ethyl-6-phenyl-phenanthridine-3,8-diamine bromide
  • Ethidium bromide
  • Homidium bromide
  • EtBr
  • EthBr
Identifiers
CAS Number
  • 1239-45-8 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
3642536
ChEBI
  • CHEBI:4883 checkY
ChEMBL
  • ChEMBL284328 checkY
ChemSpider
  • 14034 checkY
ECHA InfoCard 100.013.622 Edit this at Wikidata
EC Number
  • 214-984-6
KEGG
  • C11161 checkY
PubChem CID
  • 14710
RTECS number
  • SF7950000
UNII
  • 059NUO2Z1L checkY
UN number 2811
CompTox Dashboard (EPA)
  • DTXSID8025258 Edit this at Wikidata
InChI
  • 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 checkY
    Key: ZMMJGEGLRURXTF-UHFFFAOYSA-N checkY
  • InChI=1/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
    Key: ZMMJGEGLRURXTF-UHFFFAOYAD
SMILES
  • CC[n+]1c2cc(N)ccc2c3ccc(N)cc3c1c4ccccc4.[Br-]
Properties
Chemical formula
C21H20BrN3
Molar mass 394.294 g/mol
Appearance Purple-red solid
Melting point 260 to 262 °C (500 to 504 °F; 533 to 535 K)
Solubility in water
~40 g/l
Pharmacology
ATCvet code
QP51DX03 (WHO)
Hazards[1]
GHS labelling:
Pictograms
GHS06: ToxicGHS08: Health hazard
Signal word
Danger
Hazard statements
H302, H330, H341
Precautionary statements
P201, P202, P260, P284, P301+P312, P304+P340+P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
4
1
0
Flash point > 100 °C (212 °F; 373 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Ethidium bromide (or homidium bromide,[2] chloride salt homidium chloride)[3][4] is an intercalating agent commonly used as a fluorescent tag (nucleic acid stain) in molecular biology laboratories for techniques such as agarose gel electrophoresis. It is commonly abbreviated as EtBr, which is also an abbreviation for bromoethane. To avoid confusion, some laboratories have used the abbreviation EthBr for this salt. When exposed to ultraviolet light, it will fluoresce with an orange colour, intensifying almost 20-fold after binding to DNA. Under the name homidium, it has been commonly used since the 1950s in veterinary medicine to treat trypanosomiasis in cattle.[5] The high incidence of antimicrobial resistance makes this treatment impractical in some areas, where the related isometamidium chloride is used instead. Despite its reputation as a mutagen, tests have shown it to have low mutagenicity without metabolic activation.[6][7]

  1. ^ "GESTIS-Stoffdatenbank". gestis.dguv.de (in German). Retrieved 22 November 2021.
  2. ^ Cite error: The named reference Hom-Br-PubChem was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference Kinabo-1993 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Hom-Cl-PubChem was invoked but never defined (see the help page).
  5. ^ Stevenson P, Sones KR, Gicheru MM, Mwangi EK (May 1995). "Comparison of isometamidium chloride and homidium bromide as prophylactic drugs for trypanosomiasis in cattle at Nguruman, Kenya". Acta Tropica. 59 (2): 77–84. doi:10.1016/0001-706X(94)00080-K. PMID 7676909.
  6. ^ Lowe, Derek (2016-04-18). "The Myth of Ethidium Bromide". In the Pipeline. Retrieved 2019-02-28.
  7. ^ "Ethidium Bromide: Swap or Not | UCSB Sustainability". sustainability.ucsb.edu. Retrieved 2023-02-08.

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Ethidium bromide

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Ethidium bromide (or homidium bromide, chloride salt homidium chloride) is an intercalating agent commonly used as a fluorescent tag (nucleic acid stain)...

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Gel electrophoresis of nucleic acids

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Circular DNA are more strongly affected by ethidium bromide concentration than linear DNA if ethidium bromide is present in the gel during electrophoresis...

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Agarose gel electrophoresis

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of the buffer, and the concentration of intercalating dye such as ethidium bromide if used during electrophoresis. Smaller molecules travel faster than...

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GelRed

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and its optical properties are essentially identical to those of ethidium bromide. When exposed to ultraviolet light, it fluoresces with an orange color...

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Staining

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of one or the other is more a matter of preference and tradition. Ethidium bromide intercalates and stains DNA, providing a fluorescent red-orange stain...

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SYBR Green I

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for ethidium bromide, a potential human mutagen, as both safer to work with and free from the complex waste disposal issues of ethidium bromide. However...

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Bromoethane

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bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide)...

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Astrogliosis

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upregulation after CNS injuries, promoting axonal regeneration. Injection of ethidium bromide kills all CNS glia (oligodendrocytes and astrocytes), but leaves axons...

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SYBR Gold

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owned by Thermo Fisher Scientific SYBR Gold is more sensitive than ethidium bromide, SYBR Green I, and SYBR Green II for detecting various types of nucleic...

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Diagnostic microbiology

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chloride in water. DNA will go to the density that reflects its own, and ethidium bromide is then added to enhance the visuals the nucleic acid band provides...

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SYBR Safe

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marketed as a safer alternative to ethidium bromide. However, as the molecule itself is quite a bit larger than ethidium bromide, it does not bind to the column...

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Gel extraction

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begin, UV light is shone on the gel in order to illuminate all the ethidium bromide-stained DNA. Care must be taken to avoid exposing the DNA to mutagenic...

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Agarose

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other applications. The DNA is normally visualized by staining with ethidium bromide and then viewed under a UV light, but other methods of staining are...

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Polyacrylamide gel electrophoresis

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color under UV light. Ethidium bromide binds nucleic acid chains through the process of Intercalation. While Ethidium bromide is a popular stain it is...

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Northern blot

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the RNA to limit secondary structure. The gels can be stained with ethidium bromide (EtBr) and viewed under UV light to observe the quality and quantity...

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Fluorescence

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detection: the compound ethidium bromide, in aqueous solution, has very little fluorescence, as it is quenched by water. Ethidium bromide's fluorescence is greatly...

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Gel electrophoresis

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gel can be stained to make them visible. DNA may be visualized using ethidium bromide which, when intercalated into DNA, fluoresce under ultraviolet light...

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Electrophoretic color marker

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using either ethidium bromide or SYBR Green dyes.[citation needed] The most common electrophoretic stain in agarose gel is ethidium bromide, however, SYBR...

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DNA extraction

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a restriction enzyme, running it on an agarose gel, staining with ethidium bromide (EtBr) or a different stain and comparing the intensity of the DNA...

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Fluorescent tag

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labeling, protein labeling, and genetic labeling are widely utilized. Ethidium bromide, fluorescein and green fluorescent protein are common tags. The most...

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Trypanosoma brucei

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dimidium bromide and its derivatives were first used in 1948 in animal cases in Africa, and became known as homidium (or as ethidium bromide in molecular...

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Polymerase chain reaction

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Ethidium bromide-stained PCR products after gel electrophoresis. Two sets of primers were used to amplify a target sequence from three different tissue...

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Isometamidium chloride

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trypanocidal agent used in veterinary medicine. It consists of a single ethidium bromide like subunit linked to a fragment of the diminazene molecule.[citation...

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Cytoplasmic hybrid

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depleted of their own mitochondrial DNA by prolonged incubation with ethidium bromide, a chemical which inhibits mitochondrial DNA replication. The rho-zero...

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Fluorophore

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hydrazine), carboxyl groups (carbodiimide), thiol (maleimide, acetyl bromide), and organic azide (via click chemistry or non-specifically (glutaraldehyde))...

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Nucleic acid quantitation

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that bind to nucleic acids and selectively fluoresce when bound (e.g. Ethidium bromide). This method is useful for cases where concentration is too low to...

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Deoxyribonuclease

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dispensed circular well in an agarose gel layer, in which DNA stained by ethidium bromide is uniformly distributed. After the incubation, a circular dark zone...

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DAPI

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SAFETY DATA SHEET. kpl.com Ohta T, Tokishita S, Yamagata H (2001). "Ethidium bromide and SYBR Green I enhance the genotoxicity of UV-irradiation and chemical...

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Base pair

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compounds and are known or suspected carcinogens. Examples include ethidium bromide and acridine.[citation needed] Mismatched base pairs can be generated...

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