1239-45-8 Usage
description
Ethidium Bromide (EtBr), commonly used in research laboratories as a stain for the visualization of nucleic acids in electrophoresis gels, is a toxic chemical and a potent mutagen. When used in nucleic acid staining, ethidium bromide fluoresces a red-orange to pink color under ultraviolet light and with increased fluorescence when bound to double-stranded DNA. While it is not specifically regulated as a hazardous waste, the mutagenic properties may present health hazards and disposal concerns if it is not managed properly in the laboratory.
Uses
Different sources of media describe the Uses of 1239-45-8 differently. You can refer to the following data:
1. Ethidium bromide (EtBr) is a fluorescent dye widely used in molecular biology research. Early usage was as a veterinary trypanocide. It is a mutagenic compound that intercalates double-stranded DNA and RNA. The fluorescence of EtBr increases 21-fold upon binding to double-stranded RNA, 25-fold on binding double-stranded DNA (although histones block binding of EtBr to DNA). Ethidium bromide has been used in multiple 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 the binding to DNA, EtBr is a powerful inhibitor of DNA polymerase.Molecular Biology-grade Powder is suitable for use in gel electrophoresis and DNA isolation procedures.Aqueous Solution (10 mg/mL) is suitable for use in gel electrophoresis and DNA isolation procedures.Molecular Biology-grade Aqueous Solution (500 mg/mL) is suitable for use in gel electrophoresis.
2. 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. Antiprotozoal (Trypanosoma).
3. Intercalating agent and fluorescent label for DNA.
4. antiprotozoal, intercalcates with DNA
Health Hazards
EtBr is a potent mutagen (may cause genetic damage), and moderately toxic after an acute exposure. EtBr can be absorbed through skin, so it is important to avoid any direct contact with the chemical. EtBr is an irritant to the skin, eyes, mouth, and upper respiratory tract. It should be stored away from strong oxidizing agents in a cool, dry place, and the container must be kept undamaged and tightly closed.
Chemical Properties
Purple/maroon crystalline powder
Health Hazard
Acute toxic effects from exposure to ethidium bromide have not been thoroughly
investigated. Ethidium bromide is irritating to the eyes, skin, mucous membranes,
and upper respiratory tract.
Although there is no evidence for the carcinogenicity or teratogenicity of this
substance in humans, ethidium bromide is strongly mutagenic and therefore should
be regarded as a possible carcinogen and reproductive toxin
Flammability and Explosibility
Ethidium bromide does not pose a flammability hazard (NFPA rating = 1).
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.
Safety Profile
Because ethidium bromide can bind with DNA, it is highly toxic as a mutagen. It may potentially cause carcinogenic or teratogenic effects, although no scientific evidence showing either health effect has been found. Exposure routes of ethidium bromide are inhalation, ingestion, and skin absorption. An acute exposure to ethidium bromide causes irritation of the mouth, upper respiratory tract, skin, and eyes.
storage
Because of its mutagenicity, stock solutions of this compound should be prepared in a fume hood, and protective gloves should be worn at all times while handling this substance. Operations capable of generating ethidium bromide dust or aerosols of ethidium bromide solutions should be conducted in a fume hood to prevent exposure by inhalation.
Purification Methods
Crystallise it from MeOH or EtOH [Lamos et al. J Am Chem Soc 108 4278 1986]. Its solubility in H2O is 1%. [Beilstein 22/11 V 352.] POSSIBLE CARCINOGEN.
Incompatibilities
No incompatibilities are known.
Waste Disposal
Excess ethidium bromide and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.
Check Digit Verification of cas no
The CAS Registry Mumber 1239-45-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,3 and 9 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1239-45:
(6*1)+(5*2)+(4*3)+(3*9)+(2*4)+(1*5)=68
68 % 10 = 8
So 1239-45-8 is a valid CAS Registry Number.
InChI:InChI=1/C21H19N3.BrH/c1-2-15-16(13-6-4-3-5-7-13)11-19(23)18-12-24-20-9-8-14(22)10-17(20)21(15)18;/h3-12H,2,22-23H2,1H3;1H
1239-45-8Relevant articles and documents
1H NMR study of complexation of ethidium bromide with single-stranded noncomplementary desoxytetranucleotide 5′-d(GpApApG) in aqueous solution
Baranovskii,Djimant,Osetrov,Petrenko,Parkes,Davies,Veselkov
, p. 660 - 670 (1998)
Complexation of the ethidium bromide dye (3,8-diamino-6-phenyl-5-ethylphenanthridine) with single-stranded noncomplementary desoxytetranucleotide 5′-d(GpApApG) in aqueous salt solution was studied by one- and two-dimensional 1H NMR (500 and 600 MHz). The concentration dependences of the proton chemical shifts of the reactant molecules were measured at different temperatures (T1 = 298 K, T2 = 308 K). Investigations of self-association of the tetranucleotide showed that duplices can hardly form in solution. Therefore, dye complexes with single-stranded tetranucleotide play a major role in the equilibrium in solution; this makes it possible to analyze the specifics of interactions of aromatic ligands with single-stranded DNA. Various schemes of complexation are discussed; the equilibrium constants and the limiting values of the proton chemical shifts of ethidium bromide in the complexes are determined. The constants of dye binding to the single-stranded tetranucleotide 5′-d(GAAG) involving only purine bases is approximately an order of magnitude lower than the constants of ethidium bromide complexation with desoxytetranucleotide monomers whose sequences contain alternating types of base in the chain. The relative contents of complexes of different types are analyzed, and peculiarities of dynamic equilibrium, depending on the ratio of concentrations between the dye and the tetranucleotide, are revealed. Based on the data obtained it is concluded that the binding between ethidium bromide and the single-stranded nucleotide is sequence-specific. The estimated values of the induced chemical shifts of the dye protons are used to establish the most probable structures of the 1:1 and 2:1 complexes of ethidium bromide with single-stranded desoxytetranucleotide. 1999 Kluwer Academic/Plenum Publishers.
Improvement of ways to obtain ethidium bromide and synthesis of ethidium ethyl sulfate, a new fluorescent dye for detection of nucleic acids
Osadchii,Shubin,Kozlova,Varlamenko,Filipenko,Boyarskikh
, p. 1541 - 1548 (2012/01/14)
Two methods for synthesis of ethidium bromide, a fluorescent dye widely used in molecular biology, were improved. An analog of ethidium bromide, ethidium ethyl sulfate, was synthesized.
DNA-binding peptides searched from the solid-phase combinatorial library with the use of the magnetic beads attaching the target duplex DNA
Rowshon Alam,Maeda, Minoru,Sasaki, Shigeki
, p. 465 - 473 (2007/10/03)
We have exhibited successful and rapid screening of DNA-binding peptide ligands from solid-phase library beads with the use of the target DNA- conjugated magnetic beads. The target duplex DNA (3) has a polyether linker between two complementary sequences (T4A3G-ether linker-CT3A4) and is stable in the duplex form during the selection procedure. Finally, 71 pentapeptide sequences were identified from the solid-phase pentapeptide library. From an analysis of the peptide sequences identified in this study, it has been revealed that peptide ligands contain hydrophobic amino acids as the major component. The synthetic peptides with identified sequences and a combination of the major components have exhibited moderate to high binding affinity to the duplex DNA in competition experiments with ethidium-DNA complexes. (C) 2000 Elsevier Science Ltd.
