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changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 structure chemistry and fluorescence 2 applications toggle applications subsection 2 1 alternatives for gel 3 possible carcinogenic activity 4 handling and disposal 5 drug resistance 6 see also 7 references 8 external links toggle the table of contents ethidium bromide 32 languages العربية تۆرکجه български català čeština deutsch español euskara فارسی suomi français galego עברית हिन्दी italiano 日本語 ქართული 한국어 nederlands norsk bokmål polski português русский srpskohrvatski српскохрватски slovenščina српски srpski svenska தமிழ் türkçe українська اردو 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia dna gel stain and veterinary drug not to be confused with ethyl bromide 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 y 3d model jsmol interactive image beilstein reference 3642536 chebi chebi 4883 y chembl chembl284328 y chemspider 14034 y echa infocard 100 013 622 ec number 214 984 6 kegg c11161 y pubchem cid 14710 rtecs number sf7950000 unii 059nuo2z1l y un number 2811 comptox dashboard epa dtxsid8025258 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 y key zmmjgeglrurxtf uhfffaoysa n y 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 c 21 h 20 br n 3 molar mass 394 316 g mol 1 appearance purple red solid density 1 3739 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 signal word danger hazard statements h302 h330 h341 precautionary statements p201 p202 p260 p284 p301 p312 p304 p340 p310 nfpa 704 fire diamond 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 y verify what is y n infobox references chemical compound 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 8 structure chemistry and fluorescence edit absorption spectrum of ethidium bromide as with most fluorescent compounds ethidium bromide is aromatic its core heterocyclic moiety is generically known as a phenanthridine an isomer of which is the fluorescent dye acridine absorption maxima of etbr in aqueous solution are at 210 nm and 285 nm which correspond to ultraviolet light as a result of this excitation etbr emits orange light with wavelength 605 nm 9 10 ethidium bromide s intense fluorescence after binding with dna is probably not due to rigid stabilization of the phenyl moiety because the phenyl ring has been shown to project outside the intercalated bases in fact the phenyl group is found to be almost perpendicular to the plane of the ring system as it rotates about its single bond to find a position where it will impinge upon the ring system minimally instead the hydrophobic environment found between the base pairs is believed to be responsible by moving into this hydrophobic environment and away from the solvent the ethidium cation is forced to shed any water molecules that were associated with it as water is a highly efficient fluorescence quencher the removal of these water molecules allows the ethidium to fluoresce citation needed applications edit dna sample separated using gel electrophoresis of nucleic acids and stained with ethidium bromide which emits orange light after binding to dna ethidium bromide is commonly used to detect nucleic acids in molecular biology laboratories in the case of dna this is usually double stranded dna from pcrs restriction digests etc single stranded rna can also be detected since it usually folds back onto itself and thus provides local base pairing for the dye to intercalate detection typically involves a gel containing nucleic acids placed on or under an ultraviolet lamp since ultraviolet light is harmful to eyes and skin gels stained with ethidium bromide are usually viewed indirectly using an enclosed camera with the fluorescent images recorded as photographs where direct viewing is needed the viewer s eyes and exposed skin should be protected in the laboratory the intercalating properties have long been used to minimize chromosomal condensation when a culture is exposed to mitotic arresting agents during harvest the resulting slide preparations permit a higher degree of resolution and thus more confidence in determining structural integrity of chromosomes upon microscopic analysis citation needed ethidium bromide is also used during dna fragment separation by agarose gel electrophoresis 11 it is added to running buffer and binds by intercalating between dna base pairs when the agarose gel is illuminated using uv light dna bands become visible intercalation of etbr can alter properties of the dna molecule such as charge weight conformation and flexibility since the mobilities of dna molecules through the agarose gel are measured relative to a molecular weight standard the effects of etbr can be critical to determining the sizes of molecules 12 ethidium bromide has also been used extensively to reduce mitochondrial dna copy number in proliferating cells 13 the effect of etbr on mitochondrial dna is used in veterinary medicine to treat trypanosomiasis in cattle as etbr binds molecules of kinetoplastid dna and changes their conformation to the z dna form this form inhibits replication of kinetoplastid dna which is lethal for trypanosomes 14 the chloride salt homidium chloride has the same applications 3 4 ethidium bromide can be added to ypd media and used as an inhibitor for cell growth 15 the binding affinity of the cationic nanoparticles with dna could be evaluated by competitive binding with ethidium bromide 16 17 etbr can stain proteins as well as nucleic acids 18 alternatives for gel edit there are alternatives to ethidium bromide which are advertised as being less dangerous and having better performance 19 20 for example several sybr based dyes are used by some researchers and there are other emerging stains such as novel juice sybr dyes are less mutagenic than etbr by the ames test with liver extract 21 however sybr green i was actually found to be more mutagenic than etbr to the bacterial cells exposed to uv which is used to visualize either dye 22 this may be the case for other safer dyes but while mutagenic and toxicity details are available 23 these have not been published in peer reviewed journals the msds for sybr safe reports an ld 50 for rats of over 5 g kg which is higher than that of etbr 1 5 g kg many alternative dyes are suspended in dmso which has health implications of its own including increased skin absorption of organic compounds 21 despite the performance advantage of using sybr dyes instead of etbr for staining purposes many researchers still prefer etbr since it is considerably less expensive citation needed possible carcinogenic activity edit ethidium bromide intercalated between two adenine thymine base pairs the intercalation is said by some by whom to motivate a high mutagenicity of dna 6 most use of ethidium bromide in the laboratory 0 25 1 μg ml is below the ld50 dosage making acute toxicity unlikely testing in humans and longer studies in a mammalian system would be required to fully understand the long term risk ethidium bromide poses to lab workers but it is clear that ethidium bromide can cause mutations in mammalian and bacterial cells 24 handling and disposal edit ethidium bromide is not regulated as hazardous waste at low concentrations 25 but is treated as hazardous waste by many organizations material should be handled according to the manufacturer s safety data sheet sds citation needed the disposal of laboratory ethidium bromide remains a controversial subject 26 ethidium bromide can be degraded chemically or collected and incinerated it is common for ethidium bromide waste below a mandated concentration to be disposed of normally such as pouring it down a drain a common practice is to treat ethidium bromide with sodium hypochlorite bleach before disposal 27 according to lunn and sansone chemical degradation using bleach yields compounds which are mutagenic by the ames test data are lacking on the mutagenic effects of degradation products lunn and sansone describe more effective methods for degradation 28 elsewhere ethidium bromide removal from solutions with activated charcoal or ion exchange resin is recommended 29 various commercial products are available for this use 30 drug resistance edit trypanosomes in the gibe river valley in southwest ethiopia showed universal resistance between july 1989 and february 1993 31 this likely indicates a permanent loss of function in this area against the tested target t congolense isolated from boran cattle 31 see also edit phenanthridine agarose gel electrophoresis and gel electrophoresis of nucleic acids gelred itself derived from ethbr and gelgreen marketed as safer and more intense dna stains propidium iodide and propidium monoazide related dyes references edit gestis stoffdatenbank gestis dguv de in german retrieved 22 november 2021 homidium bromide pubchem ncbi nlm us nih retrieved 2020 09 08 cid 14710 from pubchem 1 2 kinabo ld september 1993 pharmacology of existing drugs for animal trypanosomiasis acta tropica 54 3 4 elsevier 169 183 doi 10 1016 0001 706x 93 90091 o pmid 7902656 s2cid 27564786 1 2 homidium chloride pubchem ncbi nlm us nih retrieved 2021 03 14 cid 11765 from pubchem 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 1 2 lowe derek 2016 04 18 the myth of ethidium bromide in the pipeline retrieved 2019 02 28 ethidium bromide swap or not ucsb sustainability sustainability ucsb edu retrieved 2023 02 08 lecointe pierre bichet nicole fraire claudine paoletti claude 1981 03 15 the hepatic metabolism of ethidium bromide to reactive mutagenic species biochemical and structural requirements biochemical pharmacology 30 6 601 609 doi 10 1016 0006 2952 81 90132 5 issn 0006 2952 pmid 7271898 sabnis rw 2010 handbook of biological dyes and stains synthesis and industrial application hoboken nj wiley isbn 978 0 470 40753 0 application note ethidium bromide pdf retrieved 6 april 2014 borst p november 2005 ethidium dna agarose gel electrophoresis how it started iubmb life 57 11 745 747 doi 10 1080 15216540500380855 pmid 16511967 sigmon j larcom ll october 1996 the effect of ethidium bromide on mobility of dna fragments in agarose gel electrophoresis electrophoresis 17 10 1524 1527 doi 10 1002 elps 1150171003 pmid 8957173 s2cid 10593378 diaz f bayona bafaluy mp rana m mora m hao h moraes ct november 2002 human mitochondrial dna with large deletions repopulates organelles faster than full length genomes under relaxed copy number control nucleic acids research 30 21 4626 4633 doi 10 1093 nar gkf602 pmc 135822 pmid 12409452 roy chowdhury a bakshi r wang j yildirir g liu b pappas brown v et al december 2010 the killing of african trypanosomes by ethidium bromide plos pathogens 6 12 e1001226 doi 10 1371 journal ppat 1001226 pmc 3002999 pmid 21187912 caesar r warringer j blomberg a february 2006 physiological importance and identification of novel targets for the n terminal acetyltransferase natb eukaryotic cell 5 2 368 378 doi 10 1128 ec 5 2 368 378 2006 pmc 1405896 pmid 16467477 liang h peng b dong c liu l mao j wei s et al october 2018 cationic nanoparticle as an inhibitor of cell free dna induced inflammation nature communications 9 1 4291 bibcode 2018natco 9 4291l doi 10 1038 s41467 018 06603 5 pmc 6191420 pmid 30327464 olmsted j kearns dr august 1977 mechanism of ethidium bromide fluorescence enhancement on binding to nucleic acids biochemistry 16 16 3647 3654 doi 10 1021 bi00635a022 pmid 889813 dvortsov i a lunina n a chekanovskaya l a shedova e n gening l v velikodvorskaya g a 2006 06 15 ethidium bromide is good not only for staining of nucleic acids but also for staining of proteins after polyacrylamide gel soaking in trichloroacetic acid solution analytical biochemistry 353 2 293 295 doi 10 1016 j ab 2006 03 001 issn 0003 2697 pmid 16597429 huang q fu wl 2005 comparative analysis of the dna staining efficiencies of different fluorescent dyes in preparative agarose gel electrophoresis clinical chemistry and laboratory medicine 43 8 841 842 doi 10 1515 cclm 2005 141 pmid 16201894 s2cid 27423672 madden d safer stains for dna retrieved 2009 12 08 1 2 singer vl lawlor te yue s february 1999 comparison of sybr green i nucleic acid gel stain mutagenicity and ethidium bromide mutagenicity in the salmonella mammalian microsome reverse mutation assay ames test mutation research 439 1 37 47 bibcode 1999mrgte 439 37s doi 10 1016 s1383 5718 98 00172 7 pmid 10029672 ohta t tokishita s yamagata h may 2001 ethidium bromide and sybr green i enhance the genotoxicity of uv irradiation and chemical mutagens in e coli mutation research 492 1 2 91 97 bibcode 2001mrgte 492 91o doi 10 1016 s1383 5718 01 00155 3 pmid 11377248 novel juice 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