エチジウムブロミド

Ethidium Bromide

HCID 14710CAS 1239-45-8

基本情報

標準SMILES
CC[n+]1c(-c2ccccc2)c2cc(N)ccc2c2ccc(N)cc21.[Br-]
InChIKey
ZMMJGEGLRURXTF-UHFFFAOYSA-N
分子式
C21H20N3.Br
平均分子量
394.3 g/mol
単同位体質量
393.08405974

概要

Ethidium bromide is the organic bromide salt of ethidium. It has a role as a geroprotector, an intercalator and a trypanocidal drug. It contains an ethidium.

名称と識別子

優先名称
Ethidium Bromide
IUPAC
5-ethyl-6-phenylphenanthridin-5-ium-3,8-diamine bromide
現地名
エチジウムブロミド
英語名
Ethidium bromide
分子式
C21H20BrN3
分子量
394.32

名称と別名

ETHIDIUM BROMIDE1239-45-8Homidium bromideDromilac3,8-Diamino-5-ethyl-6-phenylphenanthridinium bromideEtBrEthydium bromideBromure d'homidiumBromuro de homidioHomidii bromidum2,7-Diamino-10-ethyl-9-phenylphenanthridinium bromide2,7-Diamino-9-phenyl-10-ethylphenanthridinium bromide
名称をさらに表示
エチジウムブロミド臭化エチジウム3,8-ジアミノ-5-エチル-6-フェニルベンゾ[c]キノリン-5-イウム·ブロミド3,8-ジアミノ-5-エチル-6-フェニルフェナントリジン-5-イウム·ブロミドホミジウムブロミド3,8-ジアミノ-5-エチル-6-フェニルフェナントリジニウム·ブロミド臭化エチジウム溶液エチジウムブロマイド臭化ホミジウム3,8-ジアミノ-5-エチル-6-フェニルフェナントリジニウムブロミドエチジウムブロミド (0.5mg/mL水溶液) (スポイトボトル入り) [電気泳動用]エチジウムブロミド SOLUTION臭化エチジウム水溶液臭化エチジウム 溶液3,8-ジアミノ-5-エチル-6-フェニルベンゾ[c]キノリン-5-イウム・ブロミド3,8-ジアミノ-5-エチル-6-フェニルフェナントリジニウム・ブロミド3,8-ジアミノ-5-エチル-6-フェニルフェナントリジン-5-イウム・ブロミドEthidium bromide solutionHomidiumRd1572-Cellstain-EbEthD (bromide)Ethidium Brmide
2,7-Diamino-9-phenylphenanthridine ethobromideDTXSID8025258NSC-268986RD 1572059NUO2Z1LCHEBI:4883DTXCID605258Bromide, Ethidium

データベース識別子

CAS
1239-45-8
PubChem CID
14710
DTXSID
DTXSID8025258
ChEMBL
CHEMBL284328
ChEBI
CHEBI:4883
UNII
059NUO2Z1L
EC Number
214-984-6

物性

構造計算による物性

極性表面積
55.9 Ų
水素結合供与体数
2
水素結合受容体数
3
回転可能結合数
2
重原子数
25

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
LogP · 2 件

log Kow= -0.38 /Estimated/

-1.1

TasteBitter tasting
Density0.34 g/cm³
Color/Form · 2 件

Dark red crystals from alcohol

Maroon powder

Solubility · 4 件

Solubility in 2-methoxyethanol is 20 mg/mL; ethanol, 2 mg/mL

Soluble in 750 parts chloroform at 20 °C

Soluble in 20 parts water at 20 °C

Solubility in water, g/100ml at 20 °C: 5

物理化学的性質

融点
260 · 260-262 °C (dec.)(lit.)
比重(密度)
1.3739 · 1.3739 (rough estimate)
屈折率
1.67 · 1.6700 (estimate)
闪点
100 °C · >100°C
貯蔵温度
2 · 2-8°C
溶解性
2 O: · H2O: 10 mg/mL、不透明、強い赤色

化学的性質

化学的特性Purple/maroon crystalline powder

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P264, P270, P271, P280, P284, P301+P317, P304+P340, P316, P318, P320, P330, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H302 (97.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P260, P261, P264, P270, P271, P280, P284, P301+P317, P304+P340, P316, P318, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 2 件

Chemical: Phenanthridinium, 3,8-diamino-5-ethyl-6-phenyl-, bromide

Ethidium bromide: HSNO Approval: HSR004464 Approved with controls

Other Safety InformationIMAP assessments - Phenanthridinium, 3,8-diamino-5-ethyl-6-phenyl-, bromide: Human health tier I assessment
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards SummaryA skin, eye, and respiratory tract irritant; [ICSC] May cause irritation; Toxic by ingestion; Highly toxic by inhalation; Mutagenic effects observed in vitro; [Sigma-Aldrich MSDS] See Propidium iodide.
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: I
Chemical DangersDecomposes on heating. This produces toxic gases including hydrogen bromide (see ICSC 0282) and nitrogen oxides (see ICSCs 0930 and 1311). Reacts violently with strong oxidants.

安全と保護具

Fire FightingUse water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures · 4 件

Fresh air, rest.

Rinse and then wash skin with water and soap.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth.

Safe StorageFireproof. Separated from strong oxidants and food and feedstuffs.
Storage Conditions · 1 件

Ethidium bromide should be handled in the laboratory using the "basic prudent practices" described in Chapter 5.C. 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.

Disposal Methods · 2 件

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. For more information on disposal procedures see Chapter 7 of this volume.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage DisposalSweep spilled substance into sealable containers. Then wash away with plenty of water.

毒性情報

Interactions · 1 件

Bleomycin is an anti-tumor agent whose cytotoxicity is related to the introduction of both single-stranded and double-stranded breaks in cellular DNA. In an assay using isolated nuclei, low levels of ethidium bromide substantially increased bleomycin induced release of nuclear chromatin. Treatment of mouse L1210 leukemia cells in vitro with low levels of ethidium bromide followed 1 hr later by bleomycin produced a synergistic effect that was 8 fold greater than that expected from the additive cytotoxicity of each drug alone. Interestingly, when the order of drug addition was reversed the drug synergism was much reduced (2 fold). The combination of DNA unwinding and strand scission agents may represent a novel and rational approach to the chemotherapy of cancer.

Exposure RoutesThe substance can be absorbed into the body by inhalation and by ingestion.
Signs and Symptoms · 3 件

Cough.

Redness.

Sore throat.

ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.
Non-Human Toxicity Excerpts · 5 件

/LABORATORY ANIMALS: Acute Exposure/ Homidium was a moderate eye irritant but not a skin irritant in the rabbit. /Homidium/

/LABORATORY ANIMALS: Acute Exposure/ Respiratory impairment was seen after intravenous administration while necrosis at the injection site occurred following subcutaneous injection. /Homidium/

/LABORATORY ANIMALS: Acute Exposure/ The major signs of toxicity noted after intravenous and subcutaneous dosing /in rats/ included tremors, prostration and sedation. /Homidium/

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Peripheral nerve ultrastructure was assessed after single or multiple local injections of the intercalating dye ethidium bromide. Thirty-four adult Wistar rats of both sexes were divided into five groups and maintained in a controlled environment with rat chow and water ad libitum throughout the experiment. The experimental animals were injected with 1 microl of 0.1% ethidium bromide in 0.9% saline into the central third of the left sciatic nerve 1 (group 1), 2 (group 2), 4 (group 3), 6 (group 4) or 8 (group 5) times. In groups 2 to 5 the injections were made at 28-day intervals. Control animals received the same amount of 0.9% saline. The animals were killed at different times after injection: group 1 at 7 days (2 rats) and 15 days (2 rats); for groups 2, 3, 4 and 5, all rats were killed 10 days after the last injection and the lesions were investigated by light and transmission electron microscopy. In the acute lesions, intoxicated Schwann cells showed a vacuolated cytoplasm and separation of the sheaths from the axon. Myelin sheaths underwent progressive vesiculation and subsequent segmental demyelination. Myelin debris were withdrawn by macrophages and remyelination by Schwann cells was prominent. With the increase in the number of injections collagen fibers also increased in number and progressively enveloped smaller numbers of remyelinated axons composing new fascicles. Wallerian degeneration of fibers apparently not affected by ethidium bromide was more intense in the nerves from groups 4 and 5. The peripheral nerve repairs itself after demyelinating challenges with a profusion of collagen fibers and new fasciculations. This experimental model is valid to mimic recurrent demyelinating neuropathies.

For more Non-Human Toxicity Excerpts (Complete) data for ETHIDIUM BROMIDE (8 total), please visit the HSDB record page.

Antidote and Emergency Treatment · 2 件

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

安全データ

F
8-9
wgk
3
rtecs
SF7950000
ridadr
UN 2811 6.1/PG 1
毒性
Intercalating dye widely used to stain DNA in gels and gradients. The DNA can be visualized readily by irradiation with ultraviolet light, as little as 0.5 μg of DNA being detectable by such methods. Ethidium bromide is also added to cesium chloride density gradients, since as an intercalating molecule it binds more readily to linear DNA than to closed collinear circles of DNA (such as plasmids). Binding of ethidium bromide reduces the density of DNA, thus covalent circles of DNA have higher densities at saturating concentrations of ethidium bromide, permitting the separation of plasmid DNA. Ethidium bromide is a putative carcinogen.
hs_code
29339990

化学と産業

薬理情報

Mechanism of Action · 1 件

Ethidium bromide (EB), an intercalating drug, has been shown to prevent the in vitro interaction of the estrogen receptor (R) with DNA. We have now studied the effect of this drug on the nuclear translocation of R in order to determine whether DNA integrity is needed for this translocation. In a cell-free reconstituted system made of purified nuclei and cytosol, the pretreatment of nuclei by EB prevented approximately half of the R nuclear translocation, but was unable to extract more than 17% of the /estradiol-R complex/ previously translocated. A series of indirect evidences suggests that EB inhibits the nuclear translocation of R by interacting with nuclear DNA. The degree of the inhibition was related to the amount of drug bound to nuclei and was in agreement with the degree of ultrastructural modifications of chromatin. R was not irreversibly altered by the drug. The EB inhibition was only observed with DNA-containing particles and with estrogen receptor able to bind to DNA. In surviving uteri the drug also inhibited the R nuclear translocation. These results indicate two types of nuclear translocation of R, one sensitive and the other resistant to EB, and suggest that DNA is required for the EB-sensitive translocation.

Metabolism/Metabolites · 1 件

The metabolism of ethidium bromide by isolated rat hepatocytes is significantly enhanced by pre-treatment of animals with phenobarbitone (PB) and 3-methylcholanthrene (3-MC). Pre-treatment with PB and 3-MC results in a 2.5- and 1.5-fold increase, respectively in the amount of the principal metabolite, ethidium 8-N-glucuronide, compared with that formed by hepatocytes from untreated rats. The formation of ethidium 3-N-glucuronide is not enhanced by pre-treatment with either PB or 3-MC. Two new metabolites, hydroxyethidium glucuronide and a transient unidentified species, have been detected by HPLC and are formed only by hepatocytes from animals pre-treated with 3-MC.

MeSH Pharmacological Classification · 5 件

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA.

Drugs that bind to nicotinic cholinergic receptors (RECEPTORS, NICOTINIC) and block the actions of acetylcholine or cholinergic agonists. Nicotinic antagonists block synaptic transmission at autonomic ganglia, the skeletal neuromuscular junction, and at central nervous system nicotinic synapses.

用途と製造

Uses · 2 件

Used in the determination of nucleic acids and as an antimicrobial (Trypanosoma); [Merck Index]

Used as a DNA probe

応用分野 · 2 件

解説核酸の2塩基分子間にインターカレーションではいり込みやすい構造の有機色素.C21H20BrN3.ゲル電気泳動をした核酸の染色に利用する.臭化エチジウム固有の光吸収(ピーク300 nm)や,核酸の光吸収(ピーク260 nm)とエネルギー移動を経て現れる蛍光(ピーク590 nm)を観測することにより,核酸のバンドを検出できる.

使用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).

調製方法

純化方法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.

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