기본 정보
- 표준 SMILES
CC[n+]1c(-c2ccccc2)c2cc(N)ccc2c2ccc(N)cc21.[Br-]- InChIKey
ZMMJGEGLRURXTF-UHFFFAOYSA-N- 분자식
- C21H20N3.Br
- 평균 분자량
- 394.3 g/mol
- 단동위원소 질량
- 393.08405974
개요
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.
이름 및 식별자
- 우선 이름
- Ethidium Bromide
- IUPAC
- 5-ethyl-6-phenylphenanthridin-5-ium-3,8-diamine bromide
- 현지명
- 에티듐 브로마이드
- 영어명
- Ethidium bromide
- 분자식
- C21H20BrN3
- 분자량
- 394.32
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
1239-45-8- PubChem CID
- 14710
- DTXSID
DTXSID8025258- ChEMBL
CHEMBL284328- ChEBI
CHEBI:4883- UNII
- 059NUO2Z1L
- EC Number
- 214-984-6
물성
구조 계산 물성
- 극성 표면적
- 55.9 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 25
- 형식 전하
- 0
- 복잡도
- 419
실험 및 물리화학적 성질
LogP
log Kow= -0.38 /Estimated/
-1.1
Color/Form
Dark red crystals from alcohol
Maroon powder
Solubility
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
Melting Point
260-262 °C (decomposes)
238-240 °C
Vapor Pressure
1.2X10-12 mm Hg at 25 °C /Estimated/
Vapor pressure at 25 °C: negligible
Physical Description
Dark red solid; [Merck Index] Red to brown solid; [ICSC] Dark red powder; [Sigma-Aldrich MSDS]
RED-TO-BROWN CRYSTALS.
물리화학적 성질
- 녹는점
- 260 · 260-262 °C (dec.)(lit.)
- 밀도
- 1.3739 · 1.3739 (rough estimate)
- 굴절률
- 1.67 · 1.6700 (estimate)
- 인화점
- 100 °C · >100°C
- 저장 조건
- 2 · 2-8°C
- 용해도
- 2 O: · H2O: 10 mg/mL, 불투명, 강한 빨간색
- 물리적 상태
- 가루
- 색상
- 빨간색에서 진한 보라색까지
- 수소이온지수(pH)
- 4.4 · 4.4 (20°C, 10g/L in H2O)
- 냄새
- 무취 고체
- 수용성
- 40 g/L · 40g/L(25℃)
- Merck
- 14 · 14,4731
- BRN
- 3642536 · 3642536
- 안정성
- 안정적인. 강한 산화제와 호환되지 않습니다.
- 주요 응용
- 전광 디스플레이;포토레지스트
- 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
- InChIKey
- ZMMJGEGLRURXTF-UHFFFAOYSA-N
- SMILES
- [Br-].CC[n+]1c(-c2ccccc2)c3cc(N)ccc3c4ccc(N)cc14
- EPA
- 3 · Phenanthridinium, 3,8-diamino-5-ethyl-6-phenyl-, bromide (1239-45-8)
화학적 성질
Purple/maroon crystalline powder
안전 및 규제
GHS 분류
GHS Classification
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)
유해성 정보
Regulatory Information
Chemical: Phenanthridinium, 3,8-diamino-5-ethyl-6-phenyl-, bromide
Ethidium bromide: HSNO Approval: HSR004464 Approved with controls
Hazard Classes and Categories
Acute Tox. 4 (97.1%)
Germ cell mutagenicity - category 2
Muta. 2
Shipment Methods and Regulations
Employers /must/ ensure that labels on incoming containers of hazardous chemicals are not removed or defaced. Employers /must/ maintain any material safety data sheets that are received with incoming shipments of hazardous chemicals, and ensure that they are readily accessible to laboratory employees.
안전 및 보호
First Aid Measures
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.
Storage Conditions
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
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.
독성 정보
Interactions
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.
Signs and Symptoms
Cough.
Redness.
Sore throat.
Non-Human Toxicity Excerpts
/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
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/
Non-Human Toxicity Values
LD50 Mouse subcutaneous 110 mg/kg
LD50 Mouse intraperitoneal 20 mg/kg
LD50 Rat iv 27 mg/kg
LD50 Rat sc 80 mg/kg
For more Non-Human Toxicity Values (Complete) data for ETHIDIUM BROMIDE (6 total), please visit the HSDB record page.
안전 데이터
- wgk
- 3
- rtecs
- SF7950000
- ridadr
- UN 2811 6.1/PG 1
- 독성
- 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 번호
- 29339990
- risk_code
- 23-68-36/37/38-26-21/22-22
- hazard_code
- T,T+
- safety_code
- 36/37-45-36/37/39-28A-26-22-28-63
- 포장분류
- I
- 위험 등급
- 6.1
- 기존화학 물질
- KE-09740
- F 고인화성물질
- 8-9
- Hazard Classifications
- Acute Tox. 1 InhalationAcute Tox. 4 OralMuta. 2
- 스토리지 클래스
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- 유해 물질 데이터
- 1239-45-8(Hazardous Substances Data)
화학 및 산업
약리 정보
Mechanism of Action
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
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
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.
용도 및 제조
Uses
Used in the determination of nucleic acids and as an antimicrobial (Trypanosoma); [Merck Index]
Used as a DNA probe
응용 분야
용도Ethidium 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).
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