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Home > Encyclopedia > Ethidium bromide

Ethidium bromide

Ethidium bromide structure

Ethidium bromide 

structure
  • CAS No:

    1239-45-8

  • Formula:

    C21H20N3.Br

  • Chemical Name:

    Ethidium bromide

  • Synonyms:

    Phenanthridinium,3,8-diamino-5-ethyl-6-phenyl-,bromide (1:1);Phenanthridinium,3,8-diamino-5-ethyl-6-phenyl-,bromide;3,8-Diamino-5-ethyl-6-phenylphenanthridinium bromide;2,7-Diamino-9-phenyl-10-ethylphenanthridinium bromide;2,7-Diamino-9-phenylphenanthridine ethobromide;Dromilac;Ethidium bromide;Homidium bromide;2,7-Diamino-10-ethyl-9-phenylphenanthridinium bromide;131089-24-2;35322-47-5

  • Categories:

    Biochemical Engineering  >  Biochemical Reagents

Description

RED-TO-BROWN CRYSTALS.


RED-TO-BROWN CRYSTALS.


Ethidium bromide is an organic bromide salt. It has a role as a trypanocidal drug. It contains an ethidium.|A trypanocidal agent and possible antiviral agent that is widely used in experimental cell biology and biochemistry. Ethidium has several experimentally useful properties including binding to nucleic acids, noncompetitive inhibition of nicotinic acetylcholine receptors, and fluorescence among others. It is most commonly used as the bromide.

Ethidium bromide Basic Attributes

394.31

393.084045

3642536

214-984-6

059NUO2Z1L

1676

758630|268986

2811

DTXSID8025258

Dark red crystals from alcohol|Maroon powder

29339990

Characteristics

55.92000

2.29820

Red to dark purple powder

0.34 g/cm³

260-262 °C (dec.)(lit.)

>100°C

1.4575 (20ºC)

H2O: 40 g/L (25 ºC)

2-8°C

1.2X10-12 mm Hg at 25 deg C /Estimated/

Bitter tasting

Henry's Law constant= 1.8X10-20 atm-cu m/mole at 25 °C /Estimated/

175.1 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Hydroxyl radical reaction rate constant= 2.1X10-10 cu cm/molecule-sec at 25 °C /Estimated/

Safety Information

I

6.1

UN 2811 6.1/PG 1

3

23-68-36/37/38-26-21/22-22

36/37-45-36/37/39-28A-26-22-28-63

SF7950000

T,T+

Fireproof. Separated from strong oxidants and food and feedstuffs.

Stable. Incompatible with strong oxidizing agents.

P260-P281-P284-P310

H302-H330-H341

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.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P271, P281, P284, P301+P312, P304+P340, P308+P313, P310, P320, P330, P403+P233, P405, and P501|H302 (96.97%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P281, P284, P301+P312, P304+P340, P308+P313, P310, P311, P320, P321, P330, P403+P233, P405, and P501|Aggregated GHS information provided by 33 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

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.

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

Fireproof. Separated from strong oxidants and food and feedstuffs.

A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

The substance is irritating to the eyes and respiratory tract.

NO open flames. NO contact with strong oxidizing agents.

AVOID ALL CONTACT!

Use local exhaust. Use breathing protection.

Protective gloves.

Wear safety goggles.

Toxicity

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.

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.

Drug Information

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. (See all compounds classified as Fluorescent Dyes.)|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 and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)|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. (See all compounds classified as Nicotinic Antagonists.)|Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA. (See all compounds classified as Trypanocidal Agents.)

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.

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.

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).

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/

Bromide, Ethidium

The substance can be absorbed into the body by inhalation and by ingestion.

Cough.


Redness.

Ethidium bromide Use and Manufacturing

antiprotozoal, intercalcates with DNA

Computed Properties

Molecular Weight:394.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:393.08406
Monoisotopic Mass:393.08406
Topological Polar Surface Area:55.9
Heavy Atom Count:25
Complexity:419
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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