Physicochemical Properties
| Molecular Formula | C21H20BRN3 |
| Molecular Weight | 394.31 |
| Exact Mass | 393.084 |
| Elemental Analysis | C, 63.97; H, 5.11; Br, 20.26; N, 10.66 |
| CAS # | 1239-45-8 |
| Related CAS # | 1239-45-8 (Br); 3546-21-2; 602-52-8 (Cl) |
| PubChem CID | 14710 |
| Appearance | Brown to reddish brown solid powder |
| Melting Point | 260-262 °C (dec.)(lit.) |
| Flash Point | >100°C |
| Index of Refraction | 1.4575 (20ºC) |
| LogP | 2.298 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 25 |
| Complexity | 419 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | ZMMJGEGLRURXTF-UHFFFAOYSA-N |
| InChi Code | 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 |
| Chemical Name | 5-ethyl-6-phenylphenanthridin-5-ium-3,8-diamine;bromide |
| Synonyms | Dromilac; ETHIDIUM BROMIDE; EtBr; Homidium bromide |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Ethidium Bromide (EtBr) is occasionally added to the running buffer when using agarose gel electrophoresis to separate DNA fragments. It is utilized because the DNA banding pattern can be seen when the molecule binds to the DNA and is illuminated with a UV light source. Intercalation between base pairs is how EtBr binds. The DNA molecule's weight, charge, conformation, and flexibility are all altered by this binding. DNA has always moved less freely in the gels containing EtBr[1]. |
| ADME/Pharmacokinetics |
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. |
| Toxicity/Toxicokinetics |
Toxicity Data LC50 (rat) = 11,000-134,000 mg/m3/1hr 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. 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. |
| References |
[1]. Electrophoresis . 1996 Oct;17(10):1524-7. |
| Additional Infomation |
Ethidium bromide is the organic bromide salt of ethidium. It has a role as a trypanocidal drug, a geroprotector and an intercalator. 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. 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. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~78 mg/mL (~197.8 mM) Ethanol : ~1 mg/mL (~2.5 mM) Water : ~7 mg/mL (~17.8 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.28 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.28 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: 9.09 mg/mL (23.05 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C). (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5361 mL | 12.6804 mL | 25.3608 mL | |
| 5 mM | 0.5072 mL | 2.5361 mL | 5.0722 mL | |
| 10 mM | 0.2536 mL | 1.2680 mL | 2.5361 mL |