Molecular Formula | C10H11BrN2O2 |
Molar Mass | 271.11 |
Density | 1.66±0.1 g/cm3(Predicted) |
Melting Point | 152-154°C(lit.) |
Boling Point | 327.8±44.0 °C(Predicted) |
Solubility | DMF: soluble |
Appearance | Morphological powder |
Color | Yellow |
Maximum wavelength(λmax) | 398 nm |
BRN | 4430959 |
pKa | -3.36±0.70(Predicted) |
Storage Condition | 2-8°C |
Stability | Light Sensitive |
MDL | MFCD00036951 |
In vitro study | Bromobimanes in solution (aqueous or organic solvents of medium polarity) react with small thiols [e.g., the tripeptide thiol glutathione (GSH)], and with reactive protein thiol groups (e.g., hemoglobin). The reactions of bromobimanes with thiols are second order and dependent on pH, the active nucleophile being the thiolate anion. The reaction of bromobimane with a thiolate converts the nonfluorescent agent into water-soluble fluorescent products. The neutral agents mBBr and bBBr are moderately soluble in mediumpolarity organic solvents (acetonitrile, dichloromethane), and slightly soluble in water. The quaternary salt, qBBr, and the anionic bromobimane, SBBr, are soluble in water, but less soluble in organic solvents. Bromobimanes are yellow. The highly selective, rapid reactivity of bromobimanes toward thiols, the stability and fluorescence yield of the thiol derivatives, the ease of separation of the derivatives by reversed-phase HPLC, and the availability of both cell-penetrating and nonpenetrating forms, make the use bromobimanes an extremely powerful approach to the analysis of low molecular weight biothiols. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
WGK Germany | 3 |
FLUKA BRAND F CODES | 8 |
1mg | 5mg | 10mg | |
---|---|---|---|
1 mM | 3.689 ml | 18.443 ml | 36.885 ml |
5 mM | 0.738 ml | 3.689 ml | 7.377 ml |
10 mM | 0.369 ml | 1.844 ml | 3.689 ml |
5 mM | 0.074 ml | 0.369 ml | 0.738 ml |
maximum wavelength (& lambda;max) | 398 nm |
biological applications | Glutathione S-transferase substrates; detecting glutathione S-transferase,thiols,sulfite,homocysteine,mycothiol,sulfur compounds; thiol-reactive probes |
biological activity
Bromobimane is basically a non-fluorescent substance, and when reacted with small mercaptan, fluorescent products are generated.
in vitro studies
Bromobimanes in solution (aqueous or organic solvents of medium polarity) react with small thiols [e.g., the tripeptide thiol glutathione (GSH)], and with reactive protein thiol groups (e.g., hemoglobin). The reactions of bromobimanes with thiols are second order and dependent on pH, the active nucleophile being the thiolate anion. The reaction of bromobimane with a thiolate converts the nonfluorescent agent into water-soluble fluorescent products. The neutral agents mBBr and bBBr are moderately soluble in mediumpolarity organic solvents (acetonitrile, dichloromethane), and slightly soluble in water. The quaternary salt, qBBr, and the anionic bromobimane, SBBr, are soluble in water, but less soluble in organic solvents. Bromobimanes are yellow. The highly selective, rapid reactivity of bromobimanes toward thiols, the stability and fluorescence yield of the thiol derivatives, the ease of separation of the derivatives by reversed-phase HPLC, and the availability of both cell-penetrating and nonpenetrating forms, make the use bromobimanes an extremely powerful approach to the analysis of low molecular weight biothiols.