596105

THIOLYTE^® Monobromobimane Reagent, Fluorescent Labeling Compound

• Synonym(s): THIOLYTE^® MB Reagent, MBB
• CAS Number: 71418-44-5
• UNSPSC Code: 41116133
• NACRES: NB.23
• MDL number: MFCD00036951

Properties

• assay: ≥95% (HPLC)
• Quality Segment: 100
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: yellow
• solubility: acetonitrile: 13 mg/mL, methanol: 25 mg/mL
• shipped in: ambient
• storage temp.: 10-30°C
• SMILES string: BrCc1[n]2[n]([c](c1C)=O)[c](c(c2C)C)=O
• InChI: 1S/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3
• InChI key: AHEWZZJEDQVLOP-UHFFFAOYSA-N

Description

General description

Contains a reactive functional group (allylic bromide) that is capable of reacting with a wide variety of nucleophiles to form stable covalent adducts. Reacts extremely rapidly with thiol groups under physiological conditions to yield highly fluorescent products. A labeling reaction is typically carried out at room temperature for 2 to 60 min, pH 7.4, using an equivalent amount (or a small excess) of reagent relative to the amount of thiol. Material is chemically and photolytically stable and shows an absorption maxima at 370 to 385 nm and emits light at 477 to 484 nm (turquoise). Readily penetrates membranes. Useful as an alternative tool in labeling methodology, complementing the use of such well known fluorescent labeling reagents as fluorescein and rhodamine isothiocyanates (whose reactions are slower and yield products that fade relatively fast during irradiation) and fluorescamine (which reacts primarily with amine groups, but whose products also fade relatively rapidly).

Has been used to label E. coli thioredoxin. Weakly fluorescent but reacts with thiols to yield highly fluorescent stable thioethers.

Preparation Note

Following reconstitution, refrigerate (4°C). Stock solutions are stable for up to 3 months at 4°C. Aqueous stock solutions have a half-life of ~4 h at room temperature (20°C).

Recommended stock solution is 13 mg/ml (50 mM) in acetonitrile.

Other Notes

Mansoor, M.A., et al. 1992. Anal. Biochem.200, 218.
Zangerle, L., et al. 1992. J. Neurochem.59, 181.
Agarwal, R. and Burke, M. 1991. Arch. Biochem. Biophys.290, 1.
Martin, R.L., et al. 1989. J. Biol. Chem.264, 11768.
Bonet, A., et al. 1988. Biochem. Biophys. Res. Commun.152, 1.
Chinn, P.C. 1985. Fed. Proc.44, 1620.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

THIOLYTE is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable