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THIOLYTE® Monobromobimane Reagent, Fluorescent Labeling Compound

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Synonym(s):
THIOLYTE® MB Reagent, MBB
CAS Number:
MDL number:

assay

≥95% (HPLC)

Quality Level

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

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

Related Categories

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.

Warning

Toxicity: Standard Handling (A)

Preparation Note

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

Reconstitution

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).

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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