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34025

Sigma-Aldrich

Dibromobimane

BioReagent, suitable for fluorescence, ≥95.0% (CHN)

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About This Item

Empirical Formula (Hill Notation):
C10H10Br2N2O2
CAS Number:
68654-25-1
Molecular Weight:
350.01
Beilstein/REAXYS Number:
4189453
MDL number:
MFCD00036952
UNSPSC Code:
12352108
PubChem Substance ID:
57649022
NACRES:
NA.32

product line

BioReagent

assay

≥95.0% (CHN)

mp

170-172 °C (lit.)

solubility

DMF: soluble
acetonitrile: soluble
chloroform: soluble

fluorescence

λex 391 nm in methanol
λex 393 nm; λem 477 nm in 0.1 M Tris pH 7.0, gutathione red

suitability

suitable for fluorescence

storage temp.

2-8°C

SMILES string

CC1=C(CBr)N2N(C1=O)C(=O)C(C)=C2CBr

InChI

1S/C10H10Br2N2O2/c1-5-7(3-11)13-8(4-12)6(2)10(16)14(13)9(5)15/h3-4H2,1-2H3

InChI key

OSIYFMVMZXJKSP-UHFFFAOYSA-N

Application

Dibromobimane, a bifunctional thiol reagent, is used as a cross-linking agent for cysteine mapping and studies on protein structure/conformation and cross-linking processes.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Fluorescent thiol-specific labeling reagent

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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M Adil Khan et al.
Biochemistry, 48(41), 9745-9756 (2009-09-23)
Membrane-intrinsic enzymes are embedded in lipids, yet how such enzymes interrogate lipid substrates remains a largely unexplored fundamental question. The outer membrane phospholipid:lipid A palmitoyltransferase PagP combats host immune defenses during infection and selects a palmitate chain using its beta-barrel
T W Loo et al.
The Journal of biological chemistry, 275(50), 39272-39278 (2000-10-03)
P-glycoprotein (P-gp) can transport a wide variety of cytotoxic compounds that have diverse structures. Therefore, the drug-binding domain of the human multidrug resistance P-gp likely consists of residues from multiple transmembrane (TM) segments. In this study, we completed cysteine-scanning mutagenesis
T W Loo et al.
The Journal of biological chemistry, 272(51), 31945-31948 (1998-01-24)
We identified a thiol-reactive compound, dibromobimane (dBBn), that was a potent stimulator (8.2-fold) of the ATPase activity of Cys-less P-glycoprotein. We then used this compound together with cysteine-scanning mutagenesis to identify residues in transmembrane segment (TM) 6 and TM12 that
Qingxiu Tang et al.
The Journal of general physiology, 133(6), 555-570 (2009-05-27)
The structure of the pore is critical to understanding the molecular mechanisms underlying selective permeation and voltage-dependent gating of channels formed by the connexin gene family. Here, we describe a portion of the pore structure of unapposed hemichannels formed by
Francisco J Sánchez-Gómez et al.
Molecular pharmacology, 78(4), 723-733 (2010-07-16)
Glutathione transferase P1-1 (GSTP1-1) plays crucial roles in cancer chemoprevention and chemoresistance and is a key target for anticancer drug development. Oxidative stress or inhibitor-induced GSTP1-1 oligomerization leads to the activation of stress cascades and apoptosis in various tumor cells.
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