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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:
4189453
MDL number:
MFCD00036952
UNSPSC Code:
12352108
PubChem Substance ID:
57649022
NACRES:
NA.32

product line

BioReagent

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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.
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
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