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Sigma-Aldrich

Dibromobimane

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

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Empirical Formula (Hill Notation):
C10H10Br2N2O2
CAS Number:
Molecular Weight:
350.01
Beilstein:
4189453
MDL number:
PubChem Substance ID:
NACRES:
NA.32

product line

BioReagent

Quality Level

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

Signal Word

Warning

Hazard Statements

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

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Hai Po Helena Liang et al.
The Biochemical journal, 437(3), 455-460 (2011-05-21)
TF (tissue factor) is a transmembrane cofactor that initiates blood coagulation in mammals by binding Factor VIIa to activate Factors X and IX. The cofactor can reside in a cryptic configuration on primary cells and de-encryption may involve a redox
H Bhattacharjee et al.
The Journal of biological chemistry, 271(40), 24465-24470 (1996-10-04)
ArsA ATPase activity is allosterically activated by salts of the semimetal arsenic or antimony. Activation is associated with the presence of three cysteine residues in ArsA: Cys113, Cys172, and Cys422. To determine the distance between cysteine residues, wild type ArsA
Katrina A Black et al.
Nature communications, 11(1), 3024-3024 (2020-06-17)
The canonical mechanistic model explaining potassium channel gating is of a conformational change that alternately dilates and constricts a collar-like intracellular entrance to the pore. It is based on the premise that K+ ions maintain a complete hydration shell while
D Mornet et al.
Proceedings of the National Academy of Sciences of the United States of America, 82(6), 1658-1662 (1985-03-01)
A bifunctional fluorescent alkylating agent, dibromobimane, has been used to stabilize a preexisting primary loop in myosin subfragment 1 (S-1). The crosslink achieved joins Cys-707 (called sulfhydryl group "SH1") of the 20-kDa domain (formerly called "20K" domain) with a thiol
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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