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71028

Sigma-Aldrich

Monobromo(trimethylammonio)bimane bromide

suitable for fluorescence, ≥90.0% (HPLC)

Synonym(s):

(Trimethylammonio)monobromobimane, 5-(Bromomethyl)-N,N,N,2,6-pentamethyl-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3-methanaminium bromide, Brombimane q, Thiolye MQ, qBBr

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About This Item

Empirical Formula (Hill Notation):
C13H19Br2N3O2
CAS Number:
71418-45-6
Molecular Weight:
409.12
Beilstein/REAXYS Number:
4630658
MDL number:
MFCD00036953
UNSPSC Code:
12171500
PubChem Substance ID:
57652269
NACRES:
NA.32

assay

≥90.0% (HPLC)

form

powder

solubility

DMSO: 5 mg/mL

fluorescence

λex 380 nm; λem 475 nm in 0.1 M phosphate pH 7.5

suitability

suitable for fluorescence

storage temp.

2-8°C

SMILES string

[Br-].CC1=C(CBr)N2N(C1=O)C(=O)C(C)=C2C[N+](C)(C)C

InChI

1S/C13H19BrN3O2.BrH/c1-8-10(6-14)15-11(7-17(3,4)5)9(2)13(19)16(15)12(8)18;/h6-7H2,1-5H3;1H/q+1;/p-1

InChI key

FCRPMMVPBVOKQS-UHFFFAOYSA-M

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Biochem/physiol Actions

Monobromobimanes are essentially nonfluorescent until conjugated and readily react with low molecular weight thiols. Unlike common monobromobimanes, this carries a positive charge, thus permitting separation of conjugates by electrophoresis or cation-exchange chromatography

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Reagent for labeling thiols in biol. materials

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Analysis of biological thiols: derivatization with monobromotrimethylammoniobimane and characterization by electrophoresis and chromatography.
R C Fahey et al.
Analytical biochemistry, 107(1), 1-10 (1980-09-01)
M A Whelan et al.
European journal of immunology, 23(12), 3278-3285 (1993-12-01)
Techniques have been developed to measure the reactivity of free thiols in the HLA class I antigen-binding cleft. HLA-B27, which sequencing predicts has a free cysteine at position 67, reacts rapidly with the positively charged thiol reagent monobromotrimethyl-ammoniobimane bromide (qBBr)
M B Zucker et al.
Thrombosis and haemostasis, 55(2), 228-234 (1986-04-30)
Monobromobimane (mBBr, bimane), a compound that penetrates cells and forms a fluorescent adduct with thiol groups, was used to asses the significance of thiols in platelet function. Exposure of washed platelets for 1 min to 100 microM mBBr abolished ADP-induced
D Picot et al.
European journal of biochemistry, 196(2), 329-341 (1991-03-14)
Aspartate aminotransferase undergoes major shifts in the conformational equilibrium of the protein matrix during transamination. The present study defines the two conformational states of the enzyme by crystallographic analysis, examines the conditions under which the enzyme crystallizes in each of
Masataka Murahashi et al.
Analytical and bioanalytical chemistry, 412(23), 5799-5809 (2020-07-10)
Japanese police conduct highly sensitive and quick blood tests to detect human hemoglobin (Hb), because bloodstains left at a crime scene have probative value of circumstantial evidence in a criminal investigation. Although DNA detection from a bloodstain is a useful
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