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71028

Sigma-Aldrich

Monobromo(trimethylammonio)bimane bromide

suitable for fluorescence, ≥90.0% (HPLC)

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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
Empirical Formula (Hill Notation):
C13H19Br2N3O2
CAS Number:
Molecular Weight:
409.12
Beilstein:
4630658
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

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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This Item
426296SML3560SML3587
MU380 ≥98% (HPLC)

Sigma-Aldrich

SML3560

MU380

SCH 900776 ≥98% (HPLC)

Sigma-Aldrich

SML3587

SCH 900776

form

powder

form

powder

form

powder

form

powder

solubility

DMSO: 5 mg/mL

solubility

-

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

fluorescence

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

fluorescence

-

fluorescence

-

fluorescence

-

suitability

suitable for fluorescence

suitability

-

suitability

-

suitability

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-10 to -25°C

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 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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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
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
F Zoccarato et al.
Neuroscience letters, 274(2), 107-110 (1999-12-20)
The treatment of cerebral cortex synaptosomes with the membrane impermeable thiol reagent 5,5'-dithio-bis-(2-nitrobenzoic acid) (DTNB) induces a long-lasting partial inhibition (about 40%) of the KCl-stimulated Ca2+-dependent exocytosis of glutamate. Synaptosomes are not damaged by the treatment. The increase of cytoplasmic
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
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)

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