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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:
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 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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T T Huang et al.
Biology of reproduction, 31(4), 797-809 (1984-11-01)
The distribution of thiols and disulfides in the guinea pig spermatozoon during maturation and capacitation was studied using both membrane-permeable (mBBr) and impermeable (qBBr) forms of bromobimane, a specific fluorescent probe for thiol groups. In conjunction with the disulfide (SS)-reducing
Conformational changes in mitochondrial aspartate aminotransferase detected by a covalently attached fluorescent probe.
E Sandmeier et al.
Progress in clinical and biological research, 144B, 117-124 (1984-01-01)
K E Mate et al.
Molecular reproduction and development, 37(3), 318-325 (1994-03-01)
The acrosome of marsupial spermatozoa is a robust structure which, unlike its placental counterpart, resists disruption by detergent or freeze/thawing and does not undergo a calcium ionophore induced acrosome reaction. In this study specific fluorescent thiol labels, bromobimanes, were used
S X Yuan et al.
FEBS letters, 234(1), 218-222 (1988-07-04)
The single cysteinyl residue 26 of spinach calmodulin was labelled with the thiol-specific bimane fluorescence probe. Following application of stoichiometric quantities of Ca2+ or aluminum ions to the protein, temperature-dependent fluorescence changes (anisotropy, lifetime) could be monitored via the label.
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
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