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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

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL2818
BCCG3277
BCCD6741
BCCB3778
BCBQ0293V

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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
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.
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)
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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