A thiol-reactive fluorogenic probe
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Monobromobimane

Item No. 17097

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(bromomethyl)-2,5,6-trimethyl-1H,7H-pyrazolo[1,2-a]pyrazole-1,7-dione
CAS Number
71418-44-5
Synonyms
  • MBBr
  • NSC 608544
Molecular Formula
C10H11BrN2O2
Formula Weight
271.1
Purity
≥98%
Emission
490 nm
Excitation
398 nm
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mDMSO: 50 mg/mEthanol: 1 mg/ml
λmax
247, 383 nm
SMILES
O=C1N2N(C(CBr)=C(C)C2=O)C(C)=C1C
InChi Code
InChI=1S/C10H11BrN2O2/c1-5-7(3)12-8(4-11)6(2)10(15)13(12)9(5)14/h4H2,1-3H3
InChi Key
AHEWZZJEDQVLOP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $54

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    25 mg

    $108

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    50 mg

    $203

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    100 mg

    $351

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    Product Description

    Monobromobimane is a thiol-reactive fluorogenic probe. It is cell-permeable, reacts rapidly at physiological pH with available thiol groups, and generates a stable fluorescent signal.1 Monobromobimane can be used to evaluate or quantify a variety of compounds containing reactive sulfur or thiol groups, including H2S, glutathione, proteins, and nucleotides.2,3,4,5 The absorption and emission maxima for monobromobimane are 398 and 490 nm, respectively.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kosower, N.S., Kosower, E.M., Newton, G.L., et al. Bimane fluorescent labels: Labeling of normal human red cells under physiological conditions. Proc. Natl. Acad. Sci. USA 76(7), 3382-3386 (1979).

    2. Klingerman, C.M., Trushin, N., Prokopczyk, B., et al. H2S concentrations in the arterial blood during H2S administration in relation to its toxicity and effects on breathing. Am. J. Physiol. Regul. Integr. Comp. Physiol. 305(6), R630-R638 (2013).

    3. Rice, G.C., Bump, E.A., Shrieve, D.C., et al. Quantitative analysis of cellular glutathione by flow cytometry utilizing monochlorobimane: Some applications to radiation and drug resistance in vitro and in vivo. Cancer Res. 46(12 Pt 1), 6105-6110 (1986).

    4. Chen, Y.T., Collins, T.R.L., Guan, A., et al. Probing conformational changes in human DNA topoisomerase IIα by pulsed alkylation mass spectrometry. The Journal of Biological Chemisty 287(30), 25660-25668 (2012).

    5. Cosstick, R., McLaughlin, L.W., and Eckstein, F. Fluorescent labelling of tRNA and oligodeoxynucleotides using T4 RNA ligase. Nucleic Acids Res. 12(4), 1791-1810 (2015).

    6. Sabnis, R.W. Handbook of biological dyes and stains: Synthesis and industrial applications. (2010).