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Chemical Compound Review

Bromobimane     8-(bromomethyl)-2,3,7- trimethyl-1,5...

Synonyms: MBBR, Thiolyte MB, SureCN152679, AG-G-79681, CHEMBL1649730, ...
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Disease relevance of Bromobimane


High impact information on Bromobimane

  • Tissue extracts incubated with reduced thioredoxin are treated with a fluorescent probe (monobromobimane) to label sulfhydryl groups [5].
  • Monobromobimane labeling and protein-free thiol titration revealed significantly less extensive oxidation in the cauda epididymis when compared to that in the wild type [6].
  • Cytochalasin D (CD) and monobromobimane (MB) enhanced agglutination and prevented the inhibitory action of ADP on bovine vWf-induced platelet agglutination [7].
  • We find that two mutants, I72C and S251C, when labeled with the small, solvent-sensitive fluorophore monobromobimane, exhibit spectral changes only upon binding light-activated, phosphorylated rhodopsin [8].
  • We have determined the distribution of glutathione between different chemical states in rat liver microsomes by labeling with the thiol-specific label monobromobimane and subsequent separation by reversed phase high performance liquid chromatography [9].

Biological context of Bromobimane


Anatomical context of Bromobimane


Associations of Bromobimane with other chemical compounds


Gene context of Bromobimane

  • Monobromobimane and N-dansylaziridine labeled GPIb beta but not GPIb alpha in intact platelets [24].
  • The mechanism by which the ferredoxin-thioredoxin system activates the target enzyme, NADP-malate dehydrogenase, was investigated by analyzing the sulfhydryl status of individual protein components with [14C]iodoacetate and monobromobimane [25].
  • Two types of PC analyses are currently used, i.e., acid extraction and separation on HPLC with either precolumn derivatization (pH 8.2) with monobromobimane (mBBr) or postcolumn derivatization (pH 7.8) with Ellman's reagent [5, 5'-dithiobis(2-nitrobenzoic acid), DTNB] [26].
  • Monobromobimane occupies a distinct xenobiotic substrate site in glutathione S-transferase pi [27].
  • A highly sensitive and specific assay for Escherichia coli thioredoxin was developed using the thiol-specific reagent monobromobimane [28].

Analytical, diagnostic and therapeutic context of Bromobimane


  1. A novel mycothiol-dependent detoxification pathway in mycobacteria involving mycothiol S-conjugate amidase. Newton, G.L., Av-Gay, Y., Fahey, R.C. Biochemistry (2000) [Pubmed]
  2. Characterization of wheat thioredoxin h cDNA and production of an active Triticum aestivum protein in Escherichia coli. Gautier, M.F., Lullien-Pellerin, V., de Lamotte-Guéry, F., Guirao, A., Joudrier, P. Eur. J. Biochem. (1998) [Pubmed]
  3. The effects of monobromobimane on neuronal cell death in the hippocampus after transient global cerebral ischemia in rats. Abe, T., Takagi, N., Nakano, M., Takeo, S. Neurosci. Lett. (2004) [Pubmed]
  4. Determination of the intracellular protein thiol distribution of hepatocytes using monobromobimane derivatisation of intact cells and isolated subcellular fractions. Cotgreave, I.A., Weis, M., Berggren, M., Sandy, M.S., Moldéus, P.W. J. Biochem. Biophys. Methods (1988) [Pubmed]
  5. A strategy for the identification of proteins targeted by thioredoxin. Yano, H., Wong, J.H., Lee, Y.M., Cho, M.J., Buchanan, B.B. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  6. The nuclear form of phospholipid hydroperoxide glutathione peroxidase is a protein thiol peroxidase contributing to sperm chromatin stability. Conrad, M., Moreno, S.G., Sinowatz, F., Ursini, F., Kölle, S., Roveri, A., Brielmeier, M., Wurst, W., Maiorino, M., Bornkamm, G.W. Mol. Cell. Biol. (2005) [Pubmed]
  7. Assembly and GPIIIa content of cytoskeletal core in platelets agglutinated with bovine von Willebrand factor. Puszkin, E.G., Mauss, E.A., Zucker, M.B. Blood (1990) [Pubmed]
  8. Dynamics of arrestin-rhodopsin interactions: arrestin and retinal release are directly linked events. Sommer, M.E., Smith, W.C., Farrens, D.L. J. Biol. Chem. (2005) [Pubmed]
  9. A major fraction of endoplasmic reticulum-located glutathione is present as mixed disulfides with protein. Bass, R., Ruddock, L.W., Klappa, P., Freedman, R.B. J. Biol. Chem. (2004) [Pubmed]
  10. 20 S proteasome from Saccharomyces cerevisiae is responsive to redox modifications and is S-glutathionylated. Demasi, M., Silva, G.M., Netto, L.E. J. Biol. Chem. (2003) [Pubmed]
  11. Probing the active site of alpha-class rat liver glutathione S-transferases using affinity labeling by monobromobimane. Hu, L., Borleske, B.L., Colman, R.F. Protein Sci. (1997) [Pubmed]
  12. Reactivity of zinc finger cysteines: chemical modifications within labile zinc fingers in estrogen receptor. Atsriku, C., Scott, G.K., Benz, C.C., Baldwin, M.A. J. Am. Soc. Mass Spectrom. (2005) [Pubmed]
  13. The structure of U17 isolated from Streptomyces clavuligerus and its properties as an antioxidant thiol. Newton, G.L., Bewley, C.A., Dwyer, T.J., Horn, R., Aharonowitz, Y., Cohen, G., Davies, J., Faulkner, D.J., Fahey, R.C. Eur. J. Biochem. (1995) [Pubmed]
  14. Effects of BisGMA on glutathione metabolism and apoptosis in human gingival fibroblasts in vitro. Engelmann, J., Janke, V., Volk, J., Leyhausen, G., von Neuhoff, N., Schlegelberger, B., Geurtsen, W. Biomaterials (2004) [Pubmed]
  15. Growth-associated modifications of low-molecular-weight thiols and protein sulfhydryls in human bronchial fibroblasts. Atzori, L., Dypbukt, J.M., Sundqvist, K., Cotgreave, I., Edman, C.C., Moldéus, P., Grafström, R.C. J. Cell. Physiol. (1990) [Pubmed]
  16. Stress protein activation by the cyclopentenone prostaglandin 15-deoxy-delta12,14-prostaglandin J2 in human mesangial cells. Zhang, X., Lu, L., Dixon, C., Wilmer, W., Song, H., Chen, X., Rovin, B.H. Kidney Int. (2004) [Pubmed]
  17. Rhodopsin-G-protein interactions monitored by resonance energy transfer. Borochov-Neori, H., Montal, M. Biochemistry (1989) [Pubmed]
  18. Dynamics of the thiol status of rat spermatozoa during maturation: analysis with the fluorescent labeling agent monobromobimane. Shalgi, R., Seligman, J., Kosower, N.S. Biol. Reprod. (1989) [Pubmed]
  19. Bromobimane crosslinking studies in oligomycin-sensitive ATPase from beef heart mitochondria. Mr 31 000 protein crosslinked. Zimmer, G., Mainka, L., Heil, B.M. FEBS Lett. (1982) [Pubmed]
  20. The evolution of glutathione metabolism in phototrophic microorganisms. Fahey, R.C., Buschbacher, R.M., Newton, G.L. J. Mol. Evol. (1987) [Pubmed]
  21. Combining fluorescence detection and mass spectrometric analysis for comprehensive and quantitative analysis of redox-sensitive cysteines in native membrane proteins. Petrotchenko, E.V., Pasek, D., Elms, P., Dokholyan, N.V., Meissner, G., Borchers, C.H. Anal. Chem. (2006) [Pubmed]
  22. New method for determining cystine in leukocytes and fibroblasts. de Graaf-Hess, A., Trijbels, F., Blom, H. Clin. Chem. (1999) [Pubmed]
  23. Selective inhibition of the mitochondrial permeability transition pore at the oxidation-reduction sensitive dithiol by monobromobimane. Costantini, P., Chernyak, B.V., Petronilli, V., Bernardi, P. FEBS Lett. (1995) [Pubmed]
  24. Thiol-specific probes indicate that the beta-chain of platelet glycoprotein Ib is a transmembrane protein with a reactive endofacial sulfhydryl group. Kalomiris, E.L., Coller, B.S. Biochemistry (1985) [Pubmed]
  25. Ferredoxin-thioredoxin reductase: a catalytically active dithiol group links photoreduced ferredoxin to thioredoxin functional in photosynthetic enzyme regulation. Droux, M., Miginiac-Maslow, M., Jacquot, J.P., Gadal, P., Crawford, N.A., Kosower, N.S., Buchanan, B.B. Arch. Biochem. Biophys. (1987) [Pubmed]
  26. Derivatization of phytochelatins from Silene vulgaris, induced upon exposure to arsenate and cadmium: comparison of derivatization with Ellman's reagent and monobromobimane. Sneller, F.E., van Heerwaarden, L.M., Koevoets, P.L., Vooijs, R., Schat, H., Verkleij, J.A. J. Agric. Food Chem. (2000) [Pubmed]
  27. Monobromobimane occupies a distinct xenobiotic substrate site in glutathione S-transferase pi. Ralat, L.A., Colman, R.F. Protein Sci. (2003) [Pubmed]
  28. Determination of thiol proteins using monobromobimane labeling and high-performance liquid chromatographic analysis: application to Escherichia coli thioredoxin. Chinn, P.C., Pigiet, V., Fahey, R.C. Anal. Biochem. (1986) [Pubmed]
  29. Fully automated assay for total homocysteine, cysteine, cysteinylglycine, glutathione, cysteamine, and 2-mercaptopropionylglycine in plasma and urine. Pastore, A., Massoud, R., Motti, C., Lo Russo, A., Fucci, G., Cortese, C., Federici, G. Clin. Chem. (1998) [Pubmed]
  30. Background-free, high sensitivity staining of proteins in one- and two-dimensional sodium dodecyl sulfate-polyacrylamide gels using a luminescent ruthenium complex. Berggren, K., Chernokalskaya, E., Steinberg, T.H., Kemper, C., Lopez, M.F., Diwu, Z., Haugland, R.P., Patton, W.F. Electrophoresis (2000) [Pubmed]
  31. Sperm analysis by flow cytometry using the fluorescent thiol labeling agent monobromobimane. Seligman, J., Shalgi, R., Oschry, Y., Kosower, N.S. Mol. Reprod. Dev. (1991) [Pubmed]
  32. Two-dimensional polyacrylamide gel electrophoresis of proteins labeled with the fluorophore monobromobimane prior to first-dimensional isoelectric focusing: imaging of the fluorescent protein spot patterns using a cooled charge-coupled device. Urwin, V.E., Jackson, P. Anal. Biochem. (1993) [Pubmed]
  33. Binding of radioprotective thiols and disulfides in Chinese hamster V79 cell nuclei. Newton, G.L., Aguilera, J.A., Ward, J.F., Fahey, R.C. Radiat. Res. (1996) [Pubmed]
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