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Chemical Compound Review

BROMOPHENOL     2-bromophenol

Synonyms: o-Bromophenol, o-bromo-phenol, PubChem3841, SureCN49313, CHEMBL186007, ...
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Disease relevance of 2BR

  • In this work, we demonstrate that the substitution of Coomassie Brilliant Blue for bromophenol blue in two-dimensional electrophoresis (2-DE) buffers improves the focusing of whole proteins from Pseudomonas aeruginosa [1].
  • Reductively debrominating strains of Propionigenium maris from burrows of bromophenol-producing marine infauna [2].
  • Rhodococcus sp. RB1 nitrate reductase had an apparent molecular mass of 142 kDa and used NADH and reduced bromophenol blue or viologens as electron donors, independently of the presence of salt [3].
  • Complex formation between Chromatium vinosum ferric cytochrome c' and bromophenol blue [4].
  • Investigations of immunoblots using Borrelia burgdorferi antigen demonstrated that a band, migrating faster than the bromophenol blue front in sodium dodecyl sulfate-gel electrophoresis, reacted strongly with sera containing anti-Borrelia burgdorferi antibodies preferentially of the IgG class [5].

High impact information on 2BR

  • The formation of 2-bromophenol and bromobenzene-2,3-dihydrodiol was increased more than 10-fold in incubations of hepatocytes from beta-naphthoflavone-treated rats, as compared to those of hepatocytes from untreated rats, but recovery of 4-bromocatechol was unchanged [6].
  • 6. Neither NADH nor NADPH was effective as an electron donor, but reduced Methyl Viologen (apparent Km 998 microM) and reduced Bromophenol Blue (apparent Km 158 microM) were effective [7].
  • The pH dependence of binding of bromophenol blue and of bromocresol purple, which has a higher pKa than bromophenol blue, indicated that binding was dependent on protonation of a protein residue with a pKa of 2 [8].
  • Titration of bound bromophenol blue indicated that the deprotonated dye was bound to the strong site with approximately 20-fold greater affinity than the protonated dye [8].
  • This method was also used to isolate a form of enterotoxin that has a mobility, relative to bromophenol blue tracking dye, of 0.87 to 0.90 in 7% acrylamide gels [9].

Chemical compound and disease context of 2BR

  • The interactions of catechol (substrate), 2-hydroxy-pyridine-N-oxide (substrate analogue), and 2-bromophenol (inhibitor) with the extradiol cleaving catechol-2,3-dioxygenase from Pseudomonas putida mt-2 have been monitored through X-ray absorption spectroscopy (XAS) [10].

Biological context of 2BR


Anatomical context of 2BR


Associations of 2BR with other chemical compounds


Gene context of 2BR

  • Bromophenol red as a probe of lysozyme-active site environment: a temperature-jump study [23].
  • Two-way ANOVA showed that only the 30% S. siliquastrum-containing feed significantly (p < 0.05) increased the total bromophenol content in the fish flesh with time [24].
  • The isolated proteins (PAP I-a, PAP I-b and PAP II) were homogeneous in various methods including 7.5% and 20% gel electrophoresis or gel chromatography, and share, in the extract, 85% of the total of the acidic proteins that migrate with the bromophenol blue marker in 7.5% gels [25].

Analytical, diagnostic and therapeutic context of 2BR


  1. Substituting Coomassie Brilliant Blue for bromophenol blue in two-dimensional electrophoresis buffers improves the resolution of focusing patterns. Vilain, S., Cosette, P., Charlionet, R., Hubert, M., Lange, C., Junter, G.A., Jouenne, T. Electrophoresis (2001) [Pubmed]
  2. Reductively debrominating strains of Propionigenium maris from burrows of bromophenol-producing marine infauna. Watson, J., Matsui, G.Y., Leaphart, A., Wiegel, J., Rainey, F.A., Lovell, C.R. Int. J. Syst. Evol. Microbiol. (2000) [Pubmed]
  3. Rhodococcus sp. RB1 grows in the presence of high nitrate and nitrite concentrations and assimilates nitrate in moderately saline environments. Blasco, R., Martínez-Luque, M., Madrid, M.P., Castillo, F., Moreno-Vivián, C. Arch. Microbiol. (2001) [Pubmed]
  4. Complex formation between Chromatium vinosum ferric cytochrome c' and bromophenol blue. Mayburd, A.L., Tan, Y., Kassner, R.J. Arch. Biochem. Biophys. (2000) [Pubmed]
  5. Identification of an immunoreactive non-proteinaleous component in Borrelia burgdorferi. Eiffert, H., Lotter, H., Jarecki-Khan, K., Thomssen, R. Med. Microbiol. Immunol. (Berl.) (1991) [Pubmed]
  6. Bromobenzene metabolism in isolated rat hepatocytes. 18O2 incorporation studies. Dankovic, D., Billings, R.E., Seifert, W., Stillwell, W.G. Mol. Pharmacol. (1985) [Pubmed]
  7. Purification and characterization of the assimilatory nitrate reductase of Azotobacter vinelandii. Gangeswaran, R., Lowe, D.J., Eady, R.R. Biochem. J. (1993) [Pubmed]
  8. Interaction of bromophenol blue and related dyes with bovine neurophysin-I: use as a probe of neurophysin chemistry. Carlson, J.D., Breslow, E. Biochemistry (1981) [Pubmed]
  9. Preparative polyacrylamide gel electrophoresis purification of Clostridium perfringens enterotoxin. Enders, G.L., Duncan, C.L. Infect. Immun. (1977) [Pubmed]
  10. Substrate, substrate analogue, and inhibitor interactions with the ferrous active site of catechol 2,3-dioxygenase monitored through XAS studies. Bertini, I., Briganti, F., Mangani, S., Nolting, H.F., Scozzafava, A. FEBS Lett. (1994) [Pubmed]
  11. A kinetic study of protein-protein interactions. Koren, R., Hammes, G.G. Biochemistry (1976) [Pubmed]
  12. Detection and characterization of a dehalogenating microorganism by terminal restriction fragment length polymorphism fingerprinting of 16S rRNA in a sulfidogenic, 2-bromophenol-utilizing enrichment. Fennell, D.E., Rhee, S.K., Ahn, Y.B., Häggblom, M.M., Kerkhof, L.J. Appl. Environ. Microbiol. (2004) [Pubmed]
  13. Dose-dependent pharmacokinetics and hepatobiliary transport of bromophenol blue in the beagle. Wills, R.J., Yakatan, G.J., Pearlman, R.S. Journal of pharmaceutical sciences. (1984) [Pubmed]
  14. Additional binding sites in lysozyme. X-ray analysis of lysozyme complexes with bromophenol red and bromophenol blue. Madhusudan, n.u.l.l., Vijayan, M. Protein Eng. (1992) [Pubmed]
  15. Kinetics and thermodynamics of bromophenol blue adsorption by a mesoporous hybrid gel derived from tetraethoxysilane and bis(trimethoxysilyl)hexane. You, L., Wu, Z., Kim, T., Lee, K. Journal of colloid and interface science. (2006) [Pubmed]
  16. Identification of 2-bromohydroquinone as a metabolite of bromobenzene and o-bromophenol: implications for bromobenzene-induced nephrotoxicity. Lau, S.S., Monks, T.J., Gillette, J.R. J. Pharmacol. Exp. Ther. (1984) [Pubmed]
  17. Glutathione conjugates of 2-bromohydroquinone are nephrotoxic. Monks, T.J., Lau, S.S., Highet, R.J., Gillette, J.R. Drug Metab. Dispos. (1985) [Pubmed]
  18. Androgen-binding proteins from human hyperplastic prostate as evaluated by electrophoresis. Barahona, E., Licea, H., Torres, F., Sierra, J., Ortiz, S., Bermúdez, J.A. Arch. Androl. (1986) [Pubmed]
  19. Histomorphological and histochemical characteristics of the intestine of the Senegal sole, Solea senegalensis. Arellano, J., Dinis, M.T., Sarasquete, C. European journal of histochemistry : EJH. (1999) [Pubmed]
  20. Effect of indomethacin (a prostaglandin synthetase inhibitor) on the permeability of blood-brain and blood-CSF barriers in rat. Dey, P.K., Sharma, H.S., Rao, K.S. Indian J. Physiol. Pharmacol. (1980) [Pubmed]
  21. Acid-base characteristics of bromophenol blue-citrate buffer systems in the amorphous state. Li, J., Chatterjee, K., Medek, A., Shalaev, E., Zografi, G. Journal of pharmaceutical sciences. (2004) [Pubmed]
  22. Impact of freeze-drying on ionization of sulfonephthalein probe molecules in trehalose-citrate systems. Govindarajan, R., Chatterjee, K., Gatlin, L., Suryanarayanan, R., Shalaev, E.Y. Journal of pharmaceutical sciences. (2006) [Pubmed]
  23. Bromophenol red as a probe of lysozyme-active site environment: a temperature-jump study. Krishnamoorthy, G., Prabhananda, B.S., Gurnani, S. Biopolymers (1979) [Pubmed]
  24. Enhancement of bromophenol levels in aquacultured silver seabream (Sparus sarba). Ma, W.C., Chung, H.Y., Ang, P.O., Kim, J.S. J. Agric. Food Chem. (2005) [Pubmed]
  25. Reinvestigation of extremely acidic proteins in bovine brain. Isobe, T., Nakajima, T., Okuyama, T. Biochim. Biophys. Acta (1977) [Pubmed]
  26. Ligand-apomyoglobin interactions. Configurational adaptability of the haem-binding site. Lind, K.E., Moller, J.V. Biochem. J. (1976) [Pubmed]
  27. Procedures and computer program for deriving the Ferguson plot from electrophoresis in a single pore gradient gel: application to agarose gel and a polystyrene particle. Tietz, D., Gombocz, E., Chrambach, A. Electrophoresis (1991) [Pubmed]
  28. Multiple forms of growth inhibitors secreted from cultured rat liver cells: purification and characterization. Mashima, K., Kimura, T., Huang, W., Yano, K., Ashida, Y., Yamagata, Y., Miyazaki, K., Yamashita, J., Horio, T. J. Biochem. (1988) [Pubmed]
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