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Chemical Compound Review

Chlorobimane     8-(chloromethyl)-2,3,7- trimethyl-1,5...

Synonyms: SureCN105811, AG-H-04956, C4528_SIGMA, CHEBI:52158, NSC-602733, ...
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Disease relevance of Monochlorobimane


High impact information on Monochlorobimane


Biological context of Monochlorobimane


Anatomical context of Monochlorobimane


Associations of Monochlorobimane with other chemical compounds


Gene context of Monochlorobimane

  • Analysis of the fate of monochlorobimane in MRP transfectants revealed reduced intracellular concentrations of drug-glutathione S-conjugates associated with enhanced efflux and altered intracellular distribution [20].
  • Four of the dyes require glutathione-S-transferase (GST) to form a fluorescent conjugate, potentially conferring specificity for GSH: these included t-butoxycarbonyl-Leu-Met-7-amino-4-chloromethylcoumarin (CMAC), 7-amino-4-chloromethylcoumarin (CMAC-blue), monochlorobimane (MCB), and 5-chloromethylfluorescein diacetate (CMFDA) [21].

Analytical, diagnostic and therapeutic context of Monochlorobimane

  • Second, we have directly measured cytoplasmic GSH concentration in intact cells by laser-scanning microscopy after labeling with monochlorobimane as a GSH-specific probe [22].
  • Subcellular compartmentation studies and liver perfusions were performed using monochlorobimane and bimane S-conjugates as model compounds [23].
  • One-half of each homogenate was assayed for GSH using a HPLC approach while the other half was assayed using the monochlorobimane approach [14].
  • The cardiomyocytes were isolated by standard procedures and loaded with either CellTracker Blue CMAC or monochlorobimane by 15 min of shaking incubation in the dark at room temperature followed by centrifugation with resuspension of the cells in dye-free media [24].


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  2. Cell proliferation and hair tip growth in the Arabidopsis root are under mechanistically different forms of redox control. Sánchez-Fernández, R., Fricker, M., Corben, L.B., White, N.S., Sheard, N., Leaver, C.J., Van Montagu M, n.u.l.l., Inzé, D., May, M.J. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  3. Two-photon imaging of glutathione levels in intact brain indicates enhanced redox buffering in developing neurons and cells at the cerebrospinal fluid and blood-brain interface. Sun, X., Shih, A.Y., Johannssen, H.C., Erb, H., Li, P., Murphy, T.H. J. Biol. Chem. (2006) [Pubmed]
  4. Acute glutathione depletion restricts mitochondrial ATP export in cerebellar granule neurons. Vesce, S., Jekabsons, M.B., Johnson-Cadwell, L.I., Nicholls, D.G. J. Biol. Chem. (2005) [Pubmed]
  5. GS-X pump is functionally overexpressed in cis-diamminedichloroplatinum (II)-resistant human leukemia HL-60 cells and down-regulated by cell differentiation. Ishikawa, T., Wright, C.D., Ishizuka, H. J. Biol. Chem. (1994) [Pubmed]
  6. Enhancement of glutathione content in glutathione synthetase-deficient fibroblasts from a patient with 5-oxoprolinuria via metabolic cooperation with normal fibroblasts. Kavanagh, T.J., Raghu, G., White, C.C., Martin, G.M., Rabinovitch, P.S., Eaton, D.L. Exp. Cell Res. (1994) [Pubmed]
  7. Kinetic analysis of glutathione in anchored cells with monochlorobimane. Barhoumi, R., Bailey, R.H., Burghardt, R.C. Cytometry. (1995) [Pubmed]
  8. The molecular mechanism in activation-induced cell death of an Ag-reactive B cell clone. Hamano, T., Iwasaki, T., Ogata, A., Hashimoto, N., Kakishita, E. Clin. Exp. Immunol. (2002) [Pubmed]
  9. Evidence of prooxidant and antioxidant action of melatonin on human liver cell line HepG2. Osseni, R.A., Rat, P., Bogdan, A., Warnet, J.M., Touitou, Y. Life Sci. (2000) [Pubmed]
  10. A combined in vitro/bioinformatic investigation of redox regulatory mechanisms governing cell cycle progression. Conour, J.E., Graham, W.V., Gaskins, H.R. Physiol. Genomics (2004) [Pubmed]
  11. Proliferative capacity of human peripheral blood lymphocytes sorted on the basis of glutathione content. Kavanagh, T.J., Grossmann, A., Jaecks, E.P., Jinneman, J.C., Eaton, D.L., Martin, G.M., Rabinovitch, P.S. J. Cell. Physiol. (1990) [Pubmed]
  12. Regulation of glutathione in cardiac myocytes. Li, S., Li, X., Rozanski, G.J. J. Mol. Cell. Cardiol. (2003) [Pubmed]
  13. Use of monochlorobimane for glutathione measurements in hamster and human tumor cell lines. Cook, J.A., Pass, H.I., Russo, A., Iype, S., Mitchell, J.B. Int. J. Radiat. Oncol. Biol. Phys. (1989) [Pubmed]
  14. Monochlorobimane fluorometric method to measure tissue glutathione. Kamencic, H., Lyon, A., Paterson, P.G., Juurlink, B.H. Anal. Biochem. (2000) [Pubmed]
  15. Transport of glutathione conjugates into secretory vesicles is mediated by the multidrug-resistance protein 1. Van Luyn, M.J., Müller, M., Renes, J., Meijer, C., Scheper, R.J., Nienhuis, E.F., Mulder, N.H., Jansen, P.L., De Vries, E.G. Int. J. Cancer (1998) [Pubmed]
  16. Heterogeneity of clara cell glutathione. A possible basis for differences in cellular responses to pulmonary cytotoxicants. West, J.A., Chichester, C.H., Buckpitt, A.R., Tyler, N.K., Brennan, P., Helton, C., Plopper, C.G. Am. J. Respir. Cell Mol. Biol. (2000) [Pubmed]
  17. Selective staining by vital dyes of Müller glial cells in retinal wholemounts. Uckermann, O., Iandiev, I., Francke, M., Franze, K., Grosche, J., Wolf, S., Kohen, L., Wiedemann, P., Reichenbach, A., Bringmann, A. Glia (2004) [Pubmed]
  18. Characterization and molecular cloning of a glutathione S-transferase from the whitefly Bemisia tabaci (Hemiptera: Aleyrodidae). Rauch, N., Nauen, R. Insect Biochem. Mol. Biol. (2004) [Pubmed]
  19. Fluorescence imaging study of organic anion transport from renal proximal tubule cell to lumen. Miller, D.S., Letcher, S., Barnes, D.M. Am. J. Physiol. (1996) [Pubmed]
  20. Cellular and in vitro transport of glutathione conjugates by MRP. Shen, H., Paul, S., Breuninger, L.M., Ciaccio, P.J., Laing, N.M., Helt, M., Tew, K.D., Kruh, G.D. Biochemistry (1996) [Pubmed]
  21. Evaluation of glutathione-sensitive fluorescent dyes in cortical culture. Tauskela, J.S., Hewitt, K., Kang, L.P., Comas, T., Gendron, T., Hakim, A., Hogan, M., Durkin, J., Morley, P. Glia (2000) [Pubmed]
  22. Glutathione biosynthesis in Arabidopsis trichome cells. Gutierrez-Alcala, G., Gotor, C., Meyer, A.J., Fricker, M., Vega, J.M., Romero, L.C. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  23. Hepatic mercapturic acid formation: involvement of cytosolic cysteinylglycine S-conjugate dipeptidase activity. Jösch, C., Sies, H., Akerboom, T.P. Biochem. Pharmacol. (1998) [Pubmed]
  24. A new method of quantifying glutathione levels in freshly isolated single superfused rat cardiomyocytes. King, N., Korolchuk, S., McGivan, J.D., Suleiman, M.S. Journal of pharmacological and toxicological methods. (2004) [Pubmed]
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