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Chemical Compound Review:

Bromoethanol 2-bromoethanol

Synonyms: AGN-PC-0DA0JR, CHEMBL468583, NSC-2869, CCRIS 3862, B65586_ALDRICH, ...

Khan, S. et al., Fries, R.W. et al., Dahmén, J. et al., Yonath, A. et al., Van der Ploeg, J.R. et al., et al.

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Disease relevance of 4-01-00-01385 (Beilstein Handbook Reference)

Lipid peroxidation increased steadily 1 hr after 2-bromoethanol addition and antioxidants, iron chelators or hypoxia prevented 2-bromoethanol induced lipid peroxidation and cell lysis [1].

High impact information on 4-01-00-01385 (Beilstein Handbook Reference)

At pH 5 in the presence of bromide, 2-bromoethanol is a major product and deuterium labeling shows that the hydroxyl is predominantly on the carbon which bore the chlorine in BCNU [2].
Some of these, including bromoethanol and sodium dodecyl sulfate, had little effect on the crystals below critical concentrations at which there was a sharp volume increase and loss of x-ray pattern, which could, however, be regenerated to about 3.2-A resolution [3].
Inhibition of methylreductase by BES and 3-bromopropionate was competitive with methylcoenzyme M, but inhibition by 2-bromoethanol exhibited mixed kinetics [4].
SDS-PAGE, however, showed that this enzyme amounted to more than 50% of the total cellular protein in extracts of the mutant from 2-bromoethanol-grown cells, which was fourfold higher than in extracts of the wild-type strain grown on 2-chloroethanol [5].
Yeast alcohol dehydrogenase was inactivated by the bromohexyl analog by an active-site-directed mechanism, with a Ki = 1.5 mM and a pseudo-bimolecular rate constant of 0.03 M-1 S-1, which is 150 times larger than the bimolecular rate constant for inactivation by 2-bromoethanol [6].

Biological context of 4-01-00-01385 (Beilstein Handbook Reference)

Enzymic hydrolysis of pullulan, followed by acetylation and chromatography, gave acetylated alpha-D-Glcp-(1----6)-alpha-D-Glcp-(1----4)-alpha-D-Glcp-(1----4)-D-Glcp which, with 2-bromoethanol and boron trifluoride etherate in dichloromethane, gave the 2-bromoethyl glycoside [7].
However, cytochrome P4502E1 (CYP2E1) inhibitors/substrates were more effective at preventing 2-bromoethanol-induced GSH depletion, lipid peroxidation and cytotoxicity suggesting that 2-bromoethanol is mostly metabolically activated by CYP2E1 [1].
The latter was used for glycosylation of 2-bromoethanol [8].

Anatomical context of 4-01-00-01385 (Beilstein Handbook Reference)

The involvement of cytochrome P4502E1 in 2-bromoethanol-induced hepatocyte cytotoxicity [1].

Associations of 4-01-00-01385 (Beilstein Handbook Reference) with other chemical compounds

This suggests that 2-bromoethanol is preferably metabolised by CYP2E1 dependent monoxygenase to form 2-bromoacetaldehyde which causes cell lysis as a result of GSH depletion and lipid peroxidation [1].
Also, hepatocytes isolated from CYP2E1 induced rats were more susceptible to 2-bromoethanol and hepatocytes isolated from rats pretreated with carbon disulfide to inactivate CYP2E1 were more resistant to 2-bromoethanol treatment [1].

Gene context of 4-01-00-01385 (Beilstein Handbook Reference)

Structural analysis of denaturant-protein interactions: comparison between the effects of bromoethanol and SDS on denaturation and renaturation of triclinic lysozyme [9].

References

The involvement of cytochrome P4502E1 in 2-bromoethanol-induced hepatocyte cytotoxicity. Khan, S., Sood, C., O'Brien, P.J. Pharmacol. Toxicol. (1996) [Pubmed]
Chemistry of nitrosoureas. Intermediacy of 4,5-dihydro-1,2,3-oxadiazole in 1,3-bis(2-chloroethyl)-1-nitrosourea decomposition. Brundrett, R.B. J. Med. Chem. (1980) [Pubmed]
Crystallographic studies of protein denaturation and renaturation. 1. Effects of denaturants on volume and X-ray pattern of cross-linked triclinic lysozyme crystals. Yonath, A., Sielecki, A., Moult, J., Podjarny, A., Traub, W. Biochemistry (1977) [Pubmed]
Reversal of 2-bromoethanesulfonate inhibition of methanogenesis in Methanosarcina sp. Smith, M.R. J. Bacteriol. (1983) [Pubmed]
Adaptation of Pseudomonas sp. GJ1 to 2-bromoethanol caused by overexpression of an NAD-dependent aldehyde dehydrogenase with low affinity for halogenated aldehydes. Van der Ploeg, J.R., Kingma, J., De Vries, E.J., Van der Ven, J.G., Janssen, D.B. Arch. Microbiol. (1996) [Pubmed]
omega-haloalkyl esters of 5'-adenosine monophosphate as potential active-site-directed reagents for dehydrogenases. Fries, R.W., Bohlken, D.P., Murch, B.P., Leidal, K.G., Plapp, B.V. Arch. Biochem. Biophys. (1983) [Pubmed]
Synthesis from pullulan of spacer-arm, lipid, and ethyl glycosides of a tetrasaccharide [alpha-D-Glc-(1----6)-alpha-D-Glc-(1----4)-alpha-D-Glc-(1----4)-D-Glc] found in human urine; preparation of neoglycoproteins. Dahmén, J., Frejd, T., Magnusson, G., Noori, G., Carlström, A.S. Carbohydr. Res. (1984) [Pubmed]
2-(Trimethylsilyl)ethyl glycosides. Synthesis of the asialo-GM1-tetrasaccharide, spacer glycoside, and BSA and Sepharose glycoconjugates. Ray, A.K., Magnusson, G. Acta Chem. Scand. (1992) [Pubmed]
Structural analysis of denaturant-protein interactions: comparison between the effects of bromoethanol and SDS on denaturation and renaturation of triclinic lysozyme. Yonath, A., Podjarny, A., Honig, B., Traub, W., Sielecki, A., Herzberg, O., Moult, J. Biophys. Struct. Mech. (1977) [Pubmed]

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