Disease relevance of CHLORACETAMIDE

• Chloracetamide: an unusual cause of cosmetic dermatitis [1].
• Resolution of 2,2,2-trifluoro-1-phenylethylamine was carried out with the Pseudomonas fluorescens lipase via enantioselective alcoholysis of its chloroacetamide [2].
• Airborne contact dermatitis due to chloroacetamide in wall paint [3].
• Occupational allergic contact dermatitis from chloracetamide in glue [4].
• Occupational dermatitis to chloroacetamide [5].

High impact information on CHLORACETAMIDE

• This inactivation was shown to occur at pH 7.5 and 22 degrees C, conditions under which chemically related alkylating reagents such as chloroacetamide and chloroacetic acid (which do not possess the amino acid side chain) fail to inactivate the enzyme [6].
• To test the hypothesis that increased expression of AtGSTU19 would be sufficient to provide tolerance to chloroacetamide herbicides, a chimeric gene was produced containing the open reading frame for this GST driven by a constitutive promoter [7].
• Plants containing this transgene had a modest increase in AtGSTU19 protein, predominantly in roots, but this had no effect on tolerance to chloroacetamide herbicides [7].
• Acylation of 2,2-diphenylethylamine with chloroacetyl chloride gives the chloroacetamide (2) [8].
• Corresponding mutants are not available for Antirrhinum majus, however, organ fusions can be induced in both species by chloroacetamide inhibitors of beta-ketoacyl-CoA synthases using a chemical genetics approach [9].

Chemical compound and disease context of CHLORACETAMIDE

• Isolation and characterization of a pseudomonas oleovorans degrading the chloroacetamide herbicide acetochlor [10].
• Allergic contact dermatitis to sodium benzoate chloroacetamide in a sorbolene lotion [11].

Biological context of CHLORACETAMIDE

• Chloroacetamide hepatotoxicity: hydropic degeneration and lipid peroxidation [12].
• These compounds are based on a minimal peptidic scaffold shown previously [Chem. Biol.2005, 12, 469-475] to confer affinity for the TGase active site and bear electrophilic groups such as alpha,beta-unsaturated amide, chloroacetamide or maleimide; their general structure being Cbz-Phe-spacer-electrophile [13].
• Acid- and base-catalyzed hydrolysis of chloroacetamide herbicides [14].
• In addition, activation of the reporter gene was observed in the presence of other compounds such as acetyl chloride, tetrachlorophenol, chloroacetamide and sodium arsenite [15].

Anatomical context of CHLORACETAMIDE

• Comparative metabolism of chloroacetamide herbicides and selected metabolites in human and rat liver microsomes [16].

Associations of CHLORACETAMIDE with other chemical compounds

• In the concentration studies, subjects known to be sensitive to the test substance were tested by the Al test with costus oil (three concentrations), chloracetamide (four concentrations), or thimerosal (three concentrations); petrolatum was used as the vehicle in each case [17].
• Covalent binding of chloroacetamide herbicides to the active site cysteine of plant type III polyketide synthases [18].
• The pK values and reactivities of the thiol groups which participate in the formation of interchain disulfide bonds in Bence Jones proteins and the Fab(t) fragment of a myeloma protein (Jo) (IgGl, kappa) were determined by means of the reactions with chloroacetamide and DTNB, and of spectrophotometric titration [19].

Gene context of CHLORACETAMIDE

• Microcide and Daiichi are collaborating on the discovery of new bacterial efflux pump inhibitorsfor the treatment of drug-resistant Pseudomonas aeruginosa and other bacterial infections [20].
• CAA-resistance depended upon the simultaneous expression of CAA-inducible amidase and dehalogenase activities [21].

Analytical, diagnostic and therapeutic context of CHLORACETAMIDE

• Irradiation of tetrameric concanavalin A with a high-pressure mercury lamp in the presence of chloroacetamide and fractionation of the reaction product by affinity chromatography gave a lectin derivative showing a monomeric molecular weight at pH 7.4, with an overall yield of 25% [22].

References