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Chemical Compound Review

Microcide     2-chloroethanamide

Synonyms: Chloracetamid, CHLORACETAMIDE, sJYHCaDIKTp@, Mergal AF, C0267_ALDRICH, ...
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Disease relevance of CHLORACETAMIDE


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


Biological context of CHLORACETAMIDE


Anatomical context of CHLORACETAMIDE


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


Analytical, diagnostic and therapeutic context of CHLORACETAMIDE


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  2. Convenient synthesis of optically active 2,2,2-trifluoro-1-phenylethylamine. Kato, K., Gong, Y., Saito, T., Kimoto, H. Enantiomer. (2000) [Pubmed]
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  6. Affinity labeling of the catalytic subunit of cyclic AMP-dependent protein kinase by N alpha-tosyl-L-lysine chloromethyl ketone. Kupfer, A., Gani, V., Jiménez, J.S., Shaltiel, S. Proc. Natl. Acad. Sci. U.S.A. (1979) [Pubmed]
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  9. Functional conservation and maintenance of expression pattern of FIDDLEHEAD-like genes in Arabidopsis and Antirrhinum. Efremova, N., Schreiber, L., Bär, S., Heidmann, I., Huijser, P., Wellesen, K., Schwarz-Sommer, Z., Saedler, H., Yephremov, A. Plant Mol. Biol. (2004) [Pubmed]
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  11. Allergic contact dermatitis to sodium benzoate chloroacetamide in a sorbolene lotion. Sutton, T., Nixon, R. Australas. J. Dermatol. (2006) [Pubmed]
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  13. Synthesis and evaluation of peptidic irreversible inhibitors of tissue transglutaminase. Pardin, C., Gillet, S.M., Keillor, J.W. Bioorg. Med. Chem. (2006) [Pubmed]
  14. Acid- and base-catalyzed hydrolysis of chloroacetamide herbicides. Carlson, D.L., Than, K.D., Roberts, A.L. J. Agric. Food Chem. (2006) [Pubmed]
  15. A transformed fish cell line expressing a green fluorescent protein-luciferase fusion gene responding to cellular stress. Molina, A., Carpeaux, R., Martial, J.A., Muller, M. Toxicology in vitro : an international journal published in association with BIBRA. (2002) [Pubmed]
  16. Comparative metabolism of chloroacetamide herbicides and selected metabolites in human and rat liver microsomes. Coleman, S., Linderman, R., Hodgson, E., Rose, R.L. Environ. Health Perspect. (2000) [Pubmed]
  17. Effects of vehicles and elicitation concentration in contact dermatitis testing. I. Experimental contact sensitization in humans. Marzulli, F.N., Maibach, H.I. Contact Derm. (1976) [Pubmed]
  18. Covalent binding of chloroacetamide herbicides to the active site cysteine of plant type III polyketide synthases. Eckermann, C., Matthes, B., Nimtz, M., Reiser, V., Lederer, B., Böger, P., Schröder, J. Phytochemistry (2003) [Pubmed]
  19. Ionization and reactivities of the thiol groups which participate in the formation of interchain disulfide bonds of Bence Jones proteins and an Fab(t) fragment. Tanaka, Y., Azuma, T., Hamaguchi, K. J. Biochem. (1978) [Pubmed]
  20. MC-207110 Daiichi Seiyaku/Microcide Pharmaceuticals. Barrett, J.F. Current opinion in investigational drugs (London, England : 2000) (2001) [Pubmed]
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  22. Monovalent monomer derivative of concanavalin A produced by photochemically induced alkylation. Tanaka, I., Abe, Y., Hamada, T., Yonemitsu, O., Ishii, S. J. Biochem. (1981) [Pubmed]
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