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Chemical Compound Review

Chloromethane     chloromethane

Synonyms: Artic, Clorometano, Methylchlorid, Methylchloride, Chlor-methan, ...
 
 
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Disease relevance of chloromethane

 

High impact information on chloromethane

  • Sequence analysis, mutant properties, and measurements of enzyme activity in cell-free extracts allowed the definition of a multistep pathway for the conversion of chloromethane to formate [1].
  • Finally, an octapeptidyl chloromethane derivative proved to be a potent irreversible inhibitor of either PC1 and ruin [6].
  • Soil bacteria are heavily exposed to environmental methylating agents such as methylchloride and may have special requirements for repair of alkylation damage on DNA [7].
  • We propose that the lower polarity of the chymotrypsin active site relative to that of the subtilisin active site explains why the oxyanion pKa is higher and more sensitive to the type of chloromethane inhibitor used in the chymotrypsin derivatives than in the subtilisin derivatives [8].
  • Thrombomodulin increased the rate of inactivation of thrombin by two peptidyl chloromethane inhibitors by a similar amount [9].
 

Chemical compound and disease context of chloromethane

 

Biological context of chloromethane

  • The kinetics for the inactivation of thrombin (EC 3.4.21.5) by a series of peptides containing C-terminal arginyl chloromethane in the presence of substrate were determined [11].
  • (2) A 2-3 fold increase in the binding constant (KI) of a tripeptidyl chloromethane inhibitor was observed, but the inactivation rate constant (k i) was the same, which indicated that the nucleophilicity of the active-site histidyl residue had not changed [12].
  • The chloromethane-utilizing methylation system is absent in early growth but attains peak activity in the mid-growth phase after 72 h of incubation [13].
  • Chloromethane utilization gene cluster from Hyphomicrobium chloromethanicum strain CM2(T) and development of functional gene probes to detect halomethane-degrading bacteria [3].
  • For comparison, the amination of chloromethane by lithium dimethylamide and the reduction by borane, diborane, and borohydride ions were also examined [14].
 

Anatomical context of chloromethane

  • Previous studies from this laboratory described the kinetic characteristics of the inhibition by tosylphenylalanine chloromethane (TosPheCH2Cl) on superoxide anion production by human neutrophils (PMN) stimulated with a phorbol ester (PMA) [15].
  • We have radiolabeled the membranes of cells inactivated before or after phorbol ester stimulation, using either [3H]KBH4 reduction after reaction with unlabeled inactivator, or tritiated tosylphenylalanyl chloromethane [16].
  • All-trans-retinoyl chloromethane is a potent irreversible inactivator of bovine opsin in retinal rod outer segments [17].
  • The purpose of this study was to measure the distribution of a radiolabeled drug [3H]bicuculline methylchloride ([3H]BMC) following microinjection into the supraoptic nuclei (SON) and the dorsal hypothalamus of conscious rats [18].
  • 3. In liver microsomes from both sexes of mouse, the rates of oxidation of chloromethane and chlorzoxazone were two-fold higher than in kidney microsomes from the male, however, no sex differences in the rates of oxidation were observed [19].
 

Associations of chloromethane with other chemical compounds

 

Gene context of chloromethane

  • In order to identify physiological activators of proteinase-activated receptor-2 (PAR-2), a peptide chloromethane inhibitor (biotinyl-Ser-Lys-Gly-Arg-CH2Cl) based on the cleavage site for activation of PAR-2 was synthesised and tested with 12 trypsin-like serine proteinases [22].
  • Affinity labeling of bovine opsin by trans-retinoyl chloromethane [17].
  • Tosyl-lysyl chloromethane alters glucocorticoid-receptor complex nuclear binding and physical properties [20].
  • The major proteinase has pH optimum 8, a Ca2+-dependence maximum of 1 mM, and was inhibited by serine-proteinase inhibitors, especially tetrapeptidyl chloromethane derivatives with hydrophobic residues at the P-1 site [23].
  • Modification of B. subtilis EF-Tu by N-tosyl-L-phenylalanyl chloromethane destroyed its ability to promote protein synthesis and resulted in selective dissociation of the two binding activities of the protein for aminoacyl-tRNA [4].
 

Analytical, diagnostic and therapeutic context of chloromethane

  • PCR primers were developed for successful amplification of cmuA genes from newly isolated chloromethane utilizers and enrichment cultures [3].
  • The slope of toxicodynamics curves for depressed ChE increased about 3 times after treatment with Nef 7.5 mg/kg and pyratoxime methylchloride (2-PAM Cl) 50 mg/kg, compared with the untreated group, there was a higher significant difference (P<0.01) [24].

References

  1. A corrinoid-dependent catabolic pathway for growth of a Methylobacterium strain with chloromethane. Vannelli, T., Messmer, M., Studer, A., Vuilleumier, S., Leisinger, T. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  2. Chloromethane-dependent expression of the cmu gene cluster of Hyphomicrobium chloromethanicum. Borodina, E., McDonald, I.R., Murrell, J.C. Appl. Environ. Microbiol. (2004) [Pubmed]
  3. Chloromethane utilization gene cluster from Hyphomicrobium chloromethanicum strain CM2(T) and development of functional gene probes to detect halomethane-degrading bacteria. McAnulla, C., Woodall, C.A., McDonald, I.R., Studer, A., Vuilleumier, S., Leisinger, T., Murrell, J.C. Appl. Environ. Microbiol. (2001) [Pubmed]
  4. Modification of Bacillus subtilis elongation factor Tu by N-tosyl-L-phenylalanyl chloromethane abolishes its ability to interact with the 3'-terminal polynucleotide structure but not with the acyl bond in aminoacyl-tRNA. Jonák, J., Karas, K. FEBS Lett. (1989) [Pubmed]
  5. Site-directed mutagenesis of elongation factor Tu. The functional and structural role of residue Cys81. Anborgh, P.H., Parmeggiani, A., Jonák, J. Eur. J. Biochem. (1992) [Pubmed]
  6. Fluorescent peptidyl substrates as an aid in studying the substrate specificity of human prohormone convertase PC1 and human furin and designing a potent irreversible inhibitor. Jean, F., Boudreault, A., Basak, A., Seidah, N.G., Lazure, C. J. Biol. Chem. (1995) [Pubmed]
  7. A new protein superfamily includes two novel 3-methyladenine DNA glycosylases from Bacillus cereus, AlkC and AlkD. Alseth, I., Rognes, T., Lindbäck, T., Solberg, I., Robertsen, K., Kristiansen, K.I., Mainieri, D., Lillehagen, L., Kolstø, A.B., Bjørås, M. Mol. Microbiol. (2006) [Pubmed]
  8. 13C NMR study of how the oxyanion pKa values of subtilisin and chymotrypsin tetrahedral adducts are affected by different amino acid residues binding in enzyme subsites S1-S4. O'Sullivan, D.B., O'Connell, T.P., Mahon, M.M., Koenig, A., Milne, J.J., Fitzpatrick, T.B., Malthouse, J.P. Biochemistry (1999) [Pubmed]
  9. Effect of thrombomodulin on the kinetics of the interaction of thrombin with substrates and inhibitors. Hofsteenge, J., Taguchi, H., Stone, S.R. Biochem. J. (1986) [Pubmed]
  10. Chloromethane-induced genes define a third C1 utilization pathway in Methylobacterium chloromethanicum CM4. Studer, A., McAnulla, C., Büchele, R., Leisinger, T., Vuilleumier, S. J. Bacteriol. (2002) [Pubmed]
  11. Evaluation of inhibitor constants and alkylation rates for a series of thrombin affinity labels. Walker, B., Wikstrom, P., Shaw, E. Biochem. J. (1985) [Pubmed]
  12. Enzymatic properties of proteolytic derivatives of human alpha-thrombin. Hofsteenge, J., Braun, P.J., Stone, S.R. Biochemistry (1988) [Pubmed]
  13. Evidence for the existence of independent chloromethane- and S-adenosylmethionine-utilizing systems for methylation in Phanerochaete chrysosporium. Coulter, C., Hamilton, J.T., Harper, D.B. Appl. Environ. Microbiol. (1993) [Pubmed]
  14. Gas-phase reactions of lithium dimethylaminoborohydride and related species. Pratt, L.M., Nguyên, N.V. J. Org. Chem. (2005) [Pubmed]
  15. Aminoacyl chloromethanes as tools to study the requirements of NADPH oxidase activation in human neutrophils. Chollet-Przednowed, E., Lederer, F. Eur. J. Biochem. (1993) [Pubmed]
  16. Inhibition by aminoacyl-chloromethane protease inhibitors of superoxide anion production by phorbol-ester-stimulated human neutrophils. The labeled target is a membrane protein. Conseiller, E.C., Schott, D., Lederer, F. Eur. J. Biochem. (1990) [Pubmed]
  17. Affinity labeling of bovine opsin by trans-retinoyl chloromethane. Vaz, A.D., Schoellmann, G. Biochem. Biophys. Res. Commun. (1989) [Pubmed]
  18. Measurement of the distribution of [3H]bicuculline microinjected into the rat hypothalamus. Segura, T., Martin, D.S., Sheridan, P.J., Haywood, J.R. J. Neurosci. Methods (1992) [Pubmed]
  19. Sex, organ and species specific bioactivation of chloromethane by cytochrome P4502E1. Dekant, W., Frischmann, C., Speerschneider, P. Xenobiotica (1995) [Pubmed]
  20. Tosyl-lysyl chloromethane alters glucocorticoid-receptor complex nuclear binding and physical properties. Hubbard, J.R., Barrett, A.J., Kalimi, M. Endocrinology (1984) [Pubmed]
  21. Chloromethane: tetrahydrofolate methyl transfer by two proteins from Methylobacterium chloromethanicum strain CM4. Studer, A., Stupperich, E., Vuilleumier, S., Leisinger, T. Eur. J. Biochem. (2001) [Pubmed]
  22. Identification of potential activators of proteinase-activated receptor-2. Fox, M.T., Harriott, P., Walker, B., Stone, S.R. FEBS Lett. (1997) [Pubmed]
  23. Purification and characterization of major extracellular proteinases from Trichophyton rubrum. Asahi, M., Lindquist, R., Fukuyama, K., Apodaca, G., Epstein, W.L., McKerrow, J.H. Biochem. J. (1985) [Pubmed]
  24. Effect of neferine on toxicodynamics of dichlorvos for inhibiting rabbit cholinesterase. Xiong, Y.Q., Zeng, F.D. Acta Pharmacol. Sin. (2003) [Pubmed]
 
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