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Chemical Compound Review

Ethrisin     N-ethanoyl-2-hydroxy-benzamide

Synonyms: Nacemide, Rixamone, Arthrisin, Labazyl, Salicyl, ...
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Disease relevance of Labazyl


High impact information on Labazyl

  • When the infected mammalian host of Trypanosoma brucei brucei is injected with a solution of the iron chelator salicyl hydroxamic acid and glycerol, the aerobic and anaerobic glucose catabolism of the parasite is blocked and the parasite is rapidly destroyed [2].
  • The brominated salicyl esters also exhibit enhanced permeation of the membrane, as well as increased activity due to activation at the acyl site [3].
  • The ArCP can be posttranslationally phosphopantetheinylated on Ser52 and then loaded with a salicyl group on the phosphopantetheine (Ppant) thiol by action of the YbtE, a salicyl-AMP ligase [4].
  • Detection of the heterocyclization capacity of HMWP2 1-1491 implies salicyl-transferring and thiazoline-forming activity for the HMWP2 condensation domain (residues 101-544) and is the first demonstration of such heterocyclization ability in a nonribosomal peptide synthetase enzyme [5].
  • The salicyl group figures prominently in several potent protein-tyrosine kinase (PTK) inhibitors, including the fermentation product lavendustin A (3), the salicylsulfonyl nitrostyryl 30, and our recently reported salicyl-containing stilbene 7 [6].

Biological context of Labazyl

  • Most of them are pleiotropic and defective in one or more of the following phenotypes: cytochrome aa3, b, and c (individual or multiple defects); oligomycin inhibition of ATPase activity; respiration and its inhibition by KCN and salicyl hydroxamic acid; and growth rates in liquid and solid media at 25 degrees and 38 degrees [7].
  • 5. These results support the hypothesis that two effects are involved in the synergy between aminoglycosides and salicylate: a weak acid effect, possibly to increase the membrane potential, and an uncharacterized effect related to the salicyl structure [8].
  • Distribution of the acetyl compared with the salicyl moiety of acetylsalicylic acid. Acetylation of macromolecules in organs wherein side-effects are manifest [9].
  • Serum-independent binding and ingestion of promastigotes, which are good activators of the alternative complement pathway, is also inhibited by the anti-CR3 monoclonal antibody M1/70, by Fab anti-C3, and by an inhibitor of C3 fixation, sodium salicyl hydroxamate [10].
  • The method is based on alkaline hydrolysis of daminozide to N',N'-dimethylhydrazine (UDMH), which is recovered by distillation and subsequently derivatizated with salicyl aldehyde to salicyl aldehyde-N,N-dimethylhydrazone under strongly basic conditions [11].

Anatomical context of Labazyl

  • These isolates were slow growers (sg) regardless of temperature of incubation and their response to the respiratory inhibitors antimycin and salicyl hydroxamic acid suggested a defect in mitochondrial ribosome assembly and deficiencies in cytochromes not unlike those observed in the poky mutants of Neurospora [12].

Associations of Labazyl with other chemical compounds

  • Inhibition of in vitro lymphoproliferation by three novel iron chelators of the pyridoxal and salicyl aldehyde hydrazone classes [13].
  • These were subsequently treated with hydrazine hydrate, hydroxylamine or subjected to alkaline hydrolysis to yield new o-hydroxyaryl or salicyl containing derivatives [14].
  • The data suggest that salicyl alcohol oxidase, essential for the activation of the plant-derived precursor salicin, was originally recruited from an oxidase involved in the autogenous biosynthesis of iridoid monoterpenes and found in related chrysomelid leaf beetle species [15].

Gene context of Labazyl

  • Diaryl-substituted salicyl- and anthranyl-ketoximes as potential estrogen receptor ligands [16].
  • In the present case, however, the resulting salicyl-containing bicyclics exhibited extremely poor inhibitory potency when examined against autophosphorylation of immunoprecipitated p56lck PTK preparations [6].
  • In a survey of structure-activity effects testing 30 drugs at a fixed dose (50 microM) in six test systems, it was established that only two aromatic rings are needed and that optimal PGDH inhibition requires -CH2COOH and -OH at positions 1 and 2 in the salicyl C ring system [17].
  • There was no significant effect of salicyl hydroxamate (a blocker of the alternative oxidase), showing that the mitochondrial electron transfer chain seems to play a minor role as already indicated by the superposition of chlorophyll and DCF fluorescence [18].

Analytical, diagnostic and therapeutic context of Labazyl

  • Indeed, the pharmacological activity was highly significant and directly related to the tissue concentration of salicyl ions, which was higher after local application of the solution than after oral administration of ASA [19].


  1. Renal effects of antipyretic analgesics. Nanra, R.S. Am. J. Med. (1983) [Pubmed]
  2. Trypanosomiasis: an approach to chemotherapy by the inhibition of carbohydrate catabolism. Clarkson, A.B., Brohn, F.H. Science (1976) [Pubmed]
  3. Modification of hemoglobin with analogs of aspirin. Zaugg, R.H., Walder, J.A., Walder, R.Y., Steele, J.M., Klotz, I.M. J. Biol. Chem. (1980) [Pubmed]
  4. Tandem heterocyclization activity of the multidomain 230 kDa HMWP2 subunit of Yersinia pestis yersiniabactin synthetase: interaction of the 1-1382 and 1383-2035 fragments. Suo, Z., Walsh, C.T., Miller, D.A. Biochemistry (1999) [Pubmed]
  5. The nonribosomal peptide synthetase HMWP2 forms a thiazoline ring during biogenesis of yersiniabactin, an iron-chelating virulence factor of Yersinia pestis. Gehring, A.M., Mori, I., Perry, R.D., Walsh, C.T. Biochemistry (1998) [Pubmed]
  6. Hydroxylated 2-(5'-salicyl)naphthalenes as protein-tyrosine kinase inhibitors. Smyth, M.S., Stefanova, I., Horak, I.D., Burke, T.R. J. Med. Chem. (1993) [Pubmed]
  7. Isolation and characterization of temperature-sensitive respiratory mutants of Neurospora crassa. Pittenger, T.H., West, D.J. Genetics (1979) [Pubmed]
  8. Potentiation of susceptibility to aminoglycosides by salicylate in Escherichia coli. Aumercier, M., Murray, D.M., Rosner, J.L. Antimicrob. Agents Chemother. (1990) [Pubmed]
  9. Distribution of the acetyl compared with the salicyl moiety of acetylsalicylic acid. Acetylation of macromolecules in organs wherein side-effects are manifest. Rainsford, K.D., Schweitzer, A., Brune, K. Biochem. Pharmacol. (1983) [Pubmed]
  10. Role of macrophage complement and lectin-like receptors in binding Leishmania parasites to host macrophages. Blackwell, J.M. Immunol. Lett. (1985) [Pubmed]
  11. Determination of daminozide residues in apple pulp using HPLC-DAD-UV. Bicchi, C., Cordero, C., Rubiolo, P., Occelli, A. J. Agric. Food Chem. (2001) [Pubmed]
  12. Mutants of Arthroderma benhamiae. Howard, D.H., Dabrowa, N. Sabouraudia. (1979) [Pubmed]
  13. Inhibition of in vitro lymphoproliferation by three novel iron chelators of the pyridoxal and salicyl aldehyde hydrazone classes. van Reyk, D., Sarel, S., Hunt, N. Biochem. Pharmacol. (2000) [Pubmed]
  14. Oxazole, pyrazole and piperidine derivatives having an o-hydroxyaryl moiety with anticipated molluscicidal activity. Nawwar, G.A., Swellem, R.H., Ibrahim, A.M. Arch. Pharm. Res. (1994) [Pubmed]
  15. Salicyl alcohol oxidase of the chemical defense secretion of two chrysomelid leaf beetles. Molecular and functional characterization of two new members of the glucose-methanol-choline oxidoreductase gene family. Michalski, C., Mohagheghi, H., Nimtz, M., Pasteels, J., Ober, D. J. Biol. Chem. (2008) [Pubmed]
  16. Diaryl-substituted salicyl- and anthranyl-ketoximes as potential estrogen receptor ligands. Minutolo, F., Antonello, M., Bertini, S., Placanica, G., Rapposelli, S., Carlson, K.E., Katzenellenbogen, J.A., Macchia, M. Farmaco (2004) [Pubmed]
  17. Inhibition of prostaglandin 15-hydroxydehydrogenase by sulphasalazine and a novel series of potent analogues. Berry, C.N., Hoult, J.R., Peers, S.H., Agback, H. Biochem. Pharmacol. (1983) [Pubmed]
  18. Effect of CO2 supply on formation of reactive oxygen species in Arabidopsis thaliana. Hoffmann, A., Hammes, E., Plieth, C., Desel, C., Sattelmacher, B., Hansen, U.P. Protoplasma (2005) [Pubmed]
  19. Comparison of the concentration-effect relationship of a local antiinflammatory agent and oral acetylsalicylic acid: the value of local application. Poisson, M., Ralambosoa, C., Blehaut, H., Astoin, J. Arzneimittel-Forschung. (1985) [Pubmed]
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