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Chemical Compound Review

Methoxime     oxo-[[1-[[4- (oxoazaniumylmethylidene) pyrid...

Synonyms: LS-132721, AC1NX8W5, C13H14N4O2.2Cl, 51026-61-0, 61444-84-6 (Parent)
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Disease relevance of 4-(nitrosomethylene)-1-[[4-(nitrosomethylene)-1-pyridyl]methyl]pyridine

  • The present study demonstrates that the tabun toxicity in mice is more effectively reduced when PANPAL prophylactically is administered than in case of treatment with methoxime and cholinergic drug alone [1].
 

High impact information on 4-(nitrosomethylene)-1-[[4-(nitrosomethylene)-1-pyridyl]methyl]pyridine

  • The peaks obtained by the latter method were derivatized to the methoxime methyl ester trimethyl silyl ether and analyzed by gas-liquid chromatography-mass spectrometry [2].
  • Alprenolone methoxime is stable in isotonic phosphate vehicle but undergoes enzymatic hydrolysis to the corresponding ketone in the eye [3].
  • The (EIMS) electron ionization mass spectrometric fragmentation patterns of the methoxime- and ethoxime-trimethylsilyl (TMS) derivatives of C(4) to C(7) sugars involved as phosphates in the Calvin pathway of photosynthesis in plants were analysed by gas chromatography/EIMS using specifically labelled (13)C analogs [4].
  • The analytes were isolated from acidified human plasma by solid-phase extraction by means of Bond Elut C18 cartridges and derivatized to the pentafluorobenzyl (PFB) ester methoxime [5].
  • Their methoxime and 2,4-dinitrophenylsemicarbazone derivatives were resolved on OV-17 and OV-1 stationary phases, respectively [6].
 

Chemical compound and disease context of 4-(nitrosomethylene)-1-[[4-(nitrosomethylene)-1-pyridyl]methyl]pyridine

 

Biological context of 4-(nitrosomethylene)-1-[[4-(nitrosomethylene)-1-pyridyl]methyl]pyridine

  • Based on our determinations the new K series of reactivators is far superior to pralidoxime, methoxime and BI-6, K-27 being the outstanding compound with a tg alpha value of 3.7 (nm IC50 increase per microm reactivator) which is approximately 13 times the reactivator ability of PRX [7].
  • In vitro, methoxime seems to be the most efficacious reactivator of GF agent-inhibited acetylcholinesterase because the phosphorylation of acetylcholinesterase by GF agent markedly increases its affinity for the enzyme [8].
 

Anatomical context of 4-(nitrosomethylene)-1-[[4-(nitrosomethylene)-1-pyridyl]methyl]pyridine

 

Associations of 4-(nitrosomethylene)-1-[[4-(nitrosomethylene)-1-pyridyl]methyl]pyridine with other chemical compounds

  • The purpose of the study was to quantify in vitro the extent of oxime (pralidoxime, K-27, K-33, K-48, methoxime and BI-6) conferred protection, using paraoxon as an inhibitor [7].
  • Based on our previous in vitro work the protection conferred by the various new oximes against inhibition by paraoxon as quantified by the IC(50) shift (nM increase in the IC(50) of the inhibitor per microM oxime present) is: 0.3 (PRX), 0.4 (methoxime; MMC-4), 1 (K-33), 1.2 (BI-6), 1.5 (K-48) and 3.7 (K-27) [10].
  • Natrium thiosulphate did not significantly increase neither decrease the antidotal treatment efficacy in comparison with methoxime and atropine alone [1].
  • After purification and high-performance liquid chromatography (HPLC) samples are derivatized to give an open-chain derivative of thromboxane B2, the methoxime pentafluorobenzyl ester tris(trimethylsilyl) ether (TXB2-MO-PFB-TMS3), most suitable for negative ion chemical ionization mass spectrometry [11].
  • Steroids, mostly in the form of glucuronide and sulphate conjugates, are extracted using solid-phase cartridges, followed by enzymatic hydrolysis, re-extraction of freed steroids, formation of methoxime trimethylsilyl derivatives and analysis by sas chromatography and gas chromatography-mass spectrometry [12].
 

Gene context of 4-(nitrosomethylene)-1-[[4-(nitrosomethylene)-1-pyridyl]methyl]pyridine

  • AChE activity in the pontomedullar area was increased on increasing the dose of methoxime (p less than 0.005) [13].
 

Analytical, diagnostic and therapeutic context of 4-(nitrosomethylene)-1-[[4-(nitrosomethylene)-1-pyridyl]methyl]pyridine

  • Following conversion to the methoxime, tris-trimethylsilyl, pentafluorobenzyl derivative, samples were analysed using combined capillary column gas chromatography negative ion chemical ionisation mass spectrometry [14].
  • Methoxime analogs of selected beta-blockers were synthesized and their chemical stability established at different pH's. Subsequently, their in vivo sequential enzymatic conversion was confirmed using HPLC [15].

References

  1. Effect of methoxime combined with anticholinergic, anticonvulsant or anti-HCN drugs in tabun-poisoned mice. Sevelová, L., Vachek, J. Acta medica (Hradec Králové) / Universitas Carolina, Facultas Medica Hradec Králové. (2003) [Pubmed]
  2. Metabolism of prostacyclin and 6-keto-prostaglandin F1 alpha in man. Rosenkranz, B., Fischer, C., Weimer, K.E., Frölich, J.C. J. Biol. Chem. (1980) [Pubmed]
  3. Ocular delivery of the beta-adrenergic antagonist alprenolol by sequential bioactivation of its methoxime analogue. Prokai, L., Wu, W.M., Somogyi, G., Bodor, N. J. Med. Chem. (1995) [Pubmed]
  4. Mass spectrometric studies of the path of carbon in photosynthesis: positional isotopic analysis of (13)C-labelled C(4) to C(7) sugar phosphates. MacLeod, J.K., Flanigan, I.L., Williams, J.F., Collins, J.G. Journal of mass spectrometry : JMS. (2001) [Pubmed]
  5. Simultaneous determination of prostaglandin E1, prostaglandin E0 and 15-keto-prostaglandin E0 in human plasma by gas chromatography/negative-ion chemical-ionization tandem mass spectrometry. Hammes, W., Büchsler, U., Kinder, P., Bökens, H. Journal of chromatography. A. (1999) [Pubmed]
  6. The preparation, gas liquid chromatography, and some physical and chemical properties of certain higher aliphatic 2,4-diketones--a new lipid class. Douglas, D.E., Francis, L.E. Lipids (1977) [Pubmed]
  7. Five oximes (K-27, K-33, K-48, BI-6 and methoxime) in comparison with pralidoxime: in vitro reactivation of red blood cell acetylcholinesterase inhibited by paraoxon. Petroianu, G.A., Arafat, K., Kuca, K., Kassa, J. Journal of applied toxicology : JAT. (2006) [Pubmed]
  8. A comparison of the efficacy of acetylcholinesterase reactivators against cyclohexyl methylphosphonofluoridate (GF agent) by in vitro and in vivo methods. Kassa, J., Cabal, J. Pharmacol. Toxicol. (1999) [Pubmed]
  9. Prostaglandin E1 and E2 in bovine semen: quantification by gas chromatography. Mai, J., Kinsella, J.E. Prostaglandins (1980) [Pubmed]
  10. Five oximes (K-27, K-33, K-48, BI-6 and methoxime) in comparison with pralidoxime: survival in rats exposed to the organophosphate paraoxon. Petroianu, G.A., Nurulain, S.M., Nagelkerke, N., Al-Sultan, M.A., Kuca, K., Kassa, J. Journal of applied toxicology : JAT. (2006) [Pubmed]
  11. Measurement of thromboxane B2 in human urine by isotope dilution and negative ion chemical ionization mass spectrometry. Meese, C.O., Fischer, C., Thalheimer, P., Fürst, O. Biomed. Mass Spectrom. (1985) [Pubmed]
  12. Urinary steroid profiling. Taylor, N.F. Methods Mol. Biol. (2006) [Pubmed]
  13. Antidotal therapy and changes of acetylcholinesterase activity following isopropyl methylphosphonofluoridate intoxication in mice. Bajgar, J., Patocka, J., Jakl, A., Hrdina, V. Acta Biol. Med. Ger. (1975) [Pubmed]
  14. Analysis of picomolar concentrations of 6-oxo-prostaglandin F1 alpha in biological fluids. Barrow, S.E., Waddell, K.A., Ennis, M., Dollery, C.T., Blair, I.A. J. Chromatogr. (1982) [Pubmed]
  15. Sequential bioactivation of methoxime analogs of beta-adrenergic antagonists in the eye. Bodor, N., Prokai, L., Wu, W.M., Somogyi, G., Farag, H. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics. (1995) [Pubmed]
 
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