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Chemical Compound Review

Maleanil     1-phenylpyrrole-2,5-dione

Synonyms: Maleinanil, PubChem16335, CHEMBL76012, SureCN18713, NSC-8183, ...
 
 
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Disease relevance of NSC 8183

  • In this report we demonstrate that NEM and N-phenylmaleimide (NPM) are rapidly detoxified by E. coli [1].
  • These compounds undergo in situ cyclodimerization of the [4 + 2]-type upon dehydration of the precursor tertiary alcohols and form endo-adducts in the Diels-Alder reaction with N-phenylmaleimide [2].
 

High impact information on NSC 8183

 

Biological context of NSC 8183

  • 4. A cysteine important for the activity of murine CEH appears not to be in the active site as judged by N-phenylmaleimide inhibition in the presence and absence of either (2S,3S)-2,3-epoxy-3-(4-nitrophenyl)glycidol, a competitive inhibitor, or trans-stilbene oxide, a substrate [8].
 

Anatomical context of NSC 8183

 

Associations of NSC 8183 with other chemical compounds

 

Gene context of NSC 8183

  • Both NEM and NPM suppressed IL-2 production at doses that did not affect proliferation [10].
 

Analytical, diagnostic and therapeutic context of NSC 8183

  • We also found that crossbridges are locked in a weakly-binding state after treatment with N-phenylmaleimide (NPM) [14].
  • A combination of infrared, Raman and inelastic neutron scattering (INS) spectroscopies with density functional theory (DFT) calculations is used to provide a complete assignment of the vibrational spectra of N-phenylmaleimide and N-(perdeuterophenyl)maleimide [15].

References

  1. Glutathione-dependent conversion of N-ethylmaleimide to the maleamic acid by Escherichia coli: an intracellular detoxification process. McLaggan, D., Rufino, H., Jaspars, M., Booth, I.R. Appl. Environ. Microbiol. (2000) [Pubmed]
  2. 1,3-bis(diarylmethylidene)-2-methylidenecyclohexanes in cycloaddition and cyclodimerization reactions. The role of stereoelectronic factors. Klimova, E.I., Martínez García, M., Klimova, T., Ortega, S.H., Bakinovsky, L.V. Org. Biomol. Chem. (2003) [Pubmed]
  3. Structure/function of the human Ga1beta1,3-glucuronosyltransferase. Dimerization and functional activity are mediated by two crucial cysteine residues. Ouzzine, M., Gulberti, S., Netter, P., Magdalou, J., Fournel-Gigleux, S. J. Biol. Chem. (2000) [Pubmed]
  4. Structural characterization of weakly attached cross-bridges in the A*M*ATP state in permeabilized rabbit psoas muscle. Xu, S., Gu, J., Melvin, G., Yu, L.C. Biophys. J. (2002) [Pubmed]
  5. Behavior of N-phenylmaleimide-reacted muscle fibers in magnesium-free rigor solution. Xu, S., Yu, L.C., Schoenberg, M. Biophys. J. (1998) [Pubmed]
  6. Graphical evaluation of alkylation of myosin's SH1 and SH2: the N-phenylmaleimide reaction. Xie, L., Li, W.X., Barnett, V.A., Schoenberg, M. Biophys. J. (1997) [Pubmed]
  7. Inhibition of the light-induced H+ release from uncoupled thylakoid membranes by N-ethylmaleimide. Yamasaki, H., Okayama, S., Shibata, M., Nishimura, M. Biochem. Biophys. Res. Commun. (1992) [Pubmed]
  8. Inhibition of human and murine cytosolic epoxide hydrolase by group-selective reagents. Dietze, E.C., Stephens, J., Magdalou, J., Bender, D.M., Moyer, M., Fowler, B., Hammock, B.D. Comp. Biochem. Physiol., B (1993) [Pubmed]
  9. A model of cross-bridge attachment to actin in the A*M*ATP state based on x-ray diffraction from permeabilized rabbit psoas muscle. Gu, J., Xu, S., Yu, L.C. Biophys. J. (2002) [Pubmed]
  10. Inhibition of interleukin-2 production in the human T cell line JURKAT by nonpolar maleimides. Freed, B.M., Lempert, N., Lawrence, D.A. Toxicol. Appl. Pharmacol. (1991) [Pubmed]
  11. Interactions of sodium-proton exchange mechanism in dog red blood cells with N-phenylmaleimide. Parker, J.C., Glosson, P.S. Am. J. Physiol. (1987) [Pubmed]
  12. Human xylosyltransferase I: functional and biochemical characterization of cysteine residues required for enzymic activity. Müller, S., Schöttler, M., Schön, S., Prante, C., Brinkmann, T., Kuhn, J., Götting, C., Kleesiek, K. Biochem. J. (2005) [Pubmed]
  13. Chemical modification of milk xanthine oxidase with different modifiers. Aboul-Enein, H.Y., Refaie, M.O., El-Gazzar, H., El-Aziz, M.A. Prep. Biochem. Biotechnol. (2003) [Pubmed]
  14. Formation of ATP-insensitive weakly-binding crossbridges in single rabbit psoas fibers by treatment with phenylmaleimide or para-phenylenedimaleimide. Barnett, V.A., Ehrlich, A., Schoenberg, M. Biophys. J. (1992) [Pubmed]
  15. Vibrational spectroscopy of N-phenylmaleimide. Parker, S.F. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2006) [Pubmed]
 
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