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Chemical Compound Review

AG-D-27422     but-2-enedioic acid

Synonyms: AG-D-27437, AG-K-61366, ACMC-20995i, ACMC-20995j, ANW-16132, ...
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Disease relevance of cis-butenedioic acid


Psychiatry related information on cis-butenedioic acid

  • Patients with Alzheimer's disease received 150 mg/day and 225 mg/day Velnacrine maleate (parallel-group treatment) and placebo [5].
  • Quetiapine fumarate is an atypical antipsychotic medication approved for the treatment of patients with schizophrenia and other psychotic disorders [6].
  • METHODS: Animals isolated during 30 days were treated with U-99194a maleate (20-40 mg/kg) or saline and locomotor activity was measured 20 min after drug administration [7].
  • Under all experimental conditions, dizocilpine [MK-801, (+)-5-methyl-10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5,10-imine maleate, 500 micrograms/kg s.c. or 10 micrograms/mouse i.c.v.] prevented completely the CO-induced amnesia [8].
  • In rats killed 30 min after odour discrimination learning, dizocilpine maleate binding was significantly reduced in hippocampal sub-regions CA3, CA1 and fascia dentata and in frontal cortex [9].

High impact information on cis-butenedioic acid


Chemical compound and disease context of cis-butenedioic acid

  • Bacillus subtilis is able to grow anaerobically using alternative electron acceptors, including nitrate or fumarate [15].
  • The soluble fumarate reductase of Shewanella putrefaciens MR-1 is a periplasmic tetraheme flavocytochrome c. The crystal structures of the enzyme were solved to 2.9 A for the uncomplexed form and to 2.8 A and 2.5 A for the fumarate and the succinate-bound protein, respectively [16].
  • The global regulator FNR (for fumarate nitrate reduction) controls the transcription of >100 genes whose products facilitate adaptation of Escherichia coli to growth under O2-limiting conditions [17].
  • In the previously determined structure of QFR from Wolinella succinogenes, the site of fumarate reduction in the flavoprotein subunit A of the enzyme was identified, but the site of menaquinol oxidation was not [18].
  • Enhancement of the DNA cross-linking activity of nitrogen mustard by misonidazole and diethyl maleate in a mouse fibrosarcoma tumor in vivo [19].

Biological context of cis-butenedioic acid


Anatomical context of cis-butenedioic acid

  • Peripheral-nerve lipid abnormalities in patients on perhexiline maleate [25].
  • After maleate treatment the distribution of microvillar and lysosomal markers was unchanged, but the coated pit markers were redistributed--gp330 was concentrated in newly formed apical vacuoles, and clathrin was diffusely distributed in the apical cytoplasm or on apical coated vesicles [26].
  • Reduction of coronary blood flow during coronary artery spasm occurring spontaneously and after provocation by ergonovine maleate [27].
  • We have studied the binding of the excitatory amino acid antagonist 3H-labeled MK-801 [(+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohept-5,10-imine maleate] to extensively washed rat brain membranes [28].
  • Effects of perhexiline maleate on coronary flow distribution in the ischemic canine myocardium [22].

Associations of cis-butenedioic acid with other chemical compounds

  • Disruption of fnr abolished both nitrate and fumarate utilization as electron acceptors and anaerobic induction of narK [15].
  • When all functional NMDA receptors are blocked by dizocilpine maleate (MK-801), subsequent application of CPT leads to a partial reappearance of NMDA receptor-mediated EPSCs evoked by SCC stimulation, indicating that latent NMDA receptors are recruited [29].
  • Serial bolus injections of 0.05 mg, 0.10 mg and 0.25 mg of ergonovine maleate produced diffuse narrowing of the diameter of coronary arteries of 10 +/- 1.5%, 16 +/- 1.4% and 20 +/- 1.3% (mean +/- SEM), respectively, in the 72 patients with anginal syndromes who did not develop coronary spasm [30].
  • Here we describe that, after replacement of Glu-C66 with Gln by site-directed mutagenesis, the resulting mutant is unable to grow on fumarate and the purified enzyme lacks quinol oxidation activity [18].
  • It was high in cases with mutant TP53 and correlated with the total cellular level of the multidrug resistance-associated protein (P =.019) but not of bcl-2, bax, or bcl-x. It was also found that the dithiol oxidant diamide, in contrast to the monovalent thiol oxidant diethyl maleate, increased the sensitivity of mitochondrial membranes to mClCCP [31].

Gene context of cis-butenedioic acid


Analytical, diagnostic and therapeutic context of cis-butenedioic acid

  • The compound MK-801 [(+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d] cyclohepten-5,10-imine maleate)] is a potent anticonvulsant that is active after oral administration and whose mechanism of action is unknown [37].
  • Coronary arterial spasm was documented with arteriography during exercise-induced ST-segment elevation (three patients) or after intravenous administration of ergonovine maleate (one patient) [38].
  • The control group comprised 176 subjects with completely normal coronary arteries and a negative response to ergonovine maleate [39].
  • Whole-cell and single-channel recording techniques were used to study the action of the anticonvulsant drug MK-801 [(+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]- cyclohepten-5,10-imine maleate) on responses to excitatory amino acids in rat neocortical neurons in cell culture [40].
  • Changes in coronary arterial size due to ergonovine maleate are described and quantitated in 90 patients--18 with typical angina pectoris, 56 with atypical chest pain, nine with variant angina pectoris, and seven heart transplant (allograft) recipients [30].


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  3. Perhexiline maleate-induced cirrhosis. Pessayre, D., Bichara, M., Degott, C., Potet, F., Benhamou, J.P., Feldmann, G. Gastroenterology (1979) [Pubmed]
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  7. The dopamine D3 antagonist U-99194A maleate increases social behaviors of isolation-induced aggressive male mice. Rodríguez-Arias, M., Felip, C.M., Broseta, I., Miñarro, J. Psychopharmacology (Berl.) (1999) [Pubmed]
  8. Cholecystokinin-related peptides, after systemic or central administration, prevent carbon monoxide-induced amnesia in mice. Maurice, T., Hiramatsu, M., Kameyama, T., Hasegawa, T., Nabeshima, T. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
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  11. Structure of the Escherichia coli fumarate reductase respiratory complex. Iverson, T.M., Luna-Chavez, C., Cecchini, G., Rees, D.C. Science (1999) [Pubmed]
  12. Maleic acid and succinic acid in fermented alcoholic beverages are the stimulants of gastric acid secretion. Teyssen, S., González-Calero, G., Schimiczek, M., Singer, M.V. J. Clin. Invest. (1999) [Pubmed]
  13. Inhibition of human polymorphonuclear leukocyte function by 2-cyclohexene-1-one. A role for glutathione in cell activation. Wedner, H.J., Simchowitz, L., Stenson, W.F., Fischman, C.M. J. Clin. Invest. (1981) [Pubmed]
  14. Glutathione modulates rat and mouse hepatocyte sensitivity to tumor necrosis factor toxicity. Xu, Y., Jones, B.E., Neufeld, D.S., Czaja, M.J. Gastroenterology (1998) [Pubmed]
  15. Anaerobic transcription activation in Bacillus subtilis: identification of distinct FNR-dependent and -independent regulatory mechanisms. Cruz Ramos, H., Boursier, L., Moszer, I., Kunst, F., Danchin, A., Glaser, P. EMBO J. (1995) [Pubmed]
  16. Structure and mechanism of the flavocytochrome c fumarate reductase of Shewanella putrefaciens MR-1. Leys, D., Tsapin, A.S., Nealson, K.H., Meyer, T.E., Cusanovich, M.A., Van Beeumen, J.J. Nat. Struct. Biol. (1999) [Pubmed]
  17. Mössbauer spectroscopy as a tool for the study of activation/inactivation of the transcription regulator FNR in whole cells of Escherichia coli. Popescu, C.V., Bates, D.M., Beinert, H., Münck, E., Kiley, P.J. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  18. Essential role of Glu-C66 for menaquinol oxidation indicates transmembrane electrochemical potential generation by Wolinella succinogenes fumarate reductase. Lancaster, C.R., Gorss, R., Haas, A., Ritter, M., Mäntele, W., Simon, J., Kröger, A. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  19. Enhancement of the DNA cross-linking activity of nitrogen mustard by misonidazole and diethyl maleate in a mouse fibrosarcoma tumor in vivo. Murray, D., Meyn, R.E. Cancer Res. (1984) [Pubmed]
  20. Signal transduction in Halobacterium depends on fumarate. Marwan, W., Schäfer, W., Oesterhelt, D. EMBO J. (1990) [Pubmed]
  21. The narL gene product activates the nitrate reductase operon and represses the fumarate reductase and trimethylamine N-oxide reductase operons in Escherichia coli. Iuchi, S., Lin, E.C. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  22. Effects of perhexiline maleate on coronary flow distribution in the ischemic canine myocardium. Klassen, G.A., Sestier, F., L'Abbate, A., Mildenberger, R.R., Zborowska-Sluis, D.T. Circulation (1976) [Pubmed]
  23. Altering the anaerobic transcription factor FNR confers a hemolytic phenotype on Escherichia coli K12. Ralph, E.T., Guest, J.R., Green, J. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  24. Distinct expression profile in fumarate-hydratase-deficient uterine fibroids. Vanharanta, S., Pollard, P.J., Lehtonen, H.J., Laiho, P., Sjöberg, J., Leminen, A., Aittomäki, K., Arola, J., Kruhoffer, M., Orntoft, T.F., Tomlinson, I.P., Kiuru, M., Arango, D., Aaltonen, L.A. Hum. Mol. Genet. (2006) [Pubmed]
  25. Peripheral-nerve lipid abnormalities in patients on perhexiline maleate. Pollet, S., Hauw, J.J., Escourolle, R., Baumann, N. Lancet (1977) [Pubmed]
  26. The membrane composition of coated pits, microvilli, endosomes, and lysosomes is distinctive in the rat kidney proximal tubule cell. Rodman, J.S., Seidman, L., Farquhar, M.G. J. Cell Biol. (1986) [Pubmed]
  27. Reduction of coronary blood flow during coronary artery spasm occurring spontaneously and after provocation by ergonovine maleate. Ricci, D.R., Orlick, A.E., Doherty, P.W., Cipriano, P.R., Harrison, D.C. Circulation (1978) [Pubmed]
  28. 3H-labeled MK-801 binding to the excitatory amino acid receptor complex from rat brain is enhanced by glycine. Reynolds, I.J., Murphy, S.N., Miller, R.J. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  29. Latent N-methyl-D-aspartate receptors in the recurrent excitatory pathway between hippocampal CA1 pyramidal neurons: Ca(2+)-dependent activation by blocking A1 adenosine receptors. Klishin, A., Tsintsadze, T., Lozovaya, N., Krishtal, O. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  30. The effects of ergonovine maleate on coronary arterial size. Cipriano, P.R., Guthaner, D.F., Orlick, A.E., Ricci, D.R., Wexler, L., Silverman, J.F. Circulation (1979) [Pubmed]
  31. Mitochondrial membrane sensitivity to depolarization in acute myeloblastic leukemia is associated with spontaneous in vitro apoptosis, wild-type TP53, and vicinal thiol/disulfide status. Pallis, M., Grundy, M., Turzanski, J., Kofler, R., Russell, N. Blood (2001) [Pubmed]
  32. Electron transfer from menaquinol to fumarate. Fumarate reductase anchor polypeptide mutants of Escherichia coli. Westenberg, D.J., Gunsalus, R.P., Ackrell, B.A., Cecchini, G. J. Biol. Chem. (1990) [Pubmed]
  33. Epidermal growth factor receptor is a common mediator of quinone-induced signaling leading to phosphorylation of connexin-43: role of glutathione and tyrosine phosphatases. Abdelmohsen, K., Gerber, P.A., von Montfort, C., Sies, H., Klotz, L.O. J. Biol. Chem. (2003) [Pubmed]
  34. Mechanistic inferences from the crystal structure of fumarylacetoacetate hydrolase with a bound phosphorus-based inhibitor. Bateman, R.L., Bhanumoorthy, P., Witte, J.F., McClard, R.W., Grompe, M., Timm, D.E. J. Biol. Chem. (2001) [Pubmed]
  35. Structure of Thermus thermophilus HB8 aspartate aminotransferase and its complex with maleate. Nakai, T., Okada, K., Akutsu, S., Miyahara, I., Kawaguchi, S., Kato, R., Kuramitsu, S., Hirotsu, K. Biochemistry (1999) [Pubmed]
  36. The NR2B-selective N-methyl-D-aspartate receptor antagonist Ro 25-6981 [(+/-)-(R*,S*)-alpha-(4-hydroxyphenyl)-beta-methyl-4-(phenylmethyl)-1-piperidine propanol] potentiates the effect of nicotine on locomotor activity and dopamine release in the nucleus accumbens. Kosowski, A.R., Liljequist, S. J. Pharmacol. Exp. Ther. (2004) [Pubmed]
  37. The anticonvulsant MK-801 is a potent N-methyl-D-aspartate antagonist. Wong, E.H., Kemp, J.A., Priestley, T., Knight, A.R., Woodruff, G.N., Iversen, L.L. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  38. Coronary arterial spasm as a cause of exercise-induced ST-segment elevation in patients with variant angina. Specchia, G., de Servi, S., Falcone, C., Bramucci, E., Angoli, L., Mussini, A., Marinoni, G.P., Montemartini, C., Bobba, P. Circulation (1979) [Pubmed]
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