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Chemical Compound Review

MALEIC ANHYDRIDE     furan-2,5-dione

Synonyms: Maleinanhydrid, PubChem16845, M188_ALDRICH, M625_ALDRICH, AGN-PC-00KEFU, ...
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Disease relevance of MALEIC ANHYDRIDE


High impact information on MALEIC ANHYDRIDE


Chemical compound and disease context of MALEIC ANHYDRIDE


Biological context of MALEIC ANHYDRIDE

  • Modification of all the lysines on adrenodoxin with maleic anhydride had no effect on the interaction with either adrenodoxin reductase or cytochrome P-450scc, suggesting that the lysines are not located at the binding site for either protein [13].
  • The rigid polyampholyte blocks were formed by hydrolysis of alternating copolymers of N,N,N',N'-tetraethyl-4,4'-diaminostilbene with maleic anhydride, and the flexible coil block consists of poly(oligo(ethylene glycol)methacrylate) [14].
  • The kinetics of the stereoselective semi-hydrogenation of 4-octyne in THF by the highly active catalyst [Pd{(m,m'-(CF(3))(2)C(6)H(3))-bian}(ma)] (2) (bian = bis(imino)acenaphthene; ma = maleic anhydride) has been investigated [15].
  • Our new method allows airborne maleic anhydride to be determined with a limit of quantification of 1 microg/m3 per 12 1 of air, i.e., the concentration of about 0.01 times the occupational exposure standard (0.4 mg/m3) [16].
  • To address this problem, we suggest a novel maleic anhydride copolymer precoating technique which allows for the covalent attachment of cellulose thin films through esterification [17].

Anatomical context of MALEIC ANHYDRIDE


Associations of MALEIC ANHYDRIDE with other chemical compounds


Gene context of MALEIC ANHYDRIDE

  • TM was covalently immobilized through poly(ethylene glycol) (PEG) spacers onto thin films of poly(octadecene alt maleic anhydride) covering planar glass substrates [28].
  • This letter describes how the irreversible attachment of bovine serum albumin (BSA) to films of plasma-polymerized maleic anhydride can be measured by an indirect antibody-binding assay and how this attachment appears to be strongly affected by the polymerization conditions [29].
  • Fibronectin adsorption and exchange on two different maleic anhydride copolymer surfaces differing in hydrophobicity and surface charge density have been analyzed by quartz crystal microbalance and laser scanning microscopy with respect to adsorbed amounts, viscoelastic properties, and conformation [30].
  • The last is one of three products from the reaction of Fe(CO)(4)(MA) (MA = maleic anhydride) with NPP, the other two being Fe(CO)(3)(NPP) (7; P, P coordinated) and the unusual cyclic ylid Ph2PC(2-C5H4N)PPh2C(CH2CO2H)C(=O)(5) [31].
  • The monomer mixture was composed of UEDMA, HEMA or TEGDMA, and 0-40 mol% HEMAN (the adduct of HEMA and maleic anhydride) [32].

Analytical, diagnostic and therapeutic context of MALEIC ANHYDRIDE

  • Synthesis of a poly(vinylpyrrolidone-co-dimethyl maleic anhydride) co-polymer and its application for renal drug targeting [33].
  • Approximately 80% of the water-soluble polymer poly(vinylpyrrolidone-co-dimethyl maleic anhydride selectively accumulated in the kidney of mice 24 h after intravenous injection [34].
  • However, although the native enzyme has a sedimentation coefficient of 5.8S, dissociation by S-carboxymethylation and maleic anhydride treatment results in subunits exhibiting a single schlieren boundary on analytical ultracentrifugation with a sedimentation coefficient of 2.18S [35].
  • Feeding experiments using a deuterium labeled C16 maleic anhydride and whole cell culture of ATCC 74256 led to the isolation of phomoidride B with deuterium incorporation at C(7) and C(19) as determined by 2H NMR and electrospray mass spectrometry [36].
  • The solid-state structure of CoRu(CO)4(mu-bma)(mu-PPh2) (3a), as determined by X-ray crystallography, reveals that the two PPh2 groups are bound to the ruthenium center while the maleic anhydride pi bond is coordinated to the cobalt atom [37].


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  2. Chemical inactivation of Escherichia coli 30 S ribosomes with maleic anhydride: identification of the proteins involved in polyuridylic acid binding. Cantrell, M., Craven, G.R. J. Mol. Biol. (1977) [Pubmed]
  3. Effect of alterations of basic amino acid residues of Escherichia coli heat-stable enterotoxin II on enterotoxicity. Fujii, Y., Okamuro, Y., Hitotsubashi, S., Saito, A., Akashi, N., Okamoto, K. Infect. Immun. (1994) [Pubmed]
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  5. Solid-phase synthesis of cleavable N-arylmaleimides: applications in 1,3-dipolar cycloaddition and in thiol scavenging. Hoveyda, H.R., Hall, D.G. Org. Lett. (2001) [Pubmed]
  6. Dissociation of bovine 6S procarboxypeptidase A by reversible condensation with 2,3-dimethyl maleic anhydride: application to the partial characterization of subunit III. Puigserver, A., Desnuelle, P. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  7. Antitumor activity of tumor necrosis factor alpha conjugated with divinyl ether and maleic anhydride copolymer on solid tumors in mice. Kaneda, Y., Yamamoto, Y., Kamada, H., Tsunoda, S., Tsutsumi, Y., Hirano, T., Mayumi, T. Cancer Res. (1998) [Pubmed]
  8. Mechanism of action of a new antitumor agent, carbetimer. Ardalan, B., Paget, G.E. Cancer Res. (1986) [Pubmed]
  9. Enhancement of macrophage-induced cytotoxicity by phorbol ester tumor promoters. Laskin, D.L., Laskin, J.D., Kessler, F.K., Weinstein, I.B., Carchman, R.A. Cancer Res. (1981) [Pubmed]
  10. Induction of chemotaxis in mouse peritoneal macrophages by phorbol ester tumor promoters. Laskin, D.L., Laskin, J.D., Weinstein, I.B., Carchman, R.A. Cancer Res. (1981) [Pubmed]
  11. Chronic toxicity of styrene maleic anhydride, a male contraceptive, in rhesus monkeys (Macaca mulatta). Sethi, N., Srivastava, R.K., Singh, R.K., Bhatia, G.S., Sinha, N. Contraception. (1990) [Pubmed]
  12. Antitumor activity of sarcolysin containing crosslinked copolymers in mice. Popov, D.V. Neoplasma (1985) [Pubmed]
  13. The use of a specific fluorescence probe to study the interaction of adrenodoxin with adrenodoxin reductase and cytochrome P-450scc. Tuls, J., Geren, L., Lambeth, J.D., Millett, F. J. Biol. Chem. (1987) [Pubmed]
  14. Aggregation of rod-coil block copolymers containing rigid polyampholyte blocks in aqueous solution. Mao, M., Turner, S.R. J. Am. Chem. Soc. (2007) [Pubmed]
  15. Kinetic and spectroscopic studies of the [palladium(Ar-bian)]-catalyzed semi-hydrogenation of 4-octyne. Kluwer, A.M., Koblenz, T.S., Jonischkeit, T., Woelk, K., Elsevier, C.J. J. Am. Chem. Soc. (2005) [Pubmed]
  16. Determination of maleic anhydride in occupational atmospheres. Pfäffli, P., Hämeilä, M., Kuusimäki, L., Wirmoila, R. Journal of chromatography. A. (2002) [Pubmed]
  17. Covalent immobilization of cellulose layers onto maleic anhydride copolymer thin films. Freudenberg, U., Zschoche, S., Simon, F., Janke, A., Schmidt, K., Behrens, S.H., Auweter, H., Werner, C. Biomacromolecules (2005) [Pubmed]
  18. Role of natural killer activity in development of spontaneous metastases in murine renal cancer. Salup, R.R., Herberman, R.B., Wiltrout, R.H. J. Urol. (1985) [Pubmed]
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  20. Phospholipase A2 inhibition by alkylbenzoylacrylic acids. Köhler, T., Heinisch, M., Kirchner, M., Peinhardt, G., Hirschelmann, R., Nuhn, P. Biochem. Pharmacol. (1992) [Pubmed]
  21. Histology of the rat vas deferens after injection of a non-occlusive chemical contraceptive. Verma, K., Misro, M.M., Singh, H., Mahajan, S., Ray, A.R., Guha, S.K. J. Reprod. Fertil. (1981) [Pubmed]
  22. Differential solubilization of human erythrocyte cell membrane proteins by maleic anhydride. Vadlamudi, B.P., Dzandu, J.D., Larway, P.F. Biochem. Biophys. Res. Commun. (1975) [Pubmed]
  23. Chemical modification of L-asparaginase with comb-shaped copolymer of poly(ethylene glycol) derivative and maleic anhydride. Saito, T., Ueno, T., Sekine, T., Kodera, Y., Hiroto, M., Matsushima, A., Nishimura, H., Inada, Y. Leukemia (1997) [Pubmed]
  24. Shell-crosslinked nanostructures from amphiphilic AB and ABA block copolymers of styrene-alt-(maleic anhydride) and styrene: polymerization, assembly and stabilization in one pot. Harrisson, S., Wooley, K.L. Chem. Commun. (Camb.) (2005) [Pubmed]
  25. Breakdown of N-terminally modified peptides and an isopeptide by rumen microorganisms. Wallace, R.J., Frumholtz, P.P., Walker, N.D. Appl. Environ. Microbiol. (1993) [Pubmed]
  26. Coated reactive carriers based on copolymers of 1-vinyl-2-pyrrolidone and maleic anhydride for immobilization of enzymes. Zaharieva, E.I., Georgiev, G.G., Konstantinov, C.I. Biomaterials (1996) [Pubmed]
  27. Roles of acid/base nature and molecular weight in drug release from matrices of gelfoam and monoisopropyl ester of poly(vinyl methyl ether-maleic anhydride). Hämäläinen, K.M., Määttä, E., Piirainen, H., Marianne Sarkola, n.u.l.l., Väisänen, A., Ranta, V.P., Urtti, A. Journal of controlled release : official journal of the Controlled Release Society. (1998) [Pubmed]
  28. Covalently immobilized thrombomodulin inhibits coagulation and complement activation of artificial surfaces in vitro. Sperling, C., Salchert, K., Streller, U., Werner, C. Biomaterials (2004) [Pubmed]
  29. Control of attachment of bovine serum albumin to pulse plasma-polymerized maleic anhydride by variation of pulse conditions. Liu, S., Vareiro, M.M., Fraser, S., Jenkins, A.T. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  30. Fibronectin displacement at polymer surfaces. Renner, L., Pompe, T., Salchert, K., Werner, C. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  31. Synthetic and structural studies of the coordination behavior of 2-pyridylbis(diphenylphosphino)methane. Mague, J.T., Krinsky, J.L. Inorganic chemistry. (2001) [Pubmed]
  32. Strengthening effect of aluminum fluoride added to resin composites based on polyacid-containing polymer. Asmussen, E., Peutzfeldt, A. Dental materials : official publication of the Academy of Dental Materials. (2003) [Pubmed]
  33. Synthesis of a poly(vinylpyrrolidone-co-dimethyl maleic anhydride) co-polymer and its application for renal drug targeting. Kamada, H., Tsutsumi, Y., Sato-Kamada, K., Yamamoto, Y., Yoshioka, Y., Okamoto, T., Nakagawa, S., Nagata, S., Mayumi, T. Nat. Biotechnol. (2003) [Pubmed]
  34. A site-specific polymeric drug carrier for renal disease treatment. Kishida, A. Trends Pharmacol. Sci. (2003) [Pubmed]
  35. The subunits of human hexosaminidase A. Beutler, E., Yoshida, A., Kuhl, W., Lee, J.E. Biochem. J. (1976) [Pubmed]
  36. Studies on the biosynthesis of phomoidride B (CP-263,114): evidence for a decarboxylative homodimerization pathway. Sulikowski, G.A., Agnelli, F., Spencer, P., Koomen, J.M., Russell, D.H. Org. Lett. (2002) [Pubmed]
  37. Selective diphosphine ligand chelation and pi bond coordination in CoRu(CO)7(mu-PPh2): kinetics and X-ray structure of CoRu(CO)4(mu-bma)(mu-PPh2). Bott, S.G., Yang, K., Wang, J.C., Richmond, M.G. Inorganic chemistry. (2000) [Pubmed]
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