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Chemical Compound Review

SUCCIMIDE     pyrrolidine-2,5-dione

Synonyms: Butanimide, SUCCINIMIDE, SureCN774, PubChem13765, Succinic imide, ...
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Disease relevance of Mercuric imidosuccinate

  • Injection of carboxyfluorescein diacetate succinimide ester-labeled CTL demonstrated markedly different fates for gag-specific CTL in the presence or absence of HIV-1 infection [1].
  • Mengovirus RF RNA reacted with a succinimide ester of biotin was shown by electron microscopy to bind avidin-coupled polymethacrylate spheres [2].
  • Here we report the discovery of an unusually stabilized succinimide ring in the 1.1A structure of the Escherichia coli CheY protein, as determined from a crystal eight years old [3].
  • Two congeners Q4 and Q5 inferred in earlier analyses to be cyclic succinimide-type dehydration products of recombinant hirudin (variant 1) were structurally fully characterized [4].
  • A subset where it is more frequently seen are in adults with persistent absence seizures when the latter become finally controlled by succinimide therapy [5].

Psychiatry related information on Mercuric imidosuccinate


High impact information on Mercuric imidosuccinate

  • We demonstrate a succinimide at the C-terminus of the spliced internal protein, implicating cyclization of asparagine in resolution of the branched intermediate, and we identify an alkali-labile bond in the branched intermediate [6].
  • Protein splicing: an analysis of the branched intermediate and its resolution by succinimide formation [6].
  • This sequence of enzymatic and nonenzymatic reactions can be coupled in a single reaction mixture; the [iso-Asp3]tetragastrin that is produced upon succinimide hydrolysis can reenter the reaction sequence by enzymatic methylation, and the net result of the process is the conversion of the isomerized peptide to the normal peptide [7].
  • We hypothesize that spontaneous chemical modification of aspartyl residues in Abeta to transient succinimide induces a non-native conformation in a fraction of soluble Abeta, rendering it amyloidogenic and neurotoxic [8].
  • By using a succinimide-activated PEG derivative, PEG was conjugated to epsilon-amino groups of lysine residues of XO, which play a crucial role in binding of XO to blood vessels [9].

Chemical compound and disease context of Mercuric imidosuccinate


Biological context of Mercuric imidosuccinate

  • Deletion of the C-terminal residue of this protein does not influence the ability for phosphorylation or ring formation, but it does allow for isoaspartyl formation, verifying a succinimide as the cyclic intermediate in H15D HPr [13].
  • Moreover, since succinimide intermediates of deamidated peptides can occasionally be very stable, these peptides have the potential to act as altered self-Ags with significant implications for autoimmunity [14].
  • Cyclization of this residue to succinimide causes the final detachment of inteins from their hosts [15].
  • Metabolism of a synthetic L-isoaspartyl-containing hexapeptide in erythrocyte extracts. Enzymatic methyl esterification is followed by nonenzymatic succinimide formation [16].
  • This procedure, which can be completed in as little as 24 h with no upper limit on cell number, utilizes succinimide esters to label cell surface proteins with biotin covalently [17].

Anatomical context of Mercuric imidosuccinate

  • The metabolism of the succinimide hexapeptide in erythrocyte extracts appears to be more complex, however [16].
  • The succinimide (8b) and the pyrrolidone (3b) derivatives of 1 substituted with a phenyl group at position 1 of the butynyl chain showed the highest antimuscarinic potency with dissociation constants (KD) of 0.10 and 0.20 microM, respectively, in the ileum assay [18].
  • No antibodies were raised against the B cell epitope when the free peptides (T and B cell epitopes) were just mixed or when the T cell epitope was conjugated via m-maleimidobenzoyl succinimide ester or bis-maleimidohexane to the B cell determinant [19].
  • The Lossen rearrangement in biological systems. Inactivation of leukocyte elastase and alpha-chymotrypsin by (dl)-3-benzyl-N-(methanesulfonyloxy) succinimide [20].
  • Identification of Asp95 as the site of succinimide formation in recombinant human glial cell line-derived neurotrophic factor [21].

Associations of Mercuric imidosuccinate with other chemical compounds


Gene context of Mercuric imidosuccinate

  • We postulate that Abeta and other amyloidogenic proteins undergo a transition to beta-sheet as a result of aging-related chemical modifications of aspartyl residues to the form of succinimide or isoaspartyl methyl ester [27].
  • In vitro selectivity of several novel hydroxamate HDAC inhibitors including succinimide macrocyclic hydroxamates and the non-hydroxamate alpha-ketoamide inhibitors was investigated using isolated enzyme preparations and cellular assays [28].
  • The heterogeneous fluorescence of yeast 3-phosphoglycerate kinase, a hinge-bending enzyme with two tryptophans, has been resolved into two approximately equal components, one accessible and one inaccessible to the relatively inefficient quencher succinimide [29].
  • For this two-site immunochemiluminometric assay of intact human parathyrin (hPTH), the luminescent tracer was synthetic hPTH(53-84), conjugated via succinimide linkage to (aminobutyl)ethyl-isoluminol hemisuccinimide (abei-h) [30].
  • Major degradation products of basic fibroblast growth factor: detection of succinimide and iso-aspartate in place of aspartate [31].

Analytical, diagnostic and therapeutic context of Mercuric imidosuccinate

  • The succinimide (cyclic imide) variant was isolated from thermally stressed recombinant methionyl human growth hormone (hGH) by high performance anion-exchange chromatography, further purified by reversed-phase high performance liquid chromatography, and analyzed by tryptic mapping [32].
  • Concanavalin A (Con A) was biotinylated to various degrees using N-biotinyl-omega-aminocaproic-acid-N-hydroxy succinimide ester as the biotinylation reagent, and then analyzed by isoelectric focusing using PhastGel IEF 3-9 [33].
  • N-terminal sequence analysis can then be used to identify an internal sequence generated by cleavage of the succinimide, hence identifying the succinimide site [34].
  • The degradation products were 1) a succinimido intermediate (anhydro-daptomycin) formed by attack of side-chain carbonyl on the peptide-bond nitrogen in the asp-gly sequence and 2) a beta-asp daptomycin isomer formed by rehydration of the anhydrodaptomycin succinimide [35].
  • 5. Two capillary electrophoresis (CE) protocols were used: one for the kinetics of succinimide formation at Asp53-Gly54 (C-terminal tail) and Asp33-Gly34 (loop section), the other for the kinetics of rHir degradation [36].


  1. The antiviral activity of HIV-specific CD8+ CTL clones is limited by elimination due to encounter with HIV-infected targets. McKinney, D.M., Lewinsohn, D.A., Riddell, S.R., Greenberg, P.D., Mosier, D.E. J. Immunol. (1999) [Pubmed]
  2. Attachment of avidin-coupled spheres to linear and circular forms of mengovirus double-stranded RNA. Thornton, G.B., Robberson, D.L., Arlinghaus, R.B. J. Virol. (1981) [Pubmed]
  3. Atomic resolution structure of a succinimide intermediate in E.coli CheY. Simonovic, M., Volz, K. J. Mol. Biol. (2002) [Pubmed]
  4. Characterization of succinimide-type dehydration products of recombinant hirudin variant 1 by electrospray tandem mass spectrometry. Grossenbacher, H., Märki, W., Coulot, M., Müller, D., Richter, W.J. Rapid Commun. Mass Spectrom. (1993) [Pubmed]
  5. Acute behavioral symptomatology at disappearance of epileptiform EEG abnormality. Paradoxical or "forced" normalization. Wolf, P. Advances in neurology. (1991) [Pubmed]
  6. Protein splicing: an analysis of the branched intermediate and its resolution by succinimide formation. Xu, M.Q., Comb, D.G., Paulus, H., Noren, C.J., Shao, Y., Perler, F.B. EMBO J. (1994) [Pubmed]
  7. Conversion of isoaspartyl peptides to normal peptides: implications for the cellular repair of damaged proteins. McFadden, P.N., Clarke, S. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  8. Protein aging hypothesis of Alzheimer disease. Orpiszewski, J., Schormann, N., Kluve-Beckerman, B., Liepnieks, J.J., Benson, M.D. FASEB J. (2000) [Pubmed]
  9. Tumor-targeting chemotherapy by a xanthine oxidase-polymer conjugate that generates oxygen-free radicals in tumor tissue. Sawa, T., Wu, J., Akaike, T., Maeda, H. Cancer Res. (2000) [Pubmed]
  10. Anticancer activity of new 3-amino-pyrrolidinedione-nitrogen mustard derivatives on murine sarcoma 180. Naik, S.D., Ambaye, R.Y., Gokhale, S.V. Anticancer Res. (1987) [Pubmed]
  11. Nephrotoxic potential of N-(3,5-dichlorophenyl)glutarimide and N-(3,5-dichlorophenyl)glutaramic acid in Fischer 344 rats. Kellner-Weibel, G.L., Tchao, R., Harvison, P.J. Toxicol. Lett. (1995) [Pubmed]
  12. Induction of beta-lactamase from Shigella flexneri UCSF-129: purification by affinity chromatography and some properties. Campos, M., González, H., Alarcón, M.A., Sánchez, R. Microbios (1992) [Pubmed]
  13. The influence of protein structure on the products emerging from succinimide hydrolysis. Athmer, L., Kindrachuk, J., Georges, F., Napper, S. J. Biol. Chem. (2002) [Pubmed]
  14. CTL recognition of an altered peptide associated with asparagine bond rearrangement. Implications for immunity and vaccine design. Chen, W., Ede, N.J., Jackson, D.C., McCluskey, J., Purcell, A.W. J. Immunol. (1996) [Pubmed]
  15. Protein splicing of inteins with atypical glutamine and aspartate C-terminal residues. Amitai, G., Dassa, B., Pietrokovski, S. J. Biol. Chem. (2004) [Pubmed]
  16. Metabolism of a synthetic L-isoaspartyl-containing hexapeptide in erythrocyte extracts. Enzymatic methyl esterification is followed by nonenzymatic succinimide formation. Murray, E.D., Clarke, S. J. Biol. Chem. (1986) [Pubmed]
  17. In vitro immune modulation by antibodies coupled to tumour cells. Darling, D., Galea-Lauri, J., Gäken, J., Towner, P., Kuiper, M., Hollingsworth, S., Hirst, W., Barnard, A., Buggins, A., Mufti, G., Farzaneh, F. Gene Ther. (1997) [Pubmed]
  18. Phenyl-substituted analogues of oxotremorine as muscarinic antagonists. Nilsson, B.M., Vargas, H.M., Ringdahl, B., Hacksell, U. J. Med. Chem. (1992) [Pubmed]
  19. Peptide-induced memory (IgG) response, cross-reactive with native proteins, requires covalent linkage of a specific B cell epitope with a T cell epitope. Zegers, N.D., van Holten, C., Claasen, E., Boersma, W.J. Eur. J. Immunol. (1993) [Pubmed]
  20. The Lossen rearrangement in biological systems. Inactivation of leukocyte elastase and alpha-chymotrypsin by (dl)-3-benzyl-N-(methanesulfonyloxy) succinimide. Groutas, W.C., Giri, P.K., Crowley, J.P., Castrisos, J.C., Brubaker, M.J. Biochem. Biophys. Res. Commun. (1986) [Pubmed]
  21. Identification of Asp95 as the site of succinimide formation in recombinant human glial cell line-derived neurotrophic factor. Hui, J.O., Chow, D.T., Markell, D., Robinson, J.H., Katta, V., Nixon, L., Chang, B.S., Rohde, M.F., Haniu, M. Arch. Biochem. Biophys. (1998) [Pubmed]
  22. (18)O labeling method for identification and quantification of succinimide in proteins. Xiao, G., Bondarenko, P.V., Jacob, J., Chu, G.C., Chelius, D. Anal. Chem. (2007) [Pubmed]
  23. Analysis of drug transport kinetics in multidrug-resistant cells using a novel coumarin-vinblastine compound. Bornmann, W.G., Roepe, P.D. Biochemistry (1994) [Pubmed]
  24. Development of an electrochemical immunosensor for direct detection of interferon-gamma at the attomolar level. Dijksma, M., Kamp, B., Hoogvliet, J.C., van Bennekom, W.P. Anal. Chem. (2001) [Pubmed]
  25. Effects of alkyl-substituted gamma-butyrolactones and succinimides on the evoked and spontaneous activity of hippocampal slices in vitro. Ferrendelli, J.A., McKeon, A.C., Klunk, W.E. Exp. Neurol. (1983) [Pubmed]
  26. Aneuploidy induction in Saccharomyces cerevisiae by two solvent compounds, 1-methyl-2-pyrrolidinone and 2-pyrrolidinone. Mayer, V.W., Goin, C.J., Taylor-Mayer, R.E. Environ. Mol. Mutagen. (1988) [Pubmed]
  27. Induction of beta-sheet structure in amyloidogenic peptides by neutralization of aspartate: a model for amyloid nucleation. Orpiszewski, J., Benson, M.D. J. Mol. Biol. (1999) [Pubmed]
  28. Differential protein acetylation induced by novel histone deacetylase inhibitors. Glaser, K.B., Li, J., Pease, L.J., Staver, M.J., Marcotte, P.A., Guo, J., Frey, R.R., Garland, R.B., Heyman, H.R., Wada, C.K., Vasudevan, A., Michaelides, M.R., Davidsen, S.K., Curtin, M.L. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
  29. Resolution of the fluorescence of the buried tryptophan in yeast 3-phosphoglycerate kinase using succinimide. Varley, P.G., Dryden, D.T., Pain, R.H. Biochim. Biophys. Acta (1991) [Pubmed]
  30. Two-site immunochemiluminometric assay of intact human parathyrin in serum with use of a tracer peptide purified by reversed-phase high-performance liquid chromatography. Böhler, U., Blind, E., Vogel, G., Hitzler, W., Flentje, D., Schmidt-Gayk, H. Clin. Chem. (1989) [Pubmed]
  31. Major degradation products of basic fibroblast growth factor: detection of succinimide and iso-aspartate in place of aspartate. Shahrokh, Z., Eberlein, G., Buckley, D., Paranandi, M.V., Aswad, D.W., Stratton, P., Mischak, R., Wang, Y.J. Pharm. Res. (1994) [Pubmed]
  32. Isolation and characterization of a succinimide variant of methionyl human growth hormone. Teshima, G., Stults, J.T., Ling, V., Canova-Davis, E. J. Biol. Chem. (1991) [Pubmed]
  33. Estimation of biotinylated lectin by isoelectric focusing. Harada, H., Kondo, M., Yamaguchi, T. Electrophoresis (1990) [Pubmed]
  34. Identification of succinimide sites in proteins by N-terminal sequence analysis after alkaline hydroxylamine cleavage. Kwong, M.Y., Harris, R.J. Protein Sci. (1994) [Pubmed]
  35. Kinetics of the aspartyl transpeptidation of daptomycin, a novel lipopeptide antibiotic. Kirsch, L.E., Molloy, R.M., Debono, M., Baker, P., Farid, K.Z. Pharm. Res. (1989) [Pubmed]
  36. Chemical degradation kinetics of recombinant hirudin (HV1) in aqueous solution: effect of pH. Gietz, U., Alder, R., Langguth, P., Arvinte, T., Merkle, H.P. Pharm. Res. (1998) [Pubmed]
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