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Chemical Compound Review

sinefungin     (2S)-2,5-diamino-6- [(2R,3S,4R,5R)-5-(6...

Synonyms: CHEBI:721219, AC1L9UFC
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Disease relevance of sinefungin


High impact information on sinefungin


Chemical compound and disease context of sinefungin


Biological context of sinefungin


Anatomical context of sinefungin


Associations of sinefungin with other chemical compounds


Gene context of sinefungin

  • Whereas the peripheral, inserted structural elements of the TPMT topology are conformationally stabilized by the presence of sinefungin, a consistent increase in backbone mobility is observed for the central, conserved structural elements [4].
  • Sinefungin, a potent inhibitor of virion mRNA(guanine-7-)-methyltransferase, mRNA(nucleoside-2'-)-methyltransferase, and viral multiplication [24].
  • Surprisingly, taxol, a microtubule-stabilizing drug, induced the same morphological modifications as sinefungin although it interfered with the G2/M progression [13].
  • The crystal structures of the binary complexes of the DNA methyltransferase M.TaqI with the inhibitor Sinefungin and the reaction product S-adenosyl-L-homocysteine were determined, both at 2.6 A resolution [25].
  • Cell cycle progression was analyzed to establish that sinefungin irreversibly blocks the promastigotes in early S phase [13].

Analytical, diagnostic and therapeutic context of sinefungin


  1. Two histone H1-specific protein-lysine N-methyltransferases from Euglena gracilis. Purification and characterization. Tuck, M.T., Farooqui, J.Z., Paik, W.K. J. Biol. Chem. (1985) [Pubmed]
  2. Vesicular stomatitis viruses resistant to the methylase inhibitor sinefungin upregulate RNA synthesis and reveal mutations that affect mRNA cap methylation. Li, J., Chorba, J.S., Whelan, S.P. J. Virol. (2007) [Pubmed]
  3. Curative and preventive anticryptosporidium activities of sinefungin in an immunosuppressed adult rat model. Brasseur, P., Lemeteil, D., Ballet, J.J. Antimicrob. Agents Chemother. (1993) [Pubmed]
  4. Consequences of binding an S-adenosylmethionine analogue on the structure and dynamics of the thiopurine methyltransferase protein backbone. Scheuermann, T.H., Keeler, C., Hodsdon, M.E. Biochemistry (2004) [Pubmed]
  5. Trypanosoma brucei spliced-leader RNA methylations are required for trans splicing in vivo. McNally, K.P., Agabian, N. Mol. Cell. Biol. (1992) [Pubmed]
  6. Mutational Analysis of Encephalitozoon cuniculi mRNA Cap (Guanine-N7) Methyltransferase, Structure of the Enzyme Bound to Sinefungin, and Evidence That Cap Methyltransferase Is the Target of Sinefungin's Antifungal Activity. Zheng, S., Hausmann, S., Liu, Q., Ghosh, A., Schwer, B., Lima, C.D., Shuman, S. J. Biol. Chem. (2006) [Pubmed]
  7. Aclacinomycin 10-hydroxylase is a novel substrate-assisted hydroxylase requiring S-adenosyl-L-methionine as cofactor. Jansson, A., Koskiniemi, H., Erola, A., Wang, J., Mäntsälä, P., Schneider, G., Niemi, J. J. Biol. Chem. (2005) [Pubmed]
  8. Structures of liganded and unliganded RsrI N6-adenine DNA methyltransferase: a distinct orientation for active cofactor binding. Thomas, C.B., Scavetta, R.D., Gumport, R.I., Churchill, M.E. J. Biol. Chem. (2003) [Pubmed]
  9. Effect of 5-azacytidine and sinefungin on Streptomyces development. Fernandez, M., Soliveri, J., Novella, I.S., Yebra, M.J., Barbés, C., Sánchez, J. Gene (1995) [Pubmed]
  10. Effects of carboxylmethylation and polyamine synthesis inhibitors on methylation of Trypanosoma brucei cellular proteins and lipids. Goldberg, B., Rattendi, D., Yarlett, N., Lloyd, D., Bacchi, C.J. J. Eukaryot. Microbiol. (1997) [Pubmed]
  11. Photolabeling of CheR methyltransferase with S-adenosyl-L-methionine (AdoMet). Studies on the AdoMet binding site. Subbaramaiah, K., Simms, S.A. J. Biol. Chem. (1992) [Pubmed]
  12. An approach to the total synthesis of sinefungin. Mock, G.A., Moffatt, J.G. Nucleic Acids Res. (1982) [Pubmed]
  13. Sinefungin and taxol effects on cell cycle and cytoskeleton of Leishmania donovani promastigotes. Moulay, L., Robert-Gero, M., Brown, S., Gendron, M.C., Tournier, F. Exp. Cell Res. (1996) [Pubmed]
  14. Sinefungin shares AdoMet-uptake system to enter Leishmania donovani promastigotes. Phelouzat, M.A., Basselin, M., Lawrence, F., Robert-Gero, M. Biochem. J. (1995) [Pubmed]
  15. Two intertwined methylation activities of the MmeI restriction-modification class-IIS system from Methylophilus methylotrophus. Tucholski, J., Zmijewski, J.W., Podhajska, A.J. Gene (1998) [Pubmed]
  16. Synergism between 9-deazainosine and DL-alpha-difluoromethylornithine in treatment of experimental African trypanosomiasis. Bacchi, C.J., Berens, R.L., Nathan, H.C., Klein, R.S., Elegbe, I.A., Rao, K.V., McCann, P.P., Marr, J.J. Antimicrob. Agents Chemother. (1987) [Pubmed]
  17. Mating ability during chemically induced G1 arrest of cells of the yeast Saccharomyces cerevisiae. Bedard, D.P., Li, A.W., Singer, R.A., Johnston, G.C. J. Bacteriol. (1984) [Pubmed]
  18. Correlation between inhibition of myelin basic protein (arginine) methyltransferase by sinefungin and lack of compact myelin formation in cultures of cerebral cells from embryonic mice. Amur, S.G., Shanker, G., Cochran, J.M., Ved, H.S., Pieringer, R.A. J. Neurosci. Res. (1986) [Pubmed]
  19. Sinefungin as treatment for American Leishmania in sensitive BALB/c and resistant C57BL/6 mice. Avila, J.L., Rojas, T., Monzón, H., Convit, J. Am. J. Trop. Med. Hyg. (1990) [Pubmed]
  20. The antifungal antibiotic sinefungin as a very active inhibitor of methyltransferases and of the transformation of chick embryo fibroblasts by Rous sarcoma virus. Vedel, M., Lawrence, F., Robert-Gero, M., Lederer, E. Biochem. Biophys. Res. Commun. (1978) [Pubmed]
  21. Fate of soluble methionine in African trypanosomes: effects of metabolic inhibitors. Bacchi, C.J., Goldberg, B., Garofalo-Hannan, J., Rattendi, D., Lyte, P., Yarlett, N. Biochem. J. (1995) [Pubmed]
  22. Amoebicidal activity of the antifungal antibiotic sinefungin against Entamoeba histolytica. Ferrante, A., Ljungström, I., Huldt, G., Lederer, E. Trans. R. Soc. Trop. Med. Hyg. (1984) [Pubmed]
  23. Evaluation of sinefungin for the treatment of Trypanosoma (Nannomonas) congolense infections in goats. Zweygarth, E., Schillinger, D., Kaufmann, W., Röttcher, D. Trop. Med. Parasitol. (1986) [Pubmed]
  24. Sinefungin, a potent inhibitor of virion mRNA(guanine-7-)-methyltransferase, mRNA(nucleoside-2'-)-methyltransferase, and viral multiplication. Pugh, C.S., Borchardt, R.T., Stone, H.O. J. Biol. Chem. (1978) [Pubmed]
  25. Differential binding of S-adenosylmethionine S-adenosylhomocysteine and Sinefungin to the adenine-specific DNA methyltransferase M.TaqI. Schluckebier, G., Kozak, M., Bleimling, N., Weinhold, E., Saenger, W. J. Mol. Biol. (1997) [Pubmed]
  26. Ligand-induced conformational states of the cytosine-specific DNA methyltransferase M.HgaI-2. Baldwin, G.S., Kelly, S.M., Price, N.C., Wilson, G.W., Connolly, B.A., Artymiuk, P.J., Hornby, D.P. J. Mol. Biol. (1994) [Pubmed]
  27. Enzyme immunoassay detection of Cryptosporidium parvum inhibition by sinefungin in sporozoite infected HCT-8 enterocytic cells. Gargala, G., Delaunay, A., Favennec, L., Brasseur, P., Ballet, J.J. Int. J. Parasitol. (1999) [Pubmed]
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