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Chemical Compound Review

TOYOCAMYCIN     5-amino-9-[(2R,3R,4S,5R)-3,4- dihydroxy-5...

Synonyms: Siromycin, Vengicide, Toyokamycin, Naritheracin, Unamycin-B, ...
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Disease relevance of TOYOCAMYCIN

  • Effect of toyocamycin on the synthesis of the 70S RNA of a murine retrovirus [1].
  • The murine Eveline cell line chronically infected by Friend virus was treated with Toyocamycin (TMC), an adenosin analog and the virions released in the presence of the drug were examined for their RNA [1].
  • Genetic markers in mouse teratocarcinoma cells. Selection and partial characterization of mutants resistant to toyocamycin, DRB and podophyllotoxin [2].
  • The present study shows that the antitumor agent toyocamycin (4-amino-5-cyano-7beta-D-ribofuranosylpyrrolo(2-3d)pyrimidine) affects rRNA transcription in Ehrlich ascites cells [3].
  • A number of 7-substituted 4-aminopyrrolo[2,3-d]pyrimidine-5-carbonitrile, -5-carboxamide, and -5-thiocarboxamide derivatives related to the nucleoside antibiotics toyocamycin and sangivamycin were prepared and tested for their activity against human cytomegalovirus (HCMV) and herpes simplex virus type-1 (HSV-1) [4].

Psychiatry related information on TOYOCAMYCIN

  • Starting with commercially available tetracyanoethylene, we describe a more efficient and higher yielding synthesis of toyocamycin with regards to convenience, overall yield, and total reaction time than those syntheses previously reported [5].

High impact information on TOYOCAMYCIN

  • RH-II/Gu mostly relocalized to the nucleoli within 15 min after toyocamycin was withdrawn; only partial relocalization of nucleophosmin/B23 occurred 40 h after removal of the drug [6].
  • The marked loss of cell viability caused by toyocamycin correlates with its effect on rRNA processing, while the slow inhibition of protein synthesis appears to be secondary to the loss of ribosome synthesis [7].
  • An important proof of principle for that system was provided by demonstrating the ability of one specific small molecule inhibitor of RNA self-cleavage, toyocamycin, to control gene expression in vitro and vivo [8].
  • These measurements show that the most potent inhibitors of rhodopsin kinase, sangivamycin and toyocamycin, occur in solution preferentially in the anti conformation [9].
  • On the other hand, inhibition of rRNA processing by the nucleoside analogs 5-fluoruridine and toyocamycin decreases the rate of 45S rRNA transcription in serum-stimulated cells but has no effect on the values found in resting cultures [10].

Chemical compound and disease context of TOYOCAMYCIN


Biological context of TOYOCAMYCIN

  • The inhibitory effects on L-1210 cell growth were also determined, and toyocamycin (ID50 = 0.006 micrograms/mL) was found to be the most active compound [13].
  • Transfection of an adenosine-kinase-deficient mutant (selected for resistance to the adenosine analog toyocamycin) of Chinese hamster ovary cells with a plasmid containing the cloned adenosine kinase cDNA, leads to regaining of adenosine kinase activity in the transformed cell [14].
  • Several Toyocamycin (4) analogues were examined for their ability to inhibit HCV RNA in a replicon assay [15].

Anatomical context of TOYOCAMYCIN


Associations of TOYOCAMYCIN with other chemical compounds


Gene context of TOYOCAMYCIN

  • The adenosine kinase transformants also simultaneously lost their toyocamycin resistance and became similarly sensitive to the analog as the parental wild-type Chinese hamster ovary cells [14].
  • Toyocamycin does not affect RNA polymerase I (RNA nucleotidyltransferase EC activity when added to in vitro assay systems derived from cells grown in complete or in amino acid deficient media [3].
  • The DNA fragment -111 to +1 bp from the cap site was sufficient to drive toyocamycin-activated transcription of p16/luciferase reporter [22].
  • High-performance liquid chromatography (HPLC) and FAB mass spectrometry were used to monitor toyocamycin at all stages of strain development, fermentation and recovery [23].
  • Pyrrolopyrimidine nucleosides. Part X. Synthesis of certain 4,5-disubstituted 7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidines related to toyocamycin and sangivamycin [24].

Analytical, diagnostic and therapeutic context of TOYOCAMYCIN


  1. Effect of toyocamycin on the synthesis of the 70S RNA of a murine retrovirus. Larsen, C.J., Mauchauffé, M., Hamelin, R., Péraudeau, L., Fedele, L., Tavitian, A. Nucleic Acids Res. (1979) [Pubmed]
  2. Genetic markers in mouse teratocarcinoma cells. Selection and partial characterization of mutants resistant to toyocamycin, DRB and podophyllotoxin. Gupta, R.S., Hodgson, M. Exp. Cell Res. (1981) [Pubmed]
  3. Regulation of ribosomal RNA synthesis in mammalian cells: effect of toyocamycin. Iapalucci-Espinoza, S., Cereghini, S., Franze-Fernández, M.T. Biochemistry (1977) [Pubmed]
  4. Synthesis of non-nucleoside analogs of toyocamycin, sangivamycin, and ++thiosangivamycin: influence of various 7-substituents on antiviral activity. Renau, T.E., Wotring, L.L., Drach, J.C., Townsend, L.B. J. Med. Chem. (1996) [Pubmed]
  5. Total synthesis of the naturally occurring antibiotic toyocamycin using new and improved synthetic procedures. Porcari, A.R., Townsend, L.B. Nucleosides Nucleotides (1999) [Pubmed]
  6. Effects of cytotoxic drugs on translocation of nucleolar RNA helicase RH-II/Gu. Perlaky, L., Valdez, B.C., Busch, H. Exp. Cell Res. (1997) [Pubmed]
  7. Comparison of the cellular and RNA-dependent effects of sangivamycin and toyocamycin in human colon carcinoma cells. Cohen, M.B., Glazer, R.I. Mol. Pharmacol. (1985) [Pubmed]
  8. Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries. Yen, L., Magnier, M., Weissleder, R., Stockwell, B.R., Mulligan, R.C. RNA (2006) [Pubmed]
  9. Nucleoside inhibitors of rhodopsin kinase. Palczewski, K., Kahn, N., Hargrave, P.A. Biochemistry (1990) [Pubmed]
  10. Transcription of ribosomal RNA is differentially controlled in resting and growing BALB/c 3T3 cells. Perrone-Bizzozero, N., Iapalucci-Espinoza, S., Medrano, E.E., Franze-Fernández, M.T. J. Cell. Physiol. (1985) [Pubmed]
  11. Regulation of rRNA synthesis and processing in animal cells. Effect of nucleoside analogues. Iapalucci-Espinoza, S., Franze-Fernandez, M.T. Biochem. J. (1982) [Pubmed]
  12. Inhibition of ribosomal RNA maturation in Friend erythroleukemia cells by 5-fluorouridine and toyocamycin. Hadjiolova, K.V., Naydenova, Z.G., Hadjiolov, A.A. Biochem. Pharmacol. (1981) [Pubmed]
  13. Antiviral activity of C-5 substituted tubercidin analogues. Bergstrom, D.E., Brattesani, A.J., Ogawa, M.K., Reddy, P.A., Schweickert, M.J., Balzarini, J., De Clercq, E. J. Med. Chem. (1984) [Pubmed]
  14. Cloning and characterization of cDNA for adenosine kinase from mammalian (Chinese hamster, mouse, human and rat) species. High frequency mutants of Chinese hamster ovary cells involve structural alterations in the gene. Singh, B., Hao, W., Wu, Z., Eigl, B., Gupta, R.S. Eur. J. Biochem. (1996) [Pubmed]
  15. Synthesis of pyrrolo[2,3-d]pyrimidine nucleoside derivatives as potential anti-HCV agents. Varaprasad, C.V., Ramasamy, K.S., Girardet, J.L., Gunic, E., Lai, V., Zhong, W., An, H., Hong, Z. Bioorg. Chem. (2007) [Pubmed]
  16. Genetic and biochemical studies on mutants of CHO cells resistant to 7-deazapurine nucleosides: differences in the mechanisms of action of toyocamycin and tubercidin. Gupta, R.S., Mehta, K.D. Biochem. Biophys. Res. Commun. (1984) [Pubmed]
  17. Synthesis and cytotoxicity of 4'-C- and 5'-C-substituted toyocamycins. Gunic, E., Girardet, J.L., Pietrzkowski, Z., Esler, C., Wang, G. Bioorg. Med. Chem. (2001) [Pubmed]
  18. Induction of apoptosis in human leukemia cells by MCS-C2 via caspase-dependent Bid cleavage and cytochrome c release. Kim, M.K., Cho, Y.H., Kim, J.M., Chun, M.W., Lee, S.K., Lim, Y., Lee, C.H. Cancer Lett. (2005) [Pubmed]
  19. Nucleophosmin/B23 (NPM) oligomer is a major and stable entity in HeLa cells. Chan, P.K., Chan, F.Y. Biochim. Biophys. Acta (1995) [Pubmed]
  20. Relationship between cytotoxicity and conversion of thiosangivamycin analogs to toyocamycin analogs in cell culture medium. Renau, T.E., Lee, J.S., Kim, H., Young, C.G., Wotring, L.L., Townsend, L.B., Drach, J.C. Biochem. Pharmacol. (1994) [Pubmed]
  21. The N-terminal half of NPM dissociates from nucleoli of HeLa cells after anticancer drug treatments. Chan, P.K., Bloom, D.A., Hoang, T.T. Biochem. Biophys. Res. Commun. (1999) [Pubmed]
  22. Induction of p16/INK4a gene expression and cellular senescence by toyocamycin. Kurihara, Y., Egawa, K., Kunimoto, S., Takeuchi, T., Nose, K. Biol. Pharm. Bull. (2002) [Pubmed]
  23. Fast atom bombardment mass spectrometry and tandem mass spectrometry in antibiotics: identification of nucleoside antitumor antibiotic toyocamycin in fermentation broth. Tondeur, Y., Shorter, M., Gustafson, M.E., Pandey, R.C. Biomed. Mass Spectrom. (1984) [Pubmed]
  24. Pyrrolopyrimidine nucleosides. Part X. Synthesis of certain 4,5-disubstituted 7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidines related to toyocamycin and sangivamycin. Hinshaw, B.C., Leonoudakis, O., Schram, K.H., Townsend, L.B. J. Chem. Soc. Perkin Trans. I (1975) [Pubmed]
  25. Electrochemical study of the reduction of toyocamycin and sangivamycin in aqueous media. Bojarska, E., Pawlicki, K., Czochralska, B. Acta Biochim. Pol. (1987) [Pubmed]
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