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Fifty years of amanitin

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Abstract

Pharmacokinetic studies have provided new insights into humanAmanita poisoning, but it appears to be impossible to treat this intoxication by immunotherapy. New synthetic analogs have revealed structure-activity relationships that were unknown so far. The main toxin, α-amanitin, is in constant use as a tool in molecular biology and in biological research. First experiments have been reported in which amanitin bound to polymers could be internalized into tumor cells via a receptor-mediated endocytosis.

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References

  1. Brembach, U., and Faulstich, H., Epidermal growth factor labeled β-Amanitin Poly-L-ornithine: preparation and evidence for specific cytotoxicity. Biochemistry29 (1990) 6839–6845.

    Article  Google Scholar 

  2. Berner, R., Rudin, W., and Hecker, H., Peritrophic membranes and protease activity in the mid gut of the malaria mosquitoAnophelesstephensi insecta diptera under normal and experimental conditions. J. Ultrastruct. Res.83 (1983) 195–204.

    Article  CAS  PubMed  Google Scholar 

  3. Boege, F., Rohde, W., and Sänger, H. L., In-vitro transcription of viroid RNA into full length copies by RNA dependent RNA polymerase from healthy tomato leaf tissue. Biosci. Rep.2 (1982) 185–194.

    Article  CAS  PubMed  Google Scholar 

  4. Buku, A., Wieland, Th., Bodenmüller, H., and Faulstich, H., Über die Inhaltsstoffe des grünen Knollenblätterpilzes. LVII. Amaninamide, a new toxin ofAmanita virosa mushrooms. Experientia36 (1980) 33–34.

    Article  CAS  PubMed  Google Scholar 

  5. Carlson, D. P., and Ross, J., Human β-globin promoter and coding sequences transcribed by RNA polymerase III. Cell34 (1983) 857–864.

    Article  CAS  PubMed  Google Scholar 

  6. Carlson, D. P., and Ross, J., Alpha-amanitin-insensitive transcription of mouse β-major globin 5′-flanking and structural gene sequences correlates with messenger RNA-expression. Proc. natl Acad. Sci USA81 (1984) 7782–7786.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Cessi, C., and Fiume, L., Increased toxicity of α-amanitin when bound to a protein. Toxicon6 (1969) 309–310.

    Article  CAS  PubMed  Google Scholar 

  8. Cochet-Meilhac, M., Nuret, P., Courvalin, J. C., and Chambon, P., Animal DNA-dependent RNA polymerases. 12. Determination of the cellular number of RNA polymerase B molecules. Biochim. biophys. Acta353 (1974) 185–192.

    Article  CAS  PubMed  Google Scholar 

  9. Faulstich, H., The amatoxins. Progr. molec. subcell. Biol.7 (1980) 88–122.

    Article  CAS  Google Scholar 

  10. Faulstich, H., and Fiume, L., Protein conjugates of fungal toxins, in: Methods of Enzymology. Drug and Enzyme Targeting, pp. 225–237. Eds K. J. Widder and R. Green. Academic Press, London, New York 1985.

    Chapter  Google Scholar 

  11. Faulstich, H., Jahn, W., and Wieland, Th., Silybin inhibition of amatoxin uptake in the perfused rat liver. Arzneim. Forsch. (Drug. Res.)30 (1980) 452–454.

    CAS  Google Scholar 

  12. Faulstich, H., Kirchner, K., and Derenzini, M., Strongly enhanced toxicity of the mushroom toxin α-amanitin by an amatoxin-specific Fab or monoclonal antibody. Toxicon26 (1988) 491–499.

    Article  CAS  PubMed  Google Scholar 

  13. Fiume, L., and Laschi, R., Lesioni ultrastrutturali prodotte nelle cellule parenchimali epatiche dalla phalloidina e dalla α-amanitina. Sperimentale115 (1965) 288–297.

    CAS  PubMed  Google Scholar 

  14. Fiume, L., and Stirpe, F., Decreased RNA content in mouse liver nuclei after intoxication with α-amanitin. Biochim. biophys. Acta123 (1966) 643–645.

    Article  CAS  PubMed  Google Scholar 

  15. Flach, G., Johnson, M. H., Braude, P. R., Taylor, R. A. S., and Bolton, V. N., The transition from maternal to embryonic control in the 2 cell mouse embryo. EMBO J.1 (1982) 681–686.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Flores, R., and Semancik, G. S., Properties of a cell-free system for synthesis of citrus exocortis viroid. Proc. natl Acad. Sci. USA79 (1982) 6285–6288.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Ford, W. W., and Schlesinger, H., On the chemical properties of Amanita-toxin. J. biol. Chem.3 (1907) 279–283.

    Article  Google Scholar 

  18. Giffhorn, S., and Katz, N. R., Glucose-dependent induction of acetyl coenzyme A carboxylase EC-6.4.1.2 in rat hepatocyte cultures. Biochem. J.221 (1984) 343–350.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Hancock, R., and Hughes, M. E. Organization of DNA in the interphase nucleus. Biol. Cell44 (1982) 201–212.

    CAS  Google Scholar 

  20. Harper, M. I., and Monk, M., Evidence for translation of hypoxanthine phosphoribosyl transferase EC-2.4.2.8 enzyme on maternal messenger RNA in early mouse embryos. J. Embryol. exp. Morph.74 (1983) 15–28.

    CAS  PubMed  Google Scholar 

  21. Hatzoglou, M., Adamtziki, E., Margaritis, L., and Sekeris, C. E., Isolation and characterization of nuclear particles containing rapidly labeled heterogeneous RNA and small nuclear RNA in combination with a distinct set of polypeptides of 74000 and 72000 molecular weight. Exp. Cell Res.157 (1985) 227–241.

    Article  CAS  PubMed  Google Scholar 

  22. Kostansek, E. C., Lipscomb, W. N., Yocum, R. R., and Thiessen, W. E., The crystal structure of the mushroom toxin β-amanitin. J. Am. chem. Soc.99 (1977) 1273–1274.

    Article  CAS  PubMed  Google Scholar 

  23. Kunkel, G. R., and Pederson, T., Transcriptional boundaries of U-1 small nuclear RNA. Mol. Cell. Biol.5 (1985) 2332–2340.

    CAS  PubMed  PubMed Central  Google Scholar 

  24. Maharajan, P., Garciula, C., and Maharajan, V., State specific inhibition of sea urchin development by α-amanitin. Invertebr. Reprod. Dev.15 (1989) 13–18.

    CAS  Google Scholar 

  25. Nicoloff, H., Rieger, R., and Russev, G., Mutations in ribosomal DNA 5. Is translocation involvement of Barley nucleolus organizer regions influenced by chromatin architecture? Mutat. Res.181 147–156.

  26. Raab, H. A., Beiträge zur Kenntnis des Giftstoffs der Knollenblätterpilze. Hoppe-Seyler's Z. Physiol. Chem.207 (1932) 157–181.

    Article  CAS  Google Scholar 

  27. Radetzky, R., and Zetsche, K., Effects of specific inhibitors on the coordination of the concentrations of ribulose-bisphosphate-carboxylase subunits and their corresponding mRNAs in the alga Chlorogonium. Planta172 (1987) 38–46.

    Article  CAS  PubMed  Google Scholar 

  28. Savige, W. E., and Fontana, A., A novel synthesis of two thioether derivatives of tryptophan; covalent binding of tryptophan to cysteine sulfhydryl-groups in peptides and proteins. Int. J. Pep. Prot. Res.15 (1980) 102–112.

    Article  CAS  Google Scholar 

  29. Sekeris, C. E., Niessing, J., and Seifart, K. H., Inhibition by α-amanitin of induction of tyrosine transaminase in rat liver by cortisol. FEBS Lett.9 (1970) 41–44.

    Article  Google Scholar 

  30. Spiesmacher, E., Mühlbach, H. P., Tabler, M., and Sänger, H. L., Synthesis of dextro and levo RNA molecules of potato solanum-demissium spindle tuber viroid in isolated nuclei and its impairment by transcription inhibitors. Biosci. Rep.5 (1985) 251–266.

    Article  CAS  PubMed  Google Scholar 

  31. Theologis, A., Huynh, T. V., and Davis, R. W., Rapid induction of specific messenger RNA species by auxin in pea pisum-sativum cultivar alaska epicotyl tissue. J. molec. Biol.183 (1985) 53–68.

    Article  CAS  PubMed  Google Scholar 

  32. Vaisius, A. C., and Wieland, Th., Formation of a single phosphodiester bond by RNA polymerase B from calf thymus is not inhibited by α-amanitin. Biochemistry21 (1982) 3097–3101.

    Article  CAS  PubMed  Google Scholar 

  33. White, J. L., and Brakke, M. K., Protein changes in wheat infected with wheat streak mosaic virus and in barley infected with barley stripe mosaic virus. Physiol. Plant Path.22 (1983) 87–100.

    Article  CAS  Google Scholar 

  34. Wieland, H., and Hallermayer, R., Über die Giftstoffe des Knollenblätterpilzes. VI. Amanitin, das Hauptgift des Knollenblätterpilzes. Liebigs Ann. Chem.548 (1941) 1–18.

    Article  CAS  Google Scholar 

  35. Wieland, Th., Zeitungspapier-Test für Giftpilze. Umschau78 (1978) 611.

    Google Scholar 

  36. Wieland, Th., Peptides of Poisonous Amanita Mushrooms. Ed. A. Rich. Springer, Berlin-Heidelberg-New York 1986.

    Chapter  Google Scholar 

  37. Wieland, Th., 50 Jahre Phalloidin. Naturwissenschaften74 (1987) 367–373.

    Article  CAS  PubMed  Google Scholar 

  38. Wieland, Th., and Fischer, E., Über Elektrophorese auf Filtrierpapier. Naturwissenschaften35 (1948) 29.

    Google Scholar 

  39. Wieland, Th., and Fahrmeier, A., Oxydation und Reduktion an der γ, δ-Dihydroxyisoleucin-Seitenkette des O-Methyl-α-amanitins. Methyl-aldoamanitin, ein ungiftiges Abbauprodukt. Liebigs Ann. Chem.736 (1970) 95–99.

    Article  CAS  Google Scholar 

  40. Wieland, Th., and Faulstich, H., Amatoxins, Phallotoxins, Phallolysin and Antamanide: the biologically active components of poisonous Amanita mushrooms. Cr. Rev. Biochem.5 (1978) 185–260.

    Article  CAS  Google Scholar 

  41. Wieland, Th., Götzendörfer, Ch., Dabrowski, J., Lipscomb, W. N., and Shoham, S., Unexpected similarity of the structures of the weakly toxic amanitin (S)-sulfoxide and the highly toxic (R)-sulfoxide and sulfone as revealed by proton nuclear magnetic resonance and X-ray analysis. Biochemistry22 (1983) 1264–1271.

    Article  CAS  PubMed  Google Scholar 

  42. Yoshikawa, N., and Takahashi, T., Studies on pathogenesis in viroid infections. 15. Inhibition of hop stunt viroid replication by α-amanitin. Z. Pflanzenk. Pflanzenschutz93 (1986) 62–71.

    CAS  Google Scholar 

  43. Zanotti, G., Birr, Ch., and Wieland, Th., Analogs of amanin: synthesis of Ile3-amaninamide and its diastereoisomeric (S)-sulfoxide. Int. J. Pept. Prot. Res.18 (1981) 162–168.

    Article  CAS  Google Scholar 

  44. Zanotti, G., Wieland, Th., Benedetti, E., di Blasio, B., Pavone, V., and Pedone, C., Structure toxicity relationships in the amatoxin series. Synthesis of S-deoxy (R)-hydroxy-Ile3-amaninamide, its crystal and molecular structure and inhibitory efficiency. Int. J. Pept. Prot. Res.34 (1989) 222–228.

    Article  CAS  Google Scholar 

  45. Zanotti, G., Wieland, Th., d'Auria, G., Paolillo, L., and Trivellone, E., S-deoxo-Abu1, Ile3-amaninamide, an inactive amatoxin analogue. Int. J. Pept. Prot. Res.35 (1990) 263–270.

    Article  CAS  Google Scholar 

  46. Zanotti, G., and Wieland, Th., unpublished.

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Wienland, T., Faulstich, H. Fifty years of amanitin. Experientia 47, 1186–1193 (1991). https://doi.org/10.1007/BF01918382

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