Antibiotics pp 190-210 | Cite as

Daunomycin and Related Antibiotics

  • A. Di Marco


Daunomycin (Da) is a metabolite of Streptomyces peucetius (Grein et al., 1963) which strongly inhibits a variety of experimental tumors (Di Marco et al., 1964b). The antibiotic substance is a glycoside (Hydrochloride: C27H29NO10 · HC1) which by acid hydrolysis yields an aglycone, daunomycinone (Arcamone et al., 1964b) and a new aminosugar, daunosamine (Arcamone et al., 1964a). Dubost et al. (1963) have also described an antibiotic, rubidomycin, whose physicochemical characteristics correspond to those of daunomycin. Daunomycin is closely related to the anthracyclines. Following Brockmann’s suggestion (1963), those antibiotics that contained a tetrahydrotetracenquinone chromophore linked to a sugar should all be included in the anthracycline group. The chromophores of such antibiotics have different substituents on the nucleus (Fig. 1 and Table 1).


HeLa Cell Mitotic Index Sedimentation Coefficient Bone Marrow Aplasia Ehrlich Carcinoma 
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  1. Arcamone, F., G. Cassinelli, P. Orezzi, G. Franceschi, and R. Mondelli: Daunomycin. II. The structure and stereochemistry of daunosamine. J. Am. Chem. Soc. 86, 5335 (1964a).CrossRefGoogle Scholar
  2. Arcamone, F., G. Franceschi, P. Orezzi, G. Cassinelli, W. Barbieri, and R. Mondelli: Daunomycin. The structure of daunomycinone. J. Am. Chem. Soc. 86, 5334 (1964b).CrossRefGoogle Scholar
  3. Asheshov, I. N., and J. J. Gordon: Rutilantin: an Antibiotic substance with anti-phage activity. Biochem. J. 81, 101 (1961).PubMedGoogle Scholar
  4. Barbieri, P., A. DI Marco, R. Mazzoleni, M. Menozzi e A. Sanfilippo: Azione della Daunomicina sul metabolismo degli acidi nucleici nell’ E. coli B. Giorn. Microbiol. 19, 71 (1964).Google Scholar
  5. Bertazzoli, C., e T. Chieli: Studio tossifarmacologico della Daunomicina. Personal communication 1964.Google Scholar
  6. Bollum, F. I.: Primers in Dna polymerase reaction. In: Progress in Nucleic Acid Research (J. H. Davidson and W. E. Cohen, ed.). Academic Press 1963.Google Scholar
  7. Brindle, S. A., N. A. Giuffre, B. J. Amrein, R. C. Millonig, and D. Perlman: Antibiotic sensitivity of Ehrlich ascites cells grown in tissue culture. In: M. Finland and G. M. Savage, Antimicrobial agents and chemotherapy, p. 159. Am. Soc. Microbiol. 1961.Google Scholar
  8. Brockmann, H., and W. Lenk: Pyrromycin. Chem. Ber. 93, 1904 (1959).CrossRefGoogle Scholar
  9. Brockmann, H.: Die Actinomycine Jerstchritte. Chem. Org. Naturvt. 18, 1 (1960). Brockmann, H., u. E. Spoller: Zur Konstitution des Rhodomycins A. Naturwissenschaften 48, 716 (1961).Google Scholar
  10. Brockmann, H., u. T. Wachneldt: Eine neue Gruppe von Rhodomycinen. Naturwissenschaften 48, 717 (1961).CrossRefGoogle Scholar
  11. Brockmann, H., P. Boldt u. J. Niemeyer: Beta-Rhodomycinon and Gamma-Rhodomycinon. Chem. Ber. 96, 1356 (1963).CrossRefGoogle Scholar
  12. Calendi, E., A. DI Marco, M. Reggiani, B. Scarpinato, and L. Valentini: On physico-chemical interactions between daunomycin and nucleic acids. Biochim. et Biophys. Acta 103, 25 (1965).Google Scholar
  13. Calendi, E., and B. Scarpinato: Personal communication 1965.Google Scholar
  14. Costa, G., e G. Astaldi: Effetto della Daunomicina sulla attività proliferativa di cellule staminali ottenute in coltura da sangue umano normale. Tumori 50, 477 (1964).PubMedGoogle Scholar
  15. Davis, B. D., and E. S. Mingigli: Mutants of Escherichia coli requiring methionine or vitamin B12. J. Bacteriol. 60, 17 (1950).PubMedGoogle Scholar
  16. DI Marco, A., M. Gaetani, L. Dorigotti, M. Soldati e O. Bellini: Studi sperimentali sull’attività antineoplastica del nuovo antibiotico Daunomicina. Tumori 49, 203 (1963 a).Google Scholar
  17. DI Marco, A., M. Soldati, A. Fioretti e T. Dasdia: Ricerche sull’attività della Daunomicina su cellule normali e neoplastiche coltivate in vitro. Tumori 49, 235 (1963 b).Google Scholar
  18. DI Marco, A., M. Gaetani, L. Dorigotti, M. Soldati, and O. Bellini: Daunomycin: a new antibiotic with antitumor activity. Cancer Chemoth. Rep. 38, 31 (1964 a).Google Scholar
  19. DI Marco, A., M. Gaetani, P. Orezzi, B. Scarpinato, R. Silvestrini, M. Soldati, T. Dasdia, and L. Valentini: Daunomycin, a new antibiotic of the rhodomycin group. Nature 201, 706 (1964b).CrossRefGoogle Scholar
  20. DI Marco, A., M. Soldati, A. Fioretti, and T. Dasdia: Activity of daunomycin, a new antitumor antibiotic, on normal and neoplastic cells grown in vitro. Cancer Chemoth. Rep. 38, 39 (1964c).Google Scholar
  21. DI Marco, A., R. Silvestrini, T. Dasdia, and S. DI Marco: Nucleolar and chromosomal origin of nuclear Rna and its passage to cytoplasm. Riv. ital. istochimica (in press) (1965 a).Google Scholar
  22. DI Marco, A., R. Silvestrini, S. DI Marco, and T. Dasdia: Inhibiting effect of the new cytotoxic antibiotic daunomycin on nucleic acids and mitotic activity of HeLa cells. J. Cell Biol. 27, 545 (1965 b).Google Scholar
  23. DI Marco, A., L. Dorigotti, and M. Gaetani: Unpublished data (1965C).Google Scholar
  24. Dubost, M., P. Ganter, R. Maral, L. Ninet, S. Pinnert, J. Preud-Homme et G. H. Werner: Un nouvel antibiotique à propriétés antitumorales. Compt. Rend. 257, 1813 (1963).Google Scholar
  25. Ettlinger, L., E. Gaumann, R. Hutter, W. Keller-Schlierein, F. Kradolfer, L. Neipp, V. Prelog, P. Reusser, and H. Zarner: Cinerubine. Chem. Ber. 92, 1867 (1959).CrossRefGoogle Scholar
  26. Fuller, W.: Personal communication 1965.Google Scholar
  27. Gaetani, M.: Personal communication 1965.Google Scholar
  28. Georgiev, G. P., O. P. Samarina, M. I. Lerman, M. N. Smirnov, and A. N. Severtzov: Biosynthesis of messenger and ribosomal nucleic acids in the nucleolochromosomal apparatus of animal cells. Nature 200, 1291 (1963).PubMedCrossRefGoogle Scholar
  29. Goldberg, I. H., M. Rabinowitz, and E. Reich: Basis of actinomycin action. I Dna binding and inhibition of Rna polymerase synthetic reactions by actinomycin. Proc. Natl. Acad. Sci. U.S. 48, 2094 (1962).CrossRefGoogle Scholar
  30. Goldin, A.: Personal communication 1965.Google Scholar
  31. Grein, A., C. Spalla, A. DI Marco e G. Canevazzi: Descrizione e classificazione di un attinomicete (Streptomyces peucetius sp. nova) produttore di una sostanza ad attività antitumorale: la daunomicina. Giorn. Microbiol. 11, 109 (1963).Google Scholar
  32. Hartmann, G., H. Goller, K. Koschel, W. Kersten u. H. Kersten: Hemmung der Dna-abhängigen Rna- and Dna-Synthese durch Antibiotica. Biochem. Z. 341, 126 (1964).PubMedGoogle Scholar
  33. Hiatt, H. H.: A rapidly labeled Rna in rat liver nuclei. J. Mol. Biol. 5, 217 (1962).PubMedCrossRefGoogle Scholar
  34. Hurwitz, J., J. J. Furth, M. Malamy, and M. Alexander: The role of deoxyribonucleic acid synthesis. Iii. The inhibition of enzymatic synthesis of ribonucleic acid and deoxyribonucleic acid by actinomycin D and proflavin. Proc. Natl. Acad. Sci. U.S. 48, 1222 (1962).CrossRefGoogle Scholar
  35. Kersten, W., H. Kersten, and W. Szybalski: Physico-chemical properties of Complexes between Dna and antibiotics which affect Rna synthesis. Biochemistry (in press) (1965 a).Google Scholar
  36. Kersten, W., and H. Kersten: Die Bindung von Daunomycin, Cinerubin and Chromomycin A3 an Nucleinsäuren. Biochem. Z. 341, 174 (1965b).PubMedGoogle Scholar
  37. Lerman, L.: Structural considerations in the interaction of Dna and acridines. J. Mol. Biol. 3, 18 (1961).PubMedCrossRefGoogle Scholar
  38. Lerman, L.: Acridine mutagen and Dna structure. J. Cellular Comp. Physiol. 64, Suppl. 1, 1 (1964).CrossRefGoogle Scholar
  39. Liersch, M., u. G. Hartmann: Die Bindung von Proflavin and Actinomycin and Desoxyribonnucleinsäure. Biochem. Z. 340, 390 (1964).PubMedGoogle Scholar
  40. Lichtfield, J. T., and F. WilcoxoN: A semplified method of evaluating dose-effect experiments. J. Pharmacol. Exptl. Therap. 96, 99 (1949).Google Scholar
  41. Loustalot, P., P. A. Desaulles, and R. Meier: Characterization of the specificity of action of tumor-inhibiting compounds. Ann. N.Y. Acad. Sci. 76, 838 (1958).PubMedCrossRefGoogle Scholar
  42. Mitscher, L. A., W. Mccrae, W. W. Andres, J. A. Larry, and N. Boleanos: Ruticulomycins, new anthracycline antibiotics. J. Pharm. Sci. 53, 1139 (1964).PubMedCrossRefGoogle Scholar
  43. Ollis, W. D., I. O. Sutherland, and J. J. Gordon: Rutilantinone. Tetrahedron Letters 16, 17 (1959).CrossRefGoogle Scholar
  44. Ollis, W. D., and I. O. Sutherland: A new family of antibiotics. In: W. D. Ollis, Chemistry of natural phenolic compounds, p. 212. Oxford: Pergamon Press 1961.Google Scholar
  45. Parisi, B., and A. Soller: Studies on the antiphage activity of daunomycin. Giorn. Microbiol. 12, 183 (1964).Google Scholar
  46. Perry, R. R.: Selective effects of actinomycin D in the intracellular distribution ofGoogle Scholar
  47. Rna synthesis in tissue culture cells. Exptl. Cell Research 29, 400 (1963).CrossRefGoogle Scholar
  48. Reich, E.: In: D. Ward, E. Reich. and I. H. Goldberg, Characterization of polynucleotides with drugs. New York (1965).Google Scholar
  49. RuscoNl, A.: Personal communication 1965.Google Scholar
  50. RuscoNI, A., e E. Calendi: Azione della Daunomicina sulla sintesi nucleica in cellule di epatoma. Tumori 50, 261 (1964).Google Scholar
  51. RuscoNl, A., e E. Calendi: Personal Communication 1965.Google Scholar
  52. Sanfilippo, A., e R. Mazzoleni: Attività antifagica dell’antibiotico Daunomicina. Giorn. Microbiol. 12, 83 (1964).Google Scholar
  53. Scarpinato, B.: Personal communication 1964.Google Scholar
  54. Silvestrini, R., A. DI Marco, S. DI Marco e T. Dasdia: Azione della Daunomicina sul metabolismo degli acidi nucleici di cellule normali e neoplastiche coltivate in vitro. Tumori 49, 399 (1963).PubMedGoogle Scholar
  55. Strelitz, F., H. Flon, U. Weiss, and I. N. Asheshou • Aklavin, an antibiotic substance with antiphage activity. J. Bacteriol 72, 90 (1956).Google Scholar
  56. Tulinsky, A.: The structure of isoquinocycline A. A. X-ray crystallographic determination. J. Am. Chem. Soc. 86, 5368 (1964).CrossRefGoogle Scholar
  57. Ward, D., E. Reich, and I. H. Goldberg: Base specificity in the interaction of poly-nucleotides with antibiotic drugs. Science 149, 1259 (1965).PubMedCrossRefGoogle Scholar

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© Springer-Verlag Berlin Heidelberg 1967

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