Skip to main content
SpringerLink
Log in

Streptonigrin

  • Chapter
Mechanism of Action of Antieukaryotic and Antiviral Compounds

Part of the book series: Antibiotics ((1512,volume 5 / 2))

Abstract

Streptonigrin (Fig. 1), a metabolite produced by Streptomyces flocculus, was first isolated by Rao and Cullen (1959–60). Its activity as a broad spectrum antibiotic was summarized in a previous review (Bhuyan, 1967). A method for the biological assay of streptonigrin in biological fluids based on its antibiotic activity against Bacillus subtilis ATCC6633 has been developed by Pittillo and Woolley (1974). Exposure to streptonigrin caused a first-order decline in the viability of bacteria, implying that only one hit per cell is required for lethality (Levine and Borthwick, 1963 a). Streptonigrin is also an excellent inducer of bacteriophage production in lysogenic bacteria while inhibiting the net synthesis of host DNA (Levine and Borthwick, 1963 a; Muschel and Schmoker, 1966). A marked increase in genetic recombination was observed during a mixed bacteriophage infection in presence of the drug (Levine and Borthwick, 1963 b).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Antipov, I.G., Navitsky, V.V., Goldberg, E.D.: Myeloinhibitory effect of some antitumor antibiotics and its comparative estimation. Antibiotiki 20, 897–902 (1975)

    PubMed  CAS  Google Scholar 

  • Baumanis, E.A., Elksnite, J.E., Liepinia, V.A.: Effect of antibiotic preparation on the enzymes of serotonin metabolism in the liver of mice. Vopr. Onkol. 19, 36–39 (1973)

    PubMed  CAS  Google Scholar 

  • Bhuyan, B.K.: Phleomycin, xanthomycin, streptonigrin, nogalomycin and aurantin. In: Antibiotics, mechanism of action. Gottlieb, D., Shaw, P.D. (eds.), Vol. I, pp. 175–176. Berlin, Heidelberg, New York: Springer 1967

    Google Scholar 

  • Brazhnikova, M.G., Ponomarenko, V.I., Kovsharova, I.N., Kruglyak, E.B., Proshlyakova, V.V.: Study of bruneomycin produced by Act. Albus var. bruneomycini, and its identification with streptonigrin. Antibiotiki 13, 99–102 (1968)

    PubMed  CAS  Google Scholar 

  • Chaube, S., Kuffer, F.R., Murphy, M.L.: Comparative teratogenic effects of streptonigrin (NSC-45383) and its derivates in the rat. Cancer Chemother. Rep. 53, 23–31 (1969)

    PubMed  CAS  Google Scholar 

  • Chirigos, M.A., Luber, E., March, R., Pettigrew, H.: Antiviral chemotherapeutic assay with Friend leukemia virus in mice. Cancer Chemother. Rep. 45, 29–33 (1965)

    PubMed  CAS  Google Scholar 

  • Chirigos, M.A., Pearson, J.W., Papas, T.S., Woods, H.B., Jr., Spahn, G.: Effect of streptonigrin (NSC-45383) and analogs on oncorna replication and DNA polymerase. Cancer Chemother. Rep. 57, 305–309 (1973a)

    PubMed  CAS  Google Scholar 

  • Chirigos, M.A., Pearson, J., Spahn, G., Rutman, R.: Current studies on oncorna virus therapy. Bibl. Haematol. 39, 1208–1219 (1973b)

    PubMed  CAS  Google Scholar 

  • Chiu, Y.Y., Lipscomb, W.N.: Molecular and crystal structure of streptonigrin. J. Am. Chem. Soc. 97, 2525–2530 (1975)

    Article  PubMed  CAS  Google Scholar 

  • Cohen, M.M.: Thee specific effects of streptonigrin activity on human chromosomes in culture. Cytogenetics 2, 271–279 (1963)

    Article  Google Scholar 

  • Cohen, M.M.L: The interaction of various drugs with human chromosomes. Can. J. Genet. Cytol. 11, 1–24 (1969)

    PubMed  CAS  Google Scholar 

  • Cohen, M.M., Shaw, M.W., Craig, A.P.: The effects of streptonigrin on cultured human leukocytes. Proc. Natl. Acad. Sci. USA 50, 16–24 (1963)

    Article  PubMed  CAS  Google Scholar 

  • Cone, R., Hasan, S.K., Lowan, J.W., Morgan, A.R.: The mechanism of the degradation of DNA by streptonigrin. Can. J. Biochem. 54, 219–223 (1976)

    Article  PubMed  CAS  Google Scholar 

  • Driscoll, J.S., Hazard, G.F., Jr., Wood, H.B., Jr., Goldin, A.: Structure-antitumor activity relationships among quinone derivatives. Cancer Chemother. Rep. 4, (Pt 2, No 2), 1–362 (1974)

    CAS  Google Scholar 

  • Dudnik. J.V.: Induction of lysogenic Micrococcus lysodiekticus by antibiotics with the ability to affect DNA synthesis. Antibiotiki 2, 112–117 (1965)

    Google Scholar 

  • Dudnik, J.V., Gause, G.G.: Mechanism of bruneomycin action. Fed. Proc. 25, 1109–1112 (1966)

    CAS  Google Scholar 

  • Dudnik, J.V., Netyksa, E.M., Varik, O.Y.: Increased antibacterial effect of bruneomycin and sibiromycin in cultures with impaired reparation of DNA. Antibiotiki 16, 487–491 (1971)

    CAS  Google Scholar 

  • Dudnik, J.V., Gause, G.G., Karpov, V.L., Kozmyan, L.I., Padron, F.: On interaction in vitro of bruneomycin (streptomycin) with DNA. Antibiotiki 18, 968–973 (1973)

    PubMed  CAS  Google Scholar 

  • Ebert, P.S., Chirigos, M.A., Ellsworth, P.A.: Differential response of Friend leukemia virus and lactate dehydrogenase virus to chemotherapy and in vitro neutralization. Cancer Res. 28, 363–367 (1968)

    PubMed  CAS  Google Scholar 

  • Ebringer, L.: Are plastids derived from prokaryotic microorganisms? Action of antibiotics on chloroplasts of Euglena gracilus. J. Gen. Microbiol. 71, 35–52 (1972)

    PubMed  CAS  Google Scholar 

  • Furusawa, E., Furusawa, S., Lee, J.V.B., Petanavanich, S.: Therapeutic activity of pretazettine, a narcissus alkaloid on Rauscher leukemia ; comparison with tazettine and streptonigrin. Proc. Soc. Exp. Biol. Med. 152, 186–191 (1976)

    PubMed  CAS  Google Scholar 

  • Gause, G.G., Jr., Mikhailov, V.S.: State of DNA synthesizing system in isolated mitochondria from the mature egg of the loach (Misgurnus fossilis). Biochem. Biophys. Acta 324, 189–198 (1973)

    PubMed  CAS  Google Scholar 

  • Giraldi, A., Carco, F.P., Giraldi, M., Novati, M.: Antimitotic activity of streptonigrin. G. Ital. Chemioter. 14, 13–19 (1967)

    PubMed  CAS  Google Scholar 

  • Goldberg, E.D., Salnik, G. A.: Bruneomycin effect on energy metabolism of liver tissue in experiment. Antibiotiki 20, 66–71 (1975)

    CAS  Google Scholar 

  • Gregory, E.M., Fridovich, I.: Oxygen toxicity and the Superoxide dismutase. J. Bacteriol. 114, 1193–1197(1973)

    PubMed  CAS  Google Scholar 

  • Hassan, H.M., Fridovich, I.: Enzymatic defenses against the toxicity of oxygen and of streptonigrin in E. coli J. Bacteriol. 129, 1574–1583 (1977)

    PubMed  CAS  Google Scholar 

  • Hays, E.F.: Metabolic inhibitors and viral lymphomagenesis in thymic grafts. J. Natl. Cancer Inst. 53, 561–566 (1974)

    PubMed  CAS  Google Scholar 

  • Hochstein, P., Laszlo, J., Miller, D.: A unique, dicumarol-sensitive, non-phosphorylating oxidation of DPNH and TPNH catalyzed by streptonigrin. Biochem. Biophys. Res. Commun. 19,289–295 (1965)

    Article  PubMed  CAS  Google Scholar 

  • Ishizu, K., Dearman, H.H., Huang, M.T., White, J.R.: Electron paramagnetic resonance observation on biogenic semiquinone and 5-methyl phenylphenazinum radicals. Biochem. Biophys. Acta 165, 283–285 (1968)

    Article  PubMed  CAS  Google Scholar 

  • Iyer, V.N., Szybalski, W.: Mitomycins and porfiromycin: chemical mechanism of activation and cross-linkeng of DNA. Science 145, 55–58 (1964)

    Article  PubMed  CAS  Google Scholar 

  • Jagiello, G.: Streptonigrin effect on the first meiotic metaphase of the mouse egg. Science 157, 453–454 (1967)

    Article  PubMed  CAS  Google Scholar 

  • Kihlman, B.A.: The production of chromosomal aberrations by streptonigrin in Vicia faba. Mutat. Res. 1, 54–62 (1964)

    Article  Google Scholar 

  • Kihlman, B.A., Odmark, G.: Deoxyribonucleic acid synthesis and the production of chromosomal aberrations by streptonigrin, 8-ethoxycaffeine and 1,3,7,9-tetramethyluric acid. Mutat. Res. 2, 494–505 (1965)

    Article  PubMed  CAS  Google Scholar 

  • Kremer, W.B., Laszlo, J.: Biochemical effects of the methyl ester of streptonigrin. Biochem. Pharmacol. 15, 1111–1118(1966)

    Article  PubMed  CAS  Google Scholar 

  • Kremer, W.B., Laszlo, J.: Comparison of biochemical effects of isopropylidine azastreptonigrin (NSC-62709) with streptonigrin (NSC-45383). Cancer Chemother. Rep. 52, 19–24 (1967)

    Google Scholar 

  • Levine, M., Borthwick, M.: The action of streptonigrin on bacterial DNA metabolism and on induction of phage production in lysogenic bacteria. Virology 21, 568–574 (1963a)

    Article  PubMed  CAS  Google Scholar 

  • Levine, M., Borthwick, M.: The action of streptonigrin on genetic recombination between bacteriophages. Proc. 11th Int. Congr. Genet., Netherlands: The Hague 1963b

    Google Scholar 

  • Lown, J.W., Sim, S.K.: Studies related to antitumor antibiotics. Part VIII Cleavage of DNA by streptonigrin analogues and the relationship to antineoplastic activity. Can. J. Biochem. 54, 446–52 (1976)

    Article  PubMed  CAS  Google Scholar 

  • Mcbride, T.J., Oleson, J.J., Woolf, D.: The activity of streptonigrin against the Rauscher murine leukemia virus in vivo. Cancer Res. 26, 727–732 (1966)

    PubMed  CAS  Google Scholar 

  • Mikhailov, V.S., Gause, G.G.: The DNA-synthesizing system of isolated mitochondria of unfertilized loach eggs and its artificial activation in vitro by the antibiotic bruneomycin. Mol. Biol. 8, 108–118 (1974)

    CAS  Google Scholar 

  • Mikhailov, V.S., Gause, G.G.: Repair of damage caused by bruneomycin to DNA in isolated mitochondria of mature loach oocytes. Dokl. Akad. Nauk. SSSR 229, 1477–1480 (1976)

    PubMed  CAS  Google Scholar 

  • Miller, D.S., Laszlo, J., McCarty, K.S., Guild, W.R., Hochstein, P.: Mechanism of action of streptonigrin in leukemic cells. Cancer Res. 27, 632–638 (1967)

    PubMed  CAS  Google Scholar 

  • Mizuno, N.S.: Effects of streptonigrin on nucleic acid metabolism of tissue culture cells. Biochim. Biophys. Acta 108, 394–395 (1965)

    PubMed  CAS  Google Scholar 

  • Mizuno, N.S.: Distribution of tritiated methyl ester of streptonigrin in mice bearing sarcoma 180. Biochem. Pharmacol. 15, 394–403 (1966)

    Article  PubMed  CAS  Google Scholar 

  • Mizuno, N.S.: Comparative effects of streptonigrin derivatives on tissue culture cells. Biochem. Pharmacol. 16, 933–940 (1967)

    Article  PubMed  CAS  Google Scholar 

  • Mizuno, N.S., Gilboe, D.P.: Binding of streptonigrin to DNA. Biochim. Biophys. Acta 224, 319–327 (1970)

    PubMed  CAS  Google Scholar 

  • Mizuno, N.S., Humphrey, E.W.: Metabolism of tritiated methyl ester of streptonigrin (NSC-45384) in humans with cancer. Cancer Chemother. Rep. 41, 23–26 (1964)

    PubMed  CAS  Google Scholar 

  • Morgan, A.R., Cone, R.L., Elgert, T.M.: The mechanism of DNA strand breakage by vitamin C and Superoxide and the protective roles of catalase and Superoxide. Nucleic Acid Res. 3, 1139–1149(1976)

    PubMed  CAS  Google Scholar 

  • Muschel, L.H., Schmoker, K.: Activity of mitomycin C, other antibiotics, and serum against lysogenic bacteria. J. Bacteriol. 92, 967–971 (1966)

    PubMed  CAS  Google Scholar 

  • Nasjleti, C.E., Spencer, H.H.: Chromosome polyploidization in human leukocyte culture treated with streptonigrin and cyclophosphamide. Cancer 20, 31–35 (1967)

    Article  PubMed  CAS  Google Scholar 

  • Oberdisse, E., Neubert, D.: Influence of several antibiotics, which can form complexes with DNA, on nucleic acid synthesis of warm-blooded animal cells in vivo. Nauyn-Schmiedebergs’ Arch. Pharmakol. Exp. Pathol. 257, 47–48 (1967)

    Article  CAS  Google Scholar 

  • O’Connor, T.E., Schoop-Stansly, P., Sethi, V.S., Hadidi, A., Okano, P.: Antibiotic control of infection of human or mouse cells with oncorna virus. Collect. Pap. Annu. Symp. Fundam. Cancer Res. 27, 319 (1975)

    Google Scholar 

  • Oleson, J.J., Calderella, L.A., Mjos, K.J., Peith, A.R., Thie, R.S., Toplin, I.: The effects of streptonigrin on experimental tumors. Antibiot. Chemother. 11, 158–164 (1961)

    PubMed  CAS  Google Scholar 

  • Padron, E., Karpov, V.L., Gause, G.G., Dudnik, J.V.: Distribution of H3-bruneomycin in tumor cell. Antibiotiki 19, 387–389 (1974)

    PubMed  CAS  Google Scholar 

  • Pittillo, R.F., Woolley, C.: Biological assay of streptonigrin (NSC-45383) in body fluids and tissues of mice. Antimicrob. Agents Chemother. 5, 82–85 (1974)

    Article  PubMed  CAS  Google Scholar 

  • Price, P.J., Suk, Wa.A., Spah, G.J., Chirigos, M.A., Lane, J.A., Huebner, R.J.: Streptonigrin inhibition of 3-methylcholanthrene transformation in vitro. Proc. Soc. Exp. Biol. Med. 145, 1197–1200(1974)

    PubMed  CAS  Google Scholar 

  • Puck, T.T.: Phasing, mitotic delay and chromosomal aberration in mammalian cells. Science 144, 565–566 (1964)

    Article  PubMed  CAS  Google Scholar 

  • Pulich, W.M., Jr.: Resistance to high oxygen tension, streptonigrin and ultraviolet irradiation in the green alga Chlorella Sorokiniana strain ors. J. Cell Biol. 62, 904–907 (1974)

    Article  PubMed  CAS  Google Scholar 

  • Radding, C. M.: Incorporation of 3H-thymidine by K12 (λ) induced by streptonigrin. In: Genetics today. Geerts, S.J. (ed.) p.22. Oxford: Pergamon Press 1963

    Google Scholar 

  • Rao, K.V.: Quinone natural products; streptonigrin (NSC-45383) and lapachol (NSC-11905) structure-activity relationship. Cancer Chemother. Rep. 4 (Pt. 2, No 4), 11–17 (1974)

    CAS  Google Scholar 

  • Rao, K.V., Cullen, W.P.: Streptonigrin, an antitumor substance, I. Isolation and characterization. Antibiot. Ann., 950–953 (1959–60)

    Google Scholar 

  • Rao, K.V., Biemann, K., Woodward, R.B.: The structure of streptonigrin. J. Am. Chem. Soc. 85, 2532–2533 (1963)

    Article  CAS  Google Scholar 

  • Reilly, H.C., Sigiura, K.: An antitumor spectrum of streptonigrin. Antibiot. Chemother. 11, 174–177 (1961)

    PubMed  CAS  Google Scholar 

  • Shorin, V.A., Brazhanov, V.S.: Possibility of utilizing leukemia L1210 as a first screening model in the primary selection of new antitumor antibiotics. Antibiotiki 19, 679–684 (1974)

    PubMed  CAS  Google Scholar 

  • Soukup, S., Takacs, E., Warkany, S.: Chromosome changes in embryos treated with various teratogens. J. Embryol. Exp. Morphol. 18, 215–226 (1967)

    PubMed  CAS  Google Scholar 

  • Szybalski, W.: Structural modifications of DNA; crosslinking, circularization and single-strand interruptions. Abh. Dtsch. Akad. Berlin 4, 1–19 (1964)

    Google Scholar 

  • Teller, M.N., Wagshul, S. F., Woolley, G. S.: Transplantable human tumors in experimental chemotherapy: effects of streptonigrin on HS #1 and HEP3 in the rat. Antibiot. Chemother. 11, 165–173 (1961)

    PubMed  CAS  Google Scholar 

  • Warkany, J., Takacs, E.: Changes of endocrine glands produced by teratogenic methods. The pituitary gland. Arch. Pathol. 85, 101–113 (1968)

    PubMed  CAS  Google Scholar 

  • White, H.L., White, J.R.: Interaction of streptonigrin with DNA in vitro. Biochim. Biophys. Acta 123, 648–651 (1966)

    PubMed  CAS  Google Scholar 

  • White, H.L., White, J.R.: Lethal action and metabolic effects of streptonigrin in E. coli. Mol. Pharmacol. 4, 549–565 (1968)

    PubMed  CAS  Google Scholar 

  • White, J.R., Dearman, H.H.: Generation of free radicals from phenazine methosulfate, streptonigrin, and rubiflavin in bacterial suspensions. Proc. Natl. Acad. Sci. USA 54, 887–891 (1965)

    Article  PubMed  CAS  Google Scholar 

  • Woods, W.A., Massicot, J.G., Webb, J.H., Chirigos, M.A.: Inhibitory effect of streptonigrin on a murine sarcoma virus-induced tumor cell line (MSC) and selection of drug resistant clones. In Vitro 9, 24–30 (1973)

    Article  PubMed  CAS  Google Scholar 

  • Young, C.W., Hodas, S.: Acute effects of cytotoxic compounds on incorporation of precursors into DNA, RNA and protein of HeLa monolayers. Biochem. Pharmacol. 14, 205–214 (1965)

    Article  PubMed  CAS  Google Scholar 

  • Zee-Cheng, K.Y., Cheng, C.C.: Common receptor complement feature among some antileukemic compounds. J. Pharm. Sci. 59, 1630–1634 (1970)

    Article  PubMed  CAS  Google Scholar 

  • Zetterberg, G., Kihlman, B.A.: Production of mutation by streptonigrin in the ascomycete Ophiostoma multiannulatum. Mutat. Res. 2, 470–71 (1965)

    Article  PubMed  CAS  Google Scholar 

Download references

Authors
  1. N. S. Mizuno
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of the Army, Walter Reed Army Institute of Research, Walter Reed Army Medical Center, Washington, D.C., 20012, USA

    Fred E. Hahn Ph.D.

Rights and permissions

Reprints and permissions

Copyright information

© 1979 Springer-Verlag Berlin · Heidelberg

About this chapter

Cite this chapter

Mizuno, N.S. (1979). Streptonigrin. In: Hahn, F.E. (eds) Mechanism of Action of Antieukaryotic and Antiviral Compounds. Antibiotics, vol 5 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46407-2_19

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-46407-2_19

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-46409-6

  • Online ISBN: 978-3-642-46407-2

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation