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Streptonigrin

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Streptonigrin Basic information
Streptonigrin Chemical Properties
  • Melting point:301-303℃
  • Boiling point:595.12°C (rough estimate)
  • Density 1.4130 (rough estimate)
  • refractive index 1.6000 (estimate)
  • storage temp. 2-8°C
  • pka6.2-6.4 (1:1 aq dioxane)
  • Merck 13,8907
  • BRN 599390
Safety Information
  • Hazard Codes T+
  • Risk Statements 28
  • Safety Statements 53-28-36/37/39-45
  • RIDADR UN 3462 6.1/PG 1
  • WGK Germany 3
  • RTECS TJ7350000
  • 10-18
  • HazardClass 6.1(a)
  • PackingGroup II
  • ToxicityLD50 oral in mouse: 2330ug/kg
MSDS
Streptonigrin Usage And Synthesis
  • Chemical PropertiesBrown to red solid. Soluble in polar solvents and alkaline solutions; insoluble in most nonpolar solvents and acid solutions.
  • UsesStreptonigrin is an unusual aminoquinone with broad biological activity against bacteria, fungi, nematodes, viruses and tumour cells. Streptonigrin acts as a bioreductive agent, highly dependent on interactions with metal ions, notably iron, and plays an important role in free radical production through redox cycling of NAD(P)H:quinone oxidoreductase (NQO1).
  • DefinitionChEBI: Complex cytotoxic antibiotic obtained from Streptomyces flocculus or S. rufochronmogenus. It is used in advanced carcinoma and causes leukopenia.
  • brand nameNigrin (Pfizer).
  • Purification MethodsStreptonigrin is purified by TLC on pH 7-buffered silica gel plates (made from a slurry of Silica Gel 60 and 400mL of 0.05M phosphate buffer pH 7.0) and eluted with 5% MeOH/CHCl3. Material from the extracted band recrystallises from Me2CO or dioxane as almost black plates or needles. It is soluble in pyridine, Me2NCHO, aqueous NaHCO3 (some dec), and slightly soluble in MeOH, EtOH, EtOAc and H2O. It has UV max 248, 375-380nm ( 38,400 and 17,400). [Weinreb et al. J Am Chem Soc 104 536 1982, Rao et al. J Am Chem Soc 85 2532 1963.] Itis antineoplastic and causes severe bone marrow depression [Wilson et al. Antibiot Chemother 11 147 1961].
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