Rufocromomycin

Bezeichnung:Rufocromomycin

CAS-Nr3930-19-6

Englisch Name:Streptonigrin

CBNumberCB1333569

SummenformelC25H22N4O8

Molgewicht506.46

MOL-Datei3930-19-6.mol

Synonyma

Rufocromomycin

Rufocromomycin physikalisch-chemischer Eigenschaften

Schmelzpunkt	301-303℃
Siedepunkt	595.12°C (rough estimate)
Dichte	1.4130 (rough estimate)
Brechungsindex	1.6000 (estimate)
storage temp.	2-8°C
Löslichkeit	Chloroform:Methanol (1:1): 2 mg/ml
Aggregatzustand	A solid
pka	6.2-6.4 (1:1 aq dioxane)
Farbe	Light brown to brown
Merck	13,8907
BRN	599390

Sicherheit

Kennzeichnung gefährlicher	T+
R-Sätze:	28
S-Sätze:	53-28-36/37/39-45
RIDADR	UN 3462 6.1/PG 1
WGK Germany	3
RTECS-Nr.	TJ7350000
F	10-18
HazardClass	6.1(a)
PackingGroup	II
Toxizität	LD50 oral in mouse: 2330ug/kg

Gefahreninformationscode (GHS)

Streptonigrin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R28:Sehr giftig beim Verschlucken.
S-Sätze Betriebsanweisung:
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S28:Bei Berührung mit der Haut sofort abwaschen mit viel . . . (vom Hersteller anzugeben).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
Streptonigrin is a phenylpyridylquinoline originally isolated from S. flocculus with diverse biological activities. Streptonigrin (2.5-12.5 μM) induces DNA cleavage by calf thymus topoisomerase II in a concentration-dependent manner. It induces phage production in S. typhimurium when used at concentrations ranging from 1 to 10 μg/ml. Streptonigrin (10 μg/ml) inhibits DNA synthesis in and reduces survival of S. typhimurium bacteria. Streptonigrin is bactericidal against E. coli in an iron-dependent manner, an effect that is blocked by the iron chelators deferoxamine and orthophenanthroline. Streptonigrin (40 nM) is cytotoxic to human HT-29 colon carcinoma cells but not to BE colon carcinoma cells in which NAD(P)H:quinone oxidoreductase is not expressed. Streptonigrin (0.001-0.1 μg/ml) inhibits mitosis and induces chromatin breaks in human leukocytes in a concentration-dependent manner. In vivo, streptonigrin (0.05 mg/kg, i.p.) increases the mean survival time in rats infected with Rauscher virus.
Chemische Eigenschaften
Brown to red solid. Soluble in polar solvents and alkaline solutions; insoluble in most nonpolar solvents and acid solutions.
Verwenden
Streptonigrin is an aminoquinone antitumour antibiotic. Its antineoplastic activity requires reductive activation by Xanthine-converting enzymes. It induces apoptosis by a mechanism involving NF-κB. DNA cleavage reaction and chromosome damage by Streptonigrin are influenced by the nature of the metal ion present and dependent on the production of free radicals. Its antibiotic activity is iron-activated. Streptonigrin from Streptomyces flocculus
Verwenden
Streptonigrin 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).
Definition
ChEBI: Complex cytotoxic antibiotic obtained from Streptomyces flocculus or S. rufochronmogenus. It is used in advanced carcinoma and causes leukopenia.
Trademarks
Nigrin (Pfizer).
Biochem/physiol Actions
Streptonigrin (SN) is an aminoquinone antitumour antibiotic. Its antineoplastic activity requires reductive activation by Xanthine-converting enzymes. It induces apoptosis by a mechanism involving NF-κB. DNA cleavage reaction and chromosome damage by SN are influenced by the nature of the metal ion present and dependent on the production of free radicals. Its antibiotic activity is iron-activated.
läuterung methode
Streptonigrin 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].

Rufocromomycin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

3930-19-6, Streptonigrin Verwandte Suche:

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