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MITHRAMYCIN A

MITHRAMYCIN A Struktur
18378-89-7
CAS-Nr.
18378-89-7
Englisch Name:
MITHRAMYCIN A
Synonyma:
MITHRAMYCIN;PLICAMYCIN;2371;pa144;mitramycin;a-2371;nsc24559;MITHRACIN;luteomycin;aurelicacid
CBNumber:
CB9127380
Summenformel:
C52H76O24
Molgewicht:
1085.15
MOL-Datei:
18378-89-7.mol

MITHRAMYCIN A Eigenschaften

Schmelzpunkt:
180-183 °C
alpha 
D20 -51° (c = 0.4 in ethanol)
Siedepunkt:
761.72°C (rough estimate)
Dichte
1.1576 (rough estimate)
Brechungsindex
1.6500 (estimate)
storage temp. 
2-8°C
L?slichkeit
Soluble in DMSO (up to 20 mg/ml) or in Ethanol (up to 10 mg/ml)
Aggregatzustand
Powder
pka
4.54±0.60(Predicted)
Farbe
Red to brown
Merck 
13,7619
BRN 
5236667
Stabilit?t:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
EPA chemische Informationen
Plicamycin (18378-89-7)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xn,T+
R-S?tze: 22-26/27/28
S-S?tze: 45-38-36/37/39-28A-22
RIDADR  3249
WGK Germany  3
RTECS-Nr. PZ2800000
10
HazardClass  6.1(b)
PackingGroup  III
HS Code  29419090
Giftige Stoffe Daten 18378-89-7(Hazardous Substances Data)
Toxizit?t LD50 in mice, rats (mg/kg): 2.14, 1.74 i.v. (Slavik, Carter)
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitssch?dlich bei Verschlucken. Akute Toxizit?t oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
Sicherheit

MITHRAMYCIN A Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R22:Gesundheitssch?dlich beim Verschlucken.
R26/27/28:Sehr giftig beim Einatmen, Verschlucken und Berührung mit der Haut.

S-S?tze Betriebsanweisung:

S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).
S38:Bei unzureichender Belüftung Atemschutzger?t anlegen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S22:Staub nicht einatmen.

Beschreibung

Mithramycin is an antineoplastic antibiotic produced by Streptomyces plicatus. It is well known as the aureolic acid antitumor antibiotic that inhibits both cancer growth and bone resorption by cross-linking GC-rich DNA, thus blocking binding of Sp-family transcription factors to gene regulatory elements. Transcription of c-Src, a gene implicated in many human cancers and required for osteoclast-dependent bone resorption, is regulated by the binding of Sp factors to specific elements in its promoter. Therefore, this gene represents an important anticancer target and a potential lead target through which mithramycin displays action against osteoclastic bone resorption via an unknown mechanism. Hazards of handling this drug by the health-care personnel arise from a combination of factors: (1) its inherent toxicity and (2) the extent to which workers are exposed to the drug in the course of carrying out their duties. This exposure may be through inadvertent ingestion of the drug on foodstuffs (e.g., workers’ lunches), inhalation of drug dusts or droplets, or direct skin contact. Mithramycin has been used to decrease bone resorption in patients with humoral hypercalcemia and Paget’s disease.

Chemische Eigenschaften

yellow powder

Verwenden

Mithramycin was the first of the aureolic acid class of antitumour antibiotics, isolated from Streptomyces. Mithramycin inhibits transcription and protein synthesis by non-covalent binding with G-C-rich duplex DNA in the presence of magnesium and zinc ions. Mithramycin also induces differentiation of leukemic cells accompanied by an early decrease in c-myc expression, and selectively inhibits collagen-1 gene expression in human fibroblasts.

Application

Mithramycin, recently renamed plicamycin, was found in the culture broth of Streptomyces argillaceus and S. tanashiensis by Abbott Laboratories in 1952. It is structurally related to chromomycin A3. Mithramycin shows strong inhibitory activity against malignant cells of human origin. It acts by inhibition of the DNA-directed RNA synthesis through binding with DNA. Mithramycin is used intravenously to treat cancers of the embryonal cells, seminoma, choriocarcinoma, etc.

Indications

Plicamycin (mithramycin, Mithracin) is one of the chromomycin group of antibiotics produced by Streptomyces tanashiensis. Plicamycin binds to DNA and inhibits transcription. It also inhibits resorption of bone by osteoblasts, thus lowering serum calcium levels.Very little is known about its distribution, metabolism, and excretion. Because of its severe toxicity, plicamycin has limited clinical utility.The major indication for plicamycin therapy is in the treatment of life-threatening hypercalcemia associated with malignancy. Plicamycin also can be used in the palliative therapy of metastatic testicular carcinoma when all other known active drugs have failed.

Allgemeine Beschreibung

Chemical structure: aureolic acid

Biologische Aktivit?t

Anticancer antibiotic that selectively binds to G-C-rich DNA in the presence of Mg 2+ or Zn 2+ , inhibiting RNA and DNA polymerase action. Inhibits c-myc expression and induces myeloid differentiation of HL-60 promyelocytic leukemia cells.

l?uterung methode

Purify mithramycin A by crystallisation from CHCl3. It is soluble in MeOH, EtOH, Me2CO, EtOAc, Me2SO and H2O, and moderately soluble in CHCl3, but is slightly soluble in *C6H6 and Et2O. It is a fluorescent antitumour agent used in flow cytometry. [Thiem & Meyer Tetrahedron 37 551 1981, NMR: Yu et al. Nature 218 193 1968, Beilstein 17/1 V 672.]

MITHRAMYCIN A Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


MITHRAMYCIN A Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 176)Lieferanten
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sales@chemdad.com China 39894 58
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contact@trustwe.com China 5738 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000
marketing@targetmol.com United States 32161 58
Zhejiang Huida Biotech Co., LTD
008613515763466 8615669048680
wendy@huidabiotech.com CHINA 87 58
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86-571-88216897,88216896 13588875226
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Dideu Industries Group Limited
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1026@dideu.com China 22784 58

18378-89-7()Verwandte Suche:


  • AUREOLIC ACID
  • METHRAMYCIN A
  • MITHRAMYCIN A, FOR FLUORESCENCE
  • MITHRAMYCIN A FROM STREPTOMYCES*PLICATUS APPROX. 96
  • MITHRAMYCIN COMPLEX FROM STREPTOMYCES*PL ICATUS
  • MITHRAMYCIN FROM STREPTOMYCES PLICATUS
  • MITHRACIN
  • MITHRAMYCIN A
  • MITHRAMYCIN A, STREPTOMYCES PLICATUS
  • (2s-alpha,3beta(1r*,3r*4s*)))-droxy-7-methyl
  • 1(2h)-anthracenone,6-((2,6-dideoxy-3-o-(2,6-dideoxy-beta-d-arabino-hexopyranos
  • 6-dideoxy-alpha-d-lyxo-hexpyranosyl-(1-3)-2,6-dideoxy-beta-d-arabino-4)-o-2
  • a-2371
  • antibioticla7017
  • aurelicacid
  • aurlelicacid
  • hexpyranosyl)oxy)-3-(3,4-dihydroxy-1-methoxy-2-oxopentyl)-3,4-dihydro-8,9-dihy
  • nsc24559
  • yl)-beta-d-arabino-h)-2-((o-2,6-dideoxy-3-c-methyl-beta-d-ribohexopyranosyl-(
  • D-threo-2-Pentulose, 5-deoxy-1-C-(2S,3S)-7-2,6-dideoxy-3-O-(2,6-dideoxy-.beta.-D-arabino-hexopyranosyl)-.beta.-D-arabino-hexopyranosyloxy-3-(O-2,6-dideoxy-3-C-methyl-.beta.-D-ribo-hexopyranosyl-(1?3)-O-2,6-dideoxy-.beta.-D-lyxo-hexopyranosyl-(1?3)-2,6-did
  • mithramycin a from streptomyces plicatus
  • Mithramycin, Aureolic acid, Plicamycin
  • Mithramycin A from Streptomyces argillaceus
  • Aureolic acid, Plicamycin
  • (2S-(2alpha,3beta(1R*,3R*,4S*)))-6-((2,6-Dideoxy-3-O-(2,6-dideoxy-beta-D-arabino-hexopyranosyl)-beta-D-arabino-hexopyranosyl)oxy)-2-((O-2,6-dideoxy-3-C-methyl-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-alpha-D-lyxo-hexopyranosyl-(1->3)-2,6-dideoxy-bet
  • Mithramycin,90%
  • Plicamycin(Mithramycin)
  • (1S)-5-Deoxy-1-C-[(2S,3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1.fwdarw.3)-O-2,6-dideoxy-β-D-lyxo-hexopyranosyl-(1.fwdarw.3)-2,6-dideoxy-β-D-arabino-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-methyl-4-oxo-2-anthracenyl]-1-O-methyl-D-threo-2-pentulose
  • Plicamycin (50 mg)
  • (1S)-5-Deoxy-1-C-[(2S,3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-Methyl-β-D-ribo-hexopyranosyl-(1.fwdarw.3)-O-2,6-dideoxy-β-D-lyxo-hexopyranosyl-(1.fwdarw.3)-2,6-dideo
  • [1S(2S,3S)]-5-Deoxy-1-C-[7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-Methyl-β-D-ribo-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-lyxo-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10-dihydroxy-6-Methyl-4-oxo-2-anthracenyl]-1-O-Methyl-D-threo-2-pentulose
  • PlicatoMycin
  • Aureolic acid, Mithracin, PlicaMycin, MitraMycin, A 2371, LA 7017, NSC 23559, PA 144
  • MTM, Mithramycin A
  • Plicamycin, BC
  • D-threo-2-Pentulose, 5-deoxy-1-C-[(2S,3S)-7-[[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy]-3-[(O-2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-D-lyxo-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl)oxy]-1,2,3,4-tetrahydro-5,10...
  • MITHRAMYCIN A USP/EP/BP
  • MITHRAMYCIN
  • PLICAMYCIN
  • mitramycin
  • pa144
  • 2371
  • Mithramycin (Plicamycin)
  • luteomycin
  • (2S,3S)-3-((1S,3S,4R)-3,4-Dihydroxy-1-methoxy-2-oxopentyl)-2-(((2S,4R,5R,6R)-4-(((2S,4R,5S,6R)-4-(((2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-(((2S,4R,5R,6R)-4-(((2S,4R,5S,6R)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-8,9-dihydroxy-7-methyl-3,4-dihydroanthracen-1(2H)-one
  • 18378-89-7
  • C52H76O24
  • BioChemical
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