3D-O-(4-O-Acetyl-2,6-dideoxy-3-C-methyl-alpha-L-arabino-hexapyrano-syl)-7-methylolivomycin D

CHROMOMYCIN A3 Struktur
7059-24-7
CAS-Nr.
7059-24-7
Bezeichnung:
3D-O-(4-O-Acetyl-2,6-dideoxy-3-C-methyl-alpha-L-arabino-hexapyrano-syl)-7-methylolivomycin D
Englisch Name:
CHROMOMYCIN A3
Synonyma:
TOYOMYCIN;nsc-58514;Chromomycin;aburamycinb;Olivomycin D;CHROMOMYCIN A3;Chromoycin A3;antibioticb599;ABURAMYCIN BETA;nosyl)-7-methyl-
CBNumber:
CB8356277
Summenformel:
C57H82O26
Molgewicht:
1183.25
MOL-Datei:
7059-24-7.mol

3D-O-(4-O-Acetyl-2,6-dideoxy-3-C-methyl-alpha-L-arabino-hexapyrano-syl)-7-methylolivomycin D Eigenschaften

Schmelzpunkt:
185℃
alpha 
D23 -57° (ethanol)
Siedepunkt:
780.13°C (rough estimate)
Dichte
1.1451 (rough estimate)
Brechungsindex
1.6500 (estimate)
storage temp. 
2-8°C
Löslichkeit
Soluble in ethanol, DMSO, and ethyl acetate (10 mg/ml).
Aggregatzustand
Yellow solid
pka
4.54±0.60(Predicted)
Farbe
Yellow
Merck 
13,2258
Stabilität:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T+,T
R-Sätze: 61-28
S-Sätze: 53-28-36/37/39-45
RIDADR  UN 3462 6.1/PG 1
WGK Germany  3
RTECS-Nr. GB7875000
3-8-10
HazardClass  6.1(a)
PackingGroup  I
HS Code  29419090
Toxizität Excitation max: ~445 nm. Emission max: ~575 nm. Sol in ethanol, ethyl acetate, DMSO, methanol. LD50 in mice (mg/kg): 1.85 i.v. (Slavik, Carter).
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H300 Lebensgefahr bei Verschlucken. Akute Toxizität oral Kategorie 2 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P264, P270, P301+P310, P321, P330,P405, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P405 Unter Verschluss aufbewahren.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

3D-O-(4-O-Acetyl-2,6-dideoxy-3-C-methyl-alpha-L-arabino-hexapyrano-syl)-7-methylolivomycin D Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R61:Kann das Kind im Mutterleib schädigen.
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

Chromomycin A3 is an anthraquinone antibiotic and antitumor agent isolated from S. griseus that is used as a fluorescent probe for DNA with excitation/emission spectra of 445/575 nm. Its DNA binding is specific to two or more contiguous GC base pairs, which makes it suitable for characterizing heterochromatin in plants with species-specific AT:GC ratios. Chromomycin A3 is cytotoxic against non-small cell lung cancer and cervical cancer in vitro (IC50s = 1, 42, 60, and 40 nM for HCC44, A549, ME180, and HeLa cells, respectively). It also inhibits oxidative stress- and DNA damage-induced neuronal injury by enhancing Sp1 and Sp3 transcription factor binding.

Chemische Eigenschaften

Yellow powder

Verwenden

Chromomycin A3 is the major component of the chromomycin complex of the aureolic acid class, isolated from several Streptomyces species, and first reported in 1960. Chromomycin A3 exhibits a broad biological profile as an antibacterial, antifungal and antitumour agent. It binds reversibly to GC-specific DNA ligand in the minor groove which inhibits transcription, DNA gyrase and topoisomerase II activity. The intense UV spectrum and strong fluorescence makes chromomycin a useful stain for DNA.

Allgemeine Beschreibung

Chemical structure: aureolic acid

läuterung methode

Dissolve the antibiotic (10g) in EtOAc and add to a column of Silica Gel (Merck 0.05-0.2microns, 4x70cm) in EtOAc containing 1% oxalic acid. Elute with EtOAc+1% oxalic acid and check fractions by TLC. Pool fractions, wash with H2O thoroughly, dry and evaporate. Recrystallise the residue from EtOAc. The heptaacetate has m 214o, [] D -20o (c 1, EtOH). [Miyamoto et al. Tetrahedron 23 421 1967, Harada et al. J Am Chem Soc 91 5896 1969, Beilstein 17/5 V 673.]

3D-O-(4-O-Acetyl-2,6-dideoxy-3-C-methyl-alpha-L-arabino-hexapyrano-syl)-7-methylolivomycin D Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


3D-O-(4-O-Acetyl-2,6-dideoxy-3-C-methyl-alpha-L-arabino-hexapyrano-syl)-7-methylolivomycin D Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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7059-24-7(3D-O-(4-O-Acetyl-2,6-dideoxy-3-C-methyl-alpha-L-arabino-hexapyrano-syl)-7-methylolivomycin D)Verwandte Suche:


  • chromomycina(sub3)
  • nosyl)-7-methyl-
  • nsc-58514
  • olivomycind,3b-o-(4-o-acetyl-2,6-dideoxy-3-c-methyl-alpha-l-arabinohexopyra
  • TOYOMYCIN
  • 3BETA-O-(4-O-ACETYL-2.6-DIDEOXY-3-C-METHYL-ALPHA-L-ARABINO HEXOPYRANOSYL)-7-METHYLOLIVOMYCIN D
  • 3B-O-(4-O-ACETYL-2,6-DIDEOXY-3-C-METHYL-ALPHA-L-ARABINO-HEXOPYRANOSYL)-7-METHYLOLIVOMYCIN D
  • 3B-O-(4-O-ACETYL-2,6-DIDEXY-3-C-METHYL-ALPHA-L-ARABINO-HEXOPYRANOSYL)-7-METHYLOLIVOMYCIN
  • ABURAMYCIN BETA
  • CHROMOMYCIN A3
  • CHROMOMYCIN A3 STREPTOMYCES GRISEUS
  • 3D-O-(4-O-acetyl-2,6-dideoxy-3-C-methyl-alpha-L-arabino-hexopyranosyl)-7-methylolivomycin D
  • CHROMOMYCIN A(3), FOR FLUORESCENCE
  • CHROMOMYCIN A3 FROM STREPTOMYCESGRISEUS APPROX. 96
  • Chromomycin
  • D-threo-2-Pentulose, 1-C-(2S,3S)-7-4-O-acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-.alpha.-D-lyxo-hexopyranosyl)-.beta.-D-lyxo-hexopyranosyloxy-3-O-4-O-acetyl-2,6-dideoxy-3-C-methyl-.alpha.-L-arabino-hexopyranosyl-(1?3)-O-2,6-dideoxy-.beta.-D-arabino-h
  • chromomycin a3from streptomyces griseus
  • 3'''-O-(4-O-Acetyl-3-C-methyl-2,6-dideoxy-α-L-arabino-hexopyranosyl)-7-methylolivomycin D
  • Chromoycin A3
  • Olivomycin D
  • AburaMycin, ToyoMycin, NSC 58514, B 599-III, SR1768E
  • aburamycinb
  • antibiotic69895a
  • antibioticb599
  • Chromomycin A - CAS 7059-24-7 - Calbiochem
  • [(2R,3S,4R,6S)-6-[[(6S,7S)-6-[(2S,4R,5R,6R)-4-[(2S,4R,5R,6R)-4-[(2S,4S,5S,6S)-5-acetyloxy-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-7-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-4,10-dihydroxy-3-methyl-5-oxo-7,8-dihydro-6H-anthracen-2-yl]oxy]-4-[(2R,4R,5R,6R)-4-hydroxy-5-methoxy-6-methyloxan-2-yl]oxy-2-methyloxan-3-yl] acetate
  • D-threo-2-Pentulose, 1-C-[(2S,3S)-7-[[4-O-acetyl-2,6-dideoxy-3-O-(2,6-dideoxy-4-O-methyl-α-D-lyxo-hexopyranosyl)-β-D-lyxo-hexopyranosyl]oxy]-3-[[O-4-O-acetyl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1→3)-O-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy...
  • CHROMOMYCIN A3 USP/EP/BP
  • 7059-24-7
  • C57H82O26
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