A4262

Actinomycin D

from Streptomyces sp., ≥95% (HPLC)

• Synonym(e): Actinomycin C₁, Actinomycin IV, Dactinomycin
• Empirische Formel (Hill-System): C₆₂H₈₆N₁₂O₁₆
• CAS-Nummer: 50-76-0
• Molekulargewicht: 1255.42
• UNSPSC Code: 51282001
• NACRES: NA.76
• PubChem Substance ID: 24890842
• EC Number: 200-063-6
• Beilstein/REAXYS Number: 605235
• MDL number: MFCD00005033

Eigenschaften

• biological source: Streptomyces sp.
• Quality Segment: 200
• assay: ≥95% (HPLC)
• form: powder
• color: red, powder
• mp: 251-253
• solubility: ethanol, DMSO: soluble
• antibiotic activity spectrum: neoplastics
• mode of action: DNA synthesis | interferes
• storage temp.: 2-8°C
• SMILES string: CC(C)[C@H]1NC(=O)[C@@H](NC(=O)c2ccc(C)c3OC4=C(C)C(=O)C(N)=C(C(=O)N[C@H]5[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]6CCCN6C(=O)[C@H](NC5=O)C(C)C)C4=Nc23)[C@@H](C)OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]7CCCN7C1=O
• InChI: 1S/C62H86N12O16/c1-27(2)42-59(84)73-23-17-19-36(73)57(82)69(13)25-38(75)71(15)48(29(5)6)61(86)88-33(11)44(55(80)65-42)67-53(78)35-22-21-31(9)51-46(35)64-47-40(41(63)50(77)32(10)52(47)90-51)54(79)68-45-34(12)89-62(87)49(30(7)8)72(16)39(76)26-70(14)58(83)37-20-18-24-74(37)60(85)43(28(3)4)66-56(45)81/h21-22,27-30,33-34,36-37,42-45,48-49H,17-20,23-26,63H2,1-16H3,(H,65,80)(H,66,81)(H,67,78)(H,68,79)/t33-,34-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1
• InChI key: RJURFGZVJUQBHK-IIXSONLDSA-N

Beschreibung

General description

Chemical structure: peptide

Application

Actinomycin D is an antineoplastic antibiotic that inhibits cell proliferation with wide-ranging applications ranging from a selection agent in cell culture, use in studies of suppressing HIV-replication and programmed cell death of PC12 cells. Recommended for us in cell culture applications at 1μg/mL.

Biochem/physiol Actions

Durch die Bildung eines stabilen Komplexes mit doppelsträngiger DNA hemmt Actinomycin D die Proliferation von Zellen, wodurch die DNA-primed RNA-Synthese gehemmt und einsträngige DNA-Brüche verursacht werden. Es ist nachweislich ein Inhibitor für den Minusstrangtransfer bei der reversen Transkriptase.

Preparation Note

Actinomycin D is sold as red, shiny crystals and is soluble in acetonitrilie or acetone at 10 mg/mL and in DMSO at a minimum of 1 mg/mL. Some references also show slight solubility in water of 0.5 mg/mL.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Disclaimer

This product is hygroscopic and light-sensitive. If stored protected from light and moisture at 2-8°C, it remains unchanged, by HPLC testing, for at least 15 months. Unused dilute solutions of Actinomycin D are extremely sensitive to light and tend to adsorb to plastic and glass and should be discarded. However, frozen aliquots of concentrated stock solution are stable for at least a month.

Sicherheitshinweise

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300,H350,H360FD
• pcodes: P202 - P264 - P280 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral - Carc. 1B - Repr. 1B
• Lagerklasse: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges