01815

Actinomycin D

≥90% (HPLC), from Streptomyces sp.

• Synonym(s): Actinomycin C₁, Actinomycin IV, Dactinomycin
• Empirical Formula (Hill Notation): C₆₂H₈₆N₁₂O₁₆
• CAS Number: 50-76-0
• Molecular Weight: 1255.42
• Beilstein/REAXYS Number: 605235
• EC Number: 200-063-6
• MDL number: MFCD00005033
• UNSPSC Code: 12352200
• PubChem Substance ID: 329747361

Properties

• biological source: Streptomyces sp.
• assay: ≥90% (HPLC)
• form: powder
• color: red, powder
• mp: 251-253
• solubility: H₂O: 0.5 mg/mL; DMSO: 1 mg/mL; acetone: 10 mg/mL; acetonitrile: 10 mg/mL
• fluorescence: λ_ex 420; λ_em 443 in ethanol
• suitability: suitable for fluorescence
• 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

Description

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, and as an antibiotic in treatment of various malignant neoplasms, including Wilm′s tumour and the sarcomas. Recommended for us in cell culture applications at 1μg/mL.

Biochem/physiol Actions

Actinomycin D inhibits the proliferation of cells by forming a stable complex with double-stranded DNA, inhibiting DNA-primed RNA synthesis and causing single-stranded breaks in DNA. It has been shown to be an inhibitor of the minus-strand transfer step in reverse transcriptase.

Packaging

Product is packaged in a bottomless glass bottle with the contents inside an inserted fused cone.

Caution

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.

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

Conditions for safe storage, including any incompatibilities. Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.Storage class (TRGS 510): Non-combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials.

Safety Information

• 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
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges