A1410

Actinomycin D

from Streptomyces sp., ~98% (HPLC)

• Synonym(s): Actinomycin C₁, Actinomycin IV, Dactinomycin
• Empirical Formula (Hill Notation): C₆₂H₈₆N₁₂O₁₆
• CAS Number: 50-76-0
• Molecular Weight: 1255.42
• Beilstein: 605235
• EC Number: 200-063-6
• MDL number: MFCD00005033
• UNSPSC Code: 51282001
• PubChem Substance ID: 24890541
• NACRES: NA.85

Properties

• biological source: Streptomyces sp.
• Quality Level: 300
• Assay: ~98% (HPLC)
• form: powder
• optical activity: [α]/D alpha: 28/D (Rotation: -315 degrees (c=0.25% in methanol))
• color: red to orange; red, powder
• mp: 251-253
• solubility: DMSO: 1 mg/mL; ethanol: 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

Description

General description

Actinomycin D is a polypeptide antibiotic first described by Waksman. It is bacteriostatic in nature, especially towards gram negative bacteria, and also has anti-tumor activity.

Chemical structure: peptide

Application

Actinomycin D has a 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.

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.

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

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

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H300 - H350 - H360FD
• Precautionary Statements: P202 - P264 - P280 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 2 Oral - Carc. 1B - Repr. 1B
• Storage Class Code: 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves