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A4262 Sigma-Aldrich

Actinomycin D

from Streptomyces sp., ≥95% (HPLC)

Synonym: Actinomycin C1, Actinomycin IV, Dactinomycin

  • CAS Number 50-76-0

  • Empirical Formula (Hill Notation) C62H86N12O16

  • Molecular Weight 1255.42

  •  Beilstein/REAXYS Number 605235

  •  EC Number 200-063-6

  •  MDL number MFCD00005033

  •  PubChem Substance ID 24890842

  •  NACRES NA.76

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Properties

Related Categories A - K, Antibacterial, Antibiotics, Antibiotics A to Z, Antibiotics by Application,
Quality Level   200
biological source   Streptomyces sp.
assay   ≥95% (HPLC)
form   powder
color   red, powder
mp   251-253
solubility   ethanol, DMSO: soluble
Mode of action   DNA synthesis | interferes
antibiotic activity spectrum   neoplastics
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

Packaging

2, 5, 10, 25 mg in serum bottle

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.

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 & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
WGK 3
RTECS 
AU1575000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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