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A1410

Sigma-Aldrich

Actinomycin D

from Streptomyces sp., ~98% (HPLC)

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Synonym(s):
Actinomycin C1, Actinomycin IV, Dactinomycin
Empirical Formula (Hill Notation):
C62H86N12O16
CAS Number:
Molecular Weight:
1255.42
Beilstein:
605235
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces sp.

Quality Level

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

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This Item
A4262A9415A5156
Actinomycin D from Streptomyces sp., ~98% (HPLC)

Sigma-Aldrich

A1410

Actinomycin D

Actinomycin D from Streptomyces sp., ≥95% (HPLC)

Sigma-Aldrich

A4262

Actinomycin D

Actinomycin D from Streptomyces sp., suitable for cell culture, ≥95%

Sigma-Aldrich

A9415

Actinomycin D

assay

~98% (HPLC)

assay

≥95% (HPLC)

assay

≥95%

assay

-

form

powder

form

powder

form

powder

form

lyophilized powder

color

red to orange, red, powder

color

red, powder

color

red, powder

color

yellow to orange

mp

251-253

mp

251-253

mp

251-253

mp

-

solubility

DMSO: 1 mg/mL, ethanol: soluble

solubility

ethanol, DMSO: soluble

solubility

ethanol, DMSO: soluble (Stable in aqueous solutions at 2-8 °C.)

solubility

H2O: 20 mg/mL

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.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

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

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