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Merck
CN

01815

Sigma-Aldrich

Actinomycin D

≥90% (HPLC), from Streptomyces sp.

Synonym(s):

Actinomycin C1, Actinomycin IV, Dactinomycin

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About This Item

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:
12352200
PubChem Substance ID:
329747361

Key Documents

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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

λex 420; λem 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

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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.

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.

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.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300,H350,H360FD

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

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
BCBR0835V
BCBM3949V

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Y Maeda et al.
Journal of molecular biology, 215(2), 321-329 (1990-09-20)
The effect of intercalating drugs (the anthracycline group of antibiotics, ethidium bromide, actinomycin D) on stepwise melting of DNA was studied by differential scanning calorimetry (DSC). The DSC DNA melting profile of plasmid pJL3-TB5 DNA (5277 base-pairs in length) consists
Thomas Schwarzl et al.
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