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Merck

A9415

Actinomycin D

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

Synonym(s):

Cosmegen, Meractinomycin, 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/REAXYS Number:
605235
MDL number:
MFCD00005033
UNSPSC Code:
51282001
NACRES:
NA.76
PubChem Substance ID:
24891447
EC Number:
200-063-6

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Product Name

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

InChI key

RJURFGZVJUQBHK-IIXSONLDSA-N

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

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

biological source

Streptomyces sp.

assay

≥95%

form

powder

technique(s)

cell culture | mammalian: suitable

mp

251-253

solubility

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

antibiotic activity spectrum

neoplastics

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

Quality Level

300

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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.. 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.

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.

General description

Chemical structure: peptide

Other Notes

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

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.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000508208
0000508207
0000508206
0000508207
0000508208

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Antonio Rescifina et al.
Journal of medicinal chemistry, 49(2), 709-715 (2006-01-20)
Isoxazolidinyl polycyclic aromatic hydrocarbons (isoxazolidinyl-PAHs) have been synthesized in good yields by 1,3-dipolar cycloaddition methodology promoted by microwave irradiation. The structures of the obtained cycloadducts have been determined by NOE experiments and supported by computational studies at the AM1 level.
Arkady Khoutorsky et al.
Neuron, 78(2), 298-311 (2013-04-30)
Control of protein synthesis is critical for synaptic plasticity and memory formation. However, the molecular mechanisms linking neuronal activity to activation of mRNA translation are not fully understood. Here, we report that the translational repressor poly(A)-binding protein (PABP)-interacting protein 2A
Angela Zarama et al.
PLoS pathogens, 10(3), e1004000-e1004000 (2014-03-15)
Receptors of the signalling lymphocyte-activation molecules (SLAM) family are involved in the functional regulation of a variety of immune cells upon engagement through homotypic or heterotypic interactions amongst them. Here we show that murine cytomegalovirus (MCMV) dampens the surface expression
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H Sun et al.
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