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Merck

A1410

Actinomycin D

from Streptomyces sp., ~98% (HPLC)

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
UNSPSC Code:
51282001
NACRES:
NA.85
PubChem Substance ID:
24890541
EC Number:
200-063-6
Beilstein/REAXYS Number:
605235
MDL number:
MFCD00005033

Product Name

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

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

~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

Quality Level

300

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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.

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

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

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
0000508201
0000508200
0000508199
0000508198
0000508198

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The role of deoxyribonucleic acid in ribonucleic acid synthesis. III. The inhibition of the enzymatic synthesis of ribonucleic acid and deoxyribonucleic acid by actinomycin D and proflavin.
J HURWITZ et al.
Proceedings of the National Academy of Sciences of the United States of America, 48, 1222-1230 (1962-07-15)
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.
Paul C McDonald et al.
Gastroenterology, 157(3), 823-837 (2019-05-13)
Most pancreatic ductal adenocarcinomas (PDACs) express an activated form of KRAS, become hypoxic and dysplastic, and are refractory to chemo and radiation therapies. To survive in the hypoxic environment, PDAC cells upregulate enzymes and transporters involved in pH regulation, including
Konstantinos Boulias et al.
Molecular cell, 75(3), 631-643 (2019-07-08)
mRNAs are regulated by nucleotide modifications that influence their cellular fate. Two of the most abundant modified nucleotides are N6-methyladenosine (m6A), found within mRNAs, and N6,2'-O-dimethyladenosine (m6Am), which is found at the first transcribed nucleotide. Distinguishing these modifications in mapping
Jianzhen Li et al.
Biology of reproduction, 100(2), 468-478 (2018-11-13)
The role of androgenic steroids on ovarian development has attracted much attention in recent years, but the molecular mechanism is still largely unknown. In this study, using zebrafish as a model, we found that the trace metal zinc mediates the
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