All Photos(1)

A1410

Sigma-Aldrich

Actinomycin D

from Streptomyces sp., ~98% (HPLC)

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

Quality Level

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

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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, and as an antibiotic in treatment of various malignant neoplasms, including Wilm′s tumour and the sarcomas.

Packaging

2, 5, 10, 25, 100 mg in serum bottle

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

Certificate of Analysis

Certificate of Origin

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)
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...
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....
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...
Rolf Schreckenberg et al.
Antioxidants & redox signaling, 23(15), 1220-1232 (2015-05-16)
Research into right ventricular (RV) physiology and identification of pathomechanisms underlying RV failure have been neglected for many years, because function of the RV is often considered less important for overall hemodynamics and maintenance of blood circulation. In view of...

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service