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SBR00013

Sigma-Aldrich

Actinomycin D, Ready Made Solution

from Streptomyces sp., 2 mg/mL in DMSO

Synonym(s):

Actinomycin D solution from Streptomyces sp., Actinomycin IV, Dactinomycin

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About This Item

Empirical Formula (Hill Notation):
C62H86N12O16
CAS Number:
Molecular Weight:
1255.42
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.76
Pricing and availability is not currently available.

biological source

Streptomyces sp.

Quality Level

description

Ready Made Solution

form

liquid

storage condition

protect from light

concentration

2 mg/mL in DMSO

color

dark orange

antibiotic activity spectrum

neoplastics

Mode of action

DNA synthesis | interferes

storage temp.

−20°C

SMILES string

N21C(CCC2)C(=O)N(CC(=O)N(C(C(=O)OC(C(C(=O)NC(C1=O)C(C)C)NC(=O)c3c4nc5c(c([c](c(c5[o]c4c(cc3)C)C)=O)N)C(=O)NC6C(OC(=O)C(N(C(=O)CN(C(=O)C7N(CCC7)C(=O)C(NC6=O)C(C)C)C)C)C(C)C)C)C)C(C)C)C)C

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)

InChI key

RJURFGZVJUQBHK-UHFFFAOYSA-N

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Application

<ul>
<li><strong>Regulation of Immune Checkpoints in Cancer:</strong> Actinomycin D is pivotal in studying the ADAR-mediated RNA editing processes that regulate PVR immune checkpoints in colorectal cancer, thus demonstrating its crucial role in cancer immunotherapy research and providing insights into novel therapeutic targets (Qian et al., 2024).</li>
<li><strong>Chemotherapy and Immunotherapy Combination:</strong> The use of Actinomycin D in combined chemotherapy highlights its effectiveness in salvaging multi-chemotherapy agent and avelumab resistant choriocarcinoma, showcasing its potential in overcoming resistance to treatment in gynecological cancers (Lehmann et al., 2023).</li>
<li><strong>Advancements in Dental Medicine:</strong> Actinomycin D is used in regulating gene expression crucial for tissue regeneration and repair in dental health and it is also used to determine RNA stability assay (Pan et al., 2023).</li>
<li><strong>Cancer Progression Research:</strong> The study on hypoxia-induced lncRNA in hepatocellular carcinoma progression, where RNA-binding proteins play a critical role, aligns with Actinomycin D′s application in transcriptional inhibition and its influence on mRNA stability, essential for understanding cancer biology and developing targeted therapies (Tuo et al., 2023).</li>
</ul>

Biochem/physiol Actions

Actinomycin D is an antineoplastic antibiotic that inhibits cell proliferation. It is a cytotoxic inducer of apoptosis against tumor cells.[1] The compound inhibits the proliferation of cells in a nonspecific way by forming a stable complex with double-stranded DNA (via deoxyguanosine residues), thus inhibiting DNA-primed RNA synthesis. It also causes single strand breaks in DNA.[2][3][4]

Actinomycin D has been shown to be an inhibitor of the minus-strand transfer step in reverse transcription,[5][6] and is therefore used in studies and suppression of HIV-replication. It has also been shown to suppress programmed cell death of PC12 cells induced by etoposide, an inhibitor of topoisomerase II.[7]

In cell culture, actinomycin D is used as a selection agent. Actinomycin D binding to yeast in ribosomal RNA has been studied.[8] The sensitivity of various strains of E. coli to actinomycin D and the mechanism of binding has been studied.[9][10] Actinomycin D is also used in molecular biology as a DNA intercalator which blocks the progression of RNA polymerases.[11]

Packaging

1ML

Caution

Actinomycin D solutions are very sensitive to light.

Preparation Note

The 2 mg/mL solution may be further diluted in an appropriate buffer prior to use.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Carc. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup


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Dawson, R.M.C., et al., Eds.
Data for Biochemical Research, 256-257 (1986)
M Nakajima et al.
Neuroscience letters, 176(2), 161-164 (1994-08-01)
A rat pheochromocytoma cell line (PC12 cells) died within 24 h in the presence of etoposide (1-40 micrograms/ml), an inhibitor of topoisomerase II. This cytotoxic effect was prevented by either nerve growth (NGF) or epidermal growth factor (EGF). Cycloheximide and
The binding of actinomycin D and F to bacterial DNA.
L F Cavalieri et al.
Biochimica et biophysica acta, 166(3), 722-725 (1968-10-29)
Olivier Bensaude
Transcription, 2(3), 103-108 (2011-09-17)
This review first discusses ways in which we can evaluate transcription inhibition, describe changes in nuclear structure due to transcription inhibition, and report on genes that are paradoxically stimulated by transcription inhibition. Next, it summarizes the characteristics and mechanisms of
J Guo et al.
Journal of virology, 72(8), 6716-6724 (1998-07-11)
In this report we demonstrate that human immunodeficiency virus type 1 (HIV-1) minus-strand transfer, assayed in vitro and in endogenous reactions, is greatly inhibited by actinomycin D. Previously we showed that HIV-1 nucleocapsid (NC) protein (a nucleic acid chaperone catalyzing

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