Dactinomycin 50-76-0

Dactinomycin

The actinomycins are a class of polypeptide antibiotics isolated from soil bacteria of the genus Streptomyces, of which the most significant is actinomycin D. It was the first antibiotic isolated by Selman Waksman and his co-worker H. B. Woodruff in 1940.

Mechanism

Actinomycin D is primarily used as an investigative tool in cell biology to inhibit transcription. It does this by binding DNA at the transcription initiation complex and preventing elongation by RNA polymerase. Because it can bind DNA duplexes, it can also interfere with DNA replication, although other chemicals such as hydroxyurea are better suited for use in the laboratory as inhibitors of DNA synthesis.

Clinical use

As chemotherapy

Actinomycin D, marketed under the trade name Dactinomycin, is one of the older chemotherapy drugs, and has been used in therapy for many years. It is a clear, yellow liquid administered intravenously and most commonly used in treatment of a variety of cancers including gestational trophoblastic neoplasia, Wilms' tumor and rhabdomyosarcoma.

As an antibiotic

It was the first antibiotic shown to have anti-cancer activity, but is not normally used as such, as it is highly toxic, causing damage to genetic material.

Research use

Actinomycin D and its fluorescent derivative, 7-aminoactinomycin D (7-AAD), are used as stains in microscopy and flow cytometry applications. The affinity of these stains/compounds for GC-rich regions of DNA strands makes them excellent markers for DNA. 7-AAD binds to single stranded DNA; therefore it is a useful tool in determining apoptosis and distinguishing between dead cells and live ones.

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Systematic (IUPAC) name: 2-amino-N,N'- bis[(6S,9R,10S,13R,18aS)- 6,13-diisopropyl- 2,5,9-trimethyl- 1,4,7,11,14-pentaoxohexadecahydro- 1H-pyrrolo[2,1-i] [1,4,7,10,13] oxatetraazacyclohexadecin- 10-yl]- 4,6-dimethyl- 3-oxo- 3H-phenoxazine- 1,9-dicarboxamide
Dactinomycin CAS number: 50-76-0
ATC code: L01DA01
PubChem: 2019
DrugBank: APRD00124
Formula: C62H86N12O16
Molecular mass: 1255.42 g/mol
Dactinomycin Assay/Purity: Typically NLT 98%
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