Actinomycin


Actinomycin
Actinomycin D
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
Clinical data
MedlinePlus a682224
Pregnancy cat.  ?
Legal status  ?
Pharmacokinetic data
Protein binding 5%
Half-life 36 hours
Identifiers
CAS number 50-76-0 YesY
ATC code L01DA01
PubChem CID 2019
DrugBank APRD00124
ChemSpider 10482167 YesY
UNII 1CC1JFE158 YesY
KEGG C06770 N
ChEBI CHEBI:27666 YesY
ChEMBL CHEMBL1554 YesY
Synonyms 2-Amino- 4,6-dimethyl- 3-oxo- 3H-phenoxazine- 1,9-dicarboxylic acid bis- [(5,12-diisopropyl- 9,13,16-trimethyl- 4,7,11,14,17-pentaoxo- hexadecahydro- 10-oxa- 3a,6,13,16-tetraaza- cyclopentacyclohexadecen- 8-yl)- amide]
Chemical data
Formula C62H86N12O16 
Mol. mass 1255.42 g/mol
 N(what is this?)  (verify)

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.[1]

General structure of actinomycins


Contents

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.[2] 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, also known generically as dactinomycin, was approved by the US FDA on December 10, 1964 and launched by Merck, Sharpe and Dohme under the trade name Cosmegen[3]. It 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,[4] Wilms' tumor[5] and rhabdomyosarcoma.[6]

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.[7]

References

  1. ^ Waksman S A, Woodruff H B (1940). "Bacteriostatic and bacteriocidal substances produced by soil actinomycetes". Proc Soc Exper Biol 45: 609–614. 
  2. ^ Sobell H (1985). "Actinomycin and DNA transcription". Proc Natl Acad Sci USA 82 (16): 5328–31. doi:10.1073/pnas.82.16.5328. PMC 390561. PMID 2410919. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=390561. 
  3. ^ http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm
  4. ^ Turan T, Karacay O, Tulunay G, Boran N, Koc S, Bozok S, Kose M (2006). "Results with EMA/CO (etoposide, methotrexate, actinomycin D, cyclophosphamide, vincristine) chemotherapy in gestational trophoblastic neoplasia". Int J Gynecol Cancer 16 (3): 1432–8. doi:10.1111/j.1525-1438.2006.00606.x. PMID 16803542. 
  5. ^ Abd El-Aal H, Habib E, Mishrif M (2005). "Wilms' Tumor: The Experience of the Pediatric Unit of Kasr El-Aini Center of Radiation Oncology and Nuclear Medicine (NEMROCK)". J Egypt Natl Canc Inst 17 (4): 308–11. PMID 17102824. 
  6. ^ Khatua S, Nair C, Ghosh K (2004). "Immune-mediated thrombocytopenia following dactinomycin therapy in a child with alveolar rhabdomyosarcoma: the unresolved issues". J Pediatr Hematol Oncol 26 (11): 777–9. doi:10.1097/00043426-200411000-00020. PMID 15543019. 
  7. ^ 7-Amino-Actinomycin D, Fermentek

External links


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Look at other dictionaries:

  • actinomycin — n. [From actinomyces, the genus of the organism in which they were first found.] 1. any of various red antibiotics isolated from soil bacteria with a three ring heterocyclic nucleus with an attached peptide chain. Note: Actinomycin D is the most… …   The Collaborative International Dictionary of English

  • actinomycin C — actinomycin actinomycin n. [From actinomyces, the genus of the organism in which they were first found.] 1. any of various red antibiotics isolated from soil bacteria with a three ring heterocyclic nucleus with an attached peptide chain. Note:… …   The Collaborative International Dictionary of English

  • actinomycin D — actinomycin actinomycin n. [From actinomyces, the genus of the organism in which they were first found.] 1. any of various red antibiotics isolated from soil bacteria with a three ring heterocyclic nucleus with an attached peptide chain. Note:… …   The Collaborative International Dictionary of English

  • actinomycin F1 — actinomycin actinomycin n. [From actinomyces, the genus of the organism in which they were first found.] 1. any of various red antibiotics isolated from soil bacteria with a three ring heterocyclic nucleus with an attached peptide chain. Note:… …   The Collaborative International Dictionary of English

  • actinomycin D — n. [From actinomyces, the genus of the organism in which they were first found.] The most well known of the actinomycins ({C62H86N12O16}), a class of antibiotics which act by binding to DNA and inhibiting synthesis of RNA; they act agains gram… …   The Collaborative International Dictionary of English

  • actinomycin D — actinomycin D. См. актиномицин D. (Источник: «Англо русский толковый словарь генетических терминов». Арефьев В.А., Лисовенко Л.А., Москва: Изд во ВНИРО, 1995 г.) …   Молекулярная биология и генетика. Толковый словарь.

  • actinomycin D — n DACTINOMYCIN * * * see dactinomycin …   Medical dictionary

  • actinomycin — ☆ actinomycin [ak΄tə nōmī′sin ] n. [< ACTINOMYCETE + IN1] any of various antibiotic polypeptides derived from streptomyces soil bacteria: active against certain bacteria and fungi and some neoplasms …   English World dictionary

  • Actinomycin D — Strukturformel Allgemeines Freiname Actinomycin D Andere Namen …   Deutsch Wikipedia

  • Actinomycin — Actinomycine sind eine Klasse von Peptid Antibiotika aus Streptomyceten. Inhaltsverzeichnis 1 Struktureller Aufbau 2 Entdeckung und Nomenklatur 3 Biologische Wirkung 4 Pharmakologische Anwendung …   Deutsch Wikipedia