Aphidicolin

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Aphidicolin
Aphidicolin structure.png
Names
IUPAC name
(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.109.656 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
Properties
C20H34O4
Molar mass 338.48 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Aphidicolin is a tetracyclic diterpene antibiotic isolated from the fungus, Cephalosporum aphidicola with antiviral and antimitotic properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase. It is a specific inhibitor of DNA polymerase Alpha and Delta in eukaryotic cells and in some viruses (vaccinia [1] [2] and herpesviruses) and an apoptosis inducer in HeLa cells. Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae . [3]

Bibliography

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References

  1. DeFilippes, FM (Nov 1984). "Effect of aphidicolin on vaccinia virus: isolation of an aphidicolin-resistant mutant". Journal of Virology. 52 (2): 474–82. doi:10.1128/JVI.52.2.474-482.1984. PMC   254548 . PMID   6436508.
  2. Bucknall, R. A.; Moores, H.; Simms, R.; Hesp, B. (1 September 1973). "Antiviral Effects of Aphidicolin, a New Antibiotic Produced by Cephalosporium aphidicola". Antimicrobial Agents and Chemotherapy. 4 (3): 294–298. doi:10.1128/AAC.4.3.294. PMC   444544 . PMID   4357181.
  3. Aphidicolin product page Archived June 26, 2006, at the Wayback Machine from Fermentek