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Aphidicolin

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Aphidicolin
Names
IUPAC name (3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocycloheptanaphthalene-3,9-diol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.109.656 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1Key: NOFOAYPPHIUXJR-APNQCZIXSA-N
  • InChI=1/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1Key: NOFOAYPPHIUXJR-APNQCZIXBU
SMILES
  • OC4(O)CC31C4C3CC2(C)(CO)(O)CC12C
Properties
Chemical formula C20H34O4
Molar mass 338.48 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 and herpesviruses) and an apoptosis inducer in HeLa cells. Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae.

Bibliography

  • Dhillon VS, Husain SA, Ray GN (2003). "Expression of aphidicolin-induced fragile sites and their relationship between genetic susceptibility in breast cancer, ovarian cancer, and non-small-cell lung cancer patients". Teratogenesis, Carcinogenesis, and Mutagenesis. Suppl 1: 35–45. doi:10.1002/tcm.10068. PMID 12616595.
  • Mahy, Brian W J (2001). A dictionary of virology (3. ed.). San Diego, Calif. : Academic Press. p. 19. ISBN 978-0-12-465327-6.

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
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