Aphidicolin

Title: Aphidicolin
CAS Registry Number: 38966-21-1
CAS Name: (3a,4a,5a,17a)-3,17-Dihydroxy-4-methyl-9,15-cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanol
Additional Names: tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-8,11a-methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol
Manufacturers' Codes: ICI-69653; NSC-234714
Molecular Formula: C20H34O4
Molecular Weight: 338.48
Percent Composition: C 70.97%, H 10.12%, O 18.91%
Literature References: Novel tetracyclic diterpene antibiotic with antiviral and antimitotic properties, isolated as (+)-form from Cephalosporium aphidicola Petch. Specific inhibitor of DNA a-polymerase. Description and x-ray crystallographic determn of structure: K. M. Brundret et al., Chem. Commun. 1972, 1027. Prepn and antiviral activity: A. Borrow et al., US 3761512 (1973 to ICI). Structure and abs config: W. Dalziel et al., J. Chem. Soc. Perkin Trans. 1 1973, 2841. Total synthesis of (±)-aphidicolin: B. M. Trost et al., J. Am. Chem. Soc. 101, 1328 (1979); J. E. McMurry et al., ibid. 1331; E. J. Corey et al., ibid. 102, 1743 (1980); J. E. McMurry et al., Tetrahedron 37, Suppl. 1, 319 (1981). Antiviral effects in vitro and in vivo: R. A. Bucknall et al., Antimicrob. Agents Chemother. 4, 294 (1973). Antimitotic activity: S. Ikegami et al., Nature 275, 458 (1978). Effects on DNA synthesis in mouse sarcoma: S. Seki et al., Biochim. Biophys. Acta 610, 413 (1980). Enzymatic determn method: G. Pedrali-Noy et al., J. Biochem. Biophys. Methods 4, 113 (1981). Induction of differentiation of human myeloid leukemia cells: J. Griffin et al., Exp. Hematol. 10, 774 (1982). Effects on cell proliferation: G. Iliakis et al., Int. J. Radiat. Biol. 42, 417 (1982); on g-irradiated human fibroblasts: P. J. Smith, M. C. Paterson, Biochim. Biophys. Acta 739, 17 (1983).
Properties: Needles from ethyl acetate, mp 227-232°. [a]D27 +12° (c = 1 in methanol).
Melting point: mp 227-232°
Optical Rotation: [a]D27 +12° (c = 1 in methanol)
Derivative Type: (±)-Form
Properties: White cryst, mp 218-220°.
Melting point: mp 218-220°
Use: As a biological tool in studies of cell proliferation and differentiation.
Apholate Aphylline Apicycline Apigetrin Apiin

Aphidicolin
Aphidicolin structure.png
Identifiers
CAS number 38966-21-1 YesY
PubChem 457964
ChemSpider 10280269 YesY
ChEMBL CHEMBL29711 YesY
Jmol-3D images Image 1
Properties
Molecular formula C20H34O4
Molar mass 338.48 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Aphidicolin is defined as a tetracyclic diterpene antibiotic with antiviral and antimitotical 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 A,D in eukaryotic cells and in some viruses and an apoptosis inducer in HeLa cells.
Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae.[1]