Aphidicolin

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Structural formula
Structural formula of aphidicolin
General
Surname Aphidicolin
other names
  • (3 α , 4 α , 5 α , 17 α ) -3,17-dihydroxy-4-methyl-9,15-cyclo-C, 18-dinor-14,15-secoandrostan-4,17-dimethanol
  • (+) - 3 α , 16,17,18-tetrahydroxy-aphidicolan
Molecular formula C 20 H 34 O 4
Brief description

White, crystalline solid

External identifiers / databases
CAS number 38966-21-1
EC number 609-602-3
ECHA InfoCard 100.109.656
PubChem 38194
Wikidata Q414000
properties
Molar mass 338.49 g · mol -1
Physical state

firmly

Melting point

228-230 ° C

solubility

Soluble in water, methanol, ethanol and DMSO

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Aphidicolin is a tetracyclic diterpene from the fungus Cephalosporium aphidicola Petch, but is also found in other species.

It inhibits in eukaryotic cells , the cell division and is therefore a cytostatic . More precisely , aphidicolin reversibly inhibits the replication of DNA by disabling the DNA polymerases α and δ. The cell remains in the early S phase .

It is used in cell cultures to synchronize cells so that all cells are in the same cell cycle stage .

Individual evidence

  1. ↑ a b c data sheet aphidicolin (PDF) from Calbiochem, accessed on December 8, 2015.
  2. ↑ a b data sheet aphidicolin, analytical standard from Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).
  3. ↑ KM Brundret, W. Dalziel, B. Hesp, JAJ Jarvis, S. Neidle: X-Ray crystallographic determination of the structure of the antibiotic aphidicolin: a tetracyclic diterpenoid containing a new ring system. In: J. Chem. Soc., Chem. Commun. 1972, pp. 1027-1028; doi: 10.1039 / C39720001027 .
  4. ↑ S. Ikegami, T. Taguchi, M. Ohashi, M. Oguro, H. Nagano, Y. Mano: Aphidicolin prevents mitotic cell division by interfering with the activity of DNA polymerase-α. In: Nature . 275 (5679), 1978, pp. 458-460. PMID 692726 .
  5. ↑ LP Goscin, JJ Byrnes: DNA polymerase delta: one polypeptide, two activities. In: Biochemistry . 21 (10), 1982, pp. 2513-2518. PMID 6284202 .
  6. ↑ G. Pedrali-Noy, S. Spadari, A. Miller-Faurès, AO Miller, J. Kruppa, G. Koch: Synchronization of HeLa cell cultures by inhibition of DNA polymerase alpha with aphidicolin. In: Nucleic Acids Res. 8 (2), 1980, pp. 377-387. PMID 6775308 ; PMC 327273 (free full text, PDF).

literature

  • JA Huberman: New Views of the Biochemistry of Eucaryotic DNA Replication Revealed by Aphidicolin, an Unusual Inhibitor of DNA Polymerase α. In: Cell . 23 (3), 1981, pp. 647-648. PMID 6784928 .