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(+)-Aphidicolin

Item № 14007
CAS № 38966-21-1
Purity ≥98%
product image
                (CAS 38966-21-1)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $68.00 0.00
     5 mg $220.00 0.00
     25 mg $765.00 0.00

Pricing updated 2019-07-18. Prices are subject to change without notice.

Description
Synonyms
  • ICI 69653
  • NSC 234714

(+)-Aphidicolin is a natural tetracyclic diterpene first isolated from the fungus C. aphidicola and shown to have antiviral activity against herpes simplex.1 In eukaryotic cells, it is a cell-permeable, reversible inhibitor of DNA replication, specifically blocking the activity of DNA polymerases α, δ, and ε when used at low micromolar levels.2,3,4 Aphidicolin can be used, at 3 μM, to arrest cells in G1/S phase or to increase gene amplification frequency.5,6

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Technical Information
Formal Name
(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-8,11a-methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol
CAS Number
38966-21-1
Synonyms
  • ICI 69653
  • NSC 234714
Molecular Formula
C20H34O4
Formula Weight
338.5
Purity
≥98%
Formulation
A solid
SMILES
O[C@]1(CO)CC[C@]23[C@@](C[C@@H]1C3)([H])CC[C@@]4([H])[C@@](CO)(C)[C@H](O)CC[C@@]42C
InChI Code
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/s1
InChI Key
NOFOAYPPHIUXJR-APNQCZIXSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Bucknall, R.A., Moores, H., Simms, R., et al. Antiviral effects of aphidicolin, a new antibiotic produced by Cephalosporium aphidicola Antimicrobial Agents and Chemotherapy 4(3), 294-298 (1973).

2. Oguro, M., Suzuki-Hori, C., Nagano, H., et al. The mode of inhibitory action by aphidicolin on eukaryotic DNA polymerase α Eur. J. Biochem. 97(2), 603-607 (1979).

3. Krokan, H., Wist, E., and Krokan, R.H. Aphidicolin inhibits DNA synthesis by DNA polymerase α and isolated nuclei by a similar mechanism Nucleic Acids Research 9(18), 4709-4719 (1981).

4. Cheng, C.H., and Kuchta, R.D. DNA polymerase ε: Aphidicolin inhibition and the relationship between polymerase and exonuclease activity Biochemistry 32(33), 8568-8574 (1993).

5. Kota, K.P., Benko, J.G., Mudhasani, R., et al. High content image based analysis identifies cell cycle inhibitors as regulators of Ebola virus infection Viruses 4(10), 1865-1877 (2012).

6. Yin, D.X., and Schimke, R.T. Inhibition of apoptosis by overexpressing Bcl-2 enhances gene amplification by a mechanism independent of aphidicolin pretreatment Proc. Natl. Acad. Sci. USA 93(8), 3394-3398 (1996).

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