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APExBIO

(+)-Aphidicolin

In stock
Catalog No.
B7832
tetracyclic diterpene antibiotic
Grouped product items
SizePriceStock Qty
1mg
$82.00
In stock
5mg
$264.00
In stock
25mg
$918.00
In stock

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Aphidicolin, a tetracyclic diterpenoid, is an antibiotic with novel structure produced by the mold Cephalosporium aphidicola. Aphidicolin is an inhibitor of DNA polymerase-α [1].

DNA polymerase-α is an enzyme complex involved in initiation of DNA replication and during synthesis of Okazaki fragments on the lagging strand. The DNA polymerase-α complex consists of 4 subunits: POLA1, POLA2, PRIM1, and PRIM2. POLA1 is the catalytic subunit. POLA2 is the regulatory subunit. PRIM1 and PRIM2 are the small and the large primase subunits [2].

Aphidicolin selectively inhibited the activity of DNA polymerase-α without activity for DNA polymerase-β and mitochondrial DNA polymerase. Aphidicolin prevented cell division in sea urchin embryos [1]. Aphidicolin was a potent inhibitor of cellular deoxyribonucleic acid synthesis. Aphidicolin strongly inhibited the growth of herpes simplex virus both in tissue culture and in the rabbit eye. Aphidicolin was active against iododeoxyuridine-resistant herpes virus [3]. Aphidicolin showed antiviral activity and inhibited the incorporation of thymidine into DNA of cultured human embryonic lung cells. Aphidicolin (15 μg/ml) reduced the activity of crude and partially purified DNA polymerases from the cytosol [4].

References:
[1] Ikegami S, TAGUCHI T, OHASHI M, et al.  Aphidicolin prevents mitotic cell division by interfering with the activity of DNA polymerase-α[J]. Nature, 1978, 275(5679): 458-460.
[2] Lehman I R, Kaguni L S, Krause K H, et al.  DNA polymerase alpha[J]. J. Biol. Chem, 1989, 264.
[3] Bucknall R A, Moores H, Simms R, et al.  Antiviral effects of aphidicolin, a new antibiotic produced by Cephalosporium aphidicola[J]. Antimicrobial agents and chemotherapy, 1973, 4(3): 294-298.
[4] Ohashi M, Taguchi T, Ikegami S.  Aphidicolin: a specific inhibitor of DNA polymerases in the cytosol of rat liver[J]. Biochemical and biophysical research communications, 1978, 82(4): 1084-1090.

Physical Appearance

A white to off-white solid

Chemical Properties

StorageStore at -20°C
M.Wt338.48
Cas No.38966-21-1
FormulaC20H34O4
Solubility≥33.3mg/mL in DMSO
Chemical Name(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diol
SDFDownload SDF
Canonical SMILESO[C@@]1(CC[C@@]23[C@@]([H])(CC[C@]4([C@@](C)([C@@H](CC[C@@]43C)O)CO)[H])C[C@@H]1C2)CO
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.

Quality Control

Quality Control & MSDS

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Chemical structure

(+)-Aphidicolin