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(+)-Aphidicolin tetracyclic diterpene antibiotic

Catalog No.B7832
Size Price Stock Qty
10mM (in 1mL DMSO)
$260.00
In stock
1mg
$75.00
In stock
5mg
$242.00
In stock
25mg
$842.00
In stock

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Sample solution is provided at 25 µL, 10mM.

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Chemical structure

(+)-Aphidicolin

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Chemical Properties

Cas No. 38966-21-1 SDF Download SDF
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
Canonical SMILES O[[email protected]@]1(CC[[email protected]@]23[[email protected]@]([H])(CC[[email protected]]4([[email protected]@](C)([[email protected]@H](CC[[email protected]@]43C)O)CO)[H])C[[email protected]@H]1C2)CO
Formula C20H34O4 M.Wt 338.48
Solubility >33.3mg/mL in DMSO Storage Store at -20°C
Physical Appearance A white to off-white solid Shipping Condition Evaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tips For 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.

Background

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.