(+)-Aphidicolin

• CAT Number: R015684
• CAS Number: 38966-21-1
• Molecular Formula: C20H34O4
• Molecular Weight: 338.49
• Purity: ≥95%
• Synonyms: [3R-(3α,4α,4aα,6aβ,8β,9β,11aβ,11bβ)]-Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl- 8,11a-methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol; Aphidicolin; ICI 69653; NSC 234714; (3α,4α,5α,17α)-3,17-Dihydroxy-4-methyl-9,15-cyclo-C,18-dinor-14,15-secoa
• Target: Anti-infection
• Storage: 4°C
• IUPAC Name: (1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol
• InChI: 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
• InChIKey: NOFOAYPPHIUXJR-APNQCZIXSA-N
• SMILES: C[C@]12CC[C@H]([C@@]([C@@H]1CC[C@@H]3[C@@]24CC[C@@]([C@H](C3)C4)(CO)O)(C)CO)O

(+)-Aphidicolin（Cat No.:R015684）is a naturally occurring diterpenoid compound isolated from the fungus Cephalosporium aphidicola. It acts as a potent inhibitor of DNA polymerase, particularly DNA polymerase α, which plays a crucial role in DNA replication. By inhibiting this enzyme, (+)-aphidicolin prevents DNA synthesis, leading to cell cycle arrest and apoptosis. It is widely used in molecular biology to study DNA replication and cell division. Additionally, (+)-aphidicolin has shown potential in cancer research due to its ability to inhibit tumor cell proliferation, though its clinical application is limited due to toxicity concerns.

Reference

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3:A Comprehensive Analysis of the Dynamic Response to Aphidicolin-Mediated Replication Stress Uncovers Targets for ATM and ATMIN. Mazouzi A, Stukalov A, Müller AC, Chen D, Wiedner M, Prochazkova J, Chiang SC, Schuster M, Breitwieser FP, Pichlmair A, El-Khamisy SF, Bock C, Kralovics R, Colinge J, Bennett KL, Loizou JI.Cell Rep. 2016 Apr 14. pii: S2211-1247(16)30366-7. doi: 10.1016/j.celrep.2016.03.077. [Epub ahead of print] PMID: 27149854 Free Article
4:Inhibitory effect of Aphidicolin – a tetracyclic diterpene – on the proliferation and apoptotic induction in human cervical cancer (HeLa) cells. Yu EY, Zhao RY, Wang DS.J BUON. 2015 Nov-Dec;20(6):1480-6. PMID: 26854444
5:Semisynthesis of new aphidicolin derivatives with high activity against Trypanosoma cruzi. Santos GB, Krogh R, Magalhaes LG, Andricopulo AD, Pupo MT, Emery FS.Bioorg Med Chem Lett. 2016 Feb 15;26(4):1205-8. doi: 10.1016/j.bmcl.2016.01.033. Epub 2016 Jan 14. PMID: 26810263
6:B56δ subunit of protein phosphatase 2A decreases phosphorylation of endothelial nitric oxide synthase at serine 116: Mechanism underlying aphidicolin-stimulated NO production. Park JH, Cho DH, Lee JY, Lee HJ, Ha Y, Ahn JH, Jo I.Nitric Oxide. 2015 Aug 6;50:46-51. doi: 10.1016/j.niox.2015.08.001. [Epub ahead of print] PMID: 26255574
7:Aphidicolin inhibits cell proliferation via the p53-GADD45β pathway in AtT-20 cells. Kageyama K, Sugiyama A, Murasawa S, Asari Y, Niioka K, Oki Y, Daimon M.Endocr J. 2015;62(7):645-54. doi: 10.1507/endocrj.EJ15-0084. Epub 2015 May 1. PMID: 25948499 Free Article
8:Structural basis for inhibition of DNA replication by aphidicolin. Baranovskiy AG, Babayeva ND, Suwa Y, Gu J, Pavlov YI, Tahirov TH.Nucleic Acids Res. 2014 Dec 16;42(22):14013-21. doi: 10.1093/nar/gku1209. Epub 2014 Nov 27. PMID: 25429975 Free PMC Article
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10:Human papillomavirus episome stability is reduced by aphidicolin and controlled by DNA damage response pathways. Edwards TG, Helmus MJ, Koeller K, Bashkin JK, Fisher C.J Virol. 2013 Apr;87(7):3979-89. doi: 10.1128/JVI.03473-12. Epub 2013 Jan 30. PMID: 23365423 Free PMC Article