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38966-21-1-(+)-Aphidicolin (+)-Aphidicolin

(+)-Aphidicolin

For research use only. Not for therapeutic Use.

  • CAT Number: R015684
  • CAS Number: 38966-21-1
  • Molecular Formula: C20H34O4
  • Molecular Weight: 338.488
  • Purity: ≥95%
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Aphidicolin is a tetracyclic diterpene antibiotic isolated from the fungus, Cephalosporum aphidicola with antiviral and antimitotic properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It blocks the cell cycle at early S phase. It is a specific inhibitor of DNA polymerase A,D in eukaryotic cells and in some viruses (vaccinia and herpesviruses) and an apoptosis inducer in HeLa cells. Natural aphidicolin is a secondary metabolite of the fungus Nigrospora oryzae.


Catalog Number R015684
CAS Number 38966-21-1
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

Molecular Formula C20H34O4
Purity ≥95%
Target DNA polymerase α, δ and ε inhibitor
Storage 4°C
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 CC12CCC(C(C1CCC3C24CCC(C(C3)C4)(CO)O)(C)CO)O
Reference

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1:Targeting DNA repair with aphidicolin sensitizes primary chronic lymphocytic leukemia cells to purine analogs. Starczewska E, Beyaert M, Michaux L, Vekemans MC, Saussoy P, Bol V, Arana Echarri A, Smal C, Van Den Neste E, Bontemps F.Oncotarget. 2016 Jun 21;7(25):38367-38379. doi: 10.18632/oncotarget.9525. PMID: 27223263 Free PMC Article<br />
2:Different sensitivities of cultured mammalian cells towards aphidicolin-enhanced DNA effects in the comet assay. Speit G, Sch&uuml;tz P, Bausinger J.Mutat Res Genet Toxicol Environ Mutagen. 2016 Jun;803-804:22-6. doi: 10.1016/j.mrgentox.2016.05.001. Epub 2016 May 5. PMID: 27265376<br />
3:A Comprehensive Analysis of the Dynamic Response to Aphidicolin-Mediated Replication Stress Uncovers Targets for ATM and ATMIN. Mazouzi A, Stukalov A, M&uuml;ller 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<br />
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<br />
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<br />
6:B56&delta; 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<br />
7:Aphidicolin inhibits cell proliferation via the p53-GADD45&beta; 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<br />
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<br />
9:Aphidicolin-induced nuclear elongation in tobacco BY-2 cells. Yasuhara H, Kitamoto K.Plant Cell Physiol. 2014 May;55(5):913-27. doi: 10.1093/pcp/pcu026. Epub 2014 Feb 2. PMID: 24492257<br />
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

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