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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H34O4
Molecular Weight 338.4816
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APHIDICOLIN

SMILES

[H][C@]12C[C@@H]3C[C@]1(CC[C@]3(O)CO)[C@@]4(C)CC[C@@H](O)[C@@](C)(CO)[C@]4([H])CC2

InChI

InChIKey=NOFOAYPPHIUXJR-APNQCZIXSA-N
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

HIDE SMILES / InChI

Molecular Formula C20H34O4
Molecular Weight 338.4816
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma/Datasheet/6/a0781dat.pdf https://www.ncbi.nlm.nih.gov/pubmed/6793260

Aphidicolin, a tetracyclic diterpenoid obtained from the culture filtrates of Cephalosporium aphidicola and other fungi, inhibits the growth of eukaryotic cells and of certain animal viruses (SV40, Herpes and Vaccinia viruses) by selectively inhibiting the cellular replicative DNA polymerase alpha or the viral-induced DNA polymerases. The arrest of cellular or viral growth is thus due to inhibition of cellular or viral replicative DNA synthesis without interference with mitochondrial DNA synthesis, RNA, protein and nucleic acid precursors synthesis or other major metabolic pathways. The inhibition of all sensitive eukaryotic DNA polymerases by aphidicolin is competitive with respect to dCTP. Aphidicolin has thus proved extremely useful in elucidating the functional role of DNA polymerase alpha in nuclear DNA replication, of DNA polymerase gamma in mitochondrial DNA synthesis and both DNA polymerases beta and alpha in DNA repair synthesis. An important laboratory application of aphidicolin is the synchronization of the cell cycle of eukaryotic cells both in culture and in vivo. The properties of aphidicolinhave recently aroused considerable interest for its possible exploitation in al practice. The mechanism of action of this drug suggests in fact that it may be useful for controlling excessive cell proliferation in patients with cancer, psoriasis or other dermatitis with little or no adverse effect upon non-multiplying cells.

Approval Year

PubMed

PubMed

TitleDatePubMed
Naphthalene carboxamides as inhibitors of human cytomegalovirus DNA polymerase.
2000 Sep 18
Transcription and temporal cascade in Chilo iridescent virus infected cells.
2001
Expression of AAV Rep proteins in SV40-transformed and untransformed cells: reciprocal interaction with host DNA synthesis.
2001
Towards a virtual Arabidopsis plant.
2001
Expression of VACM-1 protein in cultured rat adrenal endothelial cells is linked to the cell cycle.
2001
DNA replication and daughter cell budding are not tightly linked in the protozoan parasite Toxoplasma gondii.
2001 Apr
The cellular response to DNA damage induced by the enediynes C-1027 and neocarzinostatin includes hyperphosphorylation and increased nuclear retention of replication protein a (RPA) and trans inhibition of DNA replication.
2001 Apr 17
Ethylene induces cell death at particular phases of the cell cycle in the tobacco TBY-2 cell line.
2001 Aug
Reduced store-operated Ca(2+) currents in rat basophilic leukaemia cells cultured under serum-free conditions.
2001 Aug
Arsenic trioxide induces G2/M growth arrest and apoptosis after caspase-3 activation and bcl-2 phosphorylation in promonocytic U937 cells.
2001 Aug 31
Inhibition of N-myc expression and induction of apoptosis by iron chelation in human neuroblastoma cells.
2001 Feb 1
The efficiency of simian foamy virus vector type-1 (SFV-1) in nondividing cells and in human PBLs.
2001 Feb 15
Cell division activity during apical hook development.
2001 Jan
Activation of deoxycytidine kinase by inhibition of DNA synthesis in human lymphocytes.
2001 Jan 15
De novo activation of the beta-phaseolin promoter by phosphatase or protein synthesis inhibitors.
2001 Jan 19
Maintenance of the DNA puff expanded state is independent of active replication and transcription.
2001 Jul
Differentiation between inducers of apoptosis and nonspecific cytotoxic drugs by means of cell analyzer and immunoassay.
2001 Jun
Treatment of drug-resistant human neuroblastoma cells with cyclodextrin inclusion complexes of aphidicolin.
2001 Jun
Regulation of zygotic gene activation in the preimplantation mouse embryo: global activation and repression of gene expression.
2001 Jun
Induction of the common fragile site FRA3B does not affect FHIT expression.
2001 Mar 29
Critical assessment of the nuclear import of plasmid during cationic lipid-mediated gene transfer.
2001 Mar-Apr
Werner helicase relocates into nuclear foci in response to DNA damaging agents and co-localizes with RPA and Rad51.
2001 May
Analysis of repair and PCNA complex formation induced by ionizing radiation in human fibroblast cell lines.
2001 May
Cloning and functional expression of cDNA encoding aphidicolan-16 beta-ol synthase: a key enzyme responsible for formation of an unusual diterpene skeleton in biosynthesis of aphidicolin.
2001 May 30
Direct regulation of the centrosome duplication cycle by the p53-p21Waf1/Cip1 pathway.
2001 May 31
Characterization of the DNA polymerase gene of varicella-zoster viruses resistant to acyclovir.
2001 Nov
A multistep model for paclitaxel-induced apoptosis in human breast cancer cell lines.
2001 Nov 1
Genetic modification of human trabecular meshwork with lentiviral vectors.
2001 Nov 20
Quiescence, cell viability, apoptosis and necrosis of smooth muscle cells using different growth inhibitors.
2001 Oct
A new flow cytometric method to follow DNA gap filling during nucleotide excision repair of UVc-induced damage.
2001 Oct 1
Total synthesis of (+/-)-stemodinone via an efficient ring-exchange strategy.
2001 Oct 19
Investigation of genetic susceptibility to non-small cell lung cancer by fragile site expression.
2002
Synchronous Arabidopsis suspension cultures for analysis of cell-cycle gene activity.
2002 Apr
Process of pigment cell specification in the sand dollar, Scaphechinus mirabilis.
2002 Apr
Segment-specific expression of alkaline phosphatase in the Tubifex embryo requires DNA replication and mRNA synthesis.
2002 Apr 15
Cell cycle specific plasmid DNA replication in the nuclear extract of Saccharomyces cerevisiae: modulation by replication protein A and proliferating cell nuclear antigen.
2002 Apr 23
Studies on fertilization in the teleost IV. Effects of aphidicolin and camptothecin on chromosome formation in fertilized medaka eggs.
2002 Aug
Dependence of DNA synthesis and in vitro development of bovine nuclear transfer embryos on the stage of the cell cycle of donor cells and recipient cytoplasts.
2002 Aug
Relationships among the cell cycle, cell proliferation, and aryl hydrocarbon receptor expression in PLHC-1 cells.
2002 Aug
Wild-type p53 inhibits replication-associated homologous recombination.
2002 Aug 29
Base excision repair of adenine/8-oxoguanine mispairs by an aphidicolin-sensitive DNA polymerase in human cell extracts.
2002 Aug 8
Action of (E)-2'-deoxy-2'-(fluoromethylene)cytidine on DNA metabolism: incorporation, excision, and cellular response.
2002 Jan
Pyrido[2, 3-d]pyrimidines and pyrimido[5',4':5, 6]pyrido[2, 3-d]pyrimidines as new antiviral agents: synthesis and biological activity.
2002 Jun
Matrix association of early- and late-replicating chromatin studied by single-cell electrophoresis.
2002 Jun 12
Inhibition of nucleotide excision repair by fludarabine in normal lymphocytes in vitro, measured by the alkaline single cell gel electrophoresis (Comet) assay.
2002 May
DNA polymerase theta purified from human cells is a high-fidelity enzyme.
2002 May 31
Patents

Sample Use Guides

s.c. M5076 mouse sarcoma model: The most effective schedule was the 7-day infusion. With the 300-mg/kg/day infusion rate,
Route of Administration: Intraperitoneal
DNA synthesis was inhibited in Ehrlich ascites tumor cells using Aphidicolin at 0.02–2 ug/mL, and at 100 ug/mL in Xenopus egg extracts
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:55:46 GMT 2023
Edited
by admin
on Sat Dec 16 09:55:46 GMT 2023
Record UNII
192TJ6PP19
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APHIDICOLIN
MI  
Common Name English
NSC-234714
Code English
APHIDICOLIN [MI]
Common Name English
8,11A-METHANO-11AH-CYCLOHEPTA(A)NAPHTHALENE-4,9-DIMETHANOL, TETRADECAHYDRO-3,9-DIHYDROXY-4,11B-DIMETHYL-, (3R,4R,4AR,6AS,8R,9R,11AS,11BS)-
Systematic Name English
9,15-CYCLO-C,18-DINOR-14,15-SECOANDROSTANE-4,17-DIMETHANOL, 3,17-DIHYDROXY-4-METHYL-, (3.ALPHA.,4.ALPHA.,5.ALPHA.,17.ALPHA.)-
Common Name English
ICI-69653
Code English
(+)-APHIDICOLIN
Common Name English
Code System Code Type Description
NSC
234714
Created by admin on Sat Dec 16 09:55:46 GMT 2023 , Edited by admin on Sat Dec 16 09:55:46 GMT 2023
PRIMARY
CAS
38966-21-1
Created by admin on Sat Dec 16 09:55:46 GMT 2023 , Edited by admin on Sat Dec 16 09:55:46 GMT 2023
PRIMARY
CHEBI
2766
Created by admin on Sat Dec 16 09:55:46 GMT 2023 , Edited by admin on Sat Dec 16 09:55:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID5036711
Created by admin on Sat Dec 16 09:55:46 GMT 2023 , Edited by admin on Sat Dec 16 09:55:46 GMT 2023
PRIMARY
MERCK INDEX
m1984
Created by admin on Sat Dec 16 09:55:46 GMT 2023 , Edited by admin on Sat Dec 16 09:55:46 GMT 2023
PRIMARY Merck Index
PUBCHEM
457964
Created by admin on Sat Dec 16 09:55:46 GMT 2023 , Edited by admin on Sat Dec 16 09:55:46 GMT 2023
PRIMARY
FDA UNII
192TJ6PP19
Created by admin on Sat Dec 16 09:55:46 GMT 2023 , Edited by admin on Sat Dec 16 09:55:46 GMT 2023
PRIMARY