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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

C[C@@]1(CO)[C@H](O)CC[C@@]2(C)[C@H]1CC[C@H]3C[C@@H]4C[C@]23CC[C@]4(O)CO

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
Cell cycle-regulated gene expression in Arabidopsis.
2002-11-01
ATF is important to late S phase-dependent regulation of DNA topoisomerase IIalpha gene expression in HeLa cells.
2002-10-08
Wild-type p53 inhibits replication-associated homologous recombination.
2002-08-29
Base excision repair of adenine/8-oxoguanine mispairs by an aphidicolin-sensitive DNA polymerase in human cell extracts.
2002-08-08
Studies on fertilization in the teleost IV. Effects of aphidicolin and camptothecin on chromosome formation in fertilized medaka eggs.
2002-08
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.
2002-08
Hydroxyurea significantly enhances tumor growth delay in vivo with herpes simplex virus thymidine kinase/ganciclovir gene therapy.
2002-08
Relationships among the cell cycle, cell proliferation, and aryl hydrocarbon receptor expression in PLHC-1 cells.
2002-08
Mismatch repair in human nuclear extracts. Time courses and ATP requirements for kinetically distinguishable steps leading to tightly controlled 5' to 3' and aphidicolin-sensitive 3' to 5' mispair-provoked excision.
2002-07-19
The fragile histidine triad/common chromosome fragile site 3B locus and repair-deficient cancers.
2002-07-15
Prolonged arrest of mammalian cells at the G1/S boundary results in permanent S phase stasis.
2002-07-15
Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones.
2002-07
Over-expression of human DNA polymerase lambda in E. coli and characterization of the recombinant enzyme.
2002-07
Enhanced nucleotide excision repair in cisplatin resistant human KB carcinoma cells.
2002-06-18
Identification of unstable sequences within the common fragile site at 3p14.2: implications for the mechanism of deletions within fragile histidine triad gene/common fragile site at 3p14.2 in tumors.
2002-06-15
Cell synchronization effect on mammalian cell permeabilization and gene delivery by electric field.
2002-06-13
Matrix association of early- and late-replicating chromatin studied by single-cell electrophoresis.
2002-06-12
Pyrido[2, 3-d]pyrimidines and pyrimido[5',4':5, 6]pyrido[2, 3-d]pyrimidines as new antiviral agents: synthesis and biological activity.
2002-06
DNA polymerase theta purified from human cells is a high-fidelity enzyme.
2002-05-31
Fragmentation and dispersal of the pericentriolar Golgi complex is required for entry into mitosis in mammalian cells.
2002-05-03
Inhibition of nucleotide excision repair by fludarabine in normal lymphocytes in vitro, measured by the alkaline single cell gel electrophoresis (Comet) assay.
2002-05
Cell cycle specific plasmid DNA replication in the nuclear extract of Saccharomyces cerevisiae: modulation by replication protein A and proliferating cell nuclear antigen.
2002-04-23
The role of the cell cycle on the efficiency of photochemical gene transfection.
2002-04-15
Segment-specific expression of alkaline phosphatase in the Tubifex embryo requires DNA replication and mRNA synthesis.
2002-04-15
Synchronous Arabidopsis suspension cultures for analysis of cell-cycle gene activity.
2002-04
Process of pigment cell specification in the sand dollar, Scaphechinus mirabilis.
2002-04
Induction of biphasic DNA double strand breaks and activation of multiple repair protein complexes by DNA topoisomerase I drug 7-ethyl-10-hydroxy-camptothecin.
2002-04
Endoreduplication is not inhibited but induced by aphidicolin in cultured cells of tobacco.
2002-04
The E2F family of transcription factors from Arabidopsis thaliana. Novel and conserved components of the retinoblastoma/E2F pathway in plants.
2002-03-22
Transcriptional regulation of mitotic genes by camptothecin-induced DNA damage: microarray analysis of dose- and time-dependent effects.
2002-03-15
Role of cell contact in the specification process of pigment founder cells in the sea urchin embryo.
2002-03
Organophosphate-based pesticides and genetic damage implicated in bladder cancer.
2002-03
Aphidicolin induces 6-thioguanine resistant mutants in human diploid fibroblasts.
2002-02-20
Tumor necrosis factor-alpha exerts interleukin-6-dependent and -independent effects on cultured skeletal muscle cells.
2002-01-30
Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53.
2002-01-17
Repair of damaged DNA by Arabidopsis cell extract.
2002-01
Action of (E)-2'-deoxy-2'-(fluoromethylene)cytidine on DNA metabolism: incorporation, excision, and cellular response.
2002-01
In vitro antiviral activity of aphidicolin and its derivates. Synergistic effects of aphidicolin with other antiviral drugs.
2002
Investigation of genetic susceptibility to non-small cell lung cancer by fragile site expression.
2002
Fragile sites in human and Macaca fascicularis chromosomes are breakpoints in chromosome evolution.
2002
Chromosomal fragile sites and relationship between genetic predisposition to small cell lung cancer.
2002
Genetic modification of human trabecular meshwork with lentiviral vectors.
2001-11-20
Cladribine induces apoptosis in human leukaemia cells by caspase-dependent and -independent pathways acting on mitochondria.
2001-11-01
A multistep model for paclitaxel-induced apoptosis in human breast cancer cell lines.
2001-11-01
Cell cycle-dependent control of polarised development by a cyclin-dependent kinase-like protein in the Fucus zygote.
2001-11
Characterization of the DNA polymerase gene of varicella-zoster viruses resistant to acyclovir.
2001-11
Post-mitotic, differentiated myotubes efficiently produce retroviral vector from hybrid adeno-retrovirus templates.
2001-10
"Caged cytoskeletons": a rapid method for the isolation of microtubule-associated proteins from synchronized plant suspension cells.
2001-10
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
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 Mon Mar 31 22:55:14 GMT 2025
Edited
by admin
on Mon Mar 31 22:55:14 GMT 2025
Record UNII
192TJ6PP19
Record Status Validated (UNII)
Record Version
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Name Type Language
APHIDICOLIN
MI  
Common Name English
ICI-69653
Preferred 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
(+)-APHIDICOLIN
Common Name English
Code System Code Type Description
NSC
234714
Created by admin on Mon Mar 31 22:55:14 GMT 2025 , Edited by admin on Mon Mar 31 22:55:14 GMT 2025
PRIMARY
CAS
38966-21-1
Created by admin on Mon Mar 31 22:55:14 GMT 2025 , Edited by admin on Mon Mar 31 22:55:14 GMT 2025
PRIMARY
CHEBI
2766
Created by admin on Mon Mar 31 22:55:14 GMT 2025 , Edited by admin on Mon Mar 31 22:55:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID5036711
Created by admin on Mon Mar 31 22:55:14 GMT 2025 , Edited by admin on Mon Mar 31 22:55:14 GMT 2025
PRIMARY
MERCK INDEX
m1984
Created by admin on Mon Mar 31 22:55:14 GMT 2025 , Edited by admin on Mon Mar 31 22:55:14 GMT 2025
PRIMARY Merck Index
PUBCHEM
457964
Created by admin on Mon Mar 31 22:55:14 GMT 2025 , Edited by admin on Mon Mar 31 22:55:14 GMT 2025
PRIMARY
FDA UNII
192TJ6PP19
Created by admin on Mon Mar 31 22:55:14 GMT 2025 , Edited by admin on Mon Mar 31 22:55:14 GMT 2025
PRIMARY