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
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
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/3931652Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3931652
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 20.0 µM [EC50] | |||
Target ID: CHEMBL612241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10699730 |
|||
Target ID: CHEMBL377 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10956199 |
0.59 µM [IC50] | ||
Target ID: CHEMBL3414 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16134946 |
0.4 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3931652 |
Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8306334
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
| Substance Class |
Chemical
Created
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| Record UNII |
192TJ6PP19
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| Record Status |
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