Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H34O4 |
Molecular Weight | 338.4823 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]1(CO)[C@]2([H])CC[C@@]3([H])C[C@]4([H])C[C@]3(CC[C@@]4(CO)O)[C@@]2(C)CC[C@@]1([H])O
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
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 |
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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 |
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Transcription and temporal cascade in Chilo iridescent virus infected cells. | 2001 |
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Expression of AAV Rep proteins in SV40-transformed and untransformed cells: reciprocal interaction with host DNA synthesis. | 2001 |
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Uracil-initiated base excision DNA repair synthesis fidelity in human colon adenocarcinoma LoVo and Escherichia coli cell extracts. | 2001 |
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Towards a virtual Arabidopsis plant. | 2001 |
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Arsenic trioxide induces G2/M growth arrest and apoptosis after caspase-3 activation and bcl-2 phosphorylation in promonocytic U937 cells. | 2001 Aug 31 |
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Maintenance of the DNA puff expanded state is independent of active replication and transcription. | 2001 Jul |
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Cell cycle-dependent control of polarised development by a cyclin-dependent kinase-like protein in the Fucus zygote. | 2001 Nov |
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Characterization of the DNA polymerase gene of varicella-zoster viruses resistant to acyclovir. | 2001 Nov |
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Cladribine induces apoptosis in human leukaemia cells by caspase-dependent and -independent pathways acting on mitochondria. | 2001 Nov 1 |
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A multistep model for paclitaxel-induced apoptosis in human breast cancer cell lines. | 2001 Nov 1 |
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Genetic modification of human trabecular meshwork with lentiviral vectors. | 2001 Nov 20 |
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Post-mitotic, differentiated myotubes efficiently produce retroviral vector from hybrid adeno-retrovirus templates. | 2001 Oct |
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"Caged cytoskeletons": a rapid method for the isolation of microtubule-associated proteins from synchronized plant suspension cells. | 2001 Oct |
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Quiescence, cell viability, apoptosis and necrosis of smooth muscle cells using different growth inhibitors. | 2001 Oct |
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Total synthesis of (+/-)-stemodinone via an efficient ring-exchange strategy. | 2001 Oct 19 |
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Transfection of large plasmids in primary human myoblasts. | 2001 Sep |
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In vitro antiviral activity of aphidicolin and its derivates. Synergistic effects of aphidicolin with other antiviral drugs. | 2002 |
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Investigation of genetic susceptibility to non-small cell lung cancer by fragile site expression. | 2002 |
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Fragile sites in human and Macaca fascicularis chromosomes are breakpoints in chromosome evolution. | 2002 |
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Synchronous Arabidopsis suspension cultures for analysis of cell-cycle gene activity. | 2002 Apr |
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Process of pigment cell specification in the sand dollar, Scaphechinus mirabilis. | 2002 Apr |
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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 Apr |
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Endoreduplication is not inhibited but induced by aphidicolin in cultured cells of tobacco. | 2002 Apr |
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The role of the cell cycle on the efficiency of photochemical gene transfection. | 2002 Apr 15 |
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Segment-specific expression of alkaline phosphatase in the Tubifex embryo requires DNA replication and mRNA synthesis. | 2002 Apr 15 |
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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 |
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Studies on fertilization in the teleost IV. Effects of aphidicolin and camptothecin on chromosome formation in fertilized medaka eggs. | 2002 Aug |
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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 |
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Hydroxyurea significantly enhances tumor growth delay in vivo with herpes simplex virus thymidine kinase/ganciclovir gene therapy. | 2002 Aug |
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Relationships among the cell cycle, cell proliferation, and aryl hydrocarbon receptor expression in PLHC-1 cells. | 2002 Aug |
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Wild-type p53 inhibits replication-associated homologous recombination. | 2002 Aug 29 |
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Base excision repair of adenine/8-oxoguanine mispairs by an aphidicolin-sensitive DNA polymerase in human cell extracts. | 2002 Aug 8 |
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Aphidicolin induces 6-thioguanine resistant mutants in human diploid fibroblasts. | 2002 Feb 20 |
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Repair of damaged DNA by Arabidopsis cell extract. | 2002 Jan |
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Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53. | 2002 Jan 17 |
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Tumor necrosis factor-alpha exerts interleukin-6-dependent and -independent effects on cultured skeletal muscle cells. | 2002 Jan 30 |
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Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones. | 2002 Jul |
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The fragile histidine triad/common chromosome fragile site 3B locus and repair-deficient cancers. | 2002 Jul 15 |
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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 Jul 19 |
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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 |
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Cell synchronization effect on mammalian cell permeabilization and gene delivery by electric field. | 2002 Jun 13 |
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Role of cell contact in the specification process of pigment founder cells in the sea urchin embryo. | 2002 Mar |
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Organophosphate-based pesticides and genetic damage implicated in bladder cancer. | 2002 Mar |
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Transcriptional regulation of mitotic genes by camptothecin-induced DNA damage: microarray analysis of dose- and time-dependent effects. | 2002 Mar 15 |
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The E2F family of transcription factors from Arabidopsis thaliana. Novel and conserved components of the retinoblastoma/E2F pathway in plants. | 2002 Mar 22 |
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Inhibition of nucleotide excision repair by fludarabine in normal lymphocytes in vitro, measured by the alkaline single cell gel electrophoresis (Comet) assay. | 2002 May |
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Fragmentation and dispersal of the pericentriolar Golgi complex is required for entry into mitosis in mammalian cells. | 2002 May 3 |
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DNA polymerase theta purified from human cells is a high-fidelity enzyme. | 2002 May 31 |
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Cell cycle-regulated gene expression in Arabidopsis. | 2002 Nov 1 |
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ATF is important to late S phase-dependent regulation of DNA topoisomerase IIalpha gene expression in HeLa cells. | 2002 Oct 8 |
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
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38966-21-1
Created by
admin on Sat Jun 26 07:15:39 UTC 2021 , Edited by admin on Sat Jun 26 07:15:39 UTC 2021
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PRIMARY | |||
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38966-21-1
Created by
admin on Sat Jun 26 07:15:39 UTC 2021 , Edited by admin on Sat Jun 26 07:15:39 UTC 2021
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PRIMARY | |||
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M1984
Created by
admin on Sat Jun 26 07:15:39 UTC 2021 , Edited by admin on Sat Jun 26 07:15:39 UTC 2021
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PRIMARY | Merck Index | ||
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457964
Created by
admin on Sat Jun 26 07:15:39 UTC 2021 , Edited by admin on Sat Jun 26 07:15:39 UTC 2021
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PRIMARY | |||
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192TJ6PP19
Created by
admin on Sat Jun 26 07:15:39 UTC 2021 , Edited by admin on Sat Jun 26 07:15:39 UTC 2021
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PRIMARY |
SUBSTANCE RECORD