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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
Structure of APHIDICOLIN

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

HIDE SMILES / InChI

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
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
Uracil-initiated base excision DNA repair synthesis fidelity in human colon adenocarcinoma LoVo and Escherichia coli cell extracts.
2001
Towards a virtual Arabidopsis plant.
2001
Arsenic trioxide induces G2/M growth arrest and apoptosis after caspase-3 activation and bcl-2 phosphorylation in promonocytic U937 cells.
2001 Aug 31
Maintenance of the DNA puff expanded state is independent of active replication and transcription.
2001 Jul
Cell cycle-dependent control of polarised development by a cyclin-dependent kinase-like protein in the Fucus zygote.
2001 Nov
Characterization of the DNA polymerase gene of varicella-zoster viruses resistant to acyclovir.
2001 Nov
Cladribine induces apoptosis in human leukaemia cells by caspase-dependent and -independent pathways acting on mitochondria.
2001 Nov 1
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
Post-mitotic, differentiated myotubes efficiently produce retroviral vector from hybrid adeno-retrovirus templates.
2001 Oct
"Caged cytoskeletons": a rapid method for the isolation of microtubule-associated proteins from synchronized plant suspension cells.
2001 Oct
Quiescence, cell viability, apoptosis and necrosis of smooth muscle cells using different growth inhibitors.
2001 Oct
Total synthesis of (+/-)-stemodinone via an efficient ring-exchange strategy.
2001 Oct 19
Transfection of large plasmids in primary human myoblasts.
2001 Sep
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
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
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
Endoreduplication is not inhibited but induced by aphidicolin in cultured cells of tobacco.
2002 Apr
The role of the cell cycle on the efficiency of photochemical gene transfection.
2002 Apr 15
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
Hydroxyurea significantly enhances tumor growth delay in vivo with herpes simplex virus thymidine kinase/ganciclovir gene therapy.
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
Aphidicolin induces 6-thioguanine resistant mutants in human diploid fibroblasts.
2002 Feb 20
Repair of damaged DNA by Arabidopsis cell extract.
2002 Jan
Homologous recombination induced by replication inhibition, is stimulated by expression of mutant p53.
2002 Jan 17
Tumor necrosis factor-alpha exerts interleukin-6-dependent and -independent effects on cultured skeletal muscle cells.
2002 Jan 30
Characterization of the bone-resorptive effect of interleukin-11 in cultured mouse calvarial bones.
2002 Jul
The fragile histidine triad/common chromosome fragile site 3B locus and repair-deficient cancers.
2002 Jul 15
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
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
Cell synchronization effect on mammalian cell permeabilization and gene delivery by electric field.
2002 Jun 13
Role of cell contact in the specification process of pigment founder cells in the sea urchin embryo.
2002 Mar
Organophosphate-based pesticides and genetic damage implicated in bladder cancer.
2002 Mar
Transcriptional regulation of mitotic genes by camptothecin-induced DNA damage: microarray analysis of dose- and time-dependent effects.
2002 Mar 15
The E2F family of transcription factors from Arabidopsis thaliana. Novel and conserved components of the retinoblastoma/E2F pathway in plants.
2002 Mar 22
Inhibition of nucleotide excision repair by fludarabine in normal lymphocytes in vitro, measured by the alkaline single cell gel electrophoresis (Comet) assay.
2002 May
Fragmentation and dispersal of the pericentriolar Golgi complex is required for entry into mitosis in mammalian cells.
2002 May 3
DNA polymerase theta purified from human cells is a high-fidelity enzyme.
2002 May 31
Cell cycle-regulated gene expression in Arabidopsis.
2002 Nov 1
ATF is important to late S phase-dependent regulation of DNA topoisomerase IIalpha gene expression in HeLa cells.
2002 Oct 8
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
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
CAS
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
PRIMARY
EPA CompTox
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
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
PUBCHEM
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
PRIMARY
FDA UNII
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
PRIMARY