(+)-Aphidicolin

CHF 100.00
In stock
BVT-0307-M0011 mgCHF 100.00
BVT-0307-M0055 mgCHF 290.00
BVT-0307-M02525 mgCHF 950.00
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Product Details
Synonyms NSC234714; BRN4689958; ICI69653
Product Type Chemical
Properties
Formula

C20H34O4

MW 338.5
Merck Index 14: 727
CAS 38966-21-1
RTECS PB9185000
Source/Host Chemicals Isolated from Phoma sp. BS 7210.
Purity Chemicals ≥98% (HPLC)
Appearance White to off-white solid.
Solubility Soluble in DMSO (50 mg/ml), methanol (10 mg/ml) or 100% ethanol; insoluble in water.
Identity Determined by 1H-NMR.
Declaration Manufactured by BioViotica.
InChi Key NOFOAYPPHIUXJR-APNQCZIXSA-N
Smiles [H][C@]12C[C@@H]3C[C@]1(CC[C@]3(O)CO)[C@@]1(C)CC[C@@H](O)[C@@](C)(CO)[C@]1([H])CC2
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage +4°C
Handling Advice Protect from light when in solution.
Use/Stability Stable for at least 1 year after receipt when stored at +4°C.
After reconstitution protect from light at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Phytotoxin.
  • Antibiotic.
  • Antiviral and antineoplastic agent.
  • Antileishmanial agent.
  • Reversible inhibitor of eukaryotic nuclear DNA replication.
  • Useful for cell synchronization.
  • Blocks the cell cycle at G1/S phase.
  • Prolongs the half life of DNA methyltransferase. DNA methylation/demethylation modulator.
  • Specific DNA polymerase α and δ inhibitor in eukaryotic cells and in some viruses of animal origin.
  • Acts synergistically with vincristine and doxorubicin.
  • Apoptosis inhibitor/inducer.
Product References
  1. X-Ray crystallographic determination of the structure of the antibiotic aphidicolin: a tetracyclicditerpenoid containing a new ring system: K.M. Brundret, et al.; J. C. S. Chem. Commun. 1027 (1972)
  2. Aphidicolin prevents mitotic cell division by interfering with the activity of DNA polymerase-alpha: S. Ikegami, et al.; Nature 275, 458 (1978)
  3. New views of the biochemistry of eucaryotic DNA replication revealed by aphidicolin, an unusual inhibitor of DNA polymerase alpha: J.A. Huberman; Cell 23, 647 (1981)
  4. Aphidicolin: a specific inhibitor of nuclear DNA replication in eukaryotes: S. Spadari, et al.; TIBS 7, 29 (1982)
  5. Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in human myeloid leukemia cell lines: K. Kuwakado, et al.; Biochem. Pharmacol. 46, 1909 (1993)
  6. Dissociation of nuclear and cytoplasmic cell cycle progression by drugs employed in cell synchronization: L. Urbani, et al.; Exp. Cell. Res. 219, 159 (1995)
  7. Drug-induced apoptosis is not necessarily dependent on macromolecular synthesis or proliferation in the p53-negative human prostate cancer cell line PC-3: M.M. Borner, et al.; Cancer Res. 55, 2122 (1995)
  8. TrkA neurogenic receptor regulates differentiation of neuroblastoma cells: W. Poluha, et al.;Oncogene10, 185 (1995)
  9. Effect of aphidicolin on DNA methyltransferase in the nucleus: I. Suetake, et al.; Cell Struct. Funct. 23, 137 (1998)
  10. Cytotoxicity of aphidicolin and its derivatives against neuroblastoma cells in vitro: synergism with doxorubicin and vincristine: M. Michaelis, et al.; Anticancer Drugs 11, 479 (2000)
  11. Antileishmanial activities of aphidicolin and its semisynthetic derivatives: O. Kayser, et al.; Antimicrob. Agents Chemother. 45, 288 (2001)
  12. Aphidicolin and bleomycin induced chromosome damage as biomarker of mutagen sensitivity: a twin study: B. Tedeschi, et al.; Mutat. Res. 546, 55 (2004)
  13. Human papillomavirus episome stability is reduced by aphidicolin and controlled by DNA damage response pathways: T. G. Edwards, et al.; J. Virol. 87, 3979 (2013)
  14. Aphidicolin-induced nuclear elongation in tobacco BY-2 cells: H. Yashura, et al.; Plant Cell Physiol. 55, 913 (2014)
  15. Active and passive demethylation of male and female pronuclear DNA in the mammalian zygote: F. Guo, et al.; Cell Stem Cell 15, 447 (2014)
  16. Structural basis for inhibition of DNA replication by aphidicolin: A.G. Baranovskiy, et al.; Nucl. Acids Res. 42, 14013 (2014)
  17. Toward a cancer drug of fungal origin: A. Kornienko, et al.; Med. Res. Rev. 35, 937 (2015)
  18. Aphidicolin: its chemistry and biosynthesis: J.R. Hanson; J. Chem. Res. 42, 395 (2018)
  19. Stability of cytoplasmic nanoviscosity during cell cycle of HeLa cells synchronized with Aphidicolin: K. Szczepanski, et al.; Sci. Rep. 9, 1 (2019) 
  20. Mitotic DNA synthesis is differentially regulated between cancer and noncancerous cells: C.L. Graber-Feesl, et al.; Mol. Cancer Res. 17, 1687 (2019)
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