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(+)-Aphidicolin

BVT-0307-M001 1 mg $75.00
BVT-0307-M005 5 mg $220.00
BVT-0307-M025 25 mg $790.00
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Additional Information

Product Data
Synonyms NSC234714; BRN4689958; ICI69653
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 ≥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.
Origin Manufactured by BioViotica.
InChi Key NOFOAYPPHIUXJR-APNQCZIXSA-N
Product Type Chemical
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.
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Product Description

  • 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. The production of aphidicolin by Nigrospora sphaerica: A.N. Starratt and S.R Loschiavo; Can. J. Microbiol. 20, 416 (1974)
  3. Aphidicolin prevents mitotic cell division by interfering with the activity of DNA polymerase-alpha: S. Ikegami, et al.; Nature 275, 458 (1978)
  4. 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)
  5. Aphidicolin: a specific inhibitor of nuclear DNA replication in eukaryotes: S. Spadari, et al.; TIBS 7, 29 (1982)
  6. Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in human myeloid leukemia cell lines: K. Kuwakado, et al.; Biochem. Pharmacol. 46, 1909 (1993)
  7. Dissociation of nuclear and cytoplasmic cell cycle progression by drugs employed in cell synchronization: L. Urbani, et al.; Exp. Cell. Res. 219, 159 (1995)
  8. 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)
  9. TrkA neurogenic receptor regulates differentiation of neuroblastoma cells: W. Poluha, et al.;Oncogene10, 185 (1995)
  10. Effect of aphidicolin on DNA methyltransferase in the nucleus: I. Suetake, et al.; Cell Struct. Funct. 23, 137 (1998)
  11. 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)
  12. Antileishmanial activities of aphidicolin and its semisynthetic derivatives: O. Kayser, et al.; Antimicrob. Agents Chemother. 45, 288 (2001)
  13. Aphidicolin and bleomycin induced chromosome damage as biomarker of mutagen sensitivity: a twin study: B. Tedeschi, et al.; Mutat. Res. 546, 55 (2004)
  14. 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)
  15. Aphidicolin-induced nuclear elongation in tobacco BY-2 cells: H. Yashura, et al.; Plant Cell Physiol. 55, 913 (2014)
  16. Active and passive demethylation of male and female pronuclear DNA in the mammalian zygote: F. Guo, et al.; Cell Stem Cell 15, 447 (2014)
  17. Structural basis for inhibition of DNA replication by aphidicolin: A.G. Baranovskiy, et al.; Nucl. Acids Res. 42, 14013 (2014)
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