Technical Data

207059
CAS Number
38966-21-1
Grade
Highly Purified
Molecular Formula
C20H34O4
Molecular Weight
338.48
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
4°C/-20°C (after reconstitution)
(+)-Aphidicolin
[3R-(3α,4α,4aα,6aβ,8β,9β,11aβ,11bβ)]-Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-8,11a-methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol; Aphidicolin; ICI 69653; NSC 234714; (3α,4α,5α,17α)-3,17-Dihydroxy-4-methyl-9,15-cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanol; (3R,4R,4aR,6aS,8R,9R,11aS,11bS)-Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-8,11a-methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol

Antibiotic. Reversible inhibitor of eukaryotic nuclear DNA replication. Useful for cell synchronization. Blocks the cell cycle at early S phase. Prolongs the half life of DNA methyltransferase. Specific DNA polymerase alpha and delta inhibitor in eukaryotic cells and in some viruses of animal origin. Acts synergistically with vincristine and doxorubicin. Apoptosis inhibitor/inducer.

Synonyms
[3R-(3α,4α,4aα,6aβ,8β,9β,11aβ,11bβ)]-Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-8,11a-methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol; Aphidicolin; ICI 69653; NSC 234714; (3α,4α,5α,17α)-3,17-Dihydroxy-4-methyl-9,15-cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanol; (3R,4R,4aR,6aS,8R,9R,11aS,11bS)-Tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-8,11a-methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol
CAS Number
38966-21-1
Molecular Formula
C20H34O4
Molecular Weight
338.48
Source
Nigrospora oryzae
Purity
≥98% (HPLC)
Appearance
Supplied as a white to off-white solid.
Solubility
Soluble in DMSO (~50mg/ml), methanol (~10mg/ml) or 100% ethanol; insoluble in H2O.
Storage and Stability
May be stored at 4°C. For long-term storage, aliquot and store at 4°C. Do not freeze. Aliquots are stable for 6 months. For maximum recovery of product, centrifuge the original vial prior to removing the cap. Further dilutions can be made in assay buffer.
Source
Phoma sp.
Purity
≥98% (HPLC)
Form
Supplied as a white to off-white solid.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.

Intended for research use only. Not for use in human, therapeutic, or diagnostic applications.

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.;Oncogene 10: 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. Aphidicolin and bleomycin induced chromosome damage as biomarker of mutagen sensitivity: a twin study: B. Tedeschi, et al.; Mutat. Res. 546: 55 (2004)
USBio References
No references available
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