CAS 38966-21-1

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)

[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.

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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207059 (+)-Aphidicolin CAS: 38966-21-1

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