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| | APHIDICOLIN Basic information |
| Product Name: | APHIDICOLIN | | Synonyms: | (3-ALPHA,4-ALPHA,5-ALPHA,17-ALPHA)-3,17-DIHYDROXY-4-METHYL-9,15-CYCLO-C,18-DINOR-14,15-SECOANDROSTANE-4,17-DIMETHANOL;(+)-APHIDICOLIN;APHIDICOLIN;(+)-APHIDICOLIN, NIGROSPORA ORYZAE;APC;,11a-beta,11b-beta))-;9-dimethanol,tetradecahydro-3,9-11a-methano-11ah-cyclohepta(a)naphthalene-4;dihydroxy-4,11b-dimethyl-,(3r-(3-alpha,4-alpha,4a-alpha,6a-beta,8-beta,9-beta | | CAS: | 38966-21-1 | | MF: | C20H34O4 | | MW: | 338.48 | | EINECS: | 609-602-3 | | Product Categories: | antibiotic;Di-Terpenoids | | Mol File: | 38966-21-1.mol |  |
| | APHIDICOLIN Chemical Properties |
| Melting point | 218-220°C | | alpha | D27 +12° (c = 1 in methanol) | | Boiling point | 394.61°C (rough estimate) | | density | 1.0057 (rough estimate) | | vapor pressure | 0.55 hPa ( 20 °C) | | refractive index | 1.4434 (estimate) | | Fp | 87℃ | | storage temp. | 2-8°C | | solubility | ethanol: soluble1mg/mL (stable at least a week at 4°C.) | | pka | 14.24±0.70(Predicted) | | form | White solid | | color | colorless | | optical activity | [α]27/D +12°, c = 1 in methanol(lit.) | | Water Solubility | Soluble in DMSO or methanol. Insoluble in water. Store solutions at -20° | | Merck | 13,734 | | BRN | 4689958 | | Stability: | Stable for 2 years from date of purchase from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month. |
| Safety Statements | 22-24 | | RIDADR | NA 1993 / PGIII | | WGK Germany | 3 | | RTECS | PB9185000 | | F | 10-21 | | HS Code | 29419090 |
| | APHIDICOLIN Usage And Synthesis |
| Description | (+)-Aphidicolin is a natural tetracyclic diterpene first isolated from the fungus C. aphidicola and shown to have antiviral activity against herpes simplex. In eukaryotic cells, it is a cell-permeable, reversible inhibitor of DNA replication, specifically blocking the activity of DNA polymerases α, δ, and ε when used at low micromolar levels. Aphidicolin can be used, at 3 μM, to arrest cells in G1/S phase or to increase gene amplification frequency. | | Chemical Properties | White crystal | | Uses | (+)-Aphidicolin is a naturally occurring tetracyclic diterpene with potential antiviral and antimitotical properties. | | Uses | Aphidicolin is a tetracyclic diterpene antibiotic isolated from fungi, notably Cephalosporium, Nigrospora, Harziella and Phoma. Aphidicolin has antibiotic, antiviral and antimitotic properties, blocking the cell cycle at early S-phase. This property has been used to synchronise cell division and is useful as a tool in cell differentiation research. Aphidicolin is a reversible inhibitor of DNA replication by inhibiting selected DNA polymerases. Aphidicolin induces apoptosis, prolongs the half-life of DNA methyltransferase, is active against Leishmania parasites and acts synergistically with the antitumour agents, vincristine and doxorubicin. | | Uses | A DNA polymerase inhibitor. Blocks the cell cycle at the early S-phase | | Definition | ChEBI: A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positi
ns 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. | | General Description | A cell-permeable tetracyclic diterpene antibiotic. Cell synchronization agent. Blocks the cell cycle at the early S-phase. Specific inhibitor of DNA polymerase α and δ in eukaryotic cells and in some viruses of animal origin. Potentiates apoptosis induced by arabinosyl nucleosides in leukemia cell lines. Also induces apoptosis in HeLaS3 cells, but inhibits vincristine-induced apoptosis in the p53-negative human prostate cancer cell line PC-3. | | Biochem/physiol Actions | Cell permeable: yes | | storage | +4°C | | References | 1) Syvaoja et al. (1990), DNA polymerases alpha, delta, and epsilon: three distinct enzymes from HeLa cells; Proc. Natl. Acad. Sci. USA, 87 6664
2) Urbani et al. (1995), Dissociation of nuclear and cytoplasmic cell cycle progression by drugs employed in cell synchronization; Exp. Cell Res., 219 159
3) Kuwakado et al. (1993), Aphidicolin potentiates apoptosis induced by arabinosyl nucleosides in human myeloid leukemia cell lines; Biochem. Pharmacol., 46 1909
4) Yin and Schimke (1996), Inhibition of apoptosis by overexpressing Bcl-2 enhances gene amplification by a mechanism independent of aphidicolin pretreatment; Proc. Natl. Acad. Sci. USA, 93 3394 |
| | APHIDICOLIN Preparation Products And Raw materials |
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