| Identification | Back Directory | [Name]
APHIDICOLIN | [CAS]
38966-21-1 | [Synonyms]
APC
ici69653
nsc-234714
APHIDICOLIN
(+)-APHIDICOLIN
,11a-beta,11b-beta))-
APHIDICOLIN USP/EP/BP
Aphidicolin, Ready Made Solution
(+)-APHIDICOLIN, NIGROSPORA ORYZAE
Aphidicolin, froM Nigrospora oryzae
APHIDICOLIN FROM NIGROSPORA SPHAERICA
Aphidicolin, 98%, from Nigrospora oryzae
Aphidicolin - CAS 38966-21-1 - Calbiochem
APHIDICOLIN FROM CEPHALOSPORIUM APHIDICO LA
InSolution Aphidicolin - CAS 38966-21-1 - Calbiochem
Aphidicolin NSC 234714 ICI 69653
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
(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
(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
8,11a-Methano-11aH-cycloheptaanaphthalene-4,9-dimethanol, tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, (3R,4R,4aR,6aS,8R,9R,11aS,11bS)-
8,11|á-Methano-11aH-cyclohepta[a]naphthalene-4,9-dimethanol,tetradecahydro-3,9-dihydroxy-4,11b-dimethyl-, (3R,4R,4aR,6aS,8R,9R,11aS,11bS)- | [EINECS(EC#)]
609-602-3 | [Molecular Formula]
C20H34O4 | [MDL Number]
MFCD00083214 | [MOL File]
38966-21-1.mol | [Molecular Weight]
338.48 |
| Chemical Properties | Back Directory | [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.) | [form ]
White solid | [pka]
14.24±0.70(Predicted) | [color ]
colorless | [biological source]
Nigrospora sphaerica | [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. |
| Hazard Information | Back Directory | [Description]
(+)-Aphidicolin is a natural tetracyclic diterpene first isolated from the fungus C. aphidicola and shown to have antiviral activity against herpes simplex.1 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.2,3,4 Aphidicolin can be used, at 3 μM, to arrest cells in G1/S phase or to increase gene amplification frequency.5,6 | [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. | [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 |
|
| Company Name: |
Merck Ltd
|
| Tel: |
+91-2262109800 +91-2262109000 |
| Website: |
www.merckgroup.com |
| Company Name: |
BOC Sciences
|
| Tel: |
1-631-485-4226; 16314854226 |
| Website: |
https://www.bocsci.com |
|