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)

Flash point:

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 Information

Safety Statements 

22-24

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

RTECS 

PB9185000

F 

10-21

HS Code 

29419090

MSDS

• Language:English Provider:SigmaAldrich

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

A DNA polymerase inhibitor. Blocks the cell cycle at the early S-phase

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

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