APHIDICOLIN Property

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

Safety Statements 

22-24

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

RTECS 

PB9185000

F 

10-21

HS Code 

29419090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

APHIDICOLIN Chemical Properties,Usage,Production

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