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HomeProduct name listAPHIDICOLIN

APHIDICOLIN

Synonym(s):APC;Aphidicolin - CAS 38966-21-1 - Calbiochem;ICI 69653;InSolution Aphidicolin - CAS 38966-21-1 - Calbiochem;NSC-234714

  • CAS NO.:38966-21-1
  • Empirical Formula: C20H34O4
  • Molecular Weight: 338.48
  • MDL number: MFCD00083214
  • EINECS: 609-602-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
APHIDICOLIN Structural

What is APHIDICOLIN?

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

The Uses of APHIDICOLIN

(+)-Aphidicolin is a naturally occurring tetracyclic diterpene with potential antiviral and antimitotical properties.

The Uses of APHIDICOLIN

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.

The Uses of APHIDICOLIN

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

What are the applications of Application

Aphidicolin is a novel tetracyclic diterpene antibiotic and also a DNA synthesis inhibitor in eukaryotes.

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

Properties of APHIDICOLIN

Melting point: 218-220°C
Boiling point: 394.61°C (rough estimate)
alpha  D27 +12° (c = 1 in methanol)
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.)
form  White solid
pka 14.24±0.70(Predicted)
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 for APHIDICOLIN

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for APHIDICOLIN

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