CYTOCHALASIN D Chemical Properties

Melting point:

255-260°C

Boiling point:

595.84°C (rough estimate)

Density 

1.1764 (rough estimate)

refractive index 

1.6310 (estimate)

Flash point:

87℃

storage temp. 

−20°C

solubility 

DMSO: soluble

pka

11.95±0.70(Predicted)

form 

White solid

color 

White

BRN 

1632828

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.

LogP

2.640 (est)

EPA Substance Registry System

Cytochalasin D (22144-77-0)

Safety Information

Hazard Codes 

T

Risk Statements 

25-63

Safety Statements 

36/37-45

RIDADR 

UN 1544 6.1/PG 2

WGK Germany 

3

RTECS 

GZ4850000

HazardClass 

6.1(a)

PackingGroup 

I

HS Code 

29337900

Hazardous Substances Data

22144-77-0(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

CYTOCHALASIN D Usage And Synthesis

Description

Cytochalasin D (22144-77-0) is a potent inhibitor of actin polymerization which also causes the disruption of actin filaments. More potent that cytochalasin B (10-fold) and does not inhibit monosaccharide transport across cell membranes. Disruption of actin microfilaments leads to activation of p53. Cell permeable

Chemical Properties

Powder

Uses

A cell cycle arresting compound used in actin polymerization studies and cytological research

Uses

Cytochalasin D acts as an anti-hypertensive drug acting on human intestinal epithelial caco-2 cells. Also has activity in HMG-CoA reductase inhibitors used in the lowering of cholesterol. Actin inhib itor, actin polymerization inhibitor affecting cell movement, growth, phagocytosis and even secretion.

Uses

Cytochalasin D is the most studied of the cytochalasins. Like most of the members of this mycotoxin class, cytochalasin D exhibits potent inhibition of actin filament function leading to cell death by apoptosis. This led to early investigation of the metabolite as an antitumour agent. Cytochalasin D has become one of the standard cellular probes for investigating the role of actin in cell biology.

Definition

ChEBI: An organic heterotricyclic compound that is a mycotoxin produced by Helminthosporium and other moulds which is cell permeable and a potent inhibitor of actin polymerisation and DNA synthesis.

General Description

Needles or fluffy white powder.

Reactivity Profile

CYTOCHALASIN D may be sensitive to exposure to heat. CYTOCHALASIN D can react with strong oxidizing agents, strong acids and strong bases. .

Fire Hazard

Flash point data for CYTOCHALASIN D are not available; however, CYTOCHALASIN D is probably combustible.

Biological Activity

Potent disruptor of actin filament function. Alters tight junction permeability. Unlike cytochalasin B, does not inhibit monosaccharide transport across the plasma membrane.

Biochem/physiol Actions

Cell permeable fungal toxin; potent inhibitor of actin polymerization. Disrupts actin microfilaments and activates the p53-dependent pathways causing arrest of the cell cycle at the G1-S transition. Inhibits smooth muscle contraction. Inhibits insulin-stimulated, but not basal, transport of glucose.

Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

target

p38MAPK | PI3K | Akt | Calcium Channel | ATPase

storage

Store at -20°C

References

1)) Goddetteand et al. (1986), Actin polymerization. The mechanism of action of cytochalasin D; J. Biol. Chem., 261 15974 2) Rubtsova et al. (1998), Disruption of actin microfilaments by cytochalasin D leads to activation of p53; FEBS Lett., 430 353

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