7(S),18(R)-Dihydroxy-16(S),18-dimethyl-10-phenyl[11]cytochalasa-6(12),13(E),19(E)-trien-1,17-dion-21(R)-acetat

Bezeichnung:7(S),18(R)-Dihydroxy-16(S),18-dimethyl-10-phenyl[11]cytochalasa-6(12),13(E),19(E)-trien-1,17-dion-21(R)-acetat

CAS-Nr22144-77-0

Englisch Name:CYTOCHALASIN D

CBNumberCB2672937

SummenformelC30H37NO6

Molgewicht507.62

MOL-Datei22144-77-0.mol

Synonyma

7(S),18(R)-Dihydroxy-16(S),18-dimethyl-10-phenyl[11]cytochalasa-6(12),13(E),19(E)-trien-1,17-dion-21(R)-acetat

7(S),18(R)-Dihydroxy-16(S),18-dimethyl-10-phenyl[11]cytochalasa-6(12),13(E),19(E)-trien-1,17-dion-21(R)-acetat physikalisch-chemischer Eigenschaften

Schmelzpunkt	255-260°C
Siedepunkt	595.84°C (rough estimate)
Dichte	1.1764 (rough estimate)
Brechungsindex	1.6310 (estimate)
Flammpunkt	87℃
storage temp.	−20°C
Löslichkeit	DMSO: soluble
pka	11.95±0.70(Predicted)
Aggregatzustand	White solid
Farbe	White
BRN	1632828
Stabilität	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 chemische Informationen	Cytochalasin D (22144-77-0)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	25-63
S-Sätze:	36/37-45
RIDADR	UN 1544 6.1/PG 2
WGK Germany	3
RTECS-Nr.	GZ4850000
HazardClass	6.1(a)
PackingGroup	I
HS Code	29337900
Giftige Stoffe Daten	22144-77-0(Hazardous Substances Data)

Gefahreninformationscode (GHS)

CYTOCHALASIN D Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R63:Kann das Kind im Mutterleib möglicherweise schädigen.
S-Sätze Betriebsanweisung:
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
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
Chemische Eigenschaften
Powder
Verwenden
A cell cycle arresting compound used in actin polymerization studies and cytological research
Verwenden
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.
Verwenden
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.
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.
Allgemeine Beschreibung
Needles or fluffy white powder.
Reaktivität anzeigen
CYTOCHALASIN D may be sensitive to exposure to heat. CYTOCHALASIN D can react with strong oxidizing agents, strong acids and strong bases. .
Brandgefahr
Flash point data for CYTOCHALASIN D are not available; however, CYTOCHALASIN D is probably combustible.
Biologische Aktivität
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.
Sicherheitsprofil
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
Lager
Store at -20°C
Einzelnachweise
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

7(S),18(R)-Dihydroxy-16(S),18-dimethyl-10-phenyl[11]cytochalasa-6(12),13(E),19(E)-trien-1,17-dion-21(R)-acetat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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