CYTOCHALASIN D

CYTOCHALASIN D Basic information
Product Name:CYTOCHALASIN D
Synonyms:CYTOCHALASIN D;CYTOCHALASIN D, ZYGOSPORIUM MANSONII;CYTOCHALASIN D, ZYGUSPORIUM MANSONII;(7S,13E,16S,18R,19E,21R)-21-(ACETYLOXY)-7,18-DIHYDROXY-16,18-DIMETHYL-10-PHENYL[11]CYTOCHALASA-6(12),13,19-TRIENE-1,17-DIONE;(11)cytochalasa-6(12),13,19-triene-1,17-dione,21-(acetyloxy)-7,18-dihydroxy-16;,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-,15-acetate;,18-dimethyl-10-phenyl-,(7s,13e,16s,18r,19e,21r)-;15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-115-acetate
CAS:22144-77-0
MF:C30H37NO6
MW:507.62
EINECS:244-804-1
Product Categories:antibiotic;Caspases/Apoptosis
Mol File:22144-77-0.mol
CYTOCHALASIN D Structure
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)
Fp 87℃
storage temp. −20°C
solubility DMSO: soluble
pka11.95±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.
LogP2.640 (est)
EPA Substance Registry SystemCytochalasin 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 Data22144-77-0(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
CYTOCHALASIN D Usage And Synthesis
DescriptionCytochalasin 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 PropertiesPowder
UsesA cell cycle arresting compound used in actin polymerization studies and cytological research
UsesCytochalasin 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.
UsesCytochalasin 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.
DefinitionChEBI: 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 DescriptionNeedles or fluffy white powder.
Reactivity ProfileCYTOCHALASIN D may be sensitive to exposure to heat. CYTOCHALASIN D can react with strong oxidizing agents, strong acids and strong bases. .
Fire HazardFlash point data for CYTOCHALASIN D are not available; however, CYTOCHALASIN D is probably combustible.
Biological ActivityPotent disruptor of actin filament function. Alters tight junction permeability. Unlike cytochalasin B, does not inhibit monosaccharide transport across the plasma membrane.
Biochem/physiol ActionsCell 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 ProfilePoison 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.
targetp38MAPK | PI3K | Akt | Calcium Channel | ATPase
storageStore at -20°C
References1)) 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
CYTOCHALASIN D Preparation Products And Raw materials
2-AZACYCLONONANONE 1-CYCLOHEXYL-2-PROPEN-1-OL 3-Pyrrolidineethanol 1,7-HEXADECADIENE 4,8-DIMETHYL-1-PHENYLNONANE CYTOCHALASIN J,cytochalasin J from A phomopsis species CYTOCHALASIN D 2-METHYL-1,5-HEXADIEN-3-OL 3-ETHYL-4-METHYL-PYRROLIDIN-2-ONE 3-METHOXY-2,2-DIMETHYLPROPYLAMINE dodec-3-en-1-al CYTOCHALASIN D, BODIPY(R) FL CONJUGATE 3,3-DIETHYLPYRROLIDINE (E)-NONA-2,8-DIEN-1-OL (R)-Pyrrolidin-3-ylmethanol DEABL 4-METHYLENECYCLOHEXYLMETHANOL 3-HEXENE-2,5-DIOL

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