| Identification | Back Directory | [Name]
CYTOCHALASIN D | [CAS]
22144-77-0 | [Synonyms]
Nsc209835
Lygosporin a
ZYGOSPORIN A
CYTOCHALACIND
CYTOCHALICIND
Cytohalasin d
CYTOCHALASIN D
19-trien-17-one
CYTOCHALASIN D(RG)
InSolution? Cytochalasin D,
Cytochalasin D, Zygosporin A
CYTOCHALASIN D, ZYGOSPORIUM MANSONII
CYTOCHALASIN D, ZYGUSPORIUM MANSONII
cytochalasin D from zygosporium masonii
CYTOCHALASIN D FROM ZYGOSPORIUMMANSONII
,18-dimethyl-10-phenyl-,(7s,13e,16s,18r,19e,21r)-
15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-115-acetate
,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-,15-acetate
(11)cytochalasa-6(12),13,19-triene-1,17-dione,21-(acetyloxy)-7,18-dihydroxy-16
1h-cycloundec(d)isoindole-1,11(2h)-dione,3-benzyl-3,3-alpha,4,5,6,6-alpha,9,10
1h-cycloundec(d)isoindole-1,11(2h)-dione,3-benzyl-3,3-alpha4,5,6,6-alpha,9,10,
7,18-dihydroxy-10-phenyl-5,16,18-trimethyl-[11]cytochalas-21-acetoxy-6(12),13,
[11]Cytochalasa-6[12],13,19-triene-1,17-dione, 21-(acetyloxy)-7,18-dihydroxy-16,18-dimethyl-10-phenyl-
7(S),18(R)-dihydroxy-16(S),18-dimethyl-10-phenyl[11]cytochalasa-6(12),13(E),19(E)-triene-1,17-dione 21(R)-acetate
(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-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19E,21R)-
1H-Cycloundec[D]isoindole-1,11(2H)-dione, 3-benzyl-3,3-.alpha.,4,5,6,6-.alpha.,9,10,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-, 15-acetate
1H-Cycloundecdisoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12-dihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)- | [EINECS(EC#)]
244-804-1 | [Molecular Formula]
C30H37NO6 | [MDL Number]
MFCD00077706 | [MOL File]
22144-77-0.mol | [Molecular Weight]
507.62 |
| Chemical Properties | Back Directory | [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 | [form ]
White solid | [pka]
11.95±0.70(Predicted) | [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) |
| Hazard Information | Back Directory | [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 antitumor agent. Cytochalasin D has become one of the standard cellular probes for investigating the role of actin in cell biology. | [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. | [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 | [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. | [target]
p38MAPK | PI3K | Akt | Calcium Channel | ATPase | [storage]
Store at -20°C, protect from light | [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 |
| Safety Data | Back Directory | [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 | [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. | [Hazardous Substances Data]
22144-77-0(Hazardous Substances Data) |
|
|