| Identification | Back Directory | [Name]
CYTOCHALASIN E | [CAS]
36011-19-5 | [Synonyms]
CYTOCHALACINE
CYTOCHALICINE
CYTOCHALASIN 3
CYTOCHALASIN E
CYTOCHALASIN E(RG)
CYTOCHALASIN E(RG) Please Call
CYTOCHALASIN E, ASPERGILLUS CLAVATUS
CYTOCHALASIN E FROM ASPERGILLUSCLAVATUS
CYTOCHALASIN E FROM ASPERGILLUS &
(7s,13e,16s,18r,19e)-18-dimethyl-10-phenyl
21,23-dioxa(13)cytochalasa-13,19-diene-1,17,22-trione,6,7-epoxy-18-hydroxy-16,
6,7-epoxy-10-phenyl-5,6,16,18-tetramethyl-21,23-dioxa-[13]cytochalas-13,19-die
(7S,13E,16S,18R,19E)-6,7-Epoxy-18-hydroxy-16,18-dimethyl-10-phenyl-21,23-dioxa[13]cytochalasa-13,19-diene-1,17,22-trione
[7β,13E,16S,18R,19E]-6,7-Epoxy-18-hydroxy-16,18-dimethyl-10-phenyl-21,23-dioxa[13]cytochalasa-13,19-diene-1,17,22-trione
21,23-Dioxa[13]cytochalasa-13,19-diene-1,17,22-trione, 6,7-epoxy-18-hydroxy-16,18-dimethyl-10-phenyl-, (7S,13E,16S,18R,19E)-
1,3Dioxacyclotridecino4,5-doxirenofisoindole-5,10,12(4H,6H)-trione, 3,13,14,14a,15,15a,16a,16b-octahydro-6-hydroxy-4,6,15,15a-tetramethyl-14-(phenylmethyl)-, (1E,4S,6R,7E,11aS,14S,14aS,15S,15aR,16aS,16bS)- | [EINECS(EC#)]
252-835-7 | [Molecular Formula]
C28H33NO7 | [MDL Number]
MFCD00005178 | [MOL File]
36011-19-5.mol | [Molecular Weight]
495.56 |
| Chemical Properties | Back Directory | [Appearance]
white powder | [Melting point ]
206 °C
| [Boiling point ]
587.59°C (rough estimate) | [density ]
1.2415 (rough estimate) | [refractive index ]
1.6290 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMF: 11 mg/ml; DMF:PBS (pH7.2) (1:30): 0.03 mg/ml; DMSO: 10 mg/ml; Ethanol: 2 mg/ml | [form ]
White solid. | [pka]
11.22±0.70(Predicted) | [color ]
White to off-white | [BRN ]
1096975 | [LogP]
1.920 (est) |
| Hazard Information | Back Directory | [Chemical Properties]
white powder | [Uses]
Cytochalasin E is one of a family of potent mycotoxins produced by a range of fungi. All members of the class exhibit profound effects on cytoskeletal proteins, resulting in pronounced morphogenic changes in animals and plants. Despite the common mode of action, there is evidence that individual members display diverse selectivity. Specifically, cytochalasin E acts as an angiogenesis inhibitor and, unlike other cytochalasins, does not inhibit glucose transport. | [Definition]
ChEBI: A natural product found in Arthrinium sacchari. | [Description]
The cytochalasins are cell-permeable fungal metabolites which inhibit actin polymerization. This interferes with such diverse processes as cell movement, growth, phagocytosis, degranulation, and secretion. Cytochalasin E is an epoxide-containing analog of cytochalasin B which potently and selectively inhibits the growth of endothelial cells (IC50 < 1 nM), impairing angiogenesis and tumor growth. This cytochalasin does not inhibit glucose transport or HIV-1 protease activity. | [Biochem/physiol Actions]
Cytochalasin E is an epoxide that exhibits anti-proliferative activity in endothelial cells in vitro. It also participates in inhibiting tumor growth and angiogenesis in vivo. Cytochalasin E also possesses antimicrobial and antiviral properties. | [References]
[1] T UDAGAWA. Cytochalasin E, an epoxide containing Aspergillus-derived fungal metabolite, inhibits angiogenesis and tumor growth.[J]. Journal of Pharmacology and Experimental Therapeutics, 2000, 294 2: 421-427.
[2] R F KLETZIEN A S J F Perdue. Cytochalasin A and B. Inhibition of sugar uptake in cultured cells.[J]. The Journal of Biological Chemistry, 1972, 247 9: 2964-2966.
[3] J F GRIFFIN C Y J A L Rampal. Inhibition of glucose transport in human erythrocytes by cytochalasins: A model based on diffraction studies.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1982, 79 12: 3759-3763. DOI: 10.1073/pnas.79.12.3759
[4] Y.B. LOMBARDO . Long-term administration of a sucrose-rich diet to normal rats: Relationship between metabolic and hormonal profiles and morphological changes in the endocrine pancreas[J]. Metabolism: clinical and experimental, 1996, 45 12: Pages 1527-1532. DOI: 10.1016/s0026-0495(96)90183-3 |
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