Cytochalasin E (CAS 36011-19-5) | Cayman Chemical
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Cytochalasin E

Item № 11331
CAS № 36011-19-5
Purity ≥98%
product image
                (CAS 36011-19-5)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     1 mg $45.00 0.00
     5 mg $180.00 0.00
     10 mg $338.00 0.00

Pricing updated 2018-11-16. Prices are subject to change without notice.

Description

The cytochalasins are cell-permeable fungal metabolites which inhibit actin polymerization.1,2,3,4 This interferes with such diverse processes as cell movement, growth, phagocytosis, degranulation, and secretion.5,6,7,8 Cytochalasin E is an epoxide-containing analog of cytochalasin B (Item No. 11328) which potently and selectively inhibits the growth of endothelial cells (IC50 < 1 nM), impairing angiogenesis and tumor growth.9 This cytochalasin does not inhibit glucose transport or HIV-1 protease activity.10,11,12

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Technical Information
Formal Name
(1E,4S,6R,7E,11aS,14S,14aS,15S,15aR,16aS,16bS)-3,13,14,14a,15,15a,16a,16b-octahydro-6-hydroxy-4,6,15,15a-tetramethyl-14-(phenylmethyl)-[1,3]dioxacyclotridecino[4,5-d]oxireno[f]isoindole-5,10,12(4H,6H)-trione
CAS Number
36011-19-5
Molecular Formula
C28H33NO7
Formula Weight
495.6
Purity
≥98%
Formulation
A crystalline solid
SMILES
O=C(OC12[C@@]([C@H]3[C@](C)(O3)[C@@H](C)[C@@]1([H])[C@H](CC4=CC=CC=C4)NC2=O)([H])/C=C/C[C@]5([H])C)O/C=C/[C@](O)(C)C5=O
InChI Code
InChI=1S/C28H33NO7/c1-16-9-8-12-19-23-27(4,35-23)17(2)21-20(15-18-10-6-5-7-11-18)29-24(31)28(19,21)36-25(32)34-14-13-26(3,33)22(16)30/h5-8,10-14,16-17,19-21,23,33H,9,15H2,1-4H3,(H,29,31)/b12-8+,14-13+/t16-,17-,19-,20-,21-,23-,26+,27+,28?/m0/s1
InChI Key
LAJXCUNOQSHRJO-KGDUIROVSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Brenner, S.L., and Korn, E.D. The effects of cytochalasins on actin polymerization and actin ATPase provide insights into the mechanism of polymerization The Journal of Biological Chemisty 255(3), 841-844 (1980).

2. Lin, D.C., Tobin, K.D., Grumet, M., et al. Cytochalasins inhibit nuclei-induced actin polymerization by blocking filament elongation Journal of Cell Biology 84, 455-460 (1980).

3. Ostlund, R.E., Jr., Leung, J.T., and Hajek, S.V. Regulation of microtubule assembly in cultured fibroblasts Journal of Cell Biology 85, 386-391 (1980).

4. Pinder, J.C., and Gratzer, W.B. Structural and dynamic states of actin in the erythrocyte Journal of Cell Biology 96(3), 768-775 (1983).

5. Flaumenhaft, R., Dilks, J.R., Rozenvayn, N., et al. The actin cytoskeleton differentially regulates platelet α-granule and dense-granule secretion Blood 105(10), 3879-3887 (2005).

6. Taheri-Talesh, N., Horio, T., Araujo-Bazán, L., et al. The tip growth apparatus of Aspergillus nidulans Molecular Biology of the Cell 19, 1439-1449 (2008).

7. dos Santos, T., Varela, J., Lynch, I., et al. Effects of transport inhibitors on the cellular uptake of carboxylated polystyrene nanoparticles in different cell lines PLoS One 6(9), 1-10 (2011).

8. Nightingale, T.D., White, I.J., Doyle, E.L., et al. Actomyosin II contractility expels von Willebrand factor from Weibel-Palade bodies during exocytosis Journal of Cell Biology 194(4), 613-629 (2011).

9. Udagawa, T., Yuan, J., Panigrahy, D., et al. Cytochalasin E, an epoxide containing Aspergillus-derived fungal metabolite, inhibits angiogenesis and tumor growth Journal of Pharmacology and Experimental Therapeutics 294(2), 421-427 (2000).

10. Kletzien, R.F., Perdue, J.F., and Springer, A. Cytochalasin A and B. Inhibition of sugar uptake in cultured cells The Journal of Biological Chemisty 247(9), 2964-2966 (1972).

11. Griffin, J.F., Rampal, A.L., and Jung, C.Y. Inhibition of glucose transport in human erythrocytes by cytochalasins: A model based on diffraction studies Proceedings of the National Academy of Sciences of the United States of America 79, 3759-3763 (1982).

12. Lombardo, Y.B., Drago, S., Chicco, A., et al. Long-term administration of a sucrose-rich diet to normal rats: Relationship between metabolic and hormonal profiles and morphological changes in the endocrine pancreas Metabolism 45(12), 1527-1532 (1996).

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