Cytochalasin E

Cytochalasin E^[1]
Names
	Preferred IUPAC name (4E,6R,8S,10E,11aS,11bS,12aR,13S,13aS,14S)-14-Benzyl-6-hydroxy-6,8,12a,13-tetramethyl-9,11a,11b,12a,13,13a,14,15-octahydro-2H-[1,3]dioxacyclotridecino[4,5-d]oxireno[2,3-f]isoindole-2,7,16(6H,8H)-trione
Identifiers
CAS Number	36011-19-5 ;
3D model (JSmol)	Interactive image;
3DMet	L06226;
ChEBI	CHEBI:68201;
ChEMBL	ChEMBL494856;
ChemSpider	4572350 ;
ECHA InfoCard	100.048.018
EC Number	252-835-7;
KEGG	C19953;
PubChem CID	5458385;
CompTox Dashboard (EPA)	DTXSID60894866 ;
	InChI 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 Key: LAJXCUNOQSHRJO-ZYGJITOWSA-N ; InChI=1/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 Key: LAJXCUNOQSHRJO-ZYGJITOWBM;
	SMILES C[C@H]1C/C=C/[C@H]2[C@H]3[C@](O3)([C@H]([C@@H]4[C@]2(C(=O)N[C@H]4CC5=CC=CC=C5)OC(=O)O/C=C/[C@@](C1=O)(C)O)C)C;
Properties
Chemical formula	C28H33NO7
Molar mass	495.572 g·mol−1
Density	1.309 g/ml
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H330, H361
Precautionary statements	P201, P202, P260, P262, P264, P270, P271, P280, P281, P284, P301+P310, P302+P350, P304+P340, P308+P313, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	Infobox references

Cytochalasin E, a member of the cytochalasin group, is an inhibitor of actin polymerization in blood platelets. It inhibits angiogenesis and tumor growth. Unlike and cytochalasin B, it does not inhibit glucose transport.

Because of its antiangiogenic effect, cytochalasin E is a potential drug for age-related macular degeneration, a kind of blindness caused by an abnormal proliferation of blood vessels in the eye.^[2]

Cytochalasin E was found to be a potent and selective inhibitor of bovine capillary endothelial (BCE) cell proliferation. Cytochalasin E differs from other cytochalasin molecules by having an epoxide, which is required for specificity and potency. Cytochalasin E is a potent antiangiogenic agent that may be useful for treatments of cancer and other pathologic angiogenesis.^[3]

References[]

^ Cytochalasin E from Aspergillus clavatus at Sigma-Aldrich
^ eyesight.org Archived 2006-05-19 at the Wayback Machine
^ Udagawa, T; Yuan, J; Panigrahy, D; Chang, YH; Shah, J; D'Amato, RJ (August 2000). "Cytochalasin E, an epoxide containing Aspergillus-derived fungal metabolite, inhibits angiogenesis and tumor growth". J. Pharmacol. Exp. Ther. 294: 421–7. PMID 10900214.

External pages[]

Cytochalasin E from Fermentek
Cytochalasin E from Cayman Chemical

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[1] Cytochalasin E from Aspergillus clavatus at Sigma-Aldrich

[2] yesight.org Archived 2006-05-19 at the Wayback Machine

[3] Udagawa, T; Yuan, J; Panigrahy, D; Chang, YH; Shah, J; D'Amato, RJ (August 2000). "Cytochalasin E, an epoxide containing Aspergillus-derived fungal metabolite, inhibits angiogenesis and tumor growth". J. Pharmacol. Exp. Ther. 294: 421–7. PMID 10900214.

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