Cytochalasin E

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

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
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.048.018
EC Number
  • 252-835-7
KEGG
  • 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 N
    Key: LAJXCUNOQSHRJO-ZYGJITOWSA-N 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
  • 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
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:
Danger
H300, H310, H330, H361
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).
N verify (what is YN ?)
Infobox references

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
  1. Cytochalasin E from Aspergillus clavatus at Sigma-Aldrich
  2. eyesight.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.

External pages

Cytochalasin E from Fermentek
Cytochalasin E from Cayman Chemical


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