Combretastatin A-1

Combretastatin A-1
Names
Preferred IUPAC name
3-Methoxy-6-[(E)-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]benzene-1,2-diol
Other names
Combretastatin A1; OXi4500
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C18H20O6/c1-21-13-8-7-12(16(19)17(13)20)6-5-11-9-14(22-2)18(24-4)15(10-11)23-3/h5-10,19-20H,1-4H3/b6-5+ checkY
    Key: YUSYSJSHVJULID-AATRIKPKSA-N checkY
  • COC1=C(C(=C(C=C1)C=CC2=CC(=C(C(=C2)OC)OC)OC)O)O
Properties
C18H20O6
Molar mass 332.352 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Combretastatin A-1 is a combretastatin and a stilbenoid. It can be found in Combretum afrum, the Eastern Cape South African Bushwillow tree.

Biological effects in mammals

It is an antiangiogenic agent acting by destabilizing tubulin, which induces cell apoptosis of proliferating endothelial cells.

Derivatives as drugs

Currently designated an orphan drug by the FDA, combretastatin A1 diphosphate (OXi4503 or CA1P) is in Phase I clinical trials for relapsed and refractory acute myeloid leukemia and myelodysplastic syndrome.

References

  1. 1 2 Pettit, G. R.; Singh, S. B.; Niven, M. L.; Hamel, E.; Schmidt, J. M. (1987). "Isolation, Structure, and Synthesis of Combretastatins A-1 and B-1, Potent New Inhibitors of Microtubule Assembly, Derived from Combretum caffrum". Journal of Natural Products. 50 (1): 119–131. doi:10.1021/np50049a016. PMID 3598594.
  2. ↑ "A Phase I Clinical Trial of OXi4503 for Relapsed and Refractory Acute Myelogenous Leukemia (AML) and Myelodysplastic Syndromes (MDS)". 7 August 2017.