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C7744 Sigma-Aldrich

Combretastatin A4

≥98% (HPLC), powder

Synonym: 1-(3,4,5-Trimethoxyphenyl)-2-(3′-hydroxy-4′-methoxyphenyl) ethane 3,4,5-trimethoxy-3′-hydroxy-4′-methoxystilbene, 2-Methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol, CA4

  • CAS Number 117048-59-6

  • Empirical Formula (Hill Notation) C18H20O5

  • Molecular Weight 316.35

  •  MDL number MFCD03453309

  •  PubChem Substance ID 329775149

  •  NACRES NA.77

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Properties

Related Categories Apoptosis Inducers, Apoptosis Inhibitors, Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
color   off-white
solubility   DMSO: >10 mg/mL
storage temp.   −20°C
SMILES string   COc1ccc(\C=C/c2cc(OC)c(OC)c(OC)c2)cc1O
InChI   1S/C18H20O5/c1-20-15-8-7-12(9-14(15)19)5-6-13-10-16(21-2)18(23-4)17(11-13)22-3/h5-11,19H,1-4H3/b6-5-
InChI key   HVXBOLULGPECHP-WAYWQWQTSA-N

Description

General description

Combretastatin A4 belong to the class of colchicinoids compounds.

Application

Combretastatin A4 has been used:
• as an anti-tubulin agent to determine the effects of isocitrate dehydrogenases (IDH1 and IDH2) proteins in G2/M phase
•  to evaluate the anti-proliferative and pro-apoptotic properties of biphenyl CA4 derivatives in both 2D and 3D cancerous and non-cancerous cell models
•  as a microtubule inhibitor to study its effects on motility of Ascaris suum L3 larvae

Packaging

5, 25 mg in glass bottle

Biochem/physiol Actions

Combretastatin A4 is a potent microtubule targeting agent (MTA).

Combretastatin A4 is a vascular disrupting agent (VDA) that targets tumor vasculature to inhibit angiogenesis. It inhibits tubulin polymerization at the colchicine-binding site of beta-tubulin. It has antitumor activity by inhibiting AKT function in human gastric cells. The inhibited AKT activation causes decreased cell proliferation, cell cycle arrest, and reduced in vitro migration/invasiveness and in vivo metastatic ability. Combretastatin A4 is a natural stilbenoid phenol.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 2
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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