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C7744

Sigma-Aldrich

Combretastatin A4

≥98% (HPLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C18H20O5
CAS Number:
117048-59-6
Molecular Weight:
316.35
MDL number:
MFCD03453309
UNSPSC Code:
12352200
PubChem Substance ID:
329775149
NACRES:
NA.77

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

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

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.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301 + H311 + H331,H318

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

C7744-25MG:
C7744-BULK:
C7744-5MG:
C7744-VAR:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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Lisa M Greene et al.
Biochemical pharmacology, 84(5), 612-624 (2012-06-19)
Recent clinical data demonstrated that the vascular targeting agent Combretastatin-A4 phosphate (CA-4P) prolonged survival of patients with advanced anaplastic thyroid cancer without any adverse side effects. However, as a single agent CA-4 failed to reduce tumour growth in the murine
Lasse Dührsen et al.
Journal of neurosurgery, 128(6), 1668-1673 (2017-07-29)
OBJECTIVE Temporal lobe epilepsy (TLE) is the most common type of pharmacoresistant focal epilepsy, for which anterior mesial temporal lobe resection (AMTLR) is a treatment option. Focal cortical dysplasia Type IIIa (FCD IIIa), a developmental lesion resulting from defects in
Julie A Sosa et al.
Surgery, 152(6), 1078-1087 (2012-11-20)
Anaplastic thyroid cancer (ATC) is an aggressive neoplasm for which a paucity of data exist about the relative role of operative procedures in disease management. The FACT trial was a randomized, controlled phase 2/3 trial assessing the safety and efficacy
Lauriane Jugé et al.
Radiology, 264(2), 436-444 (2012-06-14)
To investigate the potential value of magnetic resonance (MR) elastography and diffusion-weighted (DW) MR imaging in the detection of microstructural changes of murine colon tumors during growth and antivascular treatment. The study was approved by the regional ethics committee for
Scott L Young et al.
Expert opinion on investigational drugs, 13(9), 1171-1182 (2004-08-28)
Combretastatin A4 phosphate (CA4P) represents the lead compound in a group of novel tubulin depolymerising agents being developed as vascular targeting agents (VTAs). VTAs are drugs that induce rapid and selective vascular dysfunction in tumours. CA4P is a water-soluble prodrug
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