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Merck

C7744

Combretastatin A4

≥98% (HPLC), vascular disrupting agent, 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
UNSPSC Code:
12352200
PubChem Substance ID:
329775149
NACRES:
NA.77
MDL number:
MFCD03453309

Product Name

Combretastatin A4, ≥98% (HPLC), powder

SMILES string

COc1ccc(\C=C/c2cc(OC)c(OC)c(OC)c2)cc1O

InChI key

HVXBOLULGPECHP-WAYWQWQTSA-N

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-

assay

≥98% (HPLC)

form

powder

color

off-white

solubility

DMSO: >10 mg/mL

storage temp.

−20°C

Quality Level

100

Related Categories

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.
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.

General description

Combretastatin A4 belong to the class of colchicinoids compounds.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000487730
0000487729
0000487729
0000487730
0000271456

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Christian Damsgaard et al.
eLife, 9 (2020-08-26)
Previously, we showed that the evolution of high acuity vision in fishes was directly associated with their unique pH-sensitive hemoglobins that allow O2 to be delivered to the retina at PO2s more than ten-fold that of arterial blood (Damsgaard et
Abundance of d-2-hydroxyglutarate in G2/M is determined by FOXM1 in mutant IDH1-expressing cells
Bala Bhaskara Rao K, et al.
Febs Letters, 593(16), 2177-2193 (2019)
Medicinal chemistry of combretastatin A4: present and future directions.
Gian Cesare Tron et al.
Journal of medicinal chemistry, 49(11), 3033-3044 (2006-05-26)
De novo identification of toxicants that cause irreparable damage to parasitic nematode intestinal cells
Jasmer DP, et al.
PLoS Neglected Tropical Diseases, 14(5), e0007942-e0007942 (2020)
S Papiol et al.
Translational psychiatry, 7(6), e1159-e1159 (2017-06-28)
Preliminary studies suggest that, besides improving cognition, aerobic exercise might increase hippocampal volume in schizophrenia patients; however, results are not consistent. Individual mechanisms of volume changes are unknown but might be connected to the load of risk genes. Genome-wide association
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