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Merck

C7744

Combretastatin A4

≥98% (HPLC), vascular disrupting agent, powder

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :
C18H20O5
Numéro CAS:
117048-59-6
Poids moléculaire :
316.35
UNSPSC Code:
12352200
PubChem Substance ID:
329775149
NACRES:
NA.77
MDL number:
MFCD03453309

Principaux documents

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Nom du produit

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

Catégories apparentées

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.
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

signalword

Danger

Hazard Classifications

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

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
0000487730
0000487729
0000487729
0000487730
0000271456

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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
B Cao et al.
Molecular psychiatry, 22(9), 1352-1358 (2017-01-25)
Volume reduction and shape abnormality of the hippocampus have been associated with mood disorders. However, the hippocampus is not a uniform structure and consists of several subfields, such as the cornu ammonis (CA) subfields CA1-4, the dentate gyrus (DG) including
Thomas Nielsen et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 18(23), 6469-6477 (2012-10-17)
Combretastatin A-4 disodium phosphate (CA4P) is a promising vascular disrupting agent (VDA) in clinical trials. As CA4P acts on dividing endothelial cells, we hypothesize that CA4P affects vessels of certain sizes. The aim of this study was to evaluate the
Eric Y Huang et al.
Journal of cellular and molecular medicine, 22(7), 3661-3670 (2018-04-24)
Single nucleotide polymorphisms (SNPs) within the regulatory elements of a gene can alter gene expression, making these SNPs of prime importance for candidate gene association studies. We aimed to determine whether such regulatory variants are associated with clinical outcomes in
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
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