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Merck
CN

234200

Combretastatin A-4

A synthetic Combretum caffrum-derived cell-permeable stilbenoid phenol that competes with colchicine tubulin binding and interferes with tubulin polymerization as well as cellular microtubule assembly

Synonym(s):

Combretastatin A-4, Combretastatin A4, CA4, Tubulin Polymerization Inhibitor XVIII, NSC 817373, 2-Methoxy-5-((1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-phenol, CA-4

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About This Item

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

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Product Name

Combretastatin A-4, A synthetic Combretum caffrum-derived cell-permeable stilbenoid phenol that competes with colchicine tubulin binding and interferes with tubulin polymerization as well as cellular microtubule assembly

SMILES string

O(C)c1c(cc(cc1OC)\C=C\c2cc(c(cc2)OC)O)OC

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-AATRIKPKSA-N

assay

≥97% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

off-white

solubility

DMSO: 50 mg/mL

shipped in

ambient

storage temp.

2-8°C

Quality Level

100

Related Categories

Disclaimer

Toxicity: Standard Handling (A)

Other Notes

Tron, G.C., et al. 2006. J. Med. Chem.49, 3033.
Griggs, J., et al. 2001. Lancet Oncol.2, 82.
Pettit, G.R., et al. 1989. Experientia45, 209.
Lin, C.M., et al. 1988. Mol. Pharmacol.34, 200.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

General description

A synthetic Combretum caffrum-derived cell-permeable stilbenoid phenol that competes with colchicine (Cat No. 234115 ) tubulin binding (by 96.4% at equal molar concentration; Ki = 1.1 µM) and interferes with tubulin polymerization (IC50 = 2-3 µM) as well as cellular microtubule assembly. In addition to its antimitotic and in vitro cancer growth inhibition activity (IC50 = 7 nM in L1210 cultures), CA4 also acts as an antivascular agent and effectively induces tumor cell necrosis in vivo by targeting endothelial cytoskeleton.

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

Certificates of Analysis (COA)

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