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(e): 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
• Empirische Formel (Hill-System): C₁₈H₂₀O₅
• CAS-Nummer: 117048-59-6
• Molekulargewicht: 316.35
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD03453309
• Assay: ≥97% (HPLC)
• Form: solid
• Quality level: 100
• Storage condition: OK to freeze, protect from light

Eigenschaften

• Quality Level: 100
• 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
• 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

Beschreibung

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.

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.

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.

Legal Information

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

Disclaimer

Toxicity: Standard Handling (A)

Sicherheitshinweise

• pictograms: GHS06,GHS05
• signalword: Danger
• hcodes: H301 + H311 + H331,H318
• pcodes: P261 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1
• Lagerklasse: 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