C7744

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
• 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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS06,GHS05
• Signal Word: Danger
• Hazard Statements: H301 + H311 + H331,H318
• Precautionary Statements: 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
• 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