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Names | |
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Preferred IUPAC name 2-Methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]phenol | |
Other names Combretastatin A4 CA-4 1-(3,4,5-Trimethoxyphenyl)-2-(3′-hydroxy-4′-methoxyphenyl)ethene 3,4,5-Trimethoxy-3′-hydroxy-4′-methoxystilbene | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.159.667 |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C18H20O5 | |
Molar mass | 316.34 g/mol |
Melting point | 116 °C (241 °F; 389 K) [1] |
insoluble | |
Solubility in DMSO, Ethanol | DMSO : 63 mg/mL, Ethanol : 34 mg/mL [2] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Combretastatin A-4 is a combretastatin and a stilbenoid. It can be isolated from Combretum afrum , the Eastern Cape South African bushwillow tree or in Combretum leprosum , the mofumbo, a species found in Brazil. [3] [4]
Tubulin represents a potent target in cancer chemotherapy, given its role in cell division. Combretastatin is a naturally occurring well known tubulin polymerization inhibitor. Combretastatin A-4 comes in two stereoisomers (cis (shown top right), and trans); The cis form binds much better to the 'colchicine' site on tubulin to inhibit polymerization. [5]
Combretastatin A-4 is the active component of combretastatin A-4 phosphate, a prodrug designed to damage the vasculature (blood vessels) of cancer tumors causing central necrosis.[ citation needed ]
A large number of synthetic derivatives have been reported, [6] [7] including beta-lactam based compounds. [8]
CA4 has a half life of 1.8-4.2h in humans. CA4P(a prodrug) has a half life of 0.22-0.36h in humans. [9]