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COMBRETASTATIN A1

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COMBRETASTATIN A1 Basic information

Product Name:
COMBRETASTATIN A1
Synonyms:
  • 3-methoxy-6-[(E)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diol
  • COMBRETASTATIN A1
  • (Z)-3,4,4',5-Tetramethoxy-2',3'-dihydroxystilbene
  • (Z)-3',4,4',5'-Tetramethoxystilbene-2,3-diol
  • 3-Methoxy-6-[(Z)-3,4,5-trimethoxystyryl]-1,2-benzenediol
  • (Z)-3-Methoxy-6-(3,4,5-Trimethoxystyryl)Benzene-1,2-Diol
  • Combretastatin A1( 3-Methoxy-6-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-benzene-1,2-diol )
  • 1,2-Benzenediol, 3-methoxy-6-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]-
CAS:
109971-63-3
MF:
C18H20O6
MW:
332.35
Product Categories:
  • Combretastatin
Mol File:
109971-63-3.mol
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COMBRETASTATIN A1 Chemical Properties

Melting point:
113-115 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
Boiling point:
528.4±50.0 °C(Predicted)
Density 
1.251±0.06 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
DMF: 5 mg/ml; DMSO: 5 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml; Ethanol: 3 mg/ml
form 
A crystalline solid
pka
8.89±0.45(Predicted)
color 
White to off-white
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COMBRETASTATIN A1 Usage And Synthesis

Uses

Combretastatin A-1 is a microtubule polymerization inhibitor that binds to the colchicine-binding site of tubulin. Combretastatin A-1 inhibits the Wnt/β-catenin pathway through tubulin depolymerization mediated AKT deactivation. Combretastatin A-1 exhibits anti-tumor and anti-vascular effects[1][2][3].

in vivo

Combretastatin A-1 (1-4 mg/kg; i.v. every other day for 4 weeks) significantly reduces the tumor volume in HepG2 subcutaneous xenograft model[2].
Combretastatin A-1 (2 mg/kg; every other day for 21 days) shows enhanced apoptosis in orthotopic hepatocellular carcinoma mouse model[2].

Animal Model:Male athymic BALB/c nu/nu mice (16-18 g; 4-6 weeks old) were inoculated with HepG2 cells[2]
Dosage:1, 2, 4?mg/kg
Administration:I.v. every other day for 4 weeks
Result:Resulted in a significant tumor volume reduction at the dose of 2?mg/kg or 4?mg/kg.

References

[1] Pettit GR, et, al. Isolation, structure, and synthesis of combretastatins A-1 and B-1, potent new inhibitors of microtubule assembly, derived from Combretum caffrum. J Nat Prod. Jan-Feb 1987;50(1):119-31. DOI:10.1021/np50049a016
[2] Mao J, et, al. Combretastatin A-1 phosphate, a microtubule inhibitor, acts on both hepatocellular carcinoma cells and tumor-associated macrophages by inhibiting the Wnt/β-catenin pathway. Cancer Lett. 2016 Sep 28;380(1):134-43. DOI:10.1016/j.canlet.2016.06.020
[3] Holwell SE, et, al. Anti-tumor and anti-vascular effects of the novel tubulin-binding agent combretastatin A-1 phosphate. Anticancer Res. Nov-Dec 2002;22(6C):3933-40. PMID:12553015

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