Introduction：Basic information about CAS 109971-63-3|Combretastatin A-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Combretastatin A-1 |
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| CAS Number | 109971-63-3 | Molecular Weight | 332.348 |
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| Density | 1.3±0.1 g/cm3 | Boiling Point | 528.4±50.0 °C at 760 mmHg |
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| Molecular Formula | C18H20O6 | Melting Point | / |
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| MSDS | / | Flash Point | 273.3±30.1 °C |
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Names
| Name | combretastatin a1 |
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| Synonym | More Synonyms |
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Combretastatin A-1 BiologicalActivity
| Description | 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]. |
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| Related Catalog | Research Areas >>CancerSignaling Pathways >>Cell Cycle/DNA Damage >>Microtubule/TubulinSignaling Pathways >>Cytoskeleton >>Microtubule/Tubulin |
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| Target | Microtubule/Tubulin[1] |
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| In Vitro | Combretastatin A-1 (72 h) inhibits the growth of various tumor cell lines in vitro, including HepG2, SMMC-7721, Hepa 1-6, LM-3, Bel-7402, Huh7, BGC-803, MDA-MB-231, MCF-7, A375, NCI-1975, CT-26, HT-29, A549 cells (IC50=9.2, 12.8, 32.9, 33.8, 38.4, 728.2, 12.2, 17.6, 46.0, 61.0, 256.3, 1075.0, 2082.0, 2247.0 nM, respectively)[2]. Combretastatin A-1 (1-10 nM; 24 h) induces apoptosis by microtubule depolymerization-induced AKT inactivation and the removal of GSK-3β inhibition in HepG2 cells[2]. Combretastatin A-1 (1-50 nM; 6 h) decreases the mitochondrial membrane potential (MMP) of HepG2 cells. Combretastatin A-1 shows dose-dependently ROS accumulation in HepG2 cells[2]. Western Blot Analysis[2] Cell Line: HepG2 cells Concentration: 1, 5, 10 nM Incubation Time: 24 hours Result: Significantly decreased Mcl-1 expression, but the Bcl-2 level was unchanged. Reduced p-GSK 3β (Ser9) without altering total GSK-3β protein levels, indicating an activation of GSK-3β. Reduced AKT phosphorylation on Ser473 without an obvious change in the total AKT protein levels. |
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| 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. |
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| 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. [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. [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. |
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Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
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| Boiling Point | 528.4±50.0 °C at 760 mmHg |
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| Molecular Formula | C18H20O6 |
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| Molecular Weight | 332.348 |
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| Flash Point | 273.3±30.1 °C |
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| Exact Mass | 332.125977 |
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| PSA | 77.38000 |
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| LogP | 3.84 |
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| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
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| Index of Refraction | 1.627 |
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| InChIKey | YUSYSJSHVJULID-WAYWQWQTSA-N |
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| SMILES | COc1ccc(C=Cc2cc(OC)c(OC)c(OC)c2)c(O)c1O |
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Safety Information
| Hazard Codes | Xi |
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| HS Code | 2909499000 |
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Customs
| HS Code | 2909499000 |
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| Summary | 2909499000. ether-alcohols and their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:5.5%. General tariff:30.0% |
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Synonyms
| combretastatin A1 Z |
| Combretastatin A-1 |
| 3-methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzene-1,2-diol |
| (Z)-3',4,4',5'-Tetramethoxystilbene-2,3-diol |
| (Z)-3,4,4',5-Tetramethoxy-2',3'-dihydroxystilbene |
| Combretastatin A1( 3-Methoxy-6-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-benzene-1,2-diol ) |
| (Z)-3-Methoxy-6-(3,4,5-Trimethoxystyryl)Benzene-1,2-Diol |
| 1,2-Benzenediol, 3-methoxy-6-(2-(3,4,5-trimethoxyphenyl)ethenyl)-, (Z)- |
| (Z)-1-[3',4',5'-trimethoxyphenyl]-2-[2'',3''-dihydroxy-4''-methoxyphenyl]ethene |
| 3-Methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]-1,2-benzenediol |
| combretastatin A-2 |
| 1,2-Benzenediol, 3-methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]- |
| 3-Methoxy-6-[(Z)-3,4,5-trimethoxystyryl]-1,2-benzenediol |
| 3-Methoxy-6-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]benzene-1,2-diol |
