Combretastatin A4

Modify Date: 2024-01-03 19:39:04

Combretastatin A4 Structure
Combretastatin A4 structure
 Common Name Combretastatin A4
CAS Number 117048-59-6 Molecular Weight 316.348
Density 1.2±0.1 g/cm3 Boiling Point 490.3±45.0 °C at 760 mmHg
Molecular Formula C18H20O5 Melting Point 84.5-85.5ºC
MSDS Chinese USA Flash Point 250.3±28.7 °C
Symbol GHS05 GHS06
GHS05, GHS06		 Signal Word Danger

 Use of Combretastatin A4


Combretastatin A4 is a microtubule-targeting agent that binds β-tubulin with Kd of 0.4 μM.

 Names

Name Combretastatin A4
Synonym More Synonyms

 Combretastatin A4 Biological Activity

Description Combretastatin A4 is a microtubule-targeting agent that binds β-tubulin with Kd of 0.4 μM.
Related Catalog
Target

Kd: 0.4 μM (β-tubulin)

In Vitro Combretastatin A4 phosphate (≥ 50 µM) significantly increases the percentage of annexin-V-binding cells and significantly decreases forward scatter. Combretastatin A4 phosphate does not appreciably increase hemolysis. Hundred µM Combretastatin A4 phosphate significantly increases Fluo3-fluorescence. The effect of Combretastatin A4 phosphate (100 µM) on annexin-V-binding is significantly blunted, but not abolished, by removal of extracellular Ca2+. Combretastatin A4 phosphate (≥ 50 µM) significantly decreases GSH abundance and ATP levels but does not significantly increase ROS or ceramide[2]. Polymersomes co-encapsulating doxorubicin-combretastatin-A4 phosphate (1:10) shows strong synergistic cytotoxicity against human nasopharyngeal epidermal carcinoma (KB) cells[3]. Pretreatment with Combretastatin A4 phosphate does not influence the amount of VM in 3-D culture as well as the expression of these key molecules[4].
In Vivo DBP and MBP at 30 minutes after administration are higher in rats treated with Combretastatin A4 disodium phosphate 120 mg/10 mL/kg. The toxicokinetic parameters of Combretastatin A4 phosphate and Combretastatin A4 in rats treated with Combretastatin A4 disodium phosphate 120 mg/10 mL/kg are indicated, and the values of Cmax, T1/2, and AUC0-inf for Combretastatin A4 are 156±13 μM, 5.87±1.69 h, and 89.4±10.1 h·μM, respectively[1]. In vivo, W256 tumors show marked intratumoral hypoxia after Combretastatin A4 phosphate treatment, accompanied by increased VM formation. Combretastatin A4 phosphate exhibits only a delay in tumor growth within 2 days but rapid tumor regrowth afterward. VM density is positively related to tumor volume and tumor weight at day 8. Combretastatin A4 phosphate causes hypoxia which induces VM formation in W256 tumors through HIF-1α/EphA2/PI3K/matrix metalloproteinase (MMP) signaling pathway, resulting in the consequent regrowth of the damaged tumor[4].
Animal Admin Rats: Rats are administered a single intravenous dose of Combretastatin A4 disodium phosphate at 120 mg/10 mL/kg by bolus infusion (n=3). Blood is taken via the jugular vein and collected in heparin-coated tubes at 10 minutes and 1, 3, 6, and 24 hours after administration. Plasma is separated by centrifugation immediately after sampling. After centrifugation, an aliquot of plasma is mixed with the equivalent volume of 1% formic acid and stored at −20°C. The thawed plasma samples are purified by solid-phase extraction, and the plasma concentrations of combretastatin A4 phosphate (free base of Combretastatin A4 disodium phosphate; Combretastatin A4 phosphate) and combretastatin A4 (the metabolite of Combretastatin A4 disodium phosphate; Combretastatin A4 ) are determined by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Toxicokinetic parameters [maximum concentration (Cmax), terminal half-life (T1/2), and area under the concentration-time curve from time zero to infinity (AUC0-inf)] are obtained by non-compartmental analysis using Phoenix WinNonlin 6.3.
References

[1]. Tochinai R, et al. Combretastatin A4 disodium phosphate-induced myocardial injury. J Toxicol Pathol. 2016 Jul;29(3):163-71.

[2]. Signoretto E, et al. Stimulation of Eryptosis by Combretastatin A4 Phosphate Disodium (CA4P). Cell Physiol Biochem. 2016;38(3):969-81

[3]. Zhu J, et al. Co-Encapsulation of Combretastatin-A4 Phosphate and Doxorubicin in Polymersomes for Synergistic Therapy of Nasopharyngeal Epidermal Carcinoma. J Biomed Nanotechnol. 2015 Jun;11(6):997-1006.

[4]. Yao N, et al. Combretastatin A4 phosphate treatment induces vasculogenic mimicry formation of W256 breast carcinoma tumor in vitro and in vivo. Tumour Biol. 2015 Nov;36(11):8499-510.

 Chemical & Physical Properties

Density 1.2±0.1 g/cm3
Boiling Point 490.3±45.0 °C at 760 mmHg
Melting Point 84.5-85.5ºC
Molecular Formula C18H20O5
Molecular Weight 316.348
Flash Point 250.3±28.7 °C
Exact Mass 316.131073
PSA 57.15000
LogP 3.57
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.607
Storage condition Desiccate at -20°C
Water Solubility DMSO: >10mg/mL

 Safety Information

Symbol GHS05 GHS06
GHS05, GHS06
Signal Word Danger
Hazard Statements H301 + H311 + H331-H318
Precautionary Statements P261-P280-P301 + P310-P305 + P351 + P338-P311
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T: Toxic;
Risk Phrases R23/24/25;R41
Safety Phrases 26-36/37-39-45
RIDADR UN 2811
Packaging Group Ⅲ
Hazard Class 6.0

 Synthetic Route

3-tert-butyldimethylsilyloxy-3',4,4',5'-tetramethyloxystilbene structure

3-tert-butyldim...

CAS#:847063-26-7

~0%

2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol structure

2-methoxy-5-[2-...

CAS#:117048-62-1

Combretastatin A4 Structure

Combretastatin A4

CAS#:117048-59-6

Literature: Malysheva, Yulia B.; Combes, Sebastien; Fedorov, Alexey Yu.; Knochel, Paul; Gavryushin, Andrei E. Synlett, 2012 , vol. 23, # 8 p. 1205 - 1208
Isovanillin structure

Isovanillin

CAS#:621-59-0

Triphenyl-[(3,4,5-trimethoxyphenyl)-methyl]-phosphonium chloride structure

Triphenyl-[(3,4...

CAS#:108683-61-0

~14%

2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol structure

2-methoxy-5-[2-...

CAS#:117048-62-1

Combretastatin A4 Structure

Combretastatin A4

CAS#:117048-59-6

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 20, # 9 p. 2780 - 2784
(E)-3-(3-acetoxy-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid structure

(E)-3-(3-acetox...

CAS#:39500-10-2

~%

2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol structure

2-methoxy-5-[2-...

CAS#:117048-62-1

Combretastatin A4 Structure

Combretastatin A4

CAS#:117048-59-6

Literature: WO2007/59118 A1, ; Page/Page column 27-28 ;
3,4,5-Trimethoxybenzaldehyde structure

3,4,5-Trimethox...

CAS#:86-81-7

3-hydroxy-4-methoxybenzyltriphenylphosphonium bromide structure

3-hydroxy-4-met...

CAS#:111394-52-6

~%

2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol structure

2-methoxy-5-[2-...

CAS#:117048-62-1

Combretastatin A4 Structure

Combretastatin A4

CAS#:117048-59-6

Literature: Journal of Chemical Research, , vol. 35, # 4 p. 229 - 230
Isovanillin structure

Isovanillin

CAS#:621-59-0

Triphenyl(3,4,5-trimethoxybenzyl)phosphonium bromide structure

Triphenyl(3,4,5...

CAS#:61240-20-8

~%

2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol structure

2-methoxy-5-[2-...

CAS#:117048-62-1

Combretastatin A4 Structure

Combretastatin A4

CAS#:117048-59-6

Literature: Guo, Xiaotao; Zhang, Dan; Yu, Zhifang; Liu, Tianzhen; Li, Dachang; Li, Chunbao Journal of Chemical Research, 2011 , vol. 35, # 4 p. 229 - 230
N/A structure

N/A

CAS#:185698-55-9

~%

2-methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol structure

2-methoxy-5-[2-...

CAS#:117048-62-1

Combretastatin A4 Structure

Combretastatin A4

CAS#:117048-59-6

Literature: Chemical Communications, , vol. 48, # 44 p. 5419 - 5421

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 Synonyms

(Z)-2-Methoxy-5-[2-(3,4,5,-trimethoxyphenyl)ethenyl]phenol
(Z)-CombretastatinA4
Phenol, 2-methoxy-5-(2-(3,4,5-trimethoxyphenyl)ethenyl)-, (Z)-
(Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)phenol
3'-Hydroxy-3,4,4',5-tetramethoxy-cis-stilbene
CS A4
2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]benzolol
2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol
2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]phenol
Combretastatin A-4
3,4,5-Trimethoxy-3'-hydroxy-4'-methoxy-(Z)-stilbene
Phenol, 2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]-
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