ChemicalBook CAS DataBase List 117048-59-6

117048-59-6

Name	COMBRETASTATIN A-4
CAS	117048-59-6
Molecular Formula	C18H20O5
MDL Number	MFCD03453309
Molecular Weight	316.348
MOL File	117048-59-6.mol

Synonyms

CA4 CS-A4 Combrestatin A4 CoMbretastatin A Combretastatin A4 (Z)-CombretastatinA4 CA-4, Combretastatin A-4 combretastatin A-4 (CA-4) (Z)-2-Methoxy-5-(3,4,5-Trimethoxystyryl)Phenol (Z)-5-(3,4,5-trimethoxystyryl)-2-methoxyphenol (Z)-2-Methoxy-5-(3,4,5-trimethoxystyryl)phenol ,98% 2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)vinyl]phenol 2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol 3-[(Z)-2-(3,4,5-Trimethoxyphenyl)ethenyl]-6-methoxyphenol 5-[(Z)-2-(3,4,5-Trimethoxyphenyl)ethenyl]-2-methoxyphenol 2-Methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol Combrestatin A4( 2-Methoxy-5-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-phenol ) (Z)-2-Methoxy-5-[2-(3,4,5-triMethoxyphenyl)ethenyl]phenol, 3,4,5-TriMethoxy-3'-hydroxy-4'-Methoxy-(Z)-stilbene (Z)-2-Methoxy-5-[2-(3,4,5-trimethoxyphenyl)ethenyl]phenol,3,4,5-Trimethoxy-3hydroxy-4methoxy-(Z)-stilbene,CS-A4 1-(3,4,5-Trimethoxyphenyl)-2-(3′-hydroxy-4′-methoxyphenyl) ethane 3,4,5-trimethoxy-3′-hydroxy-4′-methoxystilbene

Chemical Properties

Appearance	Crystalline Powder
Melting point	84.5-85.5°C
Boiling point	490.3±45.0 °C(Predicted)
density	1.184±0.06 g/cm3(Predicted)
storage temp.	Desiccate at -20°C
solubility	DMSO: >10mg/mL
form	powder
pka	9.65±0.10(Predicted)
color	off-white
Merck	14,2494
InChI	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-
InChIKey	HVXBOLULGPECHP-WAYWQWQTSA-N
SMILES	C1(O)=CC(/C=C\C2=CC(OC)=C(OC)C(OC)=C2)=CC=C1OC

Safety Data

Symbol(GHS)	GHS05,GHS06
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 Codes	T
Risk Statements	23/24/25-41 less more
Safety Statements	26-36/37-39-45 less more
RIDADR	UN 2811
WGK Germany	2
HazardClass	6.1
PackingGroup	Ⅲ
HS Code	29095000
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Eye Dam. 1

Raw materials And Preparation Products

Hazard Information

Chemical Properties

Crystalline Powder

Uses

Combretastatin is a small organic molecule found in the bark of the African bush willow tree Combretum caffrum. Combretastatin-A4 Prodrug Induces Mitotic Catastrophe in Chronic Lymphocytic Leukemia Cell Line Independent of Caspase Activation and Poly(ADP-ribose) Polymerase Cleavage. A potent cytotoxic agent which strongly inhibits the polymerization of tubulin by binding to the colchicine site.

Biological Activity

Antitumor, antiangiogenic and antimetastatic agent, in vitro and in vivo . Acts by inhibiting tubulin polymerization (IC 50 = 2-3 μ M).

Description

Combrestatin A4 (CA4) is a potent inhibitor of tubulin polymerization and displays strong inhibitory activity on tumor cell growth. Combrestatin A4 was shown to inhibit tumor growth in several cell lines including IMR32 (neuroblastoma), Hs746T (gastric carcinoma), CFPAC-1 (pancreatic carcinoma), and MCF-7 (breast cancer) with IC₅₀ values of 2.16, 5.20, 3.46, and 18.47 nM, respectively. CA4 inhibits tubulin polymerization with an IC₅₀ value of 2.2 μM.

Definition

ChEBI: Combretastatin A4 is a stilbenoid.

General Description

Combretastatin A4 belong to the class of colchicinoids compounds.

Biochem/physiol Actions

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.

Anticancer Research

It is a stilbenoid compound and the active among all combretastatins isolated fromthe bark of Combretum caffrum and is used for colon, lung, and leukemia cancertherapy (Shoeb 2006).

References

[1] LICHUN SUN. Abilities of 3,4-diarylfuran-2-one analogs of combretastatin A-4 to inhibit both proliferation of tumor cell lines and growth of relevant tumors in nude mice.[J]. Anticancer research, 2004, 24 1: 179-186.
[2] DEY P. Chromatin remodeling, cancer and chemotherapy.[J]. Current medicinal chemistry, 2006, 13 24: 2909-2919. DOI: 10.2174/092986706778521850

Spectrum Detail

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