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C7744

Sigma-Aldrich

Combretastatin A4

≥98% (HPLC), powder

Sinonimo/i:

1-(3,4,5-Trimethoxyphenyl)-2-(3′-hydroxy-4′-methoxyphenyl) ethane 3,4,5-trimethoxy-3′-hydroxy-4′-methoxystilbene, 2-Methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenol, CA4

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About This Item

Formula empirica (notazione di Hill):
C18H20O5
Numero CAS:
117048-59-6
Peso molecolare:
316.35
Numero MDL:
MFCD03453309
Codice UNSPSC:
12352200
ID PubChem:
329775149
NACRES:
NA.77

Livello qualitativo

100

Saggio

≥98% (HPLC)

Stato

powder

Colore

off-white

Solubilità

DMSO: >10 mg/mL

Temperatura di conservazione

−20°C

Stringa SMILE

COc1ccc(\C=C/c2cc(OC)c(OC)c(OC)c2)cc1O

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-
HVXBOLULGPECHP-WAYWQWQTSA-N

Descrizione generale

Combretastatin A4 belong to the class of colchicinoids compounds.

Applicazioni

Combretastatin A4 has been used:
  • as an anti-tubulin agent to determine the effects of isocitrate dehydrogenases (IDH1 and IDH2) proteins in G2/M phase
  • to evaluate the anti-proliferative and pro-apoptotic properties of biphenyl CA4 derivatives in both 2D and 3D cancerous and non-cancerous cell models
  • as a microtubule inhibitor to study its effects on motility of Ascaris suum L3 larvae

Azioni biochim/fisiol

Combretastatin A4 is a potent microtubule targeting agent (MTA).
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.

Pittogrammi

Skull and crossbonesCorrosion
GHS06,GHS05

Avvertenze

Danger

Indicazioni di pericolo

H301 + H311 + H331,H318

Classi di pericolo

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1

Codice della classe di stoccaggio

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificati d'analisi (COA)

Lot/Batch Number
072M4705V
061M4746V
100M4720V
040M4714
109K47011

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Lisa M Greene et al.
Biochemical pharmacology, 84(5), 612-624 (2012-06-19)
Recent clinical data demonstrated that the vascular targeting agent Combretastatin-A4 phosphate (CA-4P) prolonged survival of patients with advanced anaplastic thyroid cancer without any adverse side effects. However, as a single agent CA-4 failed to reduce tumour growth in the murine
Lasse Dührsen et al.
Journal of neurosurgery, 128(6), 1668-1673 (2017-07-29)
OBJECTIVE Temporal lobe epilepsy (TLE) is the most common type of pharmacoresistant focal epilepsy, for which anterior mesial temporal lobe resection (AMTLR) is a treatment option. Focal cortical dysplasia Type IIIa (FCD IIIa), a developmental lesion resulting from defects in
Julie A Sosa et al.
Surgery, 152(6), 1078-1087 (2012-11-20)
Anaplastic thyroid cancer (ATC) is an aggressive neoplasm for which a paucity of data exist about the relative role of operative procedures in disease management. The FACT trial was a randomized, controlled phase 2/3 trial assessing the safety and efficacy
Lauriane Jugé et al.
Radiology, 264(2), 436-444 (2012-06-14)
To investigate the potential value of magnetic resonance (MR) elastography and diffusion-weighted (DW) MR imaging in the detection of microstructural changes of murine colon tumors during growth and antivascular treatment. The study was approved by the regional ethics committee for
Scott L Young et al.
Expert opinion on investigational drugs, 13(9), 1171-1182 (2004-08-28)
Combretastatin A4 phosphate (CA4P) represents the lead compound in a group of novel tubulin depolymerising agents being developed as vascular targeting agents (VTAs). VTAs are drugs that induce rapid and selective vascular dysfunction in tumours. CA4P is a water-soluble prodrug
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