D5817
DMXAA
≥98% (HPLC), solid, apoptosis inducer
Sinónimos:
5,6-Dimethylxanthenone-4-acetic Acid, ASA404, Vadimezan
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Acerca de este artículo
Fórmula empírica (notación de Hill):
C17H14O4
Número CAS:
Peso molecular:
282.29
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Permítanos ayudarleNombre del producto
DMXAA, ≥98% (HPLC), solid
SMILES string
Cc1ccc2C(=O)c3cccc(CC(O)=O)c3Oc2c1C
InChI key
XGOYIMQSIKSOBS-UHFFFAOYSA-N
InChI
1S/C17H14O4/c1-9-6-7-13-15(20)12-5-3-4-11(8-14(18)19)17(12)21-16(13)10(9)2/h3-7H,8H2,1-2H3,(H,18,19)
assay
≥98% (HPLC)
form
solid
color
light brown
solubility
DMSO: soluble >10 mg/mL
storage temp.
2-8°C
Quality Level
Categorías relacionadas
General description
5,6-dimethylxanthenone-4-acetic acid (DMXAA) is a flavone acetic acid derivative. It acts as a vascular disrupting agent (VDA), which damages tumor vasculature and stimulates an anti-tumor immune response. It stimulates hemorrhagic necrosis.
Application
5,6-dimethylxanthenone-4-acetic acid (DMXAA) has been used to induce type-I IFN signaling in a stimulator of interferon genes (STING) dependent manner. It has also been used to study STING-dependent signaling in the absence of infection.
Biochem/physiol Actions
DMXAA is an apoptosis inducer; anti-vascular.
Features and Benefits
This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
signalword
Warning
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
hcodes
Hazard Classifications
Acute Tox. 4 Oral
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Jing Sun et al.
Biochemical pharmacology, 82(9), 1175-1185 (2011-08-09)
The small molecule anti-tumor agent, 5,6-dimethylxanthenone-4-acetic acid (DMXAA, now called Vadimezan) is a potent macrophage and dendritic cell activating agent that, in the murine system, results in the release of large amounts of cytokines and chemokines. The mechanisms by which
Primo N Lara et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 29(22), 2965-2971 (2011-06-29)
This phase III trial was conducted to test whether the novel vascular disrupting agent ASA404 (vadimezan), when combined with first-line platinum-based chemotherapy, improves survival in patients with advanced non-small-cell lung cancer (NSCLC) versus chemotherapy alone. Patients with advanced stage IIIB
Z G Fridlender et al.
British journal of cancer, 108(6), 1288-1297 (2013-03-14)
Successful immunotherapy will require alteration of the tumour microenvironment and/or decreased immune suppression. Tumour-associated macrophages (TAMs) are one major factor affecting tumour microenvironment. We hypothesised that altering TAM phenotype would augment the efficacy of immunotherapy. We and others have reported
S M Tijono et al.
British journal of cancer, 108(6), 1306-1315 (2013-03-14)
Species selectivity of DMXAA (5,6-dimethylxanthenone-4-acetic acid, Vadimezan) for murine cells over human cells could explain in part the recent disappointing phase III trials clinical results when preclinical studies were so promising. To identify analogues with greater human clinical potential, we
AMP-activated kinase (AMPK) promotes innate immunity and antiviral defense through modulation of stimulator of interferon genes (STING) signaling
Prantner D, et al.
The Journal of Biological Chemistry, 292(1), 292-304 (2017)
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