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D5817

Sigma-Aldrich

DMXAA

≥98% (HPLC), solid, apoptosis inducer

Synonyme(s) :

5,6-Dimethylxanthenone-4-acetic Acid, ASA404, Vadimezan

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About This Item

Formule empirique (notation de Hill):
C17H14O4
Numéro CAS:
117570-53-3
Poids moléculaire :
282.29
Numéro MDL:
MFCD00870555
Code UNSPSC :
12352200
ID de substance PubChem :
24724464
Nomenclature NACRES :
NA.77

product name

DMXAA, ≥98% (HPLC), solid

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

solid

Couleur

light brown

Solubilité

DMSO: soluble >10 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

Cc1ccc2C(=O)c3cccc(CC(O)=O)c3Oc2c1C

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)

Clé InChI

XGOYIMQSIKSOBS-UHFFFAOYSA-N

Description générale

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.

Actions biochimiques/physiologiques

DMXAA is an apoptosis inducer; anti-vascular.

Caractéristiques et avantages

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.

Pictogrammes

Exclamation markEnvironment
GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H302,H400

Conseils de prudence

P273 - P301 + P312 + P330

Classification des risques

Acute Tox. 4 Oral - Aquatic Acute 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
The STING agonist DMXAA triggers a cooperation between T lymphocytes and myeloid cells that leads to tumor regression
Weiss JM, et al.
Oncoimmunology, 6(10), e1346765-e1346765 (2017)
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
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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