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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

Nom du produit

DMXAA, ≥98% (HPLC), solid

Niveau de qualité

100

Essai

≥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

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Certificats d'analyse (COA)

Lot/Batch Number
0000409771
0000409773
0000409771
0000409773
0000248660

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

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
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)
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
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
Activation of cGAS-dependent antiviral responses by DNA intercalating agents
Pepin G, et al.
Nucleic Acids Research, 45(1), 198-205 (2016)
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