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D5817

DMXAA

Name: DMXAA
Brand: SIGMA

≥98% (HPLC), solid, apoptosis inducer

Synonyme(s) :

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

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Conditionnement	Référence	Disponibilité	Prix

A propos de cet article

Formule empirique (notation de Hill) :

C₁₇H₁₄O₄

Numéro CAS:

117570-53-3

Poids moléculaire :

282.29

UNSPSC Code:

12352200

PubChem Substance ID:

24724464

NACRES:

NA.77

MDL number:

MFCD00870555

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Propriétés

Nom du produit

DMXAA, ≥98% (HPLC), solid

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

light brown

solubility

DMSO: soluble >10 mg/mL

storage temp.

2-8°C

SMILES string

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)

InChI key

XGOYIMQSIKSOBS-UHFFFAOYSA-N

Description

General description

5,6-dimethylxanthenone-4-acetic acid (DMXAA) is a flavone acetic acid derivative.[1] It acts as a vascular disrupting agent (VDA), which damages tumor vasculature and stimulates an anti-tumor immune response. It stimulates hemorrhagic necrosis.[1]

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.

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Cet article	444283	219331	178278
Sigma-Aldrich D5817 DMXAA	Sigma-Aldrich 444283 MMP-13 Inhibitor	Sigma-Aldrich 219331 β-Catenin/Tcf Inhibitor II, PKF118-310	Sigma-Aldrich 178278 Apigenin
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥95% (HPLC)	assay ≥98% (HPLC)
form solid	form solid	form solid	form crystalline solid
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMSO: soluble >10 mg/mL	solubility DMSO: 10 mg/mL	solubility DMSO: 100 mg/mL	solubility hot ethanol: 1 mg/mL, DMSO: 10 mg/mL
color light brown	color light yellow	color dark yellow	color yellow

signalword

Warning

Classe de stockage

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

Hazard Classifications

Acute Tox. 4 Oral

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Certificats d'analyse (COA)

Lot/Batch Number

0000325850

0000409771

0000409773

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Activation of mitogen-activated protein kinases by 5,6-dimethylxanthenone-4-acetic acid (DMXAA) plays an important role in macrophage stimulation.

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

Randomized phase III placebo-controlled trial of carboplatin and paclitaxel with or without the vascular disrupting agent vadimezan (ASA404) in advanced non-small-cell lung cancer.

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

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)

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Numéro d'article de commerce international

Référence	GTIN
D5817-25MG	04061833586891
D5817-5MG	04061833586907

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