All Photos(1)

Documents

D5817

DMXAA

Name: DMXAA
Brand: SIGMA

≥98% (HPLC), solid, apoptosis inducer

Synonym(s):

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

Sign Into View Organizational & Contract Pricing

All Photos(1)

About This Item

Empirical Formula (Hill Notation):

C₁₇H₁₄O₄

CAS Number:

117570-53-3

Molecular Weight:

282.29

MDL number:

MFCD00870555

UNSPSC Code:

12352200

PubChem Substance ID:

24724464

NACRES:

NA.77

product name

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

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.

Pictograms

GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Using macrophage activation to augment immunotherapy of established tumours.

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

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

Activation of cGAS-dependent antiviral responses by DNA intercalating agents

Pepin G, et al.

Nucleic Acids Research, 45(1), 198-205 (2016)

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)

View All Related Papers

Articles

Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Discover Bioactive Small Molecules for Cell Cycle

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service