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D5817

Sigma-Aldrich

DMXAA

≥98% (HPLC), solid

Synonym(s):

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

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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

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

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302 - H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

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’.

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Non-canonical NF-κB Antagonizes STING Sensor-Mediated DNA Sensing in Radiotherapy
Hou Y, et al.
Immunity, 49(3), 490-503 (2018)
Mark J McKeage
Expert opinion on investigational drugs, 17(1), 23-29 (2007-12-22)
5,6-Dimethylxanthenone-4-acetic acid (DMXAA) is a vascular disrupting agent that has demonstrated efficacy in combination with taxane-based chemotherapy in patients with advanced cancer. Complementary modes of action, a lack of pharmacokinetic interaction and distinct adverse effect profiles provide a strong rationale
Martin Früh et al.
Clinical lung cancer, 14(1), 34-39 (2012-05-29)
Small-cell lung cancer (SCLC) is a highly vascularized tumor. ASA404 is a tumor vascular disrupting agent. This is the first trial to report the effects of combining chemotherapy with ASA404 in SCLC. Patients with untreated metastatic SCLC were treated with
J Guerra et al.
Science advances, 6(21), eaax3333-eaax3333 (2020-06-05)
Inflammation is an essential part of immunity against pathogens and tumors but can promote disease if not tightly regulated. Self and non-self-nucleic acids can trigger inflammation, through recognition by the cyclic GMP-AMP (cGAMP) synthetase (cGAS) and subsequent activation of the
Shufeng Zhou et al.
Drug metabolism reviews, 34(4), 751-790 (2002-12-19)
The novel anti-tumor agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA) was developed in the Auckland Cancer Society Research Center. Its pharmacokinetic properties have been investigated using both in vitro and in vivo models, and the resulting data extrapolated to patients. The metabolism of
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