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D5817

Sigma-Aldrich

DMXAA

≥98% (HPLC), solid, apoptosis inducer

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C17H14O4
CAS-Nummer:
117570-53-3
Molekulargewicht:
282.29
MDL-Nummer:
MFCD00870555
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24724464
NACRES:
NA.77

product name

DMXAA, ≥98% (HPLC), solid

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

solid

Farbe

light brown

Löslichkeit

DMSO: soluble >10 mg/mL

Lagertemp.

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)

InChIKey

XGOYIMQSIKSOBS-UHFFFAOYSA-N

Allgemeine Beschreibung

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.

Anwendung

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. Wirkung

DMXAA is an apoptosis inducer; anti-vascular.

Leistungsmerkmale und Vorteile

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.

Piktogramme

Exclamation markEnvironment
GHS07,GHS09

Signalwort

Warning

H-Sätze

H302,H400

Gefahreneinstufungen

Acute Tox. 4 Oral - Aquatic Acute 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Die Dokumentenbibliothek aufrufen

Bruce C Baguley
The Lancet. Oncology, 4(3), 141-148 (2003-03-08)
The vascular endothelium of tumour tissue, which differs in several ways from that of normal tissues, is a potential target for selective anticancer therapy. By contrast with antiangiogenic agents, antivascular agents target the endothelial cells of existing tumour blood vessels
Gary R Martin et al.
Scientific reports, 9(1), 14281-14281 (2019-10-05)
Detection of cytoplasmic DNA by the host's innate immune system is essential for microbial and endogenous pathogen recognition. In mammalian cells, an important sensor is the stimulator of interferon genes (STING) protein, which upon activation by bacterially-derived cyclic dinucleotides (cDNs)
Christina M Buchanan et al.
Clinical science (London, England : 1979), 122(10), 449-457 (2011-12-07)
The flavone acetic acid derivative DMXAA [5,6-dimethylXAA (xanthenone-4-acetic acid), Vadimezan, ASA404] is a drug that displayed vascular-disrupting activity and induced haemorrhagic necrosis and tumour regression in pre-clinical animal models. Both immune-mediated and non-immune-mediated effects contributed to the tumour regression. The
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
Non-canonical NF-κB Antagonizes STING Sensor-Mediated DNA Sensing in Radiotherapy
Hou Y, et al.
Immunity, 49(3), 490-503 (2018)
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