DMXAA

Category	Influenza Virus
CAS	117570-53-3
Description	DMXAA is a STING agonist that induces antitumor immunological responses.

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Product Information

Synonyms	9H-Xanthene-4-acetic acid, 5,6-dimethyl-9-oxo-; 5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid; 2-(5,6-Dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid; 5,6-Dimethyl-9-oxo-9H-xanthen-4-ylacetic acid; 5,6-Dimethylxanthenone-4-acetic acid; ASA404; ASA 404; ASA404; AS1404; AS 1404; AS1404; D5817; NSC 640488; Vadimezan
IUPAC Name	2-(5,6-dimethyl-9-oxoxanthen-4-yl)acetic acid
Molecular Weight	282.29
Molecular Formula	C17H14O4
Canonical SMILES	CC1=C(C2=C(C=C1)C(=O)C3=C(O2)C(=CC=C3)CC(=O)O)C
InChI	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
Boiling Point	520.9±50.0°C at 760 mmHg
Melting Point	259-261°C
Flash Point	197.1±23.6 °C
Purity	≥95%
Density	1.321±0.06 g/cm3
Solubility	Soluble in DMSO
Appearance	Off-white Solid
Application	Antineoplastic Agents
Storage	Store at 2-8°C
Animal Admin	Male 129/Sv mice (6 to 12 week old) are used in this study. To generate subcutaneous tumors, 5×105 344SQ-ELuc cells in 100 µL PBS are injected in both posterior flanks of mice. Tumor growth is monitored every 2 to 4 days via BLI. Once tumors are established (day 10 for systemic metastases; day 7 or day 14 for subcutaneous tumors), mice are given 25 mg/kg of Vadimezan (DMXAA), or DMSO vehicle by i.p. injection. BLI is carried out at 6 and 24 hours .
Complexity	433
Exact Mass	282.08920892
Index Of Refraction	1.633
In Vitro	Vadimezan (DMXAA), the vascular disrupting agent, is a murine agonist of the stimulator of interferon genes (STING) and also a potent inducer of type I IFNs and other cytokines. Vadimezan (DMXAA) has no detrimental effect on 344SQ-ELuc cell viability. It is found that Vadimezan-mediated up regulation of the NF-κB pathway as shown by increased p65 phosphorylation in M2 macrophages. Results demonstrate that Vadimezan (DMXAA)-treated cells are protected from VSV-induced cytotoxicity at all MOIs in contrast to medium-pretreated macrophages. Vadimezan (DMXAA) effectively inhibits growth of both strains of influenza, demonstrating the potential of Vadimezan for treatment of drug-resistant strains of human influenza.
In Vivo	344SQ-ELuc NSCLC subcutaneous tumors respond dramatically to Vadimezan (DMXAA), with a marked decrease in bioluminescence (BLI) signals post-drug injection. Vadimezan (DMXAA) treatment of 344SQ-ELuc metastases yields no decrease in photon emission rates, with the tumors remaining histologically similar to controls after this treatment. As with the large subcutaneous tumors, Vadimezan (DMXAA) administration to mice with small subcutaneous tumors still leads to ~2-log decreases in photon emission at both 6 and 24 hours. In vivo, Vadimezan (DMXAA) is a more potent inducer of IFN-β mRNA and a relatively poor inducer of TNF-α mRNA. Vadimezan (DMXAA) administration leads to significantly less weight loss in influenza-infected mice.
PSA	67.51000
Target	STING, type I IFNs
Vapor Pressure	0.0±1.4 mmHg at 25°C
XLogP3-AA	3.2