A STING activator and tumor vascular disrupting agent
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DMXAA

Item No. 14617

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,6-dimethyl-9-oxo-9H-xanthene-4-acetic acid
CAS Number
117570-53-3
Synonyms
  • ASA 404
  • 5,6-Dimethylxanthenone-4-acetic Acid
  • NSC 640488
  • Vadimezan
Molecular Formula
C17H14O4
Formula Weight
282.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 14 mg/mlDMF:PBS(pH 7.2)(1:1): 0.50 mg/mlDMSO: 1 mg/ml
SMILES
O=C1C2=C(C(CC(O)=O)=CC=C2)OC3=C(C)C(C)=CC=C31
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $39

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    5 mg

    $87

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    10 mg

    $136

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    25 mg

    $290

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    Product Description

    DMXAA is a xanthene which acts as a tumor vascular disrupting agent, inducing apoptosis in tumor vascular endothelium resulting in necrosis at the tumor core.1,2 It potently activates the TANK-binding kinase 1-interferon regulatory factor 3 (TBK1/IRF3) signaling pathway in leukocytes, inducing type-I-interferon (IFN) production.3,4,5 Specifically, DMXAA activates the mitochondria- and endoplasmic reticulum-associated protein known as stimulator of interferon genes (STING), leading to TBK1/IRF3 signaling.6 DMXAA signals through mouse STING but not human STING.7 In addition, DMXAA significantly inhibits several kinases in endothelial cells, including the vascular endothelial growth factor (VEGF) receptors VEGFR1 and VEGFR2 (IC50 = 119 and 11 µM, respectively).8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McKeage, M.J., and Baguley, B.C. Disrupting established tumor blood vessels: An emerging therapeutic strategy for cancer. Cancer 116(8), 1859-1871 (2010).

    2. Thorpe, P.E. Vascular targeting agents as cancer therapeutics. Clin. Cancer Res. 10(2), 415-427 (2004).

    3. Roberts, Z.J., Goutagny, N., Perera, P.Y., et al. The chemotherapeutic agent DMXAA potently and specifically activates the TBK1-IRF-3 signaling axis. J. Exp. Med. 204(7), 1559-1569 (2007).

    4. Tang, C.K., Aoshi, T., Jounai, N., et al. The chemotherapeutic agent DMXAA as a unique IRF3-dependent type-2 vaccine adjuvant. PLoS One 8(3), (2013).

    5. Wallace, A., LaRosa, D.F., Kapoor, V., et al. The vascular disrupting agent, DMXAA, directly activates dendritic cells through a MyD88-independent mechanism and generates antitumor cytotoxic T lymphocytes. Cancer Res. 67(114), 7011-7019 (2007).

    6. Prantner, D., Perkins, D.J., Lai, W., et al. 5,6-Dimethylxanthenone-4-acetic acid (DMXAA) activates stimulator of interferon gene (STING)-dependent innate immune pathways and is regulated by mitochondrial membrane potential. The Journal of Biological Chemisty 287(47), 39776-39788 (2012).

    7. Conlon, J., Burdette, D.L., Sharma, S., et al. Mouse, but not human STING, binds and signals in response to the vascular disrupting agent 5,6-dimethylxanthenone-4-acetic acid. J. Immunol. 190(10), 5216-5225 (2013).

    8. Buchanan, C.M., Shih, J.H., Astin, J.W., et al. DMXAA (Vadimezan, ASA404) is a multi-kinase inhibitor targeting VEGFR2 in particular. Clin. Sci. (Lond.) 122(10), 449-457 (2012).