CAS Number117570-53-3
Synonyms5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid; 5,6-dimethylxanthenoneacetic acid; (5,6-Dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid; Vadimezan; 2-(5,6-Dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid; T C666 BO IVJ D1 E1 N1VQ; ASA-404; DMXAA; 5,6-Dimethylxanthenone-4-acetic acid
Molecular FormulaC17H14O4
Molecular Weight282.29
Purity≥98 (HPLC)%
Density1.3±0.1 g/cm3
Boiling Point520.9±50.0 °C at 760 mmHg
Melting Point264 °C
Appearancesolid
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 117570-53-3 |
| Catalog No. | 2A-9051115 |
| Chinese Name | 2,5-己酮可可碱 |
| Synonyms | 5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid; 5,6-dimethylxanthenoneacetic acid; (5,6-Dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid; Vadimezan; 2-(5,6-Dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid; T C666 BO IVJ D1 E1 N1VQ; ASA-404; DMXAA; 5,6-Dimethylxanthenone-4-acetic acid |
| Molecular Formula | C17H14O4 |
| Molecular Weight | 282.29 |
| Purity | ≥98 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 520.9±50.0 °C at 760 mmHg |
| Melting Point | 264 °C |
| Appearance | solid |
| Water Solubility | DMSO: 17 mg/mL, soluble |
| Storage Condition | 2-8°C |
| Application | Vadimezan (ASA-404; DMXAA) is a vascular disruptor, a stimulator of the murine interferon gene (STING), and a potent inducer of type I IFN and other cytokines. |
| HTC | 2932999099 |
| PubChem ID | 24724464 |
| MDL Number | MFCD00870555 |
| SMILES | 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 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| MSDS | msds/51115_1_117570_53_3.pdf |
| Bioactivity | Vadimezan (ASA-404; 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. Related Catalog Signaling Pathways >> Immunology/Inflammation >> Interleukin Related Signaling Pathways >> Immunology/Inflammation >> STING Research Areas >> Cancer Target STING[1], type I IFNs[2] 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[1]. 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[2]. 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[1]. 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[2]. Kinase Assay M2-polarized macrophages are treated with 20 µg/mL Vadimezan (ASA-404) or DMSO vehicle for 30 min. Cells are then lysed and protein denatured in SDS buffer and samples sent for RPPA analysis. Differential abundance of various proteins and/or their phosphorylation status in response to Vadimezan (ASA-404) is assessed[1]. Cell Assay RAW 264.7 macrophages are cultured and plated at 1×105 cells/well in a 96-well plate. After overnight incubation at 37°C, cells are treated with medium containing vehicle or Vadimezan (DMXAA) (100 μg/mL). After 6 h, the culture medium is replaced with serum-free DMEM containing VSV at the indicated MOI for 1 h. Cells are then maintained in complete DMEM with 10% FBS. Twenty-four hours later, cells are washed with PBS, fixed with 10% buffered formalin, and rinsed thoroughly with distilled water. Adherent cells are stained with crystal violet[2]. 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 [1]. References [1]. Downey CM, et al. DMXAA causes tumor site-specific vascular disruption in murine non-small cell lung cancer, and like the endogenous non-canonical cyclic dinucleotide STING agonist, 2'3'-cGAMP, induces M2 macrophage repolarization. PLoS One. 2014 Jun 18;9(6):e99988. [2]. Shirey KA, et al. The anti-tumor agent, 5,6-dimethylxanthenone-4-acetic acid (DMXAA), induces IFN-beta-mediated antiviral activity in vitro and in vivo. J Leukoc Biol. 2011 Mar;89(3):351-7. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 520.9±50.0 °C at 760 mmHg Melting Point 264 °C Molecular Formula C17H14O4 Molecular Weight 282.291 Flash Point 197.1±23.6 °C Exact Mass 282.089203 PSA 67.51000 LogP 3.60 Appearance of Characters solid | light brown Vapour Pressure 0.0±1.4 mmHg at 25°C Index of Refraction 1.633 InChIKey XGOYIMQSIKSOBS-UHFFFAOYSA-N SMILES Cc1ccc2c(=O)c3cccc(CC(=O)O)c3oc2c1C Storage condition 2-8°C Water Solubility DMSO: 17 mg/mL, soluble |
| Use of | Vadimezan (ASA-404; 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. Properties Articles39 Name vadimezan Synonym More Synonyms DMXAA (Vadimezan) Biological Activity Description Vadimezan (ASA-404; 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. Related Catalog Signaling Pathways >> Immunology/Inflammation >> Interleukin Related Signaling Pathways >> Immunology/Inflammation >> STING Research Areas >> Cancer STING[1], type I IFNs[2] 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[1]. 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[2]. References [2]. Shirey KA, et al. The anti-tumor agent, 5,6-dimethylxanthenone-4-acetic acid (DMXAA), induces IFN-beta-mediated antiviral activity in vitro and in vivo. J Leukoc Biol. 2011 Mar;89(3):351-7. Chemical & Physical Properties Molecular Formula C17H14O4 Exact Mass 282.089203 PSA 67.51000 Appearance of Characters solid | light brown Index of Refraction 1.633 InChIKey XGOYIMQSIKSOBS-UHFFFAOYSA-N |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
| Related Products in Specialty Chemicals | ||
|---|---|---|
| 3-Amino-3-(4-isopropylphenyl)propanoic acid | 117391-53-4 | 2A-9051103 |
| Endothelin 1 | 117399-94-7 | 2A-9051106 |
| 2',7'-Bis(2-carboxyethyl)-5(6)-carboxyfluorescein acetoxymethyl ester | 117464-70-7 | 2A-9051109 |
| 5(6)-Carboxyfluorescein N-succinimidyl ester | 117548-22-8 | 2A-9051113 |
| Calcium dobesilate monohydrate | 117552-78-0 | 2A-9051114 |
| Combretastatin D1 | 117709-78-1 | 2A-9051126 |
| 3-Cyano-4-methoxybenzoic acid | 117738-82-6 | 2A-9051128 |
| tert-Butyl 3S-amino-2,3,4,5-tetrahydro-1H-[1]benaepin-2-one-1-acetate tartrate | 117770-66-8 | 2A-9051129 |
| 5-Amino-2-pyridinol hydrochloride | 117865-72-2 | 2A-9051138 |
| 4-[2-(trans-4-Propylcyclohexyl)ethyl]cyclohexanone | 117923-32-7 | 2A-9051141 |
| Browse all Specialty Chemicals products » | ||
Phone:
630-322-8886
630-322-8887
Email:
Office Locations:
Chicago, IL, USA
San Francisco, CA, USA
EN
SDS