Vadimezan

Vadimezan Basic information
Product Name:Vadimezan
Synonyms:CS-1975;DMXAA (ASA404,Vadimezan);5,6-dimethylxanthenoneacetic acid;DMXAA;vadimezan;(5,6-DIMETHYL-9-OXO-XANTHEN)-4-ACETIC ACID;5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid;5,6-Dimethylxanthenone-4-acetic acid
CAS:117570-53-3
MF:C17H14O4
MW:282.29
EINECS:700-141-4
Product Categories:Inhibitors
Mol File:117570-53-3.mol
Vadimezan Structure
Vadimezan Chemical Properties
Melting point 259-261 °C
Boiling point 520.9±50.0 °C(Predicted)
density 1.321±0.06 g/cm3(Predicted)
vapor pressure 0Pa at 20℃
storage temp. 2-8°C
solubility DMSO: 17 mg/mL, soluble
pka4.21±0.10(Predicted)
form solid
color light brown
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20°C for up to 3 months.
Safety Information
Hazard Codes Xn,N
Risk Statements 22-50/53
Safety Statements 60-61
RIDADR UN 3077 9/PG 3
WGK Germany 3
RTECS ZD5536200
HS Code 2932.99.7000
MSDS Information
Vadimezan Usage And Synthesis
DescriptionDMXAA (117570-53-3) is a STING (Stimulator of Interferon Genes) agonist selective for mouse STING.1,2 Intratumoral administration of DMXAA resulted in tumor regression and complete rejection in mouse xenografts.3 Tumor regression induced by DMXAA results from a cascade of cellular events which include disruption of tumor vasculature followed by the release of chemokines which trigger the recruitment of immune cells.4 DMXAA induced expression of IFN-β resulting in a striking expansion of leukemia-specific T cells extending survival in two acute myeloid leukemia models.5
UsesVadimezan is a drug that displayed vascular-disrupting activity and induced haemorrhagic necrosis and tumour regression in pre-clinical animal models. It is a substrate for the immune adaptor protein STING in mice.
DefinitionChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 5,6-dimethyl-9-oxoxanthen-4-yl group.
General Description5,6-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.
Biochem/physiol ActionsDMXAA is an apoptosis inducer; anti-vascular.
storageStore at +4°C
References1) Prantner et al. (2012), 5,6-Dimethylzanthenone-4-acetic acid (DMXAA) activates stimulator of interferon gene (STING)-dependent innate immune pathways and is regulated by mitochondrial membrane potential; J. Biol. Chem., 287 39776 2) Conlon et al. (2013), Mouse, but not human STING, binds and signals in response to the vascular disrupting agent 5,6-dimethylxanthenone-4-acetic acid; J. Immunol., 190 5216 3) Corrales et al. (2015), Direct Activation of STING in the Tumor Microenvironment Leads to Potent and Systemic Tumor Regression and immunity; Cell Rep., 11 1018 4) Weiss et al. (2017), The STING agonist DMXAA triggers a cooperation between T lymphocytes and myeloid cells that leads to tumor regression; Oncoimmunology, 6 e1346765 5) Curran et al. (2016), STING Pathway Activation Stimulates Potent Immunity Against Acute Myeloid Leukemia; Cell Rep., 15 2357
Vadimezan Preparation Products And Raw materials
Dimethylbenzylcarbinyl acetate 2-PHENOXYPHENYLACETIC ACID Ethyl 2-(Chlorosulfonyl)acetate Acetic anhydride N,N-Dimethylformamide Poly(dimethylsiloxane) xanthenone-4-acetic acid 3-BENZOYLPHENYLACETIC ACID Vadimezan 2-Propylpiperidine Pentoxifylline 2,6-Lutidine Methyl 2,2-dimethylphenylacetate Theobromine Acetone oxime Dimethyl sulfoxide N,N-Dimethylacetamide Phenylacetic acid

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