117570-53-3 Usage
Description
5,6-Dimethylxantheonone-4-acetic acid (DMXAA) is a flavone acetic acid derivative that acts as a vascular disrupting agent (VDA). It is a STING (Stimulator of Interferon Genes) agonist selective for mouse STING. DMXAA has the ability to damage tumor vasculature and stimulate an anti-tumor immune response, leading to hemorrhagic necrosis.
Uses
Used in Anticancer Applications:
5,6-Dimethylxantheonone-4-acetic acid is used as an anticancer agent for inducing tumor regression and complete rejection in mouse xenografts. It works by disrupting tumor vasculature, releasing chemokines, and triggering the recruitment of immune cells. Additionally, DMXAA induces the expression of IFN-β, resulting in a significant expansion of leukemia-specific T cells and extending survival in acute myeloid leukemia models.
Used in Immune Response Stimulation:
5,6-Dimethylxantheonone-4-acetic acid is used as an immune response stimulator for activating the immune adaptor protein STING in mice. This activation leads to a cascade of cellular events that contribute to the anti-tumor immune response and tumor regression.
Used in Drug Development:
5,6-Dimethylxantheonone-4-acetic acid is used as a compound in drug development for its potential applications in cancer treatment. Its vascular-disrupting activity and immune-stimulating properties make it a promising candidate for further research and development in the pharmaceutical industry.
Biochem/physiol Actions
DMXAA is an apoptosis inducer; anti-vascular.
References
1) 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
Check Digit Verification of cas no
The CAS Registry Mumber 117570-53-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,7,5,7 and 0 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 117570-53:
(8*1)+(7*1)+(6*7)+(5*5)+(4*7)+(3*0)+(2*5)+(1*3)=123
123 % 10 = 3
So 117570-53-3 is a valid CAS Registry Number.
InChI:InChI=1/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)
117570-53-3Relevant articles and documents
Compound as DMXAA-Pyranoxanthone well as preparation method and application thereof
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, (2020/02/19)
The invention discloses a DMXAA-Pyranoxanthone heterozygous compound with an anti-tumor effect and a preparation method and application thereof. The DMXAA-Pyranoxanthone heterozygous compound adopts the structural formula shown as a formula I. The preparation method comprises the following steps: preparing DMXAA in three steps, preparing pyranoxanthone in two steps, and combining the DMXAA and the pyranoxanthone into the DMXAA-Pyranoxanthone heterozygous compound in two steps. The DMXAA-Pyranoxanthone heterozygous compound and a DMXAA/pyranoxanthone combined medicine have excellent in-vitro tumor cell proliferation inhibiting activity on breast cancer cells, liver cancer cells, leukemia cells, and can induce apoptosis of tumor cells through multiple targets. The DMXAA-Pyranoxanthone heterozygous compound and the DMXAA/pyranoxanthone combined medicine can be applied to preparation of cancer treating medicines.
Preparation method of DMXAA
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Paragraph 0012; 0047-0049; 0053-0055, (2020/10/21)
The invention relates to a preparation method of DMXAA. The preparation method comprises two chemical reactions: firstly, nitrifying 3, 4-dimethylbenzaldehyde with fuming nitric acid or concentrated sulfuric acid/potassium nitrate to obtain 3, 4-dimethyl-2-nitrobenzaldehyde; and then making the 3, 4-dimethyl-2-nitrobenzaldehyde directly react with o-hydroxyphenylacetic acid to obtain 5, 6-dimethylcucurbitone-4-acetic acid (DMXAA). According to the preparation method provided by the invention, an existing synthetic route is greatly shortened, reaction conditions are mild, the yield is high, andthe total yield reaches 50% or above.
5,6-DIMETHYL XANTHONE-4-ACETIC ACID DERIVATIVES AND METHOD OF PREPARING THE SAME
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, (2010/05/13)
A method of preparation of 5,6-dimethylxanthone-4-acetic acid (DMXAA) and derivatives thereof. The derivatives are represented by formula (I), wherein R represents totally 1 to 2 substitutes at 1, 2, 3, 7, and 8 position selected from a lower alkyl, halogen, CF3, CN, NO2, NH2, CH2COOH, OR2, OH, NHSO2R2, SR2, CH2CONHR2 or NHR2, and R2 represents a lower alkyl, or a lower alkyl having OH, NH2, or OCH3. The invention further provides a pharmaceutical composition having such derivatives used as excellent antitumor and antibacterial agents.