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3,4-DAA

Catalog No.GC12624

synthetic derivative of the tryptophan metabolite anthranilic acid

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3,4-DAA Chemical Structure

Cas No.: 2117759-07-4

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1mg
$24.00
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5mg
$102.00
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10mg
$181.00
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50mg
$774.00
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Sample solution is provided at 25 µL, 10mM.

Description of 3,4-DAA

N-(3,4,-Dimethoxycinnamoyl) anthranilic acid (3,4-DAA) is a synthetic derivative of the tryptophan metabolite anthranilic acid [1].

Degradation of the essential amino acid Trp by indoleamine 2,3-dioxygenase (IDO) plays an important role in immunity. IDO has been implicated in immune modulation through limiting T cell function and engage mechanisms of immune tolerance. Activation of IDO has been observed during tumor development, helping malignant cells escape eradication by the immune system [2].

3,4-DAA suppressed antigen-specific proliferation of MBP Ac1-11 TCR transgenic CD4+ T cells by arrested the cells in G1/S-phase. 3,4-DAA (200 μM) reduced the release of IL-2, IFN-γ, and TNF-α and 3,4-DAA (30 μM)increased the level of IL-4 and IL-10 in splenocytes from MBP Ac1-11 TCR transgenic T cells after antigen stimulation [1]. 3,4-DAA dose-dependently decreased IFNγ–induced cell surface expression of MHC class II and costimulatory molecules and suppressed the expression of inducible nitric oxide synthase (iNOS) and nitric oxide (NO) release from EOC20 cells and phosphorylation of STAT1α induced by IFNγ. In Mice with experimental autoimmune encephalomyelitis, oral administration of 3,4-DAA (300 mg/kg per day) exhibited fewer and milder relapses and less severe disease compared to control animals [1]. In allograft immunorejection model, administration of 3,4-DAA reduced histological severity of allograft immunorejection, decreased serum levels of TNF-α and IFN-γ, and raised serum levels of IL-10 [3].

References:
[1] Platten M, Ho P P, Youssef S, et al.  Treatment of autoimmune neuroinflammation with a synthetic tryptophan metabolite[J]. Science, 2005, 310(5749): 850-855.
[2] Hirata F, Ohnishi T, Hayaishi O.  Indoleamine 2, 3-Dioxygenase[J]. J. Biol. Chem, 1977, 252: 4637.
[3] Sun Q F, Ding J G, Sheng J F, et al.  Novel action of 3, 4‐DAA ameliorating acute liver allograft injury[J]. Cell biochemistry and function, 2011, 29(8): 673-678.

Chemical Properties of 3,4-DAA

Cas No. 2117759-07-4 SDF
Chemical Name 2-[3-(3,4-dimethoxy-phenyl)-acryloylamino]-3-hydroxy-benzoic acid
Canonical SMILES COC1=C(OC)C=C(/C=C/C(NC2=C(O)C=CC=C2C(O)=O)=O)C=C1
Formula C18H17NO6 M.Wt 343.3
Solubility DMF: 30 mg/ml,DMF:PBS (pH 7.2) (1:1): .5 mg/ml,DMSO: 20 mg/ml,Ethanol: 1 mg/ml Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 3,4-DAA

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1 mg 5 mg 10 mg
1 mM 2.9129 mL 14.5645 mL 29.129 mL
5 mM 0.5826 mL 2.9129 mL 5.8258 mL
10 mM 0.2913 mL 1.4565 mL 2.9129 mL
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