|
3,4-DAA
Cayman Chemical Item Number 10007980
Description
Local catabolism of the amino acid tryptophan by indoleamine 2,3-dioxygenase (IDO) is considered an important mechanism of regulating T-cell immunity. Inhibition of the production of T helper-1 (TH1) cytokines offers a new strategy for treating TH1 mediated autoimmune diseases such as multiple sclerosis.3,4-DAA is an orally active synthetic derivative of the tryptophan metabolite anthranilic acid. It suppresses antigen-specific proliferation of MBP Ac1-11 TCR CD4+ T-cells. At a concentration of 200 µM, 3,4-DAA reduces IFN-γ, IL-2, IL-12/23 p40, and TNFα in splenocytes from antigen-induced transgenic mice. However, at a concentration of 30 µM, IL-4, and IL-10 levels were increased. Expression of inducible nitric oxide synthase and nitric oxide release from EOC20 cells induced by IFN-γ and LPS are also suppressed by 3,4-DAA at concentration of 30-200 µM. Mice with experimental autoimmune encephalomyelitis treated orally (300 mg/kg per day) with 3,4-DAA exhibited fewer and milder relapses and less severe disease compared to control animals.1↗
Formal Name 2-[3-(3,4-dimethoxy-phenyl)-acryloylamino]-3-hydroxy-benzoic acid
Molecular Formula C18H17NO6
Formula Weight 343.3
Formulation A crystalline solid
Purity ≥95%
λmax 347 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES COc1ccc(\C=C/C(=O)Nc2c(O)cccc2C(=O)O)cc1OC
InCHI Code 1S/C18H17NO6/c1-24-14-8-6-11(10-15(14)25-2)7-9-16(21)19-17-12(18(22)23)4-3-5-13(17)20/h3-10,20H,1-2H3,(H,19,21)(H,22,23)/b9-7+
InCHI Key HUBVPPBIEOCMIE-VQHVLOKHSA-N |