Cinnabarinic acid-d4 is intended for use as an internal standard for the quantification of cinnabarinic acid by GC- or LC-MS. Cinnabarinic acid is an agonist of metabotropic glutamate receptor 4 (mGluR4) and active metabolite of 3-hydroxyanthranilic acid.1,2 It is formed via two-step oxidation of 3-hydroxyanthranilic acid. Cinnabarinic acid (100 µM) selectively induces inositol phosphate production in HEK293 cells expressing mGluR4 over HEK293 cells expressing mGluR1, mGluR2, mGluR5, mGluR6, mGluR7, or mGluR8.1 It inhibits D-amino acid oxidase (DAAO) in a cell-free assay (IC50 = 1.37 µM).3 Cinnabarinic acid (30 µM) increases levels of reactive oxygen species (ROS) and induces apoptosis in primary mouse thymocytes.4
1.Fazio, F., Lionetto, L., Molinaro, G., et al.Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptorsMol. Pharmacol.81(5)643-656(2012) 2.Subba Rao, P.V., and Vaidyanathan, C.S.Enzymic conversion of 3-hydroxyanthranilic acid into cinnabarinic acid. Partial purification and properties of rat-liver cinnabarinate synthaseBiochem. J.99(2)317-322(1966) 3.Lefin, R., Petzer, A., Cloete, S.J., et al.Phenothiazine, anthraquinone and related tricyclic derivatives as inhibitors of ?-amino acid oxidaseResults Chem.4100278(2022) 4.Hiramatsu, R., Hara, T., Akimoto, H., et al.Cinnabarinic acid generated from 3-hydroxyanthranilic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspaseJ. Cell. Biochem.103(1)42-53(2008)