Cinnabarinic Acid-d4

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)