Cinnabarinic acid

Names

[ CAS No. ]:
606-59-7

[ Name ]:
Cinnabarinic acid

[Synonym ]:
2-amino-3-oxophenoxazine-1,9-dicarboxylic acid
2-Amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
3H-Phenoxazine-1,9-dicarboxylic acid, 2-amino-3-oxo-

Biological Activity

[Description]:

Cinnabarinic acid is a specific orthosteric agonist of mGlu4 by interacting with residues of the glutamate binding pocket of mGlu4, has no activity at other mGlu receptors. Cinnabarinic acid is an endogenous metabolite of the kynurenine pathway of tryptophan. Cinnabarinic acid induces cell apoptosis[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Others

Signaling Pathways >> GPCR/G Protein >> mGluR

[Target]

mGluR4

[In Vitro]

Cinnabarinic acid (0-100 μM) does not activate mGlu1, mGlu2, mGlu5, mGlu6, mGlu7, and mGlu8 receptors as shown by measurements of [3H]InsP formation. In contrast, cinnabarinic acid acts as a partial agonist of mGlu4 receptors by increasing [3H]InsP formation by approximately 35% at 100 μM, which is 5-fold less efficacious than ACPT-I in activating mGlu4 receptors in HEK293 cells transiently transfected with rat mGlu1, -2, -4, -5, -6, -7, or -8 receptors[1]. Cinnabarinic acid (0-100 μM) reduces cAMP formation in a concentration-dependent manner with an excellent potency and efficacy. At 30 μM, cinnabarinic acid is effective at 30 μM, and substantially inhibits cAMP formation in cultured cerebellar granule cells[1].

[References]

[1]. F Fazio, et al. Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors.Mol Pharmacol. 2012 May;81(5):643-56.

[2]. Martina Ulivieri, et al. The Trace Kynurenine, Cinnabarinic Acid, Displays Potent Antipsychotic-Like Activity in Mice and Its Levels Are Reduced in the Prefrontal Cortex of Individuals Affected by Schizophrenia. Schizophr Bull. 2020 Jun 7;sbaa074.

[3]. Francesco Fazio, et al. Cinnabarinic acid and xanthurenic acid: Two kynurenine metabolites that interact with metabotropic glutamate receptors. Neuropharmacology. 2017 Jan;112(Pt B):365-372.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
536.8±50.0 °C at 760 mmHg

[ Melting Point ]:
>300ºC

[ Molecular Formula ]:
C₁₄H₈N₂O₆

[ Molecular Weight ]:
300.223

[ Flash Point ]:
278.4±30.1 °C

[ Exact Mass ]:
300.038239

[ PSA ]:
143.72000

[ LogP ]:
-0.13

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.780

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Aminophenoxazinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis of exfoliazone and chandrananimycin A.

J. Med. Chem. 56(8) , 3310-7, (2013)

A range of 2-aminophenoxazin-3-ones has been prepared by oxidative cyclocondensation of 2-aminophenols, including the natural products exfoliazone and chandrananimycin A, both synthesized for the firs...

Simultaneous determination of 3-hydroxyanthranilic and cinnabarinic acid by high-performance liquid chromatography with photometric or electrochemical detection.

Anal. Biochem. 200(2) , 273-9, (1992)

A convenient and rapid method for the simultaneous determination by HPLC of 3-hydroxyanthranilic acid and the dimer derived by its oxidation, cinnabarinic acid, is described. Buffers or biological sam...

Oxidation of 3-hydroxyanthranilic acid to the phenoxazinone cinnabarinic acid by peroxyl radicals and by compound I of peroxidases or catalase.

Biochemistry 31(34) , 8090-7, (1992)

Since 3-hydroxyanthranilic acid (3HAA), an oxidation product of tryptophan metabolism, is a powerful radical scavenger [Christen, S., Peterhans, E., & Stocker, R. (1990) Proc. Natl. Acad. Sci. U.S.A. ...