606-59-7

Usage

Uses

1. Used in Cellular and Molecular Research:
Cinnabarinic acid is used as a research tool for studying the functions of components in the kynurenine metabolic pathway and its role as a mGlu4R-specific agonist.
2. Used in Apoptosis Induction:
Cinnabarinic acid is used as an apoptosis inducer in thymocytes, which is achieved through the generation of reactive oxygen species and the induction of caspase.
3. Used in Pharmaceutical Applications:
Cinnabarinic acid may be utilized in the development of drugs targeting the mGlu4 receptor, potentially for conditions related to the immune system or neurodegenerative diseases, due to its ability to induce apoptosis in T cells at concentrations of 300-500 μM.
4. Used in Biochemical Studies:
Cinnabarinic acid can be employed in biochemical studies to understand its interactions with biopolymers and macromolecules, which may lead to the discovery of novel therapeutic applications.
5. Used in Drug Delivery Systems:
Similar to gallotannin, cinnabarinic acid may benefit from novel drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes in various applications, including its potential use in pharmaceuticals.

Biochem/physiol Actions

Cinnabarinic acid is a kynurenine pathway metabolite of tryptophan, produced by the oxidation of 3-Hydroxyanthranilic acid. Cinnabarinic acid leads to loss of mitochondrial respiration and apoptosis, and has also been shown to be an mGlu4R-specific agonist.

References

1) Lowe?et al.?(2014),?Identification of cinnabarinic acid as a novel endogenous aryl hydrocarbon receptor ligand that drives IL-22 production;? PLoS One,?9(2)?e87877 2) Hiramatsu?et al. (2008),?Cinnabarinic acid generated from 3-hydroxyanthranilic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase;? J. Cell. Biochem.,?103?42 3) Fazio?et al.?(2012),?Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors;? Mol. Pharmacol.,?81?643

InChI:InChI=1/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21)

Upstream product

• 137152-34-2 N-(3-dimethylaminopropyl)-2-nitro-3-benzyloxy-4-methoxybenzamide hydrochloride 
• 50425-08-6 2-nitro-3-benzyloxy-4-methoxybenzoyl chloride 
• 548-93-6 3-hydroxyanthranilic acid 
• 602-00-6 3-hydroxy-2-nitrobenzoic acid 
• 71489-74-2 2-nitro-3-hydroxy-4-methoxybenzoic acid 
• 83748-53-2 N-(3-dimethylaminopropyl)-2-nitro-3-benzyloxy-4-methylbenzamide hydrochloride 

Downstream Products

• 141861-80-5 (4R,4aS)-2-Amino-4,4a-dihydroxy-3-oxo-10-oxy-4,4a-dihydro-3H-phenoxazine-1,9-dicarboxylic acid 
• 141861-80-5 (4S,4aS)-2-Amino-4,4a-dihydroxy-3-oxo-10-oxy-4,4a-dihydro-3H-phenoxazine-1,9-dicarboxylic acid 
• 548-93-6 3-hydroxyanthranilic acid 

Relevant academic research and scientific papers

Plectosphaeroic acids A, B, and C, Lndoleamine 2,3-dioxygenase inhibitors produced in culture by a marine isolate of the fungus plectosphaerella cucumerina

Laboratory cultures of the fungus Plectosphaerella cucumerina obtained from marine sediments collected in Barkley Sound, British Columbia, yielded the novel alkaloids plectosphaeroic acids A (1) to C (3). The alkaloids 1-3 are inhibitors of indoleamine 2,3-dioxygenase (IDO).

Catalytic oxidation of o-aminophenols and aromatic amines by mushroom tyrosinase

The kinetics of tyrosinase acting on o-aminophenols and aromatic amines as substrates was studied. The catalytic constants of aromatic monoamines and o-diamines were both low, these results are consistent with our previous mechanism in which the slow step is the transfer of a proton by a hydroxyl to the peroxide in oxy-tyrosinase (Fenoll et al., Biochem. J. 380 (2004) 643-650). In the case of o-aminophenols, the hydroxyl group indirectly cooperates in the transfer of the proton and consequently the catalytic constants in the action of tyrosinase on these compounds are higher. In the case of aromatic monoamines, the Michaelis constants are of the same order of magnitude than for monophenols, which suggests that the monophenols bind better (higher binding constant) to the enzyme to facilitate the π-π interactions between the aromatic ring and a possible histidine of the active site. In the case of aromatic o-diamines, both the catalytic and Michaelis constants are low, the values of the catalytic constants being lower than those of the corresponding o-diphenols. The values of the Michaelis constants of the aromatic o-diamines are slightly lower than those of their corresponding o-diphenols, confirming that the aromatic o-diamines bind less well (lower binding constant) to the enzyme.

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

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 first time. The compounds were evaluated for their ability

Enantioselective total syntheses of plectosphaeroic acids B and C

Evolution of the synthetic strategy that culminated in the first total syntheses of the structurally unique plectosphaeroic acids B (2) and C (3) is described. The successful enantioselective route to (+)-2 and (+)-3 proceeds in 6 and 11 steps from the kn

Catalytic oxidative cyclocondensation of o-aminophenols to 2-amino-3H-phenoxazin-3-ones

The catalytic oxidative cyclocondensation of the o-aminophenols 1a-f was investigated. The oxidants used were air/laccase, H2O2/horseradish peroxidase, H2O2/ebselen (3), and TBHP/diphenyl diselenide 4. The products obtained were 2-amino-3H-phenoxazin-3-on

OXIDATION OF ORTHO-AMINOPHENOLS III. THE JOINT OXIDATION OF DERIVATIVES OF 3-HYDROXYANTHRANILIC ACID DIFFERING IN THE SUBSTITUENTS AT POSITION 4

The joint oxidation of 3-hydroxyanthranilic acid and its 4-methoxy-substituted derivative and also the amides of 3-hydroxyanthranilic acid and the amide of 4-chloro-3-hydroxyanthranilic acid with the amides of 4-methyl-3-hydroxyanthranilic acid always lea

Triphenodioxazine-1,8-dicarboxylic Acid as an Oxidation Product of 3-Hydroxyanthranilic Acid

The oxidation of 3-hydroxyanthranilic acid (3OHA) 1 by aqueous buffered potassium ferricyanide produces a number of coloured compounds.These include cinnabarinic acid 2 (yellow), a p-quinone dimer 3 (red) and 9-carboxy-2-hydroxy-3H-phenoxazin-3-one 4 (bro

Autoxidation of 3-Hydroxyanthranilic Acid

3-Hydroxyanthranilic acid in aqueous solution can be autoxidized to yield two different products depending on the pH at which the oxidation is performed.At acidic pH the formation of cinnabarinic acid is favored while at alkaline pHs the major product is