606-59-7 Usage
Description
Cinnabarinic acid, a natural phenoxazinone derivative, is produced through the oxidative dimerization of 3-hydroxyanthranilic acid (3-HAA), a metabolite of the amino acid tryptophan, in the kynurenic pathway. It is a dark red solid that acts as a partial receptor agonist of the metabotropic glutamate receptor 4 (mGlu4) and is effective at 100 μM without activity at other mGlu receptor subtypes.
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
Check Digit Verification of cas no
The CAS Registry Mumber 606-59-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 6 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 606-59:
(5*6)+(4*0)+(3*6)+(2*5)+(1*9)=67
67 % 10 = 7
So 606-59-7 is a valid CAS Registry Number.
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)
606-59-7Relevant articles and documents
-
Bailey,K.,Brown,B.R.
, p. 408 - 409 (1967)
-
Occurrence and characterization of a labile xanthommatin precursor in some invertebrates
Bolognese,Scherillo
, p. 225 - 226 (1974)
-
Catalytic oxidation of o-aminophenols and aromatic amines by mushroom tyrosinase
Munoz-Munoz, Jose Luis,Garcia-Molina, Francisco,Garcia-Ruiz, Pedro Antonio,Varon, Ramon,Tudela, Jose,Rodriguez-Lopez, Jose N.,Garcia-Canovas, Francisco
, p. 1974 - 1983 (2011)
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.
Enantioselective total syntheses of plectosphaeroic acids B and C
Jabri, Salman Y.,Overman, Larry E.
, p. 8766 - 8788 (2013/09/24)
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
