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Cinnabarinic acid

Katalog-Nr.GC12705

CinnabarinsÄure ist ein spezifischer orthosterischer Agonist von mGlu4, indem sie mit Resten der Glutamat-Bindungstasche von mGlu4 interagiert und keine AktivitÄt an anderen mGlu-Rezeptoren hat.

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Cinnabarinic acid Chemische Struktur

Cas No.: 606-59-7

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Sample solution is provided at 25 µL, 10mM.

Product has been cited by 1 publications

Description of Cinnabarinic acid

Cinnabarinic acid is a phenoxazinone produced by the oxidative dimerization of 3-hydroxyanthranilic acid (3-HAA) as part of the metabolism of tryptophan in the kynurenic pathway.[1],[2] It acts as a partial receptor agonist of the metabotropic glutamate receptor 4 (mGlu4), effective at 100 µM, with no activity at other mGlu receptor subtypes.[3] 3-HAA does not affect mGlu receptors, including mGlu4. Cinnabarinic acid induces apoptosis of T cells at 300-500 µM, a potency some ten times that of 3-HAA.[4]

Reference:
[1]. 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 synthase. Biochemistry Journal 99(2), 317-322 (1966).
[2]. Stone, T.W., Stoy, N., and Darlington, L.G. An expanding range of targets for kynurenine metabolites of tryptophan. Trends in Pharamacological Sciences 34(2), 136-143 (2013).
[3]. Fazio, F., Lionetto, L., Molinaro, G., et al. Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors. Molecular Pharmacology 81(5), 643-656 (2012).
[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 caspase. Journal of Cellular Biochemistry 103(1), 42-53 (2008).

Chemical Properties of Cinnabarinic acid

Cas No. 606-59-7 SDF
Chemical Name 2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
Canonical SMILES O=C1C(N)=C(C(O)=O)C2=NC3=C(C(O)=O)C=CC=C3OC2=C1
Formula C14H8N2O6 M.Wt 300.22
Löslichkeit DMSO: 25 mM (warmed) Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Cinnabarinic acid

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1 mg 5 mg 10 mg
1 mM 3.3309 mL 16.6545 mL 33.3089 mL
5 mM 666.2 μL 3.3309 mL 6.6618 mL
10 mM 333.1 μL 1.6654 mL 3.3309 mL
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