3-hydroxy-DL-Kynurenine

Names

[ CAS No. ]:
484-78-6

[ Name ]:
3-hydroxy-DL-Kynurenine

[Synonym ]:
rac 3-Hydroxy Kynurenine
Benzenebutanoic acid, a,2-diamino-3-hydroxy-g-oxo-

Biological Activity

[Description]:

3-Hydroxykynurenine, a metabolite of tryptophan, is a potential endogenous neurotoxin whose increased levels have been described in several neurodegenerative disorders. 3-Hydroxykynurenine induces neuronal apoptosis[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Neurological Disease

[Target]

Human Endogenous Metabolite

[In Vitro]

3-Hydroxykynurenine-induced neuronal cell death shows several features of apoptosis[1]. 3-Hydroxykynurenine is a metabolic intermediate of the kynurenine pathway, the major metabolic pathway of tryptophan (Trp)[1]. 3-Hydroxykynurenine acts as an endogenous neurotoxin in the brain under pathological conditions[1]. 3-Hydroxykynurenine (20-100 μM) significantly inhibits CD4+ T-cell proliferation in a dose-dependent manner with IC50 of approximately 70 μM[2]. 3-Hydroxykynurenine (20-100 μM) induces significant CD4+ T-cell-mediated cell death in a dose-dependent manner[2]. Cell Proliferation Assay[2] Cell Line: CD3/CD28 bead-stimulated CD4+ T cells Concentration: 0, 20, 40, 60, 80, and 100 μM Incubation Time: 72 hours Result: Significantly inhibited CD4+ T-cell proliferation in a dose-dependent manner with an IC50 of approximately 70 μM.

[In Vivo]

3-Hydroxykynurenine administration (560 mg/kg IP on a daily basis on days 1 to 7, days 7 to 14, or days 1 to 14) results in significant prolongation of graft survival whether administered between days 1 to 7, days 7 to 14, or days 1 to 14[2]. Animal Model: BALB/c (H2d) mice[2] Dosage: 560 mg/kg Administration: IP injection Result: There was significant prolongation of graft survival in all treatment groups in comparison to the controls.

[References]

[1]. S Okuda, et al. 3-Hydroxykynurenine, an endogenous oxidative stress generator, causes neuronal cell death with apoptotic features and region selectivity. J Neurochem. 1998 Jan;70(1):299-307.

[2]. Sarah S Zaher,et al. 3-hydroxykynurenine suppresses CD4+ T-cell proliferation, induces T-regulatory-cell development, and prolongs corneal allograft survival. Invest Ophthalmol Vis Sci. 2011 Apr 22;52(5):2640-8.

Chemical & Physical Properties

[ Density]:
1.461g/cm3

[ Boiling Point ]:
519.3ºC at 760mmHg

[ Molecular Formula ]:
C₁₀H₁₂N₂O₄

[ Molecular Weight ]:
224.21300

[ Flash Point ]:
267.9ºC

[ Exact Mass ]:
224.08000

[ PSA ]:
126.64000

[ LogP ]:
1.24060

[ Vapour Pressure ]:
1.49E-12mmHg at 25°C

[ Index of Refraction ]:
1.635

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AY6475000

CHEMICAL NAME :: Alanine, 3-(3-hydroxyanthraniloyl)-

CAS REGISTRY NUMBER :: 484-78-6

LAST UPDATED :: 198910

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C10-H12-N2-O4

MOLECULAR WEIGHT :: 224.24

WISWESSER LINE NOTATION :: ZR BQ FV1YZVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 80 mg/kg

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - tumors

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 10 mg/L

REFERENCE :: NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 222,484,1969 *** REVIEWS *** TOXICOLOGY REVIEW AEHLAU Archives of Environmental Health. (Heldref Pub., 4000 Albemarle St., NW, Washington, DC 20016) V.1- 1960- Volume(issue)/page/year: 23,6,1971

Safety Information

[ HS Code ]:
2922509090

Customs

[ HS Code ]: 2922509090

[ Summary ]:
2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%