Kinurenin

l-Kinurenin je metabolit aminokiseline l-triptofan koja se koristi u proizvodnji niacina.

l-Kinurenin
L-Kynurenine.svg L-Kynurenine-zwitterion-3D-balls.png
Općenito
Hemijski spojl-Kinurenin
Druga imena(S)-Kinurenin,
(2S)-2-Amino-4-(2-aminofenil)-4-okso-butanojska kiselina
Molekularna formulaC10H12N2O3
CAS registarski broj[http://www.nlm.nih.gov/cgi/mesh/2006/MB_cgi?term=343-65-7

CAS registarski broj-2: 2922-83-0
CAS registarski broj-3: 13441-51-5
&rn=1 343-65-7
CAS registarski broj-2: 2922-83-0

CAS registarski broj-3: 13441-51-5
]
InChI1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
Kratki opisMetabolit triptofana
Osobine1
Molarna masa20822 g mol−1
Agregatno stanjeČvrsto
Tačka topljenja
  • 191 °C, raspadanje [(S)-kinurenin]
  • 219 °C [(RS)-kinurenin]</small
1 Gdje god je moguće korištene su SI jedinice. Ako nije drugačije naznačeno, dati podaci vrijede pri standardnim uslovima.

Kinurenin se sintetizira pomoću enzima triptofan-dioksigenaza, koji se proizvodi prvenstveno, ali ne isključivo u jetri, i indoleamin 2,3-dioksigenaza, koji se stvara u mnogim tkivima kao odgovor na imunsku aktivaciju.[1] Kinurenin i njegovi daljnji proizvodi razgradnje obavljaju različite biološke funkcije, uključujući širenje krvnih žila tokom upale[2] i reguliranje imunskog odgovora.[3] Neki karcinomi povećavaju proizvodnju kinurenina, što povećava rast tumora.[1]

Dokazi upućuju na to da povećana proizvodnja kinurenina može izazvati simptome depresije povezane s interferonom u liječenju hepatitisa C.[4] Kognitivni deficiti kod shizofrenije povezani su s neravnotežom enzima koji razgrađuju kinurenin.[5] Nivo kinurenina u krvi je smanjen kod ljudi sa bipolarnim poremećajem.[6] Proizvodnja kinurenina je povećana kod Alzhemerove[7] i kardiovaskularne bolesti,[8] gdje su njegovi metaboliti povezani sa kognitivnim deficitima [9] i simptomima depresije.[10] Kynurenine is also associated with tics.[11][12]

Kinureninaza katabolizira pretvorbu kinurenina u antranilnu kiselinu[13] dok kinurenin-oksoglutarat transaminaza katabolizira svoju konverziju u kinureninsku kiselinu. Kinurenin 3-hidroksilaza pretvara kinurenin u 3-hidroksikinurenin.[14]

Kinurenin je također identificiran kao jedan od dva spoja koji čine pigment koji daje žutu boju pauku Misumena vatia.[15]

Disfunkcija kinureninskog putaUredi

Disfunkcionalna stanja različitih koraka kinureninskog puta (kao što su kinurenin, kinurenska kiselina, kinolinska kiselina, antranilna kiselina, 3-hidroksikinurenin) opisana su za brojne poremećaje, uključujući:[16]

Podregulacija kinurenin-3-monooksigenaze (KMO) može biti uzrok genetičkim polimorfizmima, citokinima ili oboje.[19][20] Nedostatak KMO dovodi do akumulacije kinurenina i do pomaka unutar triptofanskog mwetabolučkog puta prema kinureninskoj i antranilnoj kiselini.[21] Nedostatak kinurenin-3-monooksigenaze povezan je s poremećajima mozga (npr. veliki depresivni poremećaj, bipolarni poremećaj, shizofrenija, tikovi) [22] and of the liver.[11][23][24][25][26]

Također pogledajteUredi

ReferenceUredi

  1. ^ a b Opitz CA, Litzenburger UM, Sahm F, Ott M, Tritschler I, Trump S, Schumacher T, Jestaedt L, Schrenk D, Weller M, Jugold M, Guillemin GJ, Miller CL, Lutz C, Radlwimmer B, Lehmann I, von Deimling A, Wick W, Platten M (2011). "An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor". Nature. 478 (7368): 197–203. Bibcode:2011Natur.478..197O. doi:10.1038/nature10491. PMID 21976023.
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  3. ^ Nguyen NT, Kimura A, Nakahama T, Chinen I, Masuda K, Nohara K, Fujii-Kuriyama Y, Kishimoto T (2010). "Aryl hydrocarbon receptor negatively regulates dendritic cell immunogenicity via a kynurenine-dependent mechanism". Proceedings of the National Academy of Sciences. 107 (46): 19961–6. Bibcode:2010PNAS..10719961N. doi:10.1073/pnas.1014465107. PMC 2993339. PMID 21041655.
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  22. ^ Marx W, McGuinness AJ, Rocks T, Ruusunen A, Cleminson J, Walker AJ, Gomes-da-Costa S, Lane M, Sanches M, Diaz AP, Tseng PT, Lin PY, Berk M, Clarke G, O'Neil A, Jacka F, Stubbs B, Carvalho AF, Quevedo J, Soares JC, Fernandes BS (2020). "The kynurenine pathway in major depressive disorder, bipolar disorder, and schizophrenia: a meta-analysis of 101 studies". Molecular Psychiatry. 26 (8): 4158–4178. doi:10.1038/s41380-020-00951-9. PMID 33230205. S2CID 227132820 – preko doi: 10.1038/s41380-020-00951-9. PMID 33230205.CS1 održavanje: više imena: authors list (link)
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Vanjski linkoviUredi

Šablon:Intermedijari metabolizma aminokiselina Šablon:Modulatori ionotropnih glutamatnih receptora