{{위키데이터 속성 추적}}
{{chembox
| Name = 키뉴레닌<br>{{sm|l}}-Kynurenine
| Verifiedfields = changed
| verifiedrevid = 461936957
| ImageFile = L-Kynurenine.svg
| ImageSize = 200px
| ImageAlt = Skeletal formula of L-kynurenine
| ImageFile1 = L-Kynurenine-zwitterion-3D-balls.png
| ImageAlt1 = Ball-and-stick model of the L-kynurenine molecule as a zwitterion
| IUPACName = (''S'')-2-Amino-4-(2-aminophenyl)-4-oxo-butanoic acid
| OtherNames = (''S'')-Kynurenine
| SystematicName = 
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 343-65-7
| CASNo_Comment = ({{sm|d}}/{{sm|l}})
| CASNo2_Ref = {{cascite|changed|??}}
| CASNo2 = 2922-83-0
| CASNo2_Comment = ({{sm|l}})
| CASNo3_Ref = {{cascite|changed|??}}
| CASNo3 = 13441-51-5
| CASNo3_Comment = ({{sm|d}})
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 498416
| PubChem=846
| PubChem_Comment = ({{sm|d}}/{{sm|l}})
| PubChem1=1152206
| PubChem1_Comment = ({{sm|d}})
| PubChem2=161166
| PubChem2_Comment = ({{sm|l}})
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 141580
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB02070
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 57959
| UNII = 02JW4J5R44
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YGPSJZOEDVAXAB-QMMMGPOBSA-N
| SMILES=c1ccc(c(c1)C(=O)C[C@@H](C(=O)O)N)N
| MeSHName=Kynurenine
  }}
| Section2 = {{Chembox Properties
| C=10|H=12|N=2|O=3
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
| Section3 = {{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt=
  }}
| Section4 = 
| Section5 = 
| Section6 = 
}}
'''키뉴레닌'''({{llang|en|kynurenine}})은 [[니아신]] 생성에 사용되는 아미노산인 [[트립토판|L-트립토판]]의 [[대사 중간생성물]]이다.

키뉴레닌은 주로 [[간]]에서만 만들어지는 [[효소]]인 [[트립토판 2,3-이산소화효소]]와 면역 활성화에 반응하여 많은 조직에서 만들어지는 [[인돌아민 2,3-이산소화효소]]에 의해 합성된다.<ref name="pmid21976023">{{저널 인용| vauthors = 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 | title = An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor | journal = Nature | volume = 478 | issue = 7368 | pages = 197–203 | year = 2011 | pmid = 21976023 | doi = 10.1038/nature10491 }}</ref> 키뉴레닌 및 키뉴레닌의 추가적인 분해 산물들은 염증<ref>{{저널 인용| vauthors = Wang Y, Liu H, McKenzie G, Witting PK, Stasch JP, Hahn M, Changsirivathanathamrong D, Wu BJ, Ball HJ, Thomas SR, Kapoor V, Celermajer DS, Mellor AL, Keaney JF, Hunt NH, Stocker R | title = Kynurenine is an endothelium-derived relaxing factor produced during inflammation | journal = Nature Medicine | volume = 16 | issue = 3 | pages = 279–85 | year = 2010 | pmid = 20190767 | pmc = 3556275 | doi = 10.1038/nm.2092 }}</ref> 동안 [[혈관 확장]] 및 면역 반응 조절을 포함하여 다양한 생물학적 기능을 수행한다.<ref>{{저널 인용| vauthors = Nguyen NT, Kimura A, Nakahama T, Chinen I, Masuda K, Nohara K, Fujii-Kuriyama Y, Kishimoto T | title = Aryl hydrocarbon receptor negatively regulates dendritic cell immunogenicity via a kynurenine-dependent mechanism | journal = Proceedings of the National Academy of Sciences | volume = 107 | issue = 46 | pages = 19961–6 | year = 2010 | pmid = 21041655 | doi = 10.1073/pnas.1014465107 | pmc=2993339}}</ref> 일부 암은 키뉴레닌의 생성을 증가시켜 종양의 성장을 증가시킨다.<ref name="pmid21976023" />

키뉴레닌 생성의 증가는 [[C형 간염]]에 대한 [[인터페론]] 치료와 관련된 우울 증상을 유발할 수 있다는 증거가 있다.<ref>{{저널 인용| vauthors = Capuron L, Neurauter G, Musselman DL, Lawson DH, Nemeroff CB, Fuchs D, Miller AH | title = Interferon-alpha–induced changes in tryptophan metabolism | journal = Biological Psychiatry | volume = 54 | issue = 9 | pages = 906–14 | year = 2003 | pmid = 14573318 | doi = 10.1016/S0006-3223(03)00173-2 }}</ref> [[조현병]]의 인지 결핍은 키뉴레닌을 분해하는 효소의 불균형과 관련이 있다.<ref>{{저널 인용| vauthors = Wonodi I, Stine OC, Sathyasaikumar KV, Roberts RC, Mitchell BD, Hong LE, Kajii Y, Thaker GK, Schwarcz R | title = Downregulated Kynurenine 3-Monooxygenase Gene Expression and Enzyme Activity in Schizophrenia and Genetic Association with Schizophrenia Endophenotypes | journal = Archives of General Psychiatry | volume = 68 | issue = 7 | pages = 665–74 | year = 2011 | pmid = 21727251 | pmc = 3855543 | doi = 10.1001/archgenpsychiatry.2011.71 }}</ref> 키뉴레닌의 생성은 [[알츠하이머병]]<ref>{{저널 인용| vauthors = Guillemin GJ, Brew BJ, Noonan CE, Takikawa O, Cullen KM | title = Indoleamine 2,3 dioxygenase and quinolinic acid Immunoreactivity in Alzheimer's disease hippocampus | journal = Neuropathology and Applied Neurobiology | volume = 31 | issue = 4 | pages = 395–404 | year = 2005 | pmid = 16008823 | doi = 10.1111/j.1365-2990.2005.00655.x }}</ref> 및 [[심혈관계 질환]]<ref>{{저널 인용| vauthors = Wirleitner B, Rudzite V, Neurauter G, Murr C, Kalnins U, Erglis A, Trusinskis K, Fuchs D | title = Immune activation and degradation of tryptophan in coronary heart disease | journal = European Journal of Clinical Investigation | volume = 33 | issue = 7 | pages = 550–4 | year = 2003 | pmid = 12814390 | doi = 10.1046/j.1365-2362.2003.01186.x }}</ref>에서 증가하는 데, 키뉴레닌의 대사 산물들은 인지 결핍<ref>{{저널 인용| vauthors = Gulaj E, Pawlak K, Bien B, Pawlak D | title = Kynurenine and its metabolites in Alzheimer's disease patients | journal = Advances in Medical Sciences | volume = 55 | issue = 2 | pages = 204–11 | year = 2010 | pmid = 20639188 | doi = 10.2478/v10039-010-0023-6 }}</ref> 및 우울 증상<ref>{{저널 인용| vauthors = Swardfager W, Herrmann N, Dowlati Y, Oh PI, Kiss A, Walker SE, Lanctôt KL | title = Indoleamine 2,3-dioxygenase activation and depressive symptoms in patients with coronary artery disease | journal = Psychoneuroendocrinology | volume = 34 | issue = 10 | pages = 1560–6 | year = 2009 | pmid = 19540675 | doi = 10.1016/j.psyneuen.2009.05.019 }}</ref>과 관련이 있다. 키뉴레닌은 또한 [[틱 장애]]와도 관련이 있다.<ref name="pmid17665285">{{저널 인용| vauthors = Hoekstra PJ, Anderson GM, Troost PW, Kallenberg CG, Minderaa RB | title = Plasma kynurenine and related measures in tic disorder patients | journal = European Child & Adolescent Psychiatry | volume = 16 | pages = 71–7 | year = 2007 | pmid = 17665285 | doi = 10.1007/s00787-007-1009-1 }}</ref><ref name="urlKynurenine potentiates">{{저널 인용| vauthors = McCreary AC, Handley SL | title = Kynurenine potentiates the DOI head shake in mice | journal = Journal of Psychopharmacology | volume = 9 | issue = 1 | pages = 69–70 | year = 1995 | pmid = 22298697 | doi = 10.1177/026988119500900112 }}</ref>

키뉴레니네이스는 키뉴레닌의 [[안트라닐산]]<ref>[http://www.ebi.ac.uk/interpro/IEntry?ac=IPR010111 Kynureninase], European Bioinformatics Institute</ref>으로의 전환을 촉매하는 반면 [[키뉴레닌-옥소글루타르산 트랜스아미네이스]]는 키뉴레닌의 [[키뉴렌산]]으로의 전환을 촉매한다. [[키뉴레닌 3-모노옥시제네이스]]는 키뉴레닌을 [[3-하이드록시키뉴레닌]]으로 전환시킨다.<ref>{{저널 인용 | vauthors = Saito Y, Hayaishi O, Rothberg S | title = Studies on Oxygenases | journal = The Journal of Biological Chemistry | volume = 229 | issue = 2 | pages = 921–34 | date = 1957-12-01 | pmid = 13502353 | url = http://www.jbc.org/cgi/pmidlookup?view=long&pmid=13502353 }}{{깨진 링크|url=http://www.jbc.org/cgi/pmidlookup?view=long&pmid=13502353 }}</ref>

== 키뉴레닌 경로 기능 장애 ==
키뉴레닌 경로의 개별 단계(예: 키뉴레닌, [[키뉴렌산]], [[퀴놀린산]], [[안트라닐산]], [[3-하이드록시키뉴레닌]])에서의 기능 장애 상태는 다수의 장애에 대해 설명되어 왔고, 예들은 다음과 같다.<ref>{{저널 인용| vauthors = Stone TW | year = 2001 | title = Kynurenines in the CNS: from endogenous obscurity to therapeutic importance | url = | journal = Progress in Neurobiology | volume = 64 | issue = 2| pages = 185–218 | doi=10.1016/s0301-0082(00)00032-0| pmid = 11240212 }}</ref>

* [[HIV 관련 신경인지장애]]
* [[투렛 증후군]]
* [[틱 장애]]
* [[정신 질환]] (예: [[조현병]], [[주요 우울 장애]], [[불안 장애]])
* [[다발성 경화증]]
* [[헌팅턴병]]
* [[뇌증]]
* [[지질 대사]]
* [[비알코올성 지방간]]
* [[전신 홍반성 루푸스]]
* [[글루타르산뇨증 1형]]
* [[비타민 B6 결핍증|비타민 B<sub>6</sub> 결핍증]]
* [[호산구증가근육통증후군]]

[[키뉴레닌 3-모노옥시제네이스]]의 하향조절은 [[유전자]] 다형성, [[사이토카인]] 또는 둘 다에 의해 야기될 수 있다.<ref name="urlNeurobiochemie">{{웹 인용| url = http://www.klinikum.uni-muenchen.de/Institut-fuer-Laboratoriumsmedizin/de/forschung/neurobiochemie/index.html | title = Neurobiochemie | language = German | accessdate = }}</ref><ref name="pmid20658274">{{저널 인용| vauthors = Müller N, Myint AM, Schwarz MJ | title = Inflammatory biomarkers and depression | journal = Neurotox Res | volume = 19 | issue = 2 | pages = 308–18 | year = 2011 | pmid = 20658274 | doi = 10.1007/s12640-010-9210-2 }}</ref> 키뉴레닌 3-모노옥시제네이스의 결핍은 키뉴레닌의 축적을 야기하고, 키뉴레닌산 및 [[안트라닐산]]을 향한 트립토판 [[대사 경로]] 내에서의 이동을 초래한다.<ref name="pmid21727251">{{저널 인용| vauthors = Wonodi I, Stine OC, Sathyasaikumar KV, Roberts RC, Mitchell BD, Hong LE, Kajii Y, Thaker GK, Schwarcz R | title = Downregulated kynurenine 3-monooxygenase gene expression and enzyme activity in schizophrenia and genetic association with schizophrenia endophenotypes | journal = Arch. Gen. Psychiatry | volume = 68 | issue = 7 | pages = 665–74 | year = 2011 | pmid = 21727251 | pmc = 3855543 | doi = 10.1001/archgenpsychiatry.2011.71 }}</ref> 키뉴레닌 3-모노옥시제네이스 결핍증은 뇌장애(예: 조현병, 틱 장애) 및 간장애와 관련이 있다.<ref name="pmid17665285"/><ref name="pmid21693093">{{저널 인용| vauthors = Holtze M, Saetre P, Engberg G, Schwieler L, Werge T, Andreassen OA, Hall H, Terenius L, Agartz I, Jönsson EG, Schalling M, Erhardt S | title = Kynurenine 3-monooxygenase polymorphisms: relevance for kynurenic acid synthesis in patients with schizophrenia and healthy controls | journal = J Psychiatry Neurosci | volume = 37 | issue = 1 | pages = 53–7 | year = 2012 | pmid = 21693093 | pmc = 3244499 | doi = 10.1503/jpn.100175 }}</ref><ref name="pmid24567701">{{저널 인용| vauthors = Campbell BM, Charych E, Lee AW, Möller T | title = Kynurenines in CNS disease: regulation by inflammatory cytokines | journal = Front Neurosci | volume = 8 | issue = | pages = 12 | year = 2014 | pmid = 24567701 | pmc = 3915289 | doi = 10.3389/fnins.2014.00012 }}</ref><ref name="pmid24836604">{{저널 인용| vauthors = Buness A, Roth A, Herrmann A, Schmitz O, Kamp H, Busch K, Suter L | title = Identification of metabolites, clinical chemistry markers and transcripts associated with hepatotoxicity | journal = PLoS ONE | volume = 9 | issue = 5 | pages = e97249 | year = 2014 | pmid = 24836604 | pmc = 4023975 | doi = 10.1371/journal.pone.0097249 }}</ref><ref name="pmid4168935">{{저널 인용| vauthors = Hirata Y, Kawachi T, Sugimura T | title = Fatty liver induced by injection of L-tryptophan | journal = Biochim. Biophys. Acta | volume = 144 | issue = 2 | pages = 233–41 | year = 1967 | pmid = 4168935 | doi = 10.1016/0005-2760(67)90153-1 }}</ref>

== 같이 보기 ==
{{위키공용분류}}
* [[인돌아민 2,3-이산소화효소]] (IDO)
* [[트립토판 2,3-이산소화효소]] (TDO)
* [[N'-폼일키뉴레닌|''N''&prime;'-폼일키뉴레닌]]
* [[키뉴레닌 경로]]

== 각주 ==
{{각주|30em}}

{{아미노산 대사 중간생성물들}}

{{전거 통제}}

[[분류:아미노산]]
[[분류:사람의 대사산물]]
[[분류:NMDA 수용체 대항제]]