Names | |
---|---|
Preferred IUPAC name
(2S)-2-Amino-4-(2-aminophenyl)-4-oxo-butanoic acid | |
Other names
(S)-Kynurenine
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
MeSH | Kynurenine |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C10H12N2O3 | |
Molar mass | 208.217 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
l-Kynurenine is a metabolite of the amino acid l- tryptophan used in the production of niacin.
Kynurenine is synthesized by the enzyme tryptophan dioxygenase, which is made primarily but not exclusively in the liver, and indoleamine 2,3-dioxygenase, which is made in many tissues in response to immune activation. [1] Kynurenine and its further breakdown products carry out diverse biological functions, including dilating blood vessels during inflammation [2] and regulating the immune response. [3] Some cancers increase kynurenine production, which increases tumor growth. [1]
Kynurenine protects the eye by absorbing UV light, especially in the UVA region (315-400 nm). [4] Kynurenine is present in the lens and retina as one of multiple tryptophan derivatives produced in the eye, including 3-hydroxykynurenine, that together provide UV protection and aid in enhancing visual acuity. [5] [6] The use of kynurenine as a UV filter is consistent with its photostability and low photosensitization, owing to its efficient relaxation from the UV-induced excited state. [7] The concentration of this UV filter decreases with age, [8] and this loss of free kynurenine and the concomitant formation of relatively more photosensitizing kynurenine derivatives and kynurenine-protein conjugates may contribute to the formation of cataracts. [9] [10] [11]
Evidence suggests that increased kynurenine production may precipitate depressive symptoms associated with interferon treatment for hepatitis C. [12] Cognitive deficits in schizophrenia are associated with imbalances in the enzymes that break down kynurenine. [13] Blood levels of kynurenine are reduced in people with bipolar disorder. [14] Kynurenine production is increased in Alzheimer's disease [15] and cardiovascular disease [16] where its metabolites are associated with cognitive deficits [17] and depressive symptoms. [18] Kynurenine is also associated with tics. [19] [20]
Kynureninase catabolizes the conversion of kynurenine into anthranilic acid [21] while kynurenine-oxoglutarate transaminase catabolizes its conversion into kynurenic acid. Kynurenine 3-hydroxylase converts kynurenine to 3-hydroxykynurenine. [22]
Kynurenine has also been identified as one of two compounds that makes up the pigment that gives the goldenrod crab spider its yellow color. [23]
Dysfunctional states of distinct steps of the kynurenine pathway (such as kynurenine, kynurenic acid, quinolinic acid, anthranilic acid, 3-hydroxykynurenine) have been described for a number of disorders, including: [25]
Downregulation of kynurenine-3-monooxygenase (KMO) can be caused by genetic polymorphisms, cytokines, or both. [28] [29] KMO deficiency leads to an accumulation of kynurenine and to a shift within the tryptophan metabolic pathway towards kynurenine acid and anthranilic acid. [30] Kynurenine-3-monooxygenase deficiency is associated with disorders of the brain (e.g. major depressive disorder, bipolar disorder, schizophrenia, tic disorders) [31] and of the liver. [19] [32] [33] [34] [35]
It is hypothesized that the kynurenine pathway is partly responsible for the therapeutic effect of lithium on bipolar disorder. If that is the case, it could be a target of drug discovery. [36] [37]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)
Names | |
---|---|
Preferred IUPAC name
(2S)-2-Amino-4-(2-aminophenyl)-4-oxo-butanoic acid | |
Other names
(S)-Kynurenine
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
MeSH | Kynurenine |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C10H12N2O3 | |
Molar mass | 208.217 g·mol−1 |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
l-Kynurenine is a metabolite of the amino acid l- tryptophan used in the production of niacin.
Kynurenine is synthesized by the enzyme tryptophan dioxygenase, which is made primarily but not exclusively in the liver, and indoleamine 2,3-dioxygenase, which is made in many tissues in response to immune activation. [1] Kynurenine and its further breakdown products carry out diverse biological functions, including dilating blood vessels during inflammation [2] and regulating the immune response. [3] Some cancers increase kynurenine production, which increases tumor growth. [1]
Kynurenine protects the eye by absorbing UV light, especially in the UVA region (315-400 nm). [4] Kynurenine is present in the lens and retina as one of multiple tryptophan derivatives produced in the eye, including 3-hydroxykynurenine, that together provide UV protection and aid in enhancing visual acuity. [5] [6] The use of kynurenine as a UV filter is consistent with its photostability and low photosensitization, owing to its efficient relaxation from the UV-induced excited state. [7] The concentration of this UV filter decreases with age, [8] and this loss of free kynurenine and the concomitant formation of relatively more photosensitizing kynurenine derivatives and kynurenine-protein conjugates may contribute to the formation of cataracts. [9] [10] [11]
Evidence suggests that increased kynurenine production may precipitate depressive symptoms associated with interferon treatment for hepatitis C. [12] Cognitive deficits in schizophrenia are associated with imbalances in the enzymes that break down kynurenine. [13] Blood levels of kynurenine are reduced in people with bipolar disorder. [14] Kynurenine production is increased in Alzheimer's disease [15] and cardiovascular disease [16] where its metabolites are associated with cognitive deficits [17] and depressive symptoms. [18] Kynurenine is also associated with tics. [19] [20]
Kynureninase catabolizes the conversion of kynurenine into anthranilic acid [21] while kynurenine-oxoglutarate transaminase catabolizes its conversion into kynurenic acid. Kynurenine 3-hydroxylase converts kynurenine to 3-hydroxykynurenine. [22]
Kynurenine has also been identified as one of two compounds that makes up the pigment that gives the goldenrod crab spider its yellow color. [23]
Dysfunctional states of distinct steps of the kynurenine pathway (such as kynurenine, kynurenic acid, quinolinic acid, anthranilic acid, 3-hydroxykynurenine) have been described for a number of disorders, including: [25]
Downregulation of kynurenine-3-monooxygenase (KMO) can be caused by genetic polymorphisms, cytokines, or both. [28] [29] KMO deficiency leads to an accumulation of kynurenine and to a shift within the tryptophan metabolic pathway towards kynurenine acid and anthranilic acid. [30] Kynurenine-3-monooxygenase deficiency is associated with disorders of the brain (e.g. major depressive disorder, bipolar disorder, schizophrenia, tic disorders) [31] and of the liver. [19] [32] [33] [34] [35]
It is hypothesized that the kynurenine pathway is partly responsible for the therapeutic effect of lithium on bipolar disorder. If that is the case, it could be a target of drug discovery. [36] [37]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)