132685-02-0
![1,1′-Ethylidenebis[L-tryptophan] Chemical Structure](http://file.medchemexpress.cn/product_pic/hy-w585843.gif "1,1′-Ethylidenebis[L-tryptophan] Chemical Structure")
Chemical Structure
1,1′-Ethylidenebis[L-tryptophan]
- CAS No.: 132685-02-0
- Formula:C24H26N4O4
- Molecular Weight:434.49
IUPAC Name: (3S,4R,5R)-1-(2-hydroxyethyl)-2-(hydroxymethyl)piperidine-3,4,5-triol hydrochloride
InChIKey: DETVQFQGSVEQBH-PMACEKPBSA-N
SMILES: CC(N1C2=CC=CC=C2C(C[C@H](N)C(O)=O)=C1)N3C4=CC=CC=C4C(C[C@H](N)C(O)=O)=C3
Biological Activity: 1,1′-Ethylidenebis[L-tryptophan] is an orally active amino acid analog. 1,1′-Ethylidenebis[L-tryptophan] promotes the release of adrenocorticotropic hormone and corticosterone in rat plasma, and transiently inhibits CRH mRNA in the paraventricular nucleus of the hypothalamus via glucocorticoid negative feedback. 1,1′-Ethylidenebis[L-tryptophan] induces multi-tissue inflammation and fibrosis in rodents and human cells, increases the number of degranulated mast cells, and activates the IL-5 pathway in lymphocytes. 1,1′-Ethylidenebis[L-tryptophan] is activated by tryptophanyl-tRNA synthetase and replaces L-tryptophan during translation; it also interferes with tryptophan metabolism in mice via the kynurenine pathway and dynamically alters their plasma quinolinic acid levels. 1,1′-Ethylidenebis[L-tryptophan] can be used for studies on metabolism-related mechanisms[1][2][3].
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1,1′-Ethylidenebis[L-tryptophan] | 96.04% | 1,1′-Ethylidenebis[L-tryptophan] is an orally active amino acid analog. 1,1′-Ethylidenebis[L-tryptophan] promotes the release of adrenocorticotropic hormone and corticosterone in rat plasma, and transiently inhibits CRH mRNA in the paraventricular nucleus of the hypothalamus via glucocorticoid negative feedback. 1,1′-Ethylidenebis[L-tryptophan] induces multi-tissue inflammation and fibrosis in rodents and human cells, increases the number of degranulated mast cells, and activates the IL-5 pathway in lymphocytes. 1,1′-Ethylidenebis[L-tryptophan] is activated by tryptophanyl-tRNA synthetase and replaces L-tryptophan during translation; it also interferes with tryptophan metabolism in mice via the kynurenine pathway and dynamically alters their plasma quinolinic acid levels. 1,1′-Ethylidenebis[L-tryptophan] can be used for studies on metabolism-related mechanisms. | ||||||||||||||||||||
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- [1]. Brady LS, et al. 1,1'-Ethylidenebis[L-tryptophan], a contaminant implicated in L-tryptophan eosinophilia myalgia syndrome, suppresses mRNA expression of hypothalamic corticotropin-releasing hormone in Lewis (LEW/N) rat brain. Neuroimmunomodulation. 1994 Jan;1(1):59-65.
- [2]. Silver RM, et al. A murine model of the eosinophilia-myalgia syndrome induced by 1,1'-ethylidenebis (L-tryptophan). The Journal of clinical investigation. 1994 Apr;93(4):1473-80.
- [3]. Buss WC, et al. EBT, a tryptophan contaminant associated with eosinophilia myalgia syndrome, is incorporated into proteins during translation as an amino acid analog. Autoimmunity. 1996;25(1):33-45.
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