163239-22-3

163239-22-3 structure

Name: 680C91
Chemical Name: 6-Fluoro-3-[(E)-2-(3-pyridinyl)vinyl]-1H-indole
CAS Number: 163239-22-3
Molecular Formula: C₁₅H₁₁FN₂
Molecular Weight: 238.26000
Catalog: Research Areas Cancer
Create Date: 2017-03-21 19:29:03
Modify Date: 2024-01-06 11:45:44
680C91 is an orally active, selective tryptophan 2,3-dioxygenase (TDO) inhibitor with a Ki of 51 nM. TDO is the key enzyme of tryptophan catabolism. 680C91 can be used for the research of cancer immunotherapy and Alzheimer’s Disease[1][2][3][4].

Name	6-Fluoro-3-[(E)-2-(3-pyridinyl)vinyl]-1H-indole
Synonyms	PSB 0777 ammonium salt

Description	680C91 is an orally active, selective tryptophan 2,3-dioxygenase (TDO) inhibitor with a Ki of 51 nM. TDO is the key enzyme of tryptophan catabolism. 680C91 can be used for the research of cancer immunotherapy and Alzheimer’s Disease[1][2][3][4].
Related Catalog	Research Areas >> Cancer Signaling Pathways >> Others >> Others Research Areas >> Inflammation/Immunology Research Areas >> Neurological Disease
In Vitro	680C91 is a potent (Ki=51 nM) and selective TDO inhibitor with no inhibitory activity against indoleamine 2,3-dioxygenase, monoamine oxidase A and B, 5-HT uptake and 5-HT1A,1D,2A and 2C receptors at a concentration of 10 μM[2]. 680C91 inhibits the catabolism of tryptophan by rat liver cells and rat liver perfused in situ[2]. Tdo2 could regulate cell proliferation and stimulate the expression of decidual marker Dtprp in the uterine stromal cells and decidual cells. Tdo2 inhibitor 680C91 also inhibits the prolifer ation activity of uterine decidual cells at 24 h[3]. Treatment of leiomyoma smooth muscle cell (LSMC) and myometrial smooth muscle cell (MSMC) spheroids with 680C91 (25 and 50 μM) significantly represses the expression of collagen type I (COL1A1) and type III (COL3A1) in a dose-dependent manner[4]. Cell Proliferation Assay[3] Cell Line: Uterine stromal cells Concentration: 0.01, 0.05, 0.1, 0.5, 1, 5, and 10 μM Incubation Time: 24 hours Result: The proliferation activity of stromal cells was significantly decreased at 5 and 10 μM. Western Blot Analysis[4] Cell Line: MSMC and LSMC Concentration: 25 and 50 μM Incubation Time: 48 hours Result: Significantly reduced the expression of COL1A1 and COL3A1 in LSMC spheroids with no significant effect on expression of these proteins in MSMC spheroids.
In Vivo	680C91 (a dose of 15 mg/kg for acute treatment ) elevates tryptophan in brain[5]. Animal Model: Male C57Bl6/NCrl mice aged 13-18 weeks[5] Dosage: 15 mg/kg Administration: Administered per os Result: Caused a significant increase in brain tryptophan.
References	[1]. M Salter, et al. The effects of an inhibitor of tryptophan 2,3-dioxygenase and a combined inhibitor of tryptophan 2,3-dioxygenase and 5-HT reuptake in the rat. Neuropharmacology. 1995 Feb;34(2):217-27. [2]. M Salter, et al. The effects of a novel and selective inhibitor of tryptophan 2,3-dioxygenase on tryptophan and serotonin metabolism in the rat. Biochem Pharmacol. 1995 May 17;49(10):1435-42. [3]. Dang-Dang Li, et al. Differential expression and regulation of Tdo2 during mouse decidualization. J Endocrinol. 2013 Dec 2;220(1):73-83. [4]. Tsai-Der Chuang, et al. Tryptophan catabolism is dysregulated in leiomyomas. Fertil Steril. 2021 Oct;116(4):1160-1171. [5]. Sophie Imbeault, et al. Effects of IDO1 and TDO2 inhibition on cognitive deficits and anxiety following LPS-induced neuroinflammation. Acta Neuropsychiatr. 2020 Feb;32(1):43-53.

Molecular Formula	C₁₅H₁₁FN₂
Molecular Weight	238.26000
Exact Mass	238.09100
PSA	28.68000
LogP	3.87240

Symbol	GHS05
Signal Word	Danger
Hazard Statements	H318
Precautionary Statements	P280-P305 + P351 + P338
Hazard Codes	C
RIDADR	NONH for all modes of transport

1158522-08-7	940364-43-2
134104-43-1	2227206-25-7
131615-57-1	6906-52-1
930439-75-1	1360966-95-5
1018584-77-4	1375289-11-4