Physicochemical Properties
| Molecular Formula | C15H11FN2 |
| Molecular Weight | 238.26 |
| Exact Mass | 238.091 |
| CAS # | 163239-22-3 |
| PubChem CID | 10014426 |
| Appearance | Light yellow to brown solid powder |
| LogP | 3.872 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 18 |
| Complexity | 305 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | FC1C=C2C(C(/C=C/C3=CC=CN=C3)=CN2)=CC=1 |
| InChi Key | YBSDQTBCNYWBMX-ONEGZZNKSA-N |
| InChi Code | InChI=1S/C15H11FN2/c16-13-5-6-14-12(10-18-15(14)8-13)4-3-11-2-1-7-17-9-11/h1-10,18H/b4-3+ |
| Chemical Name | 6-fluoro-3-[(E)-2-pyridin-3-ylethenyl]-1H-indole |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro |
A potent (Ki=51 nM) and selective TDO inhibitor, 680C91 exhibits no inhibitory activity at concentrations of 10 μM against indoleamine 2,3-dioxygenase, monoamine oxidases A and B, 5-HT uptake, and 5-HT1A,1D,2A, and 2C receptors[2]. Rat liver perfusion in situ and rat liver cells' ability to catabolize tryptophan is inhibited by 680C91[2]. Tdo2 may control cell division and promote the expression of the decidual marker Dtprp in decidual and uterine stromal cells. At 24 hours, the uterine decidual cells' ability to proliferate is likewise inhibited by the Tdo2 inhibitor 680C91[3]. The expression of collagen type I (COL1A1) and type III (COL3A1) is significantly suppressed in a dose-dependent manner when 680C91 (25 and 50 μM) is applied to spheroids of leiomyoma smooth muscle cell (LSMC) and myometrial smooth muscle cell (MSMC)[4]. |
| ln Vivo | In acute treatment, a dose of 15 mg/kg of 680C91 raises tryptophan levels in the brain[5]. |
| Cell Assay |
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 stromal cells' proliferation activity was considerably reduced at 5 and 10 μM. |
| Animal Protocol |
Animal Model: C57Bl6/NCrl male mice, 13–18 weeks of age[5] Dosage: 15 mg/kg Administration: Administered per os Result: caused a notable rise in tryptophan in the brain. |
| References |
[1]. Differential expression and regulation of Tdo2 during mouse decidualization. J Endocrinol. 2013 Dec 2;220(1):73-83. [2].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. [3].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. [4].Differential expression and regulation of Tdo2 during mouse decidualization. J Endocrinol. 2013 Dec 2;220(1):73-83. [5].Tryptophan catabolism is dysregulated in leiomyomas. Fertil Steril. 2021 Oct;116(4):1160-1171. [6].Effects of IDO1 and TDO2 inhibition on cognitive deficits and anxiety following LPS-induced neuroinflammation. Acta Neuropsychiatr. 2020 Feb;32(1):43-53. |
| Additional Infomation | 680C91 is a fluoroindole that is 6-fluoroindole in which the hydrogen at position 3 has been replaced by a 2-(pyridin-3-yl)vinyl group (trans configuration). It is a selective inhibitor of tryptophan 2,3-dioxygenase (TDO), which directs the conversion of trypophan to kynurenin. It has a role as an EC 1.13.11.11 (tryptophan 2,3-dioxygenase) inhibitor. It is a fluoroindole, a member of pyridines and an olefinic compound. |
Solubility Data
| Solubility (In Vitro) |
DMSO : 48~125 mg/mL ( 201.46~524.64 mM ) Ethanol : 25 mg/mL |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1971 mL | 20.9855 mL | 41.9710 mL | |
| 5 mM | 0.8394 mL | 4.1971 mL | 8.3942 mL | |
| 10 mM | 0.4197 mL | 2.0985 mL | 4.1971 mL |