680C91 | CAS#163239-22-3| TDO inhibitor

680C91
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 465266

CAS#: 163239-22-3

Description: 680C91 is a Tryptophan 2,3-Dioxygenase (TDO) inhibitor.

Chemical Structure

680C91

CAS# 163239-22-3

Instruction

Theoretical Analysis

MedKoo Cat#: 465266
Name: 680C91
CAS#: 163239-22-3
Chemical Formula: C15H13FN2
Exact Mass: 240.11
Molecular Weight: 240.281
Elemental Analysis: C, 74.98; H, 5.45; F, 7.91; N, 11.66

Price and Availability

Size	Price	Availability
5mg	USD 290	2 Weeks
25mg	USD 700	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: 680C91; 680 C91; 680-C91;

IUPAC/Chemical Name: 6-fluoro-3-(2-(pyridin-3-yl)ethyl)-1H-indole

InChi Key: NPQZULRNTQFUHN-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H13FN2/c16-13-5-6-14-12(10-18-15(14)8-13)4-3-11-2-1-7-17-9-11/h1-2,5-10,18H,3-4H2

SMILES Code: FC1=CC=C2C(NC=C2CCC3=CN=CC=C3)=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	23.8	100.00
	Ethanol	11.9	50.00

Preparing Stock Solutions

The following data is based on the product molecular weight 240.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Chuang TD, Quintanilla D, Boos D, Khorram O. Tryptophan catabolism is dysregulated in leiomyomas. Fertil Steril. 2021 Jun 8:S0015-0282(21)00434-9. doi: 10.1016/j.fertnstert.2021.05.081. Epub ahead of print. PMID: 34116832.

2: Cecchi M, Paccosi S, Silvano A, Eid AH, Parenti A. Dexamethasone Induces the Expression and Function of Tryptophan-2-3-Dioxygenase in SK-MEL-28 Melanoma Cells. Pharmaceuticals (Basel). 2021 Mar 4;14(3):211. doi: 10.3390/ph14030211. PMID: 33806305; PMCID: PMC7998133.

3: Abuin-Martínez C, Vidal R, Gutiérrez-López MD, Pérez-Hernández M, Giménez- Gómez P, Morales-Puerto N, O'Shea E, Colado MI. Increased kynurenine concentration attenuates serotonergic neurotoxicity induced by 3,4-methylenedioxymethamphetamine (MDMA) in rats through activation of aryl hydrocarbon receptor. Neuropharmacology. 2021 Apr 1;187:108490. doi: 10.1016/j.neuropharm.2021.108490. Epub 2021 Feb 16. PMID: 33607146.

4: Perez-Pardo P, Grobben Y, Willemsen-Seegers N, Hartog M, Tutone M, Muller M, Adolfs Y, Pasterkamp RJ, Vu-Pham D, van Doornmalen AM, van Cauter F, de Wit J, Gerard Sterrenburg J, Uitdehaag JCM, de Man J, Buijsman RC, Zaman GJR, Kraneveld AD. Pharmacological validation of TDO as a target for Parkinson's disease. FEBS J. 2021 Jul;288(14):4311-4331. doi: 10.1111/febs.15721. Epub 2021 Feb 18. PMID: 33471408.

5: Paccosi S, Cecchi M, Silvano A, Fabbri S, Parenti A. Different effects of tryptophan 2,3-dioxygenase inhibition on SK-Mel-28 and HCT-8 cancer cell lines. J Cancer Res Clin Oncol. 2020 Dec;146(12):3155-3163. doi: 10.1007/s00432-020-03351-2. Epub 2020 Aug 10. PMID: 32776284; PMCID: PMC7679327.

6: Li Y, Zhang S, Wang R, Cui M, Liu W, Yang Q, Kuang C. Synthesis of novel tryptanthrin derivatives as dual inhibitors of indoleamine 2,3-dioxygenase 1 and tryptophan 2,3-dioxygenase. Bioorg Med Chem Lett. 2020 Jun 1;30(11):127159. doi: 10.1016/j.bmcl.2020.127159. Epub 2020 Mar 29. PMID: 32247733.

7: Imbeault S, Goiny M, Liu X, Erhardt S. Effects of IDO1 and TDO2 inhibition on cognitive deficits and anxiety following LPS-induced neuroinflammation. Acta Neuropsychiatr. 2020 Feb;32(1):43-53. doi: 10.1017/neu.2019.44. Epub 2019 Dec 20. PMID: 31753057.

8: Duhalde Vega M, Aparicio JL, Mandour MF, Retegui LA. The autoimmune response elicited by mouse hepatitis virus (MHV-A59) infection is modulated by liver tryptophan-2,3-dioxygenase (TDO). Immunol Lett. 2020 Jan;217:25-30. doi: 10.1016/j.imlet.2019.11.004. Epub 2019 Nov 11. PMID: 31726186.

9: Venkateswaran N, Lafita-Navarro MC, Hao YH, Kilgore JA, Perez-Castro L, Braverman J, Borenstein-Auerbach N, Kim M, Lesner NP, Mishra P, Brabletz T, Shay JW, DeBerardinis RJ, Williams NS, Yilmaz OH, Conacci-Sorrell M. MYC promotes tryptophan uptake and metabolism by the kynurenine pathway in colon cancer. Genes Dev. 2019 Sep 1;33(17-18):1236-1251. doi: 10.1101/gad.327056.119. Epub 2019 Aug 15. PMID: 31416966; PMCID: PMC6719621.

10: Mathsyaraja H, Freie B, Cheng PF, Babaeva E, Catchpole JT, Janssens D, Henikoff S, Eisenman RN. Max deletion destabilizes MYC protein and abrogates Eµ-Myc lymphomagenesis. Genes Dev. 2019 Sep 1;33(17-18):1252-1264. doi: 10.1101/gad.325878.119. Epub 2019 Aug 8. PMID: 31395740; PMCID: PMC6719623.

11: Zhang S, Qi F, Fang X, Yang D, Hu H, Huang Q, Kuang C, Yang Q. Tryptophan 2,3-dioxygenase inhibitory activities of tryptanthrin derivatives. Eur J Med Chem. 2018 Dec 5;160:133-145. doi: 10.1016/j.ejmech.2018.10.017. Epub 2018 Oct 10. PMID: 30321802.

12: Bostian AC, Maddukuri L, Reed MR, Savenka T, Hartman JH, Davis L, Pouncey DL, Miller GP, Eoff RL. Kynurenine Signaling Increases DNA Polymerase Kappa Expression and Promotes Genomic Instability in Glioblastoma Cells. Chem Res Toxicol. 2016 Jan 19;29(1):101-8. doi: 10.1021/acs.chemrestox.5b00452. Epub 2015 Dec 30. PMID: 26651356; PMCID: PMC4718841.

13: Li DD, Gao YJ, Tian XC, Yang ZQ, Cao H, Zhang QL, Guo B, Yue ZP. Differential expression and regulation of Tdo2 during mouse decidualization. J Endocrinol. 2013 Dec 2;220(1):73-83. doi: 10.1530/JOE-13-0429. PMID: 24190896.

14: Salter M, Hazelwood R, Pogson CI, Iyer R, Madge DJ, Jones HT, Cooper BR, Cox RF, Wang CM, Wiard RP. The effects of a selective inhibitor of tryptophan 2,3-dioxygenase and a combined inhibitor of tryptophan 2,3-dioxygenase and 5-HT reuptake on serotonergic function in the rat. Adv Exp Med Biol. 1996;398:61-5. doi: 10.1007/978-1-4613-0381-7_7. PMID: 8906241.

15: Salter M, Hazelwood R, Pogson CI, Iyer R, Madge DJ. 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. doi: 10.1016/0006-2952(95)00006-l. PMID: 7539265.

16: Salter M, Hazelwood R, Pogson CI, Iyer R, Madge DJ, Jones HT, Cooper BR, Cox RF, Wang CM, Wiard RP. 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. doi: 10.1016/0028-3908(94)00147-k. PMID: 7617147.

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