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

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680C91
CAS# 163239-22-3

Theoretical Analysis

MedKoo Cat#: 465266
Name: 680C91
CAS#: 163239-22-3
Chemical Formula: C15H13FN2
Exact Mass: 240.1063
Molecular Weight: 240.2814
Elemental Analysis: C, 74.98; H, 5.45; F, 7.91; N, 11.66

Price and Availability

Size Price Availability Quantity
5.0mg USD 290.0 2 Weeks
25.0mg USD 700.0 2 Weeks
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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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 23.83 100.0
Ethanol 11.91 50.0

Preparing Stock Solutions

The following data is based on the product molecular weight 240.2814 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.

Recalculate based on batch purity %
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

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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.

680C91

5.0mg / USD 290.0