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MedKoo Cat#: 555321 | Name: TC-2153 HCl
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Description:

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

TC-2153 is a potent inhibitor of STEP (STriatal-Enriched protein tyrosine Phosphatase) that forms a reversible covalent bond with the catalytic cysteine in STEP. TC-2153 increases tyrosine phosphorylation of STEP substrates ERK1/2, Pyk2, and GluN2B in cell cultures. TC-2153 improves cognitive function in transgenic AD mice.

Chemical Structure

TC-2153 HCl
TC-2153 HCl
CAS#1381769-23-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 555321

Name: TC-2153 HCl

CAS#: 1381769-23-8 (HCl)

Chemical Formula: C7H5ClF3NS5

Exact Mass: 354.8670

Molecular Weight: 355.87

Elemental Analysis: C, 23.63; H, 1.42; Cl, 9.96; F, 16.02; N, 3.94; S, 45.04

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
25mg USD 1,250.00 2 Weeks
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Related CAS #
1092771-94-2 (free base) 1381769-23-8 (HCl)
Synonym
TC-2153; TC 2153; TC2153;
IUPAC/Chemical Name
8-(Trifluoromethyl)-1,2,3,4,5-benzopentathiepin-6-amine hydrochloride
InChi Key
PYFSCYSDPQMEGZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C7H4F3NS5.ClH/c8-7(9,10)3-1-4(11)6-5(2-3)12-14-16-15-13-6;/h1-2H,11H2;1H
SMILES Code
NC1=C2SSSSSC2=CC(C(F)(F)F)=C1.[H]Cl
Appearance
Solid powder
Purity
>95 % (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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Certificate of Analysis
View CoA: current batch, Lot# S21G11M04
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 355.87 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
1: Garcia-Forn M, Martínez-Torres S, Barriga GG, Alberch J, Milà M, Azkona G, Pérez-Navarro E. Pharmacogenetic modulation of STEP improves motor and cognitive function in a mouse model of Huntington's disease. Neurobiol Dis. 2018 Aug 31. pii: S0969-9961(18)30517-5. doi: 10.1016/j.nbd.2018.08.024. [Epub ahead of print] PubMed PMID: 30176350. 2: Saavedra A, Ballesteros JJ, Tyebji S, Martínez-Torres S, Blázquez G, López-Hidalgo R, Azkona G, Alberch J, Martín ED, Pérez-Navarro E. Proteolytic Degradation of Hippocampal STEP(61) in LTP and Learning. Mol Neurobiol. 2018 Jun 12. doi: 10.1007/s12035-018-1170-1. [Epub ahead of print] PubMed PMID: 29948948. 3: Sinyakova NA, Kulikova EA, Englevskii NA, Kulikov AV. Effects of Fluoxetine and Potential Antidepressant 8-Trifluoromethyl 1,2,3,4,5-Benzopentathiepin-6-Amine Hydrochloride (TC-2153) on Behavior of Danio rerio Fish in the Novel Tank Test and Brain Content of Biogenic Amines and Their Metabolites. Bull Exp Biol Med. 2018 Mar;164(5):620-623. doi: 10.1007/s10517-018-4045-6. Epub 2018 Mar 26. PubMed PMID: 29577201. 4: Castonguay D, Dufort-Gervais J, Ménard C, Chatterjee M, Quirion R, Bontempi B, Schneider JS, Arnsten AFT, Nairn AC, Norris CM, Ferland G, Bézard E, Gaudreau P, Lombroso PJ, Brouillette J. The Tyrosine Phosphatase STEP Is Involved in Age-Related Memory Decline. Curr Biol. 2018 Apr 2;28(7):1079-1089.e4. doi: 10.1016/j.cub.2018.02.047. Epub 2018 Mar 22. PubMed PMID: 29576474; PubMed Central PMCID: PMC5901906. 5: Kampshoff CS, van Dongen JM, van Mechelen W, Schep G, Vreugdenhil A, Twisk JWR, Bosmans JE, Brug J, Chinapaw MJM, Buffart LM. Long-term effectiveness and cost-effectiveness of high versus low-to-moderate intensity resistance and endurance exercise interventions among cancer survivors. J Cancer Surviv. 2018 Jun;12(3):417-429. doi: 10.1007/s11764-018-0681-0. Epub 2018 Mar 1. PubMed PMID: 29497963; PubMed Central PMCID: PMC5956032. 6: Chatterjee M, Kurup PK, Lundbye CJ, Hugger Toft AK, Kwon J, Benedict J, Kamceva M, Banke TG, Lombroso PJ. STEP inhibition reverses behavioral, electrophysiologic, and synaptic abnormalities in Fmr1 KO mice. Neuropharmacology. 2018 Jan;128:43-53. doi: 10.1016/j.neuropharm.2017.09.026. Epub 2017 Sep 21. PubMed PMID: 28943283. 7: Kulikova E, Kulikov A. Striatal-enriched Tyrosine Protein Phosphatase (STEP) in the Mechanisms of Depressive Disorders. Curr Protein Pept Sci. 2017 Aug 30;18(11):1152-1162. doi: 10.2174/1389203718666170710121532. Review. PubMed PMID: 28699511. 8: Siemsen BM, Lombroso PJ, McGinty JF. Intra-prelimbic cortical inhibition of striatal-enriched tyrosine phosphatase suppresses cocaine seeking in rats. Addict Biol. 2018 Jan;23(1):219-229. doi: 10.1111/adb.12504. Epub 2017 Mar 28. PubMed PMID: 28349660; PubMed Central PMCID: PMC5617773. 9: Xu J, Kurup P, Baguley TD, Foscue E, Ellman JA, Nairn AC, Lombroso PJ. Inhibition of the tyrosine phosphatase STEP61 restores BDNF expression and reverses motor and cognitive deficits in phencyclidine-treated mice. Cell Mol Life Sci. 2016 Apr;73(7):1503-14. doi: 10.1007/s00018-015-2057-1. Epub 2015 Oct 8. PubMed PMID: 26450419; PubMed Central PMCID: PMC4801664. 10: Xu J, Kurup P, Azkona G, Baguley TD, Saavedra A, Nairn AC, Ellman JA, Pérez-Navarro E, Lombroso PJ. Down-regulation of BDNF in cell and animal models increases striatal-enriched protein tyrosine phosphatase 61 (STEP61 ) levels. J Neurochem. 2016 Jan;136(2):285-94. doi: 10.1111/jnc.13295. Epub 2015 Sep 17. PubMed PMID: 26316048; PubMed Central PMCID: PMC4769989. 11: Azkona G, Saavedra A, Aira Z, Aluja D, Xifró X, Baguley T, Alberch J, Ellman JA, Lombroso PJ, Azkue JJ, Pérez-Navarro E. Striatal-enriched protein tyrosine phosphatase modulates nociception: evidence from genetic deletion and pharmacological inhibition. Pain. 2016 Feb;157(2):377-86. doi: 10.1097/j.pain.0000000000000329. PubMed PMID: 26270590; PubMed Central PMCID: PMC4809206. 12: Kulikova EA, Tikhonova MA, Volcho KP, Khomenko TM, Salakhutdinov NF, Kulikov AV, Popova NK. [Comparison of behavioral effects of fluoxetine, imipramine and new psychotropic drug TC-2153 on mice with hereditary predisposition to catalepsy]. Zh Vyssh Nerv Deiat Im I P Pavlova. 2015 Jan-Feb;65(1):105-12. Russian. PubMed PMID: 25966577. 13: Baguley TD, Nairn AC, Lombroso PJ, Ellman JA. Synthesis of benzopentathiepin analogs and their evaluation as inhibitors of the phosphatase STEP. Bioorg Med Chem Lett. 2015 Mar 1;25(5):1044-6. doi: 10.1016/j.bmcl.2015.01.020. Epub 2015 Jan 20. PubMed PMID: 25666825; PubMed Central PMCID: PMC4334692. 14: Robinson R. A novel phosphatase inhibitor may be a STEP toward ameliorating cognitive dysfunction. PLoS Biol. 2014 Aug 5;12(8):e1001924. doi: 10.1371/journal.pbio.1001924. eCollection 2014 Aug. PubMed PMID: 25093574; PubMed Central PMCID: PMC4122348. 15: Xu J, Chatterjee M, Baguley TD, Brouillette J, Kurup P, Ghosh D, Kanyo J, Zhang Y, Seyb K, Ononenyi C, Foscue E, Anderson GM, Gresack J, Cuny GD, Glicksman MA, Greengard P, Lam TT, Tautz L, Nairn AC, Ellman JA, Lombroso PJ. Inhibitor of the tyrosine phosphatase STEP reverses cognitive deficits in a mouse model of Alzheimer's disease. PLoS Biol. 2014 Aug 5;12(8):e1001923. doi: 10.1371/journal.pbio.1001923. eCollection 2014 Aug. PubMed PMID: 25093460; PubMed Central PMCID: PMC4122355. 16: Kulikov AV, Tikhonova MA, Kulikova EA, Volcho KP, Khomenko TM, Salakhutdinov NF, Popova NK. A new synthetic varacin analogue, 8-(trifluoromethyl)-1,2,3,4,5-benzopentathiepin-6-amine hydrochloride (TC-2153), decreased hereditary catalepsy and increased the BDNF gene expression in the hippocampus in mice. Psychopharmacology (Berl). 2012 Jun;221(3):469-78. doi: 10.1007/s00213-011-2594-8. Epub 2011 Nov 30. PubMed PMID: 22127556. 17: Kulikov AV, Tikhonova MA, Kulikova EA, Khomenko TM, Korchagina DV, Volcho KP, Salachutdinov HF, Popova NK. [Effect of new potential psychotropic drug, 8-(trifluoromethyl)-1,2,3,4,5-benzopentathiepin-6-amine hydrochloride, on the expression of serotonin-related genes in mouse brain]. Mol Biol (Mosk). 2011 Mar-Apr;45(2):282-8. Russian. PubMed PMID: 21634115.