Cat. No.: HY-124379

TPCK

(Synonyms: L-1-Tosylamido-2-phenylethyl chloromethyl ketone; L-TPCK)

1 Cited Publications

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Based on 1 publication(s) in Google Scholar

TPCK (L-1-Tosylamido-2-phenylethyl chloromethyl ketone; L-TPCK) is an effective serine protease inhibitor and also a blocker of the PDK1/Akt pathway. TPCK can modify the E7 protein in actively keratinocyte cells. TPCK can induce cellular apoptosis, suppress tumor growth, reduce hypoxic-ischemic brain injury in rat pups, and affect vascular permeability in inflamed rats.

For research use only. We do not sell to patients.

Purity: 98.05%
CAS No.: 402-71-1
Formula: C₁₇H₁₈ClNO₃S
Molecular Weight:351.85

Storage:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

TPCK Chemical Structure

CAS No.: 402-71-1

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Use of MCE Products

Fluorescent Dye

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Publications (1)
Solvent & Solubility
- In Vitro
- In Vivo
Purity & Documentation
References
Help & FAQs
Classifications
Bioz

Biological Activity

Description

Cellular Effect

Cell Line	Type	Value	Description	References
HEK293	IC₅₀	10.8 μM Compound: TPCK	Inhibition of TNFalpha-induced NFkappaB (unknown origin) activation expressed in HEK293 cells after 6 hrs by luciferase reporter gene assay Inhibition of TNFalpha-induced NFkappaB (unknown origin) activation expressed in HEK293 cells after 6 hrs by luciferase reporter gene assay	[PMID: 23316950]
HEK293	IC₅₀	11.1 μM Compound: TPCK	Cytotoxicity against HEK293 cells Cytotoxicity against HEK293 cells	[PMID: 24533857]
HEK293	IC₅₀	3.76 μM Compound: TPCK	Inhibition of TNF-alpha-induced NFkappaB activation in human HEK293 cells after 6 hrs by luciferase reporter gene assay Inhibition of TNF-alpha-induced NFkappaB activation in human HEK293 cells after 6 hrs by luciferase reporter gene assay	[PMID: 21261296]
HEK293	IC₅₀	3.8 μM Compound: TPCK	Inhibition of TNFalpha-induced NF-kappaB activity expressed in human HEK 293 cells after 6 hrs by luciferase reporter gene assay Inhibition of TNFalpha-induced NF-kappaB activity expressed in human HEK 293 cells after 6 hrs by luciferase reporter gene assay	[PMID: 22850207]
HEK293	IC₅₀	3.8 μM Compound: TPCK	Cytotoxicity against human HEK293 cells assessed as cell survival by SRB assay Cytotoxicity against human HEK293 cells assessed as cell survival by SRB assay	[PMID: 23316950]
HEK293	IC₅₀	3.8 μM Compound: TPCK	Inhibition of TNFalpha-induced nuclear factor-kappa-B activation in human HEK293 cells at by luciferase reporter gene assay Inhibition of TNFalpha-induced nuclear factor-kappa-B activation in human HEK293 cells at by luciferase reporter gene assay	[PMID: 23994869]
HEK293	IC₅₀	3.8 μM Compound: TPCK	Inhibition of TNF-alpha-induced NF-kappaB activity in HEK293 cells after 6 hrs by luciferase reporter gene assay Inhibition of TNF-alpha-induced NF-kappaB activity in HEK293 cells after 6 hrs by luciferase reporter gene assay	[PMID: 24533857]
HEK293	IC₅₀	3.8 μM Compound: TPCK	Inhibition of TNF-alpha-induced NF-kappaB activity in HEK293 cells after 6 hrs by luciferase reporter gene assay Inhibition of TNF-alpha-induced NF-kappaB activity in HEK293 cells after 6 hrs by luciferase reporter gene assay	[PMID: 24992702]
HEK293	IC₅₀	3.8 μM Compound: TPCK	Inhibition of TNFalpha-induced NF-kappaB activity (unknown origin) transfected in HEK293 cells after 6 hrs by luciferase reporter gene assay Inhibition of TNFalpha-induced NF-kappaB activity (unknown origin) transfected in HEK293 cells after 6 hrs by luciferase reporter gene assay	[PMID: 26343828]
HEK293	IC₅₀	3.8 μM Compound: TPCK	Inhibition of TNF-alpha-activated NFkappaB (unknown origin) transfected in HEK293 cells after 6 hrs by luciferase reporter gene assay Inhibition of TNF-alpha-activated NFkappaB (unknown origin) transfected in HEK293 cells after 6 hrs by luciferase reporter gene assay	[PMID: 27196335]
HEK293	IC₅₀	4.9 μM Compound: N-tosyl-L-phenylalanine-chloromethyl ketone	Inhibition of TNF-alpha-induced NFkappaB activation in human HEK293 cells after 6 hrs by luciferase assay Inhibition of TNF-alpha-induced NFkappaB activation in human HEK293 cells after 6 hrs by luciferase assay	[PMID: 21978950]
HEK293	IC₅₀	5.05 μM Compound: TPCK	Inhibition of TNF-alpha activated nuclear factor-kappa B in HEK293 cells after 6 hrs by luciferase reporter gene assay Inhibition of TNF-alpha activated nuclear factor-kappa B in HEK293 cells after 6 hrs by luciferase reporter gene assay	[PMID: 26048799]
HEK293	IC₅₀	5.09 μM Compound: TPCK	Inhibition of NF-kappaB expressed in human HEK293 cells by luciferase reporter gene based luminometric analysis Inhibition of NF-kappaB expressed in human HEK293 cells by luciferase reporter gene based luminometric analysis	[PMID: 21105712]
HEK293	IC₅₀	5.09 μM Compound: TPCK	Inhibition of TNFalpha-activated NF-kappaB expressed in HEK293 cells by luciferase reporter gene assay Inhibition of TNFalpha-activated NF-kappaB expressed in HEK293 cells by luciferase reporter gene assay	[PMID: 22115839]
HEK293	IC₅₀	5.09 μM Compound: TPCK	Inhibition of TNF-alpha activated NF-kappaB expressed in HEK293 cells by luciferase reporter gene assay Inhibition of TNF-alpha activated NF-kappaB expressed in HEK293 cells by luciferase reporter gene assay	[PMID: 22386564]
HEK293	IC₅₀	5.09 μM Compound: TPCK	Inhibition of TNFalpha-induced NF-kappaB activity expressed in HEK293 cells by luciferase reporter gene assay Inhibition of TNFalpha-induced NF-kappaB activity expressed in HEK293 cells by luciferase reporter gene assay	[PMID: 23142320]
HEK293	IC₅₀	5.09 μM Compound: TPCK	Inhibition of TNF-alpha induced NF-kappaB transcriptional activity in HEK293 cells expressing NF-kappaB-Luc measured after 48 hrs by luciferase assay Inhibition of TNF-alpha induced NF-kappaB transcriptional activity in HEK293 cells expressing NF-kappaB-Luc measured after 48 hrs by luciferase assay	[PMID: 27155469]
HEK293	IC₅₀	5.09 μM Compound: TPCK	Inhibition of TNFalpha-activated nuclear factor-kappa B activity (unknown origin) expressed in HEK293 cells incubated for 6 hrs by luciferase reporter gene based assay Inhibition of TNFalpha-activated nuclear factor-kappa B activity (unknown origin) expressed in HEK293 cells incubated for 6 hrs by luciferase reporter gene based assay	[PMID: 27210437]
HEK293	IC₅₀	5.1 μM Compound: TPCK	Inhibition of TNFalpha-induced human NFkappaB activity in HEK293 cells incubated for 6 hrs followed by compound wash out measured after 5 mins by by luciferase assay Inhibition of TNFalpha-induced human NFkappaB activity in HEK293 cells incubated for 6 hrs followed by compound wash out measured after 5 mins by by luciferase assay	[PMID: 22712432]
HEK293	IC₅₀	5.3 μM Compound: TPCK	Inhibition of TNFalpha-induced NFkappaB activation in human HEK293 cells after 6 hrs by luciferase assay Inhibition of TNFalpha-induced NFkappaB activation in human HEK293 cells after 6 hrs by luciferase assay	[PMID: 32163285]

In Vitro

TPCK shows slight toxicity to mammalian cells (CC₅₀ = 138.8 µM), but it significantly inhibits the pre-flagellate morphology of L. amazonensis PH8 and Josefa strains (IC₅₀ values of 14.6 µM and 31.7 µM, respectively), with an IC₅₀ value of 11.3 µM for the pre-flagellate morphology of L. infantum. Additionally, TPCK is also effective against the intracellular amastigote form, showing IC₅₀ values of 14.2 µM and 16.6 µM for L. amazonensis PH8 and Josefa strains, and 21.7 µM for the amastigote form of L. infantum^[2].
TPCK (40 μM, 1 h) enhances wortmannin-dependent caspase activity in LNCaP cells but inhibits TRAIL-dependent caspase activity^[3].
TPCK (40 μM, 1 h) inhibits the formation of TRAIL-DISC in PC3 cells but does not inhibit the formation of Fas-DISC and reduces caspase2 levels^[3].
TPCK (0-40 μM, 24 h) kills PC3 cells in a dose-dependent manner, inducing apoptosis^[3].
TPCK (40 μM, 3 h) reduces the level of BAD-ser136 in LNCaP cells and eliminates AR in the cytoplasm and granules^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Western Blot Analysis^[3]

Cell Line:

PC3; LNCaP
Concentration:

40 μM
Incubation Time:

1 h; 3 h
Result:

Reduced the level of caspase-2 and inhibited TRAIL-induced activation of caspase-3, -7, -8, and -9. Did not reduce BAD levels, but reduced the level of BAD-ser136 and eliminated AR in the cytosol and granules.

Cell Viability Assay^[3]

Cell Line:

PC3
Concentration:

0, 2.5, 5, 10, 20, 40 μM
Incubation Time:

24 h
Result:

Killed PC3 cells in a dose-dependent manner.

In Vivo

TPCK (15-60 mg/kg, intraperitoneal injection, three times a week for ten doses) reduces the activity of anti-Leishmania parasites in mice^[2].
TPCK (5-100 mg/kg, intraperitoneal injection, single dose) diminishes DNA fragmentation, nitric oxide production, and brain damage in a neonatal mouse model of hypoxic-ischemic brain injury^[4].
TPCK (0.5-20 mg/kg, injected into the air sac, single dose) increases vascular permeability in inflamed rats, which then decline^[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:

BALB/c mice infected with L. amazonensis ^[2]
Dosage:

15, 30, 45, 60 mg/kg; three times a week; 10 times
Administration:

Intraperitoneal injection (i.p.)
Result:

Reduced lesion size and parasite burden in foot pads and spleen.

Animal Model:

7-day-old rats with right carotid artery ligation^[4]
Dosage:

5, 10, 20, 50, 100 mg/kg; single dose
Administration:

Intraperitoneal injection (i.p.)
Result:

Reduced the weight of the right hemisphere of the brain, reduced the number of DNA breaks in cells, abolished the increase in nitrate/nitrite metabolites within 6 hours after injury, and reduced DNA fragmentation, nitric oxide production, and brain damage.

Animal Model:

Carrageenan-air sac inflammation rats^[5]
Dosage:

0.5, 4, 20 mg/kg; single dose
Administration:

Injection into the air sac
Result:

Showed that vascular permeability increased rapidly and then gradually decreased.

Chemical Information

CAS No. 402-71-1
Appearance Solid
Molecular Weight 351.85
Formula C₁₇H₁₈ClNO₃S
Color White to off-white
SMILES

CC1=CC=C(C=C1)S(N[C@@H](CC2=CC=CC=C2)C(CCl)=O)(=O)=O
Synonyms

L-1-Tosylamido-2-phenylethyl chloromethyl ketone; L-TPCK
Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Publications (1)

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Journal Impact Factor

Int J Biol Macromol

Evaluation and mechanism of immune enhancement effects of Pleurotus ferulae polysaccharides-gold nanoparticles. [Abstract]

2023 Feb 1:227:1015-1026. PMID: 36460244

Solvent & Solubility

In Vitro:

DMSO : 100 mg/mL (284.21 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

2.8421 mL

14.2106 mL

28.4212 mL

5 mM

0.5684 mL

2.8421 mL

5.6842 mL

10 mM

0.2842 mL

1.4211 mL

2.8421 mL

Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molarity Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Dilution Calculator

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

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In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

Stock Solution Working Solution

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline

Solubility: ≥ 2.5 mg/mL (7.11 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Working solution concentration: 0.22 mg/mL

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (281 KB)
SDS (615 KB)
- English - EN (615 KB)
- Français - FR (615 KB)
- Deutsch - DE (615 KB)
- Norwegian - NO (615 KB)
- Español - ES (615 KB)
- Swedish - SV (615 KB)
- Italian - IT (615 KB)
- Korean - KR (615 KB)
- Portuguese - PT (615 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. H Stöppler, et al. The serine protease inhibitors TLCK and TPCK react with the RB-binding core of HPV-18 E7 protein and abolish its RB-binding capability. Virology. 1996 Mar 15;217(2):542-53. [Content Brief]

[2]. Patrícia de A Machado, et al. Effects of a Serine Protease Inhibitor N- p-Tosyl-L-phenylalanine Chloromethyl Ketone (TPCK) on Leishmania amazonensis and Leishmania infantum. Pharmaceutics.2022 Jun 29;14(7):1373. [Content Brief]

[3]. M H LeBlanc, et al. N-tosyl-L-phenylalanyl-chloromethylketone reduces hypoxic-ischemic brain injury in rat pups. Eur J Pharmacol. 2000 Mar 3;390(3):249-56 [Content Brief]

[4]. K Watanabe, et al. Vascular permeability changes by proteinase inhibitors in carrageenin-induced inflammation in rats. Agents Actions. 1986 Mar;17(5-6):472-7. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	2.8421 mL	14.2106 mL	28.4212 mL	71.0530 mL
	5 mM	0.5684 mL	2.8421 mL	5.6842 mL	14.2106 mL
	10 mM	0.2842 mL	1.4211 mL	2.8421 mL	7.1053 mL
	15 mM	0.1895 mL	0.9474 mL	1.8947 mL	4.7369 mL
	20 mM	0.1421 mL	0.7105 mL	1.4211 mL	3.5527 mL
	25 mM	0.1137 mL	0.5684 mL	1.1368 mL	2.8421 mL
	30 mM	0.0947 mL	0.4737 mL	0.9474 mL	2.3684 mL
	40 mM	0.0711 mL	0.3553 mL	0.7105 mL	1.7763 mL
	50 mM	0.0568 mL	0.2842 mL	0.5684 mL	1.4211 mL
	60 mM	0.0474 mL	0.2368 mL	0.4737 mL	1.1842 mL
	80 mM	0.0355 mL	0.1776 mL	0.3553 mL	0.8882 mL
	100 mM	0.0284 mL	0.1421 mL	0.2842 mL	0.7105 mL

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TPCK

Bioactive Compound Library Max

Bioactive Compound Library

Anti-Infection Compound Library

Apoptosis Compound Library

Immunology/Inflammation Compound Library

Kinase Inhibitor Library

Metabolism/Protease Compound Library

PI3K/Akt/mTOR Compound Library

Anti-Cancer Compound Library

Anti-Aging Compound Library

Oxygen Sensing Compound Library

Glycolysis Compound Library

Cytoskeleton Compound Library

Anti-Pancreatic Cancer Compound Library

Anti-Cancer Metabolism Compound Library

Anti-Obesity Compound Library

Glucose Metabolism Compound Library

Anti-Colorectal Cancer Compound Library

Anti-Prostate Cancer Compound Library

Cancer Stem Cells Compound Library

Coagulation and Anti-coagulation Compound Library

Protease Inhibitor Library

Cysteine Targeted Covalent Library

Cell Death Library

Serine/Threonine Kinase Inhibitor Library

Multi-Target Compound Library

MCE Bioactive Compound Library

Kinase Inhibitor Library Mini

Protein Kinase Compound Library

Non-Alcoholic Fatty Liver Disease (NAFLD) Compound Library

High-Throughput Bioactive Compound Library

Posttranslational Modification Library

Publications Citing Use of MedChemExpress (MCE) TPCK

Biological Activity

Chemical Information

Publications (1)

Solvent & Solubility

Purity & Documentation

References

Help & FAQs

Complete Stock Solution Preparation Table

TPCK Related Classifications

HY-124379 Related Classifications