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TPCK

CAT: 0804-HY-124379-04Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-124379-04Size:25 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
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[1][2][3][4][5].
CAS Number
402-71-1
Product Name Alternative
L-1-Tosylamido-2-phenylethyl chloromethyl ketone; L-TPCK
UNSPSC
12352005
Hazard Statement
H315, H318, H335
Target
Apoptosis; HPV; PDK-1; Ser/Thr Protease
Type
Reference compound
Related Pathways
Anti-infection; Apoptosis; Metabolic Enzyme/Protease; PI3K/Akt/mTOR
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/tpck.html
Purity
99.0
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
CC1=CC=C(C=C1)S(N[C@@H](CC2=CC=CC=C2)C(CCl)=O)(=O)=O
Molecular Formula
C17H18ClNO3S
Molecular Weight
351.85
Precautions
H315, H318, H335
References & Citations
[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.|[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.|[3]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.|[4]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|[5]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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Nalpha-Tosyl-L-phenylalanine chloromethyl ketone

N-tosyl-L-phenylalanyl chloromethyl ketone is the N-tosyl derivative of L-phenylalanyl chloromethyl ketone. It has a role as an alkylating agent and a serine proteinase inhibitor. It is a sulfonamide and an alpha-chloroketone. It contains a L-phenylalanyl group.

CAS Number402-71-1
PubChem CID439647
IUPAC NameN-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide
Molecular FormulaC17H18ClNO3S
Molecular Weight351.8
XLogP3.6
Topological Polar Surface Area71.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Heavy Atom Count23
Formal Charge0
Complexity475
SMILES
CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CC2=CC=CC=C2)C(=O)CCl
InChI
InChI=1S/C17H18ClNO3S/c1-13-7-9-15(10-8-13)23(21,22)19-16(17(20)12-18)11-14-5-3-2-4-6-14/h2-10,16,19H,11-12H2,1H3/t16-/m0/s1
InChIKey
MQUQNUAYKLCRME-INIZCTEOSA-N
Chemical Structure
2D Structure
2D structure of Nalpha-Tosyl-L-phenylalanine chloromethyl ketone
CAS: 402-71-1
CID: 439647
Formula: C17H18ClNO3S
MW: 351.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight351.8
XLogP33.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass351.0695923
Monoisotopic Mass351.0695923
Topological Polar Surface Area71.6 Ų
Heavy Atom Count23
Formal Charge0
Complexity475
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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