Molecular structure of TPCK, CAS Number: 402-71-1
TPCK (CAS 402-71-1)
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Alternate Names:
(S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone; (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone; TPCK;Tosyl-L-phenylalanyl-chloromethane
Application:
TPCK is a serine/cysteine protease inhibitor, which acts as an alkylating agent that interferes with translation
CAS Number:
402-71-1
Purity:
≥98%
Molecular Weight:
351.85
Molecular Formula:
C17H18ClNO3S
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
TPCK, N-p-Tosyl-L-phenylalanine chloromethyl ketone, is a serine protease and cysteine protease inhibitor capable of alkylating nucleophilic residues at the alpha-chloro ketone, irreversibly disabling the protease. Alkylation of IkappaB kinase beta with TPCK inhibits NF-kappaB activation, which has been reported to block association of NF-kappaB to the promoter region for COX-2 transcription, attenuating COX-2 activity. TPCK has also been reported to suppress p53-mediated apoptosis. TPCK is an inhibitor of CTRL. TPCK is an inhibitor of Granzyme.
TPCK (CAS 402-71-1) References
- Serine protease inhibitor TPCK prevents Taxol-induced cell death and blocks c-Raf-1 and Bcl-2 phosphorylation in human breast carcinoma cells. | Huang, Y., et al. 1999. Oncogene. 18: 3431-9. PMID: 10376521
- Another biological effect of tosylphenylalanylchloromethane (TPCK): it prevents p47phox phosphorylation and translocation upon neutrophil stimulation. | Gillibert, M., et al. 2005. Biochem J. 386: 549-56. PMID: 15498025
- N-tosyl-L-phenylalanine chloromethyl ketone inhibits NF-kappaB activation by blocking specific cysteine residues of IkappaB kinase beta and p65/RelA. | Ha, KH., et al. 2009. Biochemistry. 48: 7271-8. PMID: 19591457
- TPCK-induced apoptosis and labelling of the largest subunit of RNA polymerase II in Jurkat cells. | Fabian, Z., et al. 2009. Apoptosis. 14: 1154-64. PMID: 19653099
- TPCK targets elements of mitotic spindle and induces cell cycle arrest in prometaphase. | Fabian, Z. and Fearnhead, HO. 2010. Biochem Biophys Res Commun. 395: 458-64. PMID: 20381455
- Protease inhibitor TPCK represses Ha-ras (Val12) transformation and nuclear factor-kappa B activation. | Denko, N., et al. 1997. Int J Oncol. 10: 895-900. PMID: 21533459
- TPCK inhibits AGC kinases by direct activation loop adduction at phenylalanine-directed cysteine residues. | Anjum, R., et al. 2012. FEBS Lett. 586: 3471-6. PMID: 22967899
- The serine peptidase inhibitor TPCK induces several morphophysiological changes in the opportunistic fungal pathogen Candida parapsilosis sensu stricto. | Gandra, RM., et al. 2019. Med Mycol. 57: 1024-1037. PMID: 30753649
- N-p-Tosyl-L-phenylalanine chloromethyl ketone (TPCK) inhibits HIV-1 by suppressing the activity of viral protease. | Trivedi, J., et al. 2020. Biochem Biophys Res Commun. 527: 167-172. PMID: 32446362
- The serine peptidase inhibitor N-ρ-tosyl-l-phenylalanine chloromethyl ketone (TPCK) affects the cell biology of Candida haemulonii species complex. | Souto, XM., et al. 2021. Fungal Biol. 125: 378-388. PMID: 33910679
- Effects of a Serine Protease Inhibitor N-p-Tosyl-L-phenylalanine Chloromethyl Ketone (TPCK) on Leishmania amazonensis and Leishmania infantum. | Machado, PA., et al. 2022. Pharmaceutics. 14: PMID: 35890269
- Differential suppression by protease inhibitors and cytokines of apoptosis induced by wild-type p53 and cytotoxic agents. | Lotem, J. and Sachs, L. 1996. Proc Natl Acad Sci U S A. 93: 12507-12. PMID: 8901612
- Lipopolysaccharide-induced expression of cyclooxygenase-2 in mouse macrophages is inhibited by chloromethylketones and a direct inhibitor of NF-kappa B translocation. | Abate, A., et al. 1998. Prostaglandins Other Lipid Mediat. 56: 277-90. PMID: 9990673
Inhibitor of:
C1q-A, C1rb, Chymotrypsin, CPB, CTRL, Desc4, EG436523, FBXW24, GLYAT, Granzyme, granzyme A, HYAL4, ICAP-1, Mesotrypsinogen, Protease, Prss28, PRSS44, PRSS50, SerpinA1e, SerpinB9g, Spi10, Spi11, stefin A2, TLCK, and TMPRSS11E.Activator of:
1700074P13Rik, IκB-α, KLK9, LOC646960, PRSS35, Prss47, and Trypsin-10.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
TPCK, 1 g | sc-201297 | 1 g | $178.00 |