Tosyl-L-phenylalanine
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Tosyl-L-phenylalanine

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Category
L-Amino Acids
Catalog number
BAT-004208
CAS number
13505-32-3
Molecular Formula
C16H17NO4S
Molecular Weight
319.40
Tosyl-L-phenylalanine
IUPAC Name
(2S)-2-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoic acid
Synonyms
Tos-L-Phe-OH; N-(P-Toluenesulfonyl)-L-Phenylalanine
Appearance
White to off-white solid
Purity
≥ 98% (HPLC)
Density
1.303 g/cm3
Melting Point
162-166 °C
Boiling Point
517.7°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C16H17NO4S/c1-12-7-9-14(10-8-12)22(20,21)17-15(16(18)19)11-13-5-3-2-4-6-13/h2-10,15,17H,11H2,1H3,(H,18,19)/t15-/m0/s1
InChI Key
CGRCVIZBNRUWLY-HNNXBMFYSA-N
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(CC2=CC=CC=C2)C(=O)O
1. The serine peptidase inhibitor N-ρ-tosyl-l-phenylalanine chloromethyl ketone (TPCK) affects the cell biology of Candida haemulonii species complex
X M Souto, L S Ramos, S S C Oliveira, M H Branquinha, A L S Santos Fungal Biol. 2021 May;125(5):378-388. doi: 10.1016/j.funbio.2020.12.004. Epub 2020 Dec 23.
Candida haemulonii species complex (C. haemulonii, C. haemulonii var. vulnera and Candida duobushaemulonii) is composed by emerging and multidrug-resistant (MDR) yeasts. Candidiasis, the disease caused by these species, is difficult to treat and culminates in clinical failures and patient death. It is well-known that Candida peptidases play important roles in the fungus-host interactions, and hence these enzymes are promising targets for developing new antifungal drugs. Recently, serine-type peptidases were described in clinical isolates of C. haemulonii complex with the ability to cleave relevant key host proteins. Herein, the effects of serine peptidase inhibitors (SPIs) on the cell biology of this fungal complex were evaluated. Initially, eight distinct SPIs (phenylmethylsulfonyl fluoride - PMSF, 4-(2-aminoethyl) benzenesulfonyl fluoride hydrochloride - AEBSF, N-α-tosyl-l-lysine chloromethyl ketone hydrochloride - TLCK, N-p-tosyl-l-phenylalanine chloromethyl ketone - TPCK, simeprevir, boceprevir, danoprevir and telaprevir) were tested on the fungal growth. TPCK showed the best efficacy in controlling cell proliferation, being selected for the following experiments. This SPI induced changes in the architecture of yeast cells, as observed by scanning electron microscopy, besides injuries at the plasma membrane and reduction in the ergosterol content. TPCK also diminished the ability of yeasts to adhere to abiotic (polystyrene and glass) and biotic (murine macrophages) surfaces in a typically concentration-dependent manner. In addition, the 24 h-treatment of the mature biofilm promoted a decrease in biomass, viability and extracellular matrix. Altogether, our results highlight that SPIs may be promising new therapeutic agents in the treatment of candidiasis caused by emergent, opportunistic and MDR species forming the C. haemulonii complex.
2. N-p-Tosyl-L-phenylalanine chloromethyl ketone (TPCK) inhibits HIV-1 by suppressing the activity of viral protease
Jay Trivedi, Payel Ghosh, Debashis Mitra Biochem Biophys Res Commun. 2020 Jun 18;527(1):167-172. doi: 10.1016/j.bbrc.2020.04.096. Epub 2020 Apr 29.
Human Immunodeficiency Virus (HIV), the etiological agent for Acquired Immunodeficiency Syndrome (AIDS), continues to kill humans despite stupendous advances in antiviral research. With the presently available combination antiretroviral therapeutic arsenal, AIDS is now a manageable disease but with no cure available till date. The development of novel antivirals consumes an extensive amount of time and resources. Hence, repurposing of the established gold standard molecules for their anti-HIV application is enormously advantageous. In this study, we report that N-p-Tosyl-L-phenylalanine chloromethyl ketone (TPCK) inhibits HIV-1 replication in a highly-conserved manner. Further, TPCK inhibits HIV-1 replication at the late stages of its life cycle by impeding viral protease (PR) enzyme activity. Additionally, our results demonstrate that the combination of TPCK with established HIV-1 PR inhibitors shows significant synergistic inhibitory potential, suggesting the potential use of TPCK in cART regimen. Collectively, we report the anti-HIV activity of TPCK, which should be further characterized for its translational applications.
3. Effects of a Serine Protease Inhibitor N- p-Tosyl-L-phenylalanine Chloromethyl Ketone (TPCK) on Leishmania amazonensis and Leishmania infantum
Patrícia de A Machado, Pollyanna S Gomes, Monique P D Carneiro, Victor Midlej, Elaine S Coimbra, Herbert L de Matos Guedes Pharmaceutics. 2022 Jun 29;14(7):1373. doi: 10.3390/pharmaceutics14071373.
Studies have previously demonstrated the importance of serine proteases in Leishmania. A well-known serine protease inhibitor, TPCK, was used in the present study to evaluate its in vitro and in vivo antileishmanial effects and determine its mechanism of action. Despite slight toxicity against mammalian cells (CC50 = 138.8 µM), TPCK was selective for the parasite due to significant activity against L. amazonensis and L. infantum promastigote forms (IC50 = 14.6 and 31.7 µM for L. amazonensis PH8 and Josefa strains, respectively, and 11.3 µM for L. infantum) and intracellular amastigotes (IC50 values = 14.2 and 16.6 µM for PH8 and Josefa strains, respectively, and 21.7 µM for L. infantum). Leishmania parasites treated with TPCK presented mitochondrial alterations, oxidative stress, modifications in lipid content, flagellar alterations, and cytoplasmic vacuoles, all of which are factors that could be considered as contributing to the death of the parasites. Furthermore, BALB/c mice infected with L. amazonensis and treated with TPCK had a reduction in lesion size and parasite loads in the footpad and spleen. In BALB/c mice infected with L. infantum, TPCK also caused a reduction in the parasite loads in the liver and spleen. Therefore, we highlight the antileishmanial effect of the assessed serine protease inhibitor, proposing a potential therapeutic target in Leishmania as well as a possible new alternative treatment for leishmaniasis.
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