K777 [K11777]
| Code | Size | Price |
|---|
| AG-CR1-0158-M001 | 1 mg | £50.00 |
Quantity:
| AG-CR1-0158-M005 | 5 mg | £170.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
-20°C
Storage:
Short Term: +4°C. Long Term: -20°C
Documents
Further Information
Alternate Names/Synonyms:
K-777; K-11777; N-Pip-F-hF-VS Phenyl; N-Pip-phenylalanine-homophenylalanine-vinyl sulfone phenyl; N-Methyl-piperazinyl-L-phenylalanyl-L-homophenylalanyl-vinyl sulfone
Appearance:
Solid.
CAS:
233277-99-1
EClass:
32160000
Form (Short):
liquid
Handling Advice:
Keep cool and dry.
InChi:
InChI=1S/C32H38N4O4S/c1-35-20-22-36(23-21-35)32(38)34-30(25-27-13-7-3-8-14-27)31(37)33-28(18-17-26-11-5-2-6-12-26)19-24-41(39,40)29-15-9-4-10-16-29/h2-16,19,24,28,30H,17-18,20-23,25H2,1H3,(H,33,37)(H,34,38)/b24-19+/t28-,30-/m0/s1
InChiKey:
RHJLQMVZXQKJKB-FPHSVDBKSA-N
Long Description:
Chemical. CAS: 233277-99-1. Formula: C32H38N4O4S. MW: 574.7. Synthetic. Broad-range cathepsin inhibitor (for all known cathepsins) useful for inflammasome inhibition. Inhibits cathepsins B, L, S, C, V, K and papain in cell-free assays. Inhibits cathepsin X as well. Suppresses particle-induced NLRP3 activation and IL-1beta secretion more efficiently than Ca074Me (cathepsin B inhibitor), which in contrast suppresses nigericin-induced IL-1beta secretion. Selectively inhibits particle-induced cell death but not nigericin- or sAdT-induced cell death. Potent and selective CCR4 antagonist. Potent, irreversible cysteine protease inhibitor. Potent cysteine protease cruzain (cruzipain) inhibitor. Active against Trypanosoma cruzi the causative agent of Chagas' disease, a parasitic infection which is a leading cause of heart disease. Antiparasitic agent with anti-trypanosomal , anti-leishmanial, anti-schistosomiasis, anti-amebiasis (EhCP1 (E. Histolytica cysteine proteinase 1)), anti-anthelmintic (hookworm first-stage larvae) and anti-cryptosporidial activity. Shown to have antiviral activity by targeting cathepsin-mediated cell entry.
MDL:
MFCD14105618
Molecular Formula:
C32H38N4O4S
Molecular Weight:
574.7
Other data:
Contains ~10% other isomer product.
Package Type:
Plastic Vial
Product Description:
Broad-range cathepsin inhibitor (for all known cathepsins) useful for inflammasome inhibition. Inhibits cathepsins B, L, S, C, V, K and papain in cell-free assays. Inhibits cathepsin X as well. Suppresses particle-induced NLRP3 activation and IL-1beta secretion more efficiently than Ca074Me (cathepsin B inhibitor), which in contrast suppresses nigericin-induced IL-1beta secretion. Selectively inhibits particle-induced cell death but not nigericin- or sAdT-induced cell death. Potent and selective CCR4 antagonist. Potent, irreversible cysteine protease inhibitor. Potent cysteine protease cruzain (cruzipain) inhibitor. Active against Trypanosoma cruzi the causative agent of Chagas' disease, a parasitic infection which is a leading cause of heart disease. Antiparasitic agent with anti-trypanosomal , anti-leishmanial, anti-schistosomiasis, anti-amebiasis (EhCP1 (E. Histolytica cysteine proteinase 1)), anti-anthelmintic (hookworm first-stage larvae) and anti-cryptosporidial activity. Shown to have antiviral activity by targeting cathepsin-mediated cell entry.
Purity:
>98% (NMR)
SMILES:
CN1CCN(C(N[C@@](C(N[C@@](/C=C/S(C2=CC=CC=C2)(=O)=O)([H])CCC3=CC=CC=C3)=O)([H])CC4=CC=CC=C4)=O)CC1
Solubility Chemicals:
Soluble in DMSO. Insoluble in water.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Cysteine protease inhibitors cure an experimental Trypanosoma cruzi infection: J. Engel, et al.; J. Exp. Med. 188, 725 (1998) | In vitro evaluation of the disposition of A novel cysteine protease inhibitor: W. Jacobsen, et al.; Drug Metab. Dispos. 28, 1343 (2000) | Leishmania tropica: cysteine proteases are essential for growth and pathogenicity: H. Mahmoudzadeh-Niknam, et al.; Exp. Parasitol. 106, 158 (2004) | A cysteine protease inhibitor protects dogs from cardiac damage during infection by Trypanosoma cruzi: S.C. Barr, et al.; Antimicrob. Agents Chemother. 49, 5160 (2005) | Use of recombinant Entamoeba histolytica cysteine proteinase 1 to identify a potent inhibitor of amebic invasion in a human colonic model: S.G. Melendez-Lopez, et al.; Eukaryot. Cell 6, 1130 (2007) | Schistosomiasis mansoni: novel chemotherapy using a cysteine protease inhibitor: M.H. Abdulla, et al.; PLoS Med. 4, e14 (2007) | Vinyl sulfones as antiparasitic agents and a structural basis for drug design: I.D. Kerr, et al.; J. Biol. Chem. 284, 25697 (2009) | In vitro and in vivo studies of the trypanocidal properties of WRR-483 against Trypanosoma cruzi: Y.T. Chen, et al.; PLoS Negl. Trop. Dis. 4, e825 (2010) | Cure of hookworm infection with a cysteine protease inhibitor: J.J. Vermeire, et al.; PLoS Negl. Trop. Dis. 6, e1680 (2012) | Mapping inhibitor binding modes on an active cysteine protease via NMR spectroscopy: G.M. Lee, et al.; Biochem. 51, 10087 (2012) | Active cathepsins B, L, and S in murine and human pancreatitis: V. Lyo, et al.; Am. J. Physiol. Gastrointest. Liver Physiol. 303, G894 (2012) | Internalization of CCR4 and inhibition of chemotaxis by K777, a potent and selective CCR4 antagonist: T. Sato, et al.; Pharmacology 91, 305 (2013) | A cysteine protease inhibitor rescues mice from a lethal Cryptosporidium parvum infection: M. Ndao, et al.; Antimicrob. Agents Chemother. 57, 6063 (2013) | Reversible cysteine protease inhibitors show promise for a Chagas Disease cure: M. Ndao, et al.; Antimicrob. Agents Chemother. 58, 1167 (2014) | Protease inhibitors targeting coronavirus and filovirus entry: Y. Zhou, et al.; Antiviral Res. 116, 76 (2015) | Multiple cathepsins promote inflammasome-independent, particle-induced cell death during NLRP3-dependent IL-1beta activation: G.M. Orlowski, et al.; J. Leukoc. Biol. 102, 7 (2017)