| Identification | Back Directory | [Name]
Z-PHE-DL-ALA-FLUOROMETHYLKETONE | [CAS]
197855-65-5 | [Synonyms]
CS-1504
Z-PHE-DL-ALA-FLUOROMETHYLKETONE
Nalpha-[(Benzyloxy)Carbonyl]-N-(4-Fluoro-3-Oxo-2-Butanyl)Phenylalaninamide
Nalpha-[(Benzyloxy)Carbonyl]-N-(4-Fluoro-3-Oxo-2-Butanyl)Phenylalaninamide z-fa-fmk
Carbamic acid,N-[(1S)-2-[(3-fluoro-1-methyl-2-oxopropyl)amino]-2-oxo-1-(phenylmethyl)ethyl]-,phenylmethyl ester | [Molecular Formula]
C21H23FN2O4 | [MDL Number]
MFCD02684535 | [MOL File]
197855-65-5.mol | [Molecular Weight]
386.42 |
| Chemical Properties | Back Directory | [Boiling point ]
630.5±55.0 °C(Predicted) | [density ]
1?+-.0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMF: 5 mg/ml; DMSO: 5 mg/ml | [form ]
White solid | [pka]
11.07±0.46(Predicted) | [color ]
White to off-white | [InChIKey]
ASXVEBPEZMSPHB-PKHIMPSTSA-N | [SMILES]
C(OCC1=CC=CC=C1)(=O)N[C@@H](CC1=CC=CC=C1)C(NC(C)C(=O)CF)=O |
| Hazard Information | Back Directory | [Description]
Z-FA-FMK is an irreversible inhibitor of cysteine proteases, including cathepsins B, L, and S, cruzain, and papain.1 It also inhibits effector caspases-2, -3, -6, and -7 (IC50 = 6-32 μM) without affecting the initiator caspases-8 and -10.2 Z-FA-FMK also modulates infection by certain bacteria, parasites, and viruses.3,4,5 It can be used both in cells and in vivo.4,5 | [Uses]
Z-FA-FMK is an irreversible cysteine protease inhibitor. It also inhibits papain and cruzain. | [in vivo]
Z-FA-FMK (1 mg/kg; intratumor injection; every 2 d, for 27 d; SCID mice with HT1080 xenograft) blocks reovirus infection in vivo[2].
Z-FA-FMK (8 mg/kg; i.v.; every 2 d, once; male BALB/c mice) markedly lessens the degree of impairment seen in D-GalN/TNF-α-induced kidney injury[3]. | Animal Model: | SCID mice with HT1080 xenograft (6-8 weeks)[2] | | Dosage: | 1 mg/kg | | Administration: | Intratumor injection; every 2 days, for 27 days | | Result: | Blocked reovirus replication activity in both tumor and heart tissues. |
| Animal Model: | Male BALB/c mice[3] | | Dosage: | 8 mg/kg | | Administration: | Intravenous injection; once, 1 hour later, intraperitoneal injection D-GalN (700 mg/kg) and TNF-α (15 μg/kg). | | Result: | Decreased in the D-GalN/TNF-α-induced degenerative changes.
Decreased in the number of activated caspase-3-positive tubular epithelial cell.
Increased in kidney GSH levels, CAT, SOD and GPx activities and decreased in kidney LPO levels, LDH activity, serum AST and ALT activities, uric acid, and urea levels were determined.
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| [IC 50]
Cathepsin B; cathepsin L; Caspase-2; Caspase-3; Caspase-6; Caspase-7 | [References]
[1] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[2] FRANCISCO J LOPEZ-HERNANDEZ. Z-FA-fmk inhibits effector caspases but not initiator caspases 8 and 10, and demonstrates that novel anticancer retinoid-related molecules induce apoptosis via the intrinsic pathway.[J]. Molecular Cancer Therapeutics, 2003, 2 3: 255-263.
[3] GUENTER HARTH . Peptide-fluoromethyl ketones arrest intracellular replication and intercellular transmission of Trypanosoma cruzi[J]. Molecular and biochemical parasitology, 1993, 58 1: Pages 17-24. DOI: 10.1016/0166-6851(93)90086-d
[4] CLARE P LAWRENCE. The cathepsin B inhibitor, z-FA-FMK, inhibits human T cell proliferation in vitro and modulates host response to pneumococcal infection in vivo.[J]. Journal of immunology, 2006, 177 6: 3827-3836. DOI: 10.4049/jimmunol.177.6.3827
[5] MANBOK KIM. Z-FA-FMK as a novel potent inhibitor of reovirus pathogenesis and oncolysis in vivo.[J]. Antiviral Therapy, 2010, 15 6: 897-905. DOI: 10.3851/imp1646 |
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