Z-FF-FMK is a cell-permeant and irreversible inhibitor of cathepsin B and cathepsin L.
CAT No: HB00021
Synonyms/Alias:Z-FF-FMK;105608-85-3;CHEMBL2368566;benzyl N-[(2S)-1-[[(2S)-4-fluoro-3-oxo-1-phenylbutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate;Z-Phe-PheCH2F;SCHEMBL18328618;CAILNONEKASNSH-ZEQRLZLVSA-N;EX-A3847;BDBM50491472;Carbamic acid, N-[(1S)-2-[[(1S)-3-fluoro-2-oxo-1-(phenylmethyl)propyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-, phenylmethyl ester;HY-141867;CS-0311254;Z-Phe-Phe-fluoromethyl ketone, >=98% (TLC), solid;Carbamicacid,N-[(1S)-2-[[(1S)-3-fluoro-2-oxo-1-(phenylmethyl)propyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-,phenylmethylester;
Z-FF-FMK, also known as Benzyloxycarbonyl-Phe-Phe-fluoromethyl ketone, is a synthetic peptide-based irreversible inhibitor commonly utilized in biochemical and cellular research. As a dipeptidyl fluoromethyl ketone, it is structurally engineered to target and covalently modify the active sites of specific proteases. Its unique design incorporates a benzyloxycarbonyl (Z) protecting group and a phenylalanine-phenylalanine (Phe-Phe) sequence, capped with a fluoromethyl ketone moiety, enabling selective and potent inhibition of target enzymes. The compound's specificity and stability have made it a valuable reagent in studies exploring protease function, substrate identification, and regulatory mechanisms in complex biological systems.
Protease inhibition: Z-FF-FMK is widely employed as a potent and selective inhibitor of cysteine proteases, particularly those in the caspase and cathepsin families. By covalently binding to the catalytic cysteine residue within the enzyme's active site, it effectively blocks proteolytic activity. This property allows researchers to dissect the roles of specific proteases in apoptosis, protein turnover, and other regulated cellular processes. Its irreversible mode of action ensures sustained inhibition, making it especially useful in time-course experiments or mechanistic studies where transient inhibition would be insufficient.
Apoptosis pathway analysis: The compound is frequently used in cell biology to investigate the molecular events underlying programmed cell death. By inhibiting caspase activity, Z-FF-FMK enables the assessment of caspase-dependent and caspase-independent apoptotic pathways. Researchers utilize it to differentiate between proteolytic events that are essential for apoptosis execution and those that are secondary or unrelated, thereby clarifying the contribution of individual caspases or related proteases in cellular fate decisions.
Substrate profiling and enzyme characterization: In enzymology, Z-FF-FMK serves as a valuable tool for profiling protease substrate preferences and for characterizing enzyme kinetics. Its dipeptide structure can mimic natural substrates, while the fluoromethyl ketone group acts as a reactive warhead for irreversible binding. By employing the inhibitor in in vitro assays, scientists can map active site specificity, determine inhibitor constants, and elucidate the structural requirements for substrate recognition among various protease isoforms.
Cellular pathway dissection: The inhibitor is instrumental in dissecting complex signaling pathways that involve proteolytic processing of key regulatory proteins. By selectively blocking protease activity, researchers can evaluate the downstream effects on signal transduction, transcriptional regulation, and cellular differentiation. This approach is particularly valuable in studies where multiple proteases may have overlapping or compensatory roles, as the compound's selectivity helps isolate the function of individual enzymes within larger networks.
Peptide-based drug discovery research: Z-FF-FMK's structural features and mechanism of action make it a reference compound in the development and evaluation of novel peptide-based protease inhibitors. Its use in screening assays and structure-activity relationship studies provides insights into the design of next-generation inhibitors with improved selectivity, potency, or pharmacological properties. As such, it plays a critical role in advancing early-stage research aimed at identifying new chemical entities for potential therapeutic applications, supporting the broader field of protease-targeted drug discovery.
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