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Literature summary for 3.4.22.15 extracted from

  • Myers, M.C.; Shah, P.P.; Beavers, M.P.; Napper, A.D.; Diamond, S.L.; Smith, A.B.; Huryn, D.M.
    Design, synthesis, and evaluation of inhibitors of cathepsin L: Exploiting a unique thiocarbazate chemotype (2008), Bioorg. Med. Chem. Lett., 18, 3646-3651.
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

Crystallization (Comment) Organism
docking studies using inhibitor S-[2-[(2-ethylphenyl)amino]-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarbothioate reveal the simultaneous occupation of the S2, S3, and S1' subsites by hydrophobic and aromatic functionalities of the thiocarbazate. A key hydrogen bond is observed between the Gly66 backbone NH and the amino acid derived carbonyl of the diacyl hydrazine Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethyl 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarboxylate unreactive to transesterification by cysteine and dithiothreitol nucleophiles. Inhibitor remains intact for greater than 24 h when incubated with cathepsin L under stoichiometric conditions, and in the presence of assay buffer Homo sapiens
S-(2-oxo-1-phenylpyrrolidin-3-yl) 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarbothioate
-
Homo sapiens
S-[2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarbothioate
-
Homo sapiens
S-[2-[(2-ethylphenyl)amino]-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarbothioate
-
Homo sapiens
S-[2-[(2-ethylphenyl)amino]-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl]hydrazinecarbothioate
-
Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000007
-
-
Homo sapiens 2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethyl 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarboxylate
0.000041
-
-
Homo sapiens S-[2-(3,4-dihydroquinolin-1(2H)-yl)-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarbothioate
0.000056
-
-
Homo sapiens S-[2-[(2-ethylphenyl)amino]-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarbothioate
0.00011
-
-
Homo sapiens S-(2-oxo-1-phenylpyrrolidin-3-yl) 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propanoyl]hydrazinecarbothioate
0.000115
-
-
Homo sapiens S-[2-[(2-ethylphenyl)amino]-2-oxoethyl] 2-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl]hydrazinecarbothioate