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Literature summary for 3.4.22.28 extracted from

  • Kuo, C.J.; Shie, J.J.; Fang, J.M.; Yen, G.R.; Hsu, J.T.; Liu, H.G.; Tseng, S.N.; Chang, S.C.; Lee, C.Y.; Shih, S.R.; Liang, P.H.
    Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents (2008), Bioorg. Med. Chem., 16, 7388-7398.
    View publication on PubMed

Application

Application Comment Organism
drug development 3C protease inhibitors as anti-enterovirus anti-EV71 agents enterovirus

Cloned(Commentary)

Cloned (Comment) Organism
expressed with pET16b vector contained a N- or C-terminal hexa-His tag in Escherichia coli, protease with a C-terminus His-tag has specific activity equal to that of the tag-free enzyme, but the enzyme with N-terminal His-tag displays 10fold lower activity, indicating that additional N-terminal amino acids interfered with the protease activity enterovirus

Inhibitors

Inhibitors Comment Organism Structure
ethyl 4-[2-(4-cinnamoyl)amino-1-oxo-3-phenyl]propylamino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
-
enterovirus
ethyl 4-[2-(tert-butoxycarbonyl)amino-1-oxo-3-phenyl]propylamino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
-
enterovirus
ethyl 4-[2-[3,4-(methylenedioxy)cinnamoyl]amino-1-oxo-3-phenyl]propylamino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
-
enterovirus
ethyl 4-[2-[4-(dimethylamino)cinnamoyl]amino-1-oxo-3-phenyl]propyl-amino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
-
enterovirus
N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
-
enterovirus
Nalpha-[(2E)-3-(1,3-benzodioxol-5-yl)prop-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
-
enterovirus
Nalpha-[(2E)-3-(4-chloro-2-fluorophenyl)prop-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
-
enterovirus
Nalpha-[(2E)-3-(4-methylphenyl)prop-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
-
enterovirus
Nalpha-[(2E)-4-(5-methyl-1,2-oxazol-3-yl)but-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
-
enterovirus
Nalpha-[(benzyloxy)carbonyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
-
enterovirus
Nalpha-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
-
enterovirus

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0058
-
4-(4-dimethylaminophenylazo)benzoic acid-KTSAVLQSGFRKME-5-[(2-aminoethyl)amino]naphthalene-1-sulfonic acid
-
enterovirus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information enterovirus chymotrypsin-like protease is required for viral replication ?
-
?

Organism

Organism UniProt Comment Textmining
enterovirus
-
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant enzymes are purified by using a Ni-NTA column enterovirus

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
additional information
-
EV71 3C protease shows substantially better activity (60fold) against the substrate peptide TSAVLQSGFRKM compared to other tested substrates enterovirus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4-(4-dimethylaminophenylazo)benzoic acid-KTSAVLQSGFRKME-5-[(2-aminoethyl)amino]naphthalene-1-sulfonic acid + H2O fluorogenic substrate enterovirus 4-(4-dimethylaminophenylazo)benzoic acid-KTSAVLQ + SGFRKME-5-[(2-aminoethyl)amino]naphthalene-1-sulfonic acid
-
?
DEAMEQGVSDYI + H2O
-
enterovirus DEAMEQ + GVSDYI
-
?
IEALFQGPPKFR + H2O
-
enterovirus IEALFQ + GPPKFR
-
?
additional information chymotrypsin-like protease is required for viral replication enterovirus ?
-
?
QTGTIQGDRVAD + H2O
-
enterovirus QTGTIQ + GDRVAD
-
?
RQAVTQGFPTEL + H2O
-
enterovirus RQAVTQ + GFPTEL
-
?
TSAVLQSGFRKM + H2O
-
enterovirus TSAVLQ + SGFRKM
-
?
YFCSEQGEIQWN + H2O
-
enterovirus YFCSEQ + GEIQWN
-
?

Synonyms

Synonyms Comment Organism
3C protease
-
enterovirus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
-
assay at enterovirus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
27
-
4-(4-dimethylaminophenylazo)benzoic acid-KTSAVLQSGFRKME-5-[(2-aminoethyl)amino]naphthalene-1-sulfonic acid
-
enterovirus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
6.5
-
assay at enterovirus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 0.007 microM enterovirus Nalpha-[(2E)-3-(4-chloro-2-fluorophenyl)prop-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 0.018 microM enterovirus 2-[2-[4-(dimethylamino)cinnamoyl]amino-1-oxo-3-phenyl]propyl amino-3-(2-oxo-3-pyrrolidyl)-propan-1-al
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 0.026 microM enterovirus Nalpha-[(2E)-3-(4-methylphenyl)prop-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 0.031 microM enterovirus Nalpha-[(benzyloxy)carbonyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 0.096 microM enterovirus N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 0.16 microM enterovirus 2-(2-[3,4-(methylenedioxy)cinnamoyl]amino-1-oxo-3-phenyl)propyl amino-3-(2-oxo-3-pyrrolidyl)-propan-1-al
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 0.94 microM enterovirus Nalpha-[(2E)-4-(5-methyl-1,2-oxazol-3-yl)but-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 1.3 microM enterovirus ethyl 4-[2-(4-cinnamoyl)amino-1-oxo-3-phenyl]propylamino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 1.8 microM enterovirus ethyl 4-[2-[3,4-(methylenedioxy)cinnamoyl]amino-1-oxo-3-phenyl]propylamino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is 2.9 microM enterovirus ethyl 4-[2-[4-(dimethylamino)cinnamoyl]amino-1-oxo-3-phenyl]propyl-amino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
additional information
-
concentration required to reduce the virus-induced cell death by 50% relative to the virus control is above 20 microM enterovirus ethyl 4-[2-(tert-butoxycarbonyl)amino-1-oxo-3-phenyl]propylamino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
additional information
-
IC50 value is above 0.02 mM enterovirus ethyl 4-[2-(tert-butoxycarbonyl)amino-1-oxo-3-phenyl]propylamino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
additional information
-
IC50 value is below 0.5 microM enterovirus Nalpha-[(benzyloxy)carbonyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
additional information
-
IC50 value is below 0.5 microM enterovirus N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-Nalpha-[(2E)-3-phenylprop-2-enoyl]-L-phenylalaninamide
additional information
-
IC50 value is below 0.5 microM enterovirus Nalpha-[(2E)-3-(4-methylphenyl)prop-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
additional information
-
IC50 value is below 0.5 microM enterovirus Nalpha-[(2E)-3-(4-chloro-2-fluorophenyl)prop-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
additional information
-
IC50 value is below 0.5 microM enterovirus Nalpha-[(2E)-4-(5-methyl-1,2-oxazol-3-yl)but-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
additional information
-
IC50 value is below 0.5 microM enterovirus Nalpha-[(2E)-3-(1,3-benzodioxol-5-yl)prop-2-enoyl]-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
additional information
-
IC50 value is below 0.5 microM enterovirus Nalpha-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}-N-{(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}-L-phenylalaninamide
0.0082
-
-
enterovirus ethyl 4-[2-[4-(dimethylamino)cinnamoyl]amino-1-oxo-3-phenyl]propyl-amino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
0.01
-
-
enterovirus ethyl 4-[2-(4-cinnamoyl)amino-1-oxo-3-phenyl]propylamino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate
0.0106
-
-
enterovirus ethyl 4[2-[3,4-(methylenedioxy)cinnamoyl]amino-1-oxo-3-phenyl]propylamino-5-(2-oxo-3-pyrrolidyl)-2-pentenoate