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Literature summary for 3.4.21.91 extracted from

  • Takagi, Y.; Matsui, K.; Nobori, H.; Maeda, H.; Sato, A.; Kurosu, T.; Orba, Y.; Sawa, H.; Hattori, K.; Higashino, K.; Numata, Y.; Yoshida, Y.
    Discovery of novel cyclic peptide inhibitors of dengue virus NS2B-NS3 protease with antiviral activity (2017), Bioorg. Med. Chem. Lett., 27, 3586-3590 .
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
cyclo(D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-seryl-4-phenyl-L-phenylalanyl-L-seryl-D-arginyl)
-
Dengue virus type 2
cyclo(D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-seryl-4-phenyl-L-phenylalanyl-L-seryl-D-phenylalanyl)
-
Dengue virus type 2
cyclo(L-alanylglycyl-L-alanyl-L-arginyl-L-lysyl-L-serylglycyl-L-cysteinyl)
-
Dengue virus type 2
cyclo(L-alanylglycyl-L-lysyl-L-alanyl-L-lysyl-L-serylglycyl-L-cysteinyl)
-
Dengue virus type 2
cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-alanyl-L-serylglycyl-L-cysteinyl)
-
Dengue virus type 2
cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-alanylglycyl-L-cysteinyl)
-
Dengue virus type 2
cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-L-phenylalanyl-L-cysteinyl)
-
Dengue virus type 2
cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-serylglycyl-L-alanyl)
-
Dengue virus type 2
cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-serylglycyl-L-cysteinyl)
-
Dengue virus type 2
cyclo(L-arginyl-L-lysyl-L-seryl-4-phenyl-L-phenylalanyl-L-seryl-D-phenylalanyl-D-prolyl-L-arginyl)
-
Dengue virus type 2
cyclo(L-arginyl-L-lysyl-L-seryl-4-phenyl-L-phenylalanyl-L-seryl-D-phenylalanyl-D-prolyl-L-lysyl)
-
Dengue virus type 2
cyclo[3-(1-naphthyl)-L-alanyl-D-phenylalanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-alanyl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[3-(1-naphthyl)-L-alanyl-D-phenylalanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[3-(1-naphthyl)-L-alanyl-D-phenylalanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-N6-[CH2NH]-L-alanyl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[3-(2-naphthyl)-D-alanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-3-(2-naphthyl)-D-alanyl-(2S)-2-amino-4-phenylbutanoyl-L-phenylalanyl]
-
Dengue virus type 2
cyclo[3-(2-naphthyl)-D-alanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-D-phenylalanyl-(2S)-2-amino-4-phenylbutanoyl-L-phenylalanyl]
-
Dengue virus type 2
cyclo[3-(2-naphthyl)-L-alanyl-D-phenylalanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[3-(2-naphthyl)-L-alanyl-L-seryl-D-phenylalanyl-D-prolyl-L-lysyl-L-arginyl-L-lysyl-L-seryl]
-
Dengue virus type 2
cyclo[D-alanyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanyl]
-
Dengue virus type 2
cyclo[L-alany-(2R)-2-phenylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[L-alany-(2S)-2-phenylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[L-alanyl-(2R)-2-amino-4-phenylbutanoylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[L-alanyl-(2S)-2-amino-4-phenylbutanoylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[L-alanyl-D-phenylalanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[L-alanyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanyl]
-
Dengue virus type 2
cyclo[L-alanyl-L-phenylalanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
-
Dengue virus type 2
cyclo[L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2R)-2-amino-4-phenylbutanoyl-L-cysteinyl]
-
Dengue virus type 2
cyclo[L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-alanyl]
-
Dengue virus type 2
cyclo[L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-cysteinyl]
-
Dengue virus type 2
cyclo[L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-phenylglycyl-L-cysteinyl]
-
Dengue virus type 2
cyclo[L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanyl-D-prolyl-L-lysyl]
-
Dengue virus type 2
cyclo[L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanyl-L-prolyl-L-lysyl]
-
Dengue virus type 2
cyclo[L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanylglycyl-L-lysyl]
-
Dengue virus type 2
additional information discovery of cyclic peptide inhibitors of dengue virus NS2B-NS3 protease with antiviral activity. The introduction of aromatic residues at the appropriate positions and conformational restriction generates the most promising cyclic peptide. Cyclic peptides with proper positioning of additional arginines and aromatic residues exhibit antiviral activity against DENV. Replacing the C-terminal amide bond of the polybasic amino acid sequence with an amino methylene moiety stabilizes the cyclic peptides against hydrolysis by NS2BNS3 protease, while maintaining their enzyme inhibitory activity and antiviral activity Dengue virus type 2

Organism

Organism UniProt Comment Textmining
Dengue virus type 2
-
DENV-2
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information NS2B-NS3 protease is a trypsin-like protease with a serine protease catalytic triad (His51, Asp75, Ser135) that has a polybasic substrate recognition profile Dengue virus type 2 ?
-
?

Synonyms

Synonyms Comment Organism
dengue virus NS2B-NS3 protease
-
Dengue virus type 2
DENV-2 NS2B-NS3 protease
-
Dengue virus type 2
NS2B-NS3 protease
-
Dengue virus type 2

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00095
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanyl-D-prolyl-L-lysyl]
0.0011
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[3-(2-naphthyl)-D-alanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-3-(2-naphthyl)-D-alanyl-(2S)-2-amino-4-phenylbutanoyl-L-phenylalanyl]
0.0015
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[3-(2-naphthyl)-L-alanyl-D-phenylalanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
0.0016
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[3-(1-naphthyl)-L-alanyl-D-phenylalanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
0.0017
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[3-(1-naphthyl)-L-alanyl-D-phenylalanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-alanyl-(2S)-2-amino-4-phenylbutanoyl]
0.0017
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[3-(2-naphthyl)-D-alanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-D-phenylalanyl-(2S)-2-amino-4-phenylbutanoyl-L-phenylalanyl]
0.0021
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[3-(1-naphthyl)-L-alanyl-D-phenylalanyl-D-arginyl-L-arginyl-L-arginyl-L-lysyl-N6-[CH2NH]-L-alanyl-(2S)-2-amino-4-phenylbutanoyl]
0.0023
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-seryl-4-phenyl-L-phenylalanyl-L-seryl-D-arginyl)
0.0026
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[3-(2-naphthyl)-L-alanyl-L-seryl-D-phenylalanyl-D-prolyl-L-lysyl-L-arginyl-L-lysyl-L-seryl]
0.0033
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[D-alanyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanyl]
0.0037
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(D-arginyl-L-arginyl-L-arginyl-L-lysyl-L-seryl-4-phenyl-L-phenylalanyl-L-seryl-D-phenylalanyl)
0.0038
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(L-arginyl-L-lysyl-L-seryl-4-phenyl-L-phenylalanyl-L-seryl-D-phenylalanyl-D-prolyl-L-lysyl)
0.0038
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(L-arginyl-L-lysyl-L-seryl-4-phenyl-L-phenylalanyl-L-seryl-D-phenylalanyl-D-prolyl-L-arginyl)
0.005
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanylglycyl-L-lysyl]
0.0076
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alanyl-D-phenylalanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
0.0092
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-cysteinyl]
0.0151
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alany-(2R)-2-phenylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
0.0162
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alanyl-(2R)-2-amino-4-phenylbutanoylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
0.0184
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-alanyl]
0.0198
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alanyl-L-phenylalanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
0.0221
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-phenylglycyl-L-cysteinyl]
0.0222
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alany-(2S)-2-phenylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
0.0256
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alanyl-(2S)-2-amino-4-phenylbutanoylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl]
0.0285
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alanyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanyl]
0.0387
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-(2R)-2-amino-4-phenylbutanoyl-L-cysteinyl]
0.0393
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-seryl-L-phenylalanyl-L-cysteinyl)
0.052
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo[L-arginyl-L-lysyl-L-seryl-(2S)-2-amino-4-phenylbutanoyl-L-seryl-D-phenylalanyl-L-prolyl-L-lysyl]
0.0574
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-serylglycyl-L-alanyl)
0.114
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-serylglycyl-L-cysteinyl)
0.2
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(L-alanylglycyl-L-alanyl-L-arginyl-L-lysyl-L-serylglycyl-L-cysteinyl)
0.2
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(L-alanylglycyl-L-lysyl-L-alanyl-L-lysyl-L-serylglycyl-L-cysteinyl)
0.2
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-alanyl-L-serylglycyl-L-cysteinyl)
0.2
-
pH and temperature not specified in the publication Dengue virus type 2 cyclo(L-alanylglycyl-L-lysyl-L-arginyl-L-lysyl-L-alanylglycyl-L-cysteinyl)

General Information

General Information Comment Organism
physiological function the two-component viral protease NS2B-NS3 is required for the production of mature viruses and plays a key role in maintaining infectivity Dengue virus type 2