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Literature summary for 3.4.22.B70 extracted from

  • Qiao, Z.; Wang, W.; Wang, L.; Wen, D.; Zhao, Y.; Wang, Q.; Meng, Q.; Chen, G.; Wu, Y.; Zhou, H.
    Design, synthesis, and biological evaluation of benzodiazepine-based SUMO-specific protease 1 inhibitors (2011), Bioorg. Med. Chem. Lett., 21, 6389-6392.
    View publication on PubMed

Application

Application Comment Organism
drug development SENP1 is a potential therapeutic target for the treatment of prostate cancers Homo sapiens

Cloned(Commentary)

Cloned (Comment) Organism
cloning of the His-tagged catalytic domain of SENP1, SENP1c, aa419-aa643, from PC-3 cell cDNA library, cloned into pET28a(+) vector, and expressed in Escherichia coli strain BL21 Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(2Z)-3-(naphthalen-2-yl)-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]prop-2-enamide
-
Homo sapiens
1-(1H-indol-3-ylmethyl)-3-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]urea 3% inhibition at 0.02 mM Homo sapiens
1-(3-hydroxy-4-methylphenyl)-3-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]urea 5% inhibition at 0.02 mM Homo sapiens
1-(5-aminopentyl)-3-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]urea 43% inhibition at 0.02 mM Homo sapiens
1-(cyclohexylmethyl)-3-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]urea 5% inhibition at 0.02 mM Homo sapiens
1-(naphthalen-2-ylmethyl)-3-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]urea 26% inhibition at 0.02 mM Homo sapiens
1-naphthalen-1-yl-3-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]urea 7% inhibition at 0.02 mM Homo sapiens
1-naphthalen-2-yl-3-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]urea 30% inhibition at 0.02 mM Homo sapiens
1-[2-(1H-indol-3-yl)ethyl]-3-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]urea 24% inhibition at 0.02 mM Homo sapiens
1-[2-(naphthalen-2-yl)ethyl]-3-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]urea 45% inhibition at 0.02 mM Homo sapiens
3-[(acetyloxy)amino]-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]benzamide
-
Homo sapiens
3-[(benzyloxy)amino]-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]benzamide
-
Homo sapiens
4-methyl-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]benzenesulfonamide 17% inhibition at 0.02 mM Homo sapiens
4-[(benzyloxy)amino]-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]benzamide
-
Homo sapiens
benzyl (3-[[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]phenyl)carbamate
-
Homo sapiens
benzyl (4-[[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]phenyl)carbamate
-
Homo sapiens
benzyl [4-(2-oxo-2-[[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]amino]ethoxy)phenyl]carbamate 23% inhibition at 0.02 mM Homo sapiens
additional information design, synthesis, and biological evaluation of benzodiazepine-based SUMO-specific protease 1 inhibitors, structure–activity relationship, overview Homo sapiens
N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]pyridine-2-carboxamide 7% inhibition at 0.02 mM Homo sapiens
naphthalen-2-yl [2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]sulfamate
-
Homo sapiens
phenyl [2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamate
-
Homo sapiens
phenyl [[1-(2-hydroxyethyl)-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]carbamate
-
Homo sapiens
phenyl [[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]carbamate
-
Homo sapiens
phenyl [[2-oxo-1-(4-oxobutyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]carbamate
-
Homo sapiens
tert-butyl [3-([[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]amino)propyl]carbamate 4% inhibition at 0.02 mM Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
pro-small ubiquitin-related modifier + H2O Homo sapiens SENP1 processes the precursor SUMO to its mature form by catalyzing the cleavage of a scissile peptide bond small ubiquitin-related modifier + ?
-
?
small ubiquitin-related modifier-protein + H2O Homo sapiens SUMO-specific proteases, SENPs, reversibly remove small ubiquitin-related modifier-protein, SUMO, from the SUMOylated proteins small ubiquitin-related modifier-protein + protein
-
r

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged catalytic domain SENP1c, aa419-aa643 from Escherichia coli strain BL21 by nickel affinity chromatography Homo sapiens

Source Tissue

Source Tissue Comment Organism Textmining
PC-3 cell
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
pro-small ubiquitin-related modifier + H2O SENP1 processes the precursor SUMO to its mature form by catalyzing the cleavage of a scissile peptide bond Homo sapiens small ubiquitin-related modifier + ?
-
?
small ubiquitin-related modifier-protein + H2O SUMO-specific proteases, SENPs, reversibly remove small ubiquitin-related modifier-protein, SUMO, from the SUMOylated proteins Homo sapiens small ubiquitin-related modifier-protein + protein
-
r

Subunits

Subunits Comment Organism
More in the crystal structure of human SENP1 complexed with unprocessed SUMO1, PDB: 2IY1, the catalytic Cys603 is located in a cleft which, upon substrate binding, closes to form a channel-like structure Homo sapiens

Synonyms

Synonyms Comment Organism
SENP1
-
Homo sapiens
SUMO-specific protease
-
Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0092
-
pH and temperature not specified in the publication Homo sapiens benzyl (3-[[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]phenyl)carbamate
0.0155
-
pH and temperature not specified in the publication Homo sapiens benzyl (4-[[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]phenyl)carbamate
0.0212
-
pH and temperature not specified in the publication Homo sapiens naphthalen-2-yl [2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]sulfamate
0.0218
-
pH and temperature not specified in the publication Homo sapiens (2Z)-3-(naphthalen-2-yl)-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]prop-2-enamide
0.0272
-
pH and temperature not specified in the publication Homo sapiens phenyl [[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]carbamate
0.1
-
pH and temperature not specified in the publication Homo sapiens 4-[(benzyloxy)amino]-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]benzamide
0.1
-
pH and temperature not specified in the publication Homo sapiens 3-[(benzyloxy)amino]-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]benzamide
0.1
-
pH and temperature not specified in the publication Homo sapiens 3-[(acetyloxy)amino]-N-[2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]benzamide
0.1
-
pH and temperature not specified in the publication Homo sapiens phenyl [[1-(2-hydroxyethyl)-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]carbamate
0.1
-
pH and temperature not specified in the publication Homo sapiens phenyl [2-oxo-1-(2-oxoethyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamate
0.1
-
pH and temperature not specified in the publication Homo sapiens phenyl [[2-oxo-1-(4-oxobutyl)-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl]carbamoyl]carbamate