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Literature summary for 3.4.21.77 extracted from

  • Singh, P.; Williams, S.A.; Shah, M.H.; Lectka, T.; Pritchard, G.J.; Isaacs, J.T.; Denmeade, S.R.
    Mechanistic insights into the inhibition of prostate specific antigen by beta-lactam class compounds (2008), Proteins, 70, 1416-1428.
    View publication on PubMed
Search for more literature for 3.4.21.77

Application

Application Comment Organism
medicine biomarker used in the diagnosis of prostate cancer and to monitor therapeutic response. Design and development of potent and specific inhibitors of PSA Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
((2R,3R)-3-benzyl-1-(ethylsulfonyl)-4-oxoazetidin-2-yl)methyl benzoate
-
 Homo sapiens
((2R,3R)-3-benzyl-4-oxo-1-(phenylsulfonyl)azetidin-2-yl)methyl benzoate
-
 Homo sapiens
((2R,3R)-3-benzyl-4-oxo-1-tosylazetidin-2-yl)methyl benzoate
-
 Homo sapiens
((2S,3S)-3-benzyl-1-(ethylsulfonyl)-4-oxoazetidin-2-yl)methyl benzoate
-
 Homo sapiens
((2S,3S)-3-benzyl-4-oxo-1-(phenylsulfonyl)azetidin-2-yl)methyl benzoate
-
 Homo sapiens
((2S,3S)-3-benzyl-4-oxo-1-tosylazetidin-2-yl)methyl benzoate
-
 Homo sapiens
(2R,3R)-benzyl 1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carboxylate
-
 Homo sapiens
(2R,3R)-benzyl 1-benzoyl-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carboxylate
-
 Homo sapiens
(2R,3R)-benzyl 3-benzyl-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-4-oxoazetidine-2-carboxylate
-
 Homo sapiens
(2R,3R)-ethyl 3-benzyl-4-oxo-1-tosylazetidine-2-carboxylate
-
 Homo sapiens
(2S,3S)-benzyl 1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carboxylate
-
 Homo sapiens
(2S,3S)-benzyl 1-benzoyl-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carboxylate
-
 Homo sapiens
(2S,3S)-benzyl 3-benzyl-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-4-oxoazetidine-2-carboxylate
-
 Homo sapiens
(2S,3S)-ethyl 3-benzyl-4-oxo-1-tosylazetidine-2-carboxylate
-
 Homo sapiens
(3-benzyl-1-(ethylsulfonyl)-4-oxoazetidin-2-yl)methyl benzoate
-
 Homo sapiens
(3-benzyl-4-oxo-1-tosylazetidin-2-yl)methyl benzoate
-
 Homo sapiens
3-(2-((2R,3R)-3-benzyl-2-((4-carboxybenzyloxy)carbonyl)-4-oxoazetidin-1-yl)-2-oxoethyl)benzoic acid
-
 Homo sapiens
3-(2-((2S,3S)-3-benzyl-2-((4-carboxybenzyloxy)carbonyl)-4-oxoazetidin-1-yl)-2-oxoethyl)benzoic acid
-
 Homo sapiens
3-(2-(3-benzyl-2-((4-carboxybenzyloxy)carbonyl)-4-oxoazetidin-1-yl)-2-oxoethyl)benzoic acid
-
 Homo sapiens
4-(((2R,3R)-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
-
 Homo sapiens
4-(((2R,3R)-3-benzyl-1-(2-(3-((4-carboxybenzyloxy)carbonyl)phenyl)acetyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
-
 Homo sapiens
4-(((2R,3R)-3-benzyl-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
-
 Homo sapiens
4-(((2S,3S)-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
-
 Homo sapiens
4-(((2S,3S)-3-benzyl-1-(2-(3-((4-carboxybenzyloxy)carbonyl)phenyl)acetyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
-
 Homo sapiens
4-(((2S,3S)-3-benzyl-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
-
 Homo sapiens
4-((1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
-
 Homo sapiens
4-((3-benzyl-1-(2-(3-((4-carboxybenzyloxy)carbonyl)phenyl)acetyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
-
 Homo sapiens
4-((3-benzyl-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
-
 Homo sapiens
benzyl 1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carboxylate
-
 Homo sapiens
benzyl 1-benzoyl-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carboxylate
-
 Homo sapiens
benzyl 3-benzyl-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-4-oxoazetidine-2-carboxylate
-
 Homo sapiens
benzyl 3-benzyl-4-oxo-1-(phenylsulfonyl)azetidine-2-carboxylate
-
 Homo sapiens
additional information beta-lactams inhibit PSA in a time-dependent fashion, beta-lactams bind covalently with PSA. Specificity of a lactam inhibitor toward PSA can be strengthened by optimizing its C-3 side chain to maximize the hydrophobic and the polar interactions in the S-1 pocket Homo sapiens

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
HSSKLQ-7-amido-4-trifluoromethyl-coumarin + H2O
-
 Homo sapiens ?
-
 ?

Synonyms

Synonyms Comment Organism
prostate specific antigen
-
 Homo sapiens
PSA
-
 Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00034
-
-
 Homo sapiens benzyl 1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carboxylate
0.0011
-
-
 Homo sapiens (2S,3S)-ethyl 3-benzyl-4-oxo-1-tosylazetidine-2-carboxylate
0.00143
-
-
 Homo sapiens benzyl 3-benzyl-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-4-oxoazetidine-2-carboxylate
0.0022
-
-
 Homo sapiens (3-benzyl-1-(ethylsulfonyl)-4-oxoazetidin-2-yl)methyl benzoate
0.00308
-
-
 Homo sapiens benzyl 3-benzyl-4-oxo-1-(phenylsulfonyl)azetidine-2-carboxylate
0.0035
-
-
 Homo sapiens 4-((1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
0.0058
-
-
 Homo sapiens 4-((3-benzyl-1-(2-(3-((4-carboxybenzyloxy)carbonyl)phenyl)acetyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
0.009
-
-
 Homo sapiens 4-((3-benzyl-1-(2-(3-(benzyloxycarbonyl)phenyl)acetyl)-4-oxoazetidine-2-carbonyloxy)methyl)benzoic acid
0.01
-
-
 Homo sapiens benzyl 1-benzoyl-3-(4-hydroxybenzyl)-4-oxoazetidine-2-carboxylate
0.1
-
-
 Homo sapiens (2R,3R)-ethyl 3-benzyl-4-oxo-1-tosylazetidine-2-carboxylate