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Literature summary for 3.4.21.1 extracted from

  • Nakamura, H.; Watanabe, M.; Ban, H.S.; Nabeyama, W.; Asai, A.
    Synthesis and biological evaluation of boron peptide analogues of Belactosin C as proteasome inhibitors (2009), Bioorg. Med. Chem. Lett., 19, 3220-3224.
    View publication on PubMed

Application

Application Comment Organism
drug development design of a new class of boron peptides as inhibitors of the chymotrypsin-like activity of the 20S proteasome based around the structure of Belactosin C, proteasome inhibitors with therapeutic utility Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
Belactosin C irreversible inhibitor Homo sapiens
MG-132 reversible inhibitor Homo sapiens
additional information boron peptides selectively inhibit the chymotrypsin-like activity (beta5) of 20S proteasome Homo sapiens
N-(tert-butoxycarbonyl)-L-alanyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide irreversible inhibitor Homo sapiens
N-(tert-butoxycarbonyl)-L-alanyl-N6-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N-(naphthalen-2-ylmethyl)-6-oxo-L-lysinamide irreversible inhibitor Homo sapiens
N-(tert-butoxycarbonyl)-L-leucyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide irreversible inhibitor Homo sapiens
N-(tert-butoxycarbonyl)-L-phenylalanyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide irreversible inhibitor Homo sapiens
N-(tert-butoxycarbonyl)glycyl-N1-benzyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-L-glutamamide irreversible inhibitor, significant inhibition of 20S proteasome chymotrypsin-like (beta5) activity, inhibitory potency is similar to that of Belactosin C Homo sapiens
N-(tert-butoxycarbonyl)glycyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide irreversible inhibitor, possesses the greatest inhibition of the chymotrypsin-like activity, inhibitory potency is similar to that of Belactosin C. Increases the G2/M cell distribution in a similar manner to that of PS-341, and induces apoptosis at more than 0.001 mM concentration of compound in HeLa cells Homo sapiens
N-(tert-butoxycarbonyl)glycyl-N6-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N-(naphthalen-2-ylmethyl)-6-oxo-L-lysinamide irreversible inhibitor Homo sapiens
N2-(tert-butoxycarbonyl)-N4-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-aspartamide irreversible inhibitor Homo sapiens
N2-(tert-butoxycarbonyl)-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide irreversible inhibitor Homo sapiens
N2-(tert-butoxycarbonyl)-N6-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N-(naphthalen-2-ylmethyl)-6-oxo-L-lysinamide irreversible inhibitor Homo sapiens
PS-341 reversible inhibitor Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
20S proteasome
-
Homo sapiens
-
-

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
erythrocyte
-
Homo sapiens
-
HeLa cell
-
Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
succinyl-Leu-Leu-Val-Tyr-7-amido-4-methylcoumarin + H2O
-
Homo sapiens succinyl-Leu-Leu-Val-Tyr + 7-amino-4-methylcoumarin
-
?

Synonyms

Synonyms Comment Organism
chymotrypsin
-
Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00002
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens PS-341
0.00007
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens MG-132
0.00028
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N-(tert-butoxycarbonyl)glycyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide
0.00054
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N-(tert-butoxycarbonyl)glycyl-N1-benzyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-L-glutamamide
0.00084
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N-(tert-butoxycarbonyl)-L-alanyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide
0.00147
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N-(tert-butoxycarbonyl)-L-phenylalanyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide
0.0015
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N-(tert-butoxycarbonyl)-L-leucyl-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide
0.00274
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N-(tert-butoxycarbonyl)glycyl-N6-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N-(naphthalen-2-ylmethyl)-6-oxo-L-lysinamide
0.00412
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N2-(tert-butoxycarbonyl)-N6-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N-(naphthalen-2-ylmethyl)-6-oxo-L-lysinamide
0.00428
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N-(tert-butoxycarbonyl)-L-alanyl-N6-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N-(naphthalen-2-ylmethyl)-6-oxo-L-lysinamide
0.00451
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N2-(tert-butoxycarbonyl)-N4-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-aspartamide
0.01
-
at 37°C for 1 h, in 20 mM Tris buffer, pH 8.0, 0.5 mM EDTA and 0.035% SDS Homo sapiens N2-(tert-butoxycarbonyl)-N5-[(1R)-1-(dihydroxyboranyl)-3-methylbutyl]-N1-(naphthalen-2-ylmethyl)-L-glutamamide