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Literature summary for 3.2.1.24 extracted from

  • Fiaux, H.; Popowycz, F.; Favre, S.; Schuetz, C.; Vogel, P.; Gerber-Lemaire, S.; Juillerat-Jeanneret, L.
    Functionalized pyrrolidines inhibit alpha-mannosidase activity and growth of human glioblastoma and melanoma cells (2005), J. Med. Chem., 48, 4237-4246.
    View publication on PubMed
Search for more literature for 3.2.1.24

Inhibitors

Inhibitors Comment Organism Structure
(1S,2R,3R,8R,8aR)-3-[(arylmethoxy)methyl]octahydroindolizine-1,2,8-triol
-
 Canavalia ensiformis
(2R,3R,4S)-2-([(1R)-2,3-dihydro-1H-inden-1-ylamino]methyl)pyrrolidine-3,4-diol IC50 is 0.017 mM Canavalia ensiformis
(2R,3R,4S)-2-[(benzylamino)methyl]pyrrolidine-3,4-diol IC50 is 0.06 mM Canavalia ensiformis
(2R,3R,4S)-2-[([(1R)-2-benzyloxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol 92% inhibition at 1 mM, IC50 is 0.058 mM Canavalia ensiformis
(2R,3R,4S)-2-[([(1R)-2-hydroxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol complete and selective inhibition at 1 mM, IC50 is 700 nM Canavalia ensiformis
(2R,3R,4S)-2-[([(1R)-2-hydroxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol potent and selective inhibition Homo sapiens
(2R,3R,4S)-2-[([(1R)-2-methoxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol 77% inhibition at 1 mM Canavalia ensiformis
(2R,3R,4S)-2-[([(1R,2S)-2-hydroxy-1,2-diphenylethyl]amino)methyl]pyrrolidine-3,4-diol 88% inhibition at 1 mM, IC50 is 0.11 mM Canavalia ensiformis
(2R,3R,4S)-2-[([(1S)-2-hydroxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol 92% inhibition at 1 mM, IC50 is 0.1 mM Canavalia ensiformis
(2R,3R,4S)-2-[([(1S)-2-hydroxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol
-
 Homo sapiens
(2R,3R,4S)-2-[([(1S,2R)-2-hydroxy-1,2-diphenylethyl]amino)methyl]pyrrolidine-3,4-diol 84% inhibition at 1 mM, IC50 is 0.128 mM Canavalia ensiformis
(2R,3R,4S,5R)-2-[(benzylamino)methyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol IC50 is 0.0062 mM Canavalia ensiformis
(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[([(1R)-2-hydroxy-1,2-diphenylethyl]amino)methyl]pyrrolidine-3,4-diol 98% inhibition at 1 mM, IC50 is 0.0042 mM Canavalia ensiformis
(2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 2-fluorobenzoate 83% inhibition at 1 mM, IC50 is 0.063 mM Canavalia ensiformis
(2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 2-fluorobenzoate
-
 Homo sapiens
(2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 3-bromobenzoate 79% inhibition at 1 mM Canavalia ensiformis
(2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 3-bromobenzoate
-
 Homo sapiens
(2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 4-bromobenzoate 92% inhibition at 1 mM Canavalia ensiformis
(2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 4-bromobenzoate
-
 Homo sapiens
(2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 4-fluorobenzoate 92% inhibition at 1 mM, IC50 is 0.060 mM Canavalia ensiformis
(2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 4-fluorobenzoate
-
 Homo sapiens
3-bromo-N-[(2S)-2-[([(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl]benzamide 95% inhibition at 1 mM, IC50 is 0.089 mM Canavalia ensiformis
3-bromo-N-[(2S)-2-[([(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl]benzamide
-
 Homo sapiens
additional information inhibition of growth of glioblastoma and melanoma cells by pyrrolidine-3,4-diol derivatives, overview Homo sapiens
swainsonine IC50 is 400 nM Canavalia ensiformis
swainsonine 20% inhibition of glioblastoma cell growth at 0.25 mM Homo sapiens

Organism

Organism UniProt Comment Textmining
Canavalia ensiformis
-
 Jack bean
-
Homo sapiens
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
glioblastoma cell
-
 Homo sapiens
-
melanoma cell
-
 Homo sapiens
-

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
37
-
 assay at Canavalia ensiformis

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.000135
-
 (2R,3R,4S)-2-[([(1R)-2-hydroxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol 37°C Canavalia ensiformis
0.0012
-
 (2R,3R,4S,5R)-2-[(benzylamino)methyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol 37°C Canavalia ensiformis
0.00135
-
 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[([(1R)-2-hydroxy-1,2-diphenylethyl]amino)methyl]pyrrolidine-3,4-diol 37°C Canavalia ensiformis
0.0023
-
 (2R,3R,4S)-2-([(1R)-2,3-dihydro-1H-inden-1-ylamino]methyl)pyrrolidine-3,4-diol 37°C Canavalia ensiformis
0.0074
-
 (2R,3R,4S)-2-[(benzylamino)methyl]pyrrolidine-3,4-diol 37°C Canavalia ensiformis
0.016
-
 (2R,3R,4S)-2-[([(1R)-2-benzyloxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol 37°C Canavalia ensiformis
0.019
-
 (2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 4-fluorobenzoate 37°C Canavalia ensiformis
0.024
-
 (2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 2-fluorobenzoate 37°C Canavalia ensiformis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.0004
-
 IC50 is 400 nM Canavalia ensiformis swainsonine
0.0007
-
 complete and selective inhibition at 1 mM, IC50 is 700 nM Canavalia ensiformis (2R,3R,4S)-2-[([(1R)-2-hydroxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol
0.0042
-
 98% inhibition at 1 mM, IC50 is 0.0042 mM Canavalia ensiformis (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[([(1R)-2-hydroxy-1,2-diphenylethyl]amino)methyl]pyrrolidine-3,4-diol
0.0062
-
 IC50 is 0.0062 mM Canavalia ensiformis (2R,3R,4S,5R)-2-[(benzylamino)methyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol
0.017
-
 IC50 is 0.017 mM Canavalia ensiformis (2R,3R,4S)-2-([(1R)-2,3-dihydro-1H-inden-1-ylamino]methyl)pyrrolidine-3,4-diol
0.058
-
 92% inhibition at 1 mM, IC50 is 0.058 mM Canavalia ensiformis (2R,3R,4S)-2-[([(1R)-2-benzyloxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol
0.06
-
 92% inhibition at 1 mM, IC50 is 0.060 mM Canavalia ensiformis (2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 4-fluorobenzoate
0.06
-
 IC50 is 0.06 mM Canavalia ensiformis (2R,3R,4S)-2-[(benzylamino)methyl]pyrrolidine-3,4-diol
0.063
-
 83% inhibition at 1 mM, IC50 is 0.063 mM Canavalia ensiformis (2S)-2-[([(2R,3S,4S)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl 2-fluorobenzoate
0.089
-
 95% inhibition at 1 mM, IC50 is 0.089 mM Canavalia ensiformis 3-bromo-N-[(2S)-2-[([(2R,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]methyl)amino]-2-phenylethyl]benzamide
0.1
-
 92% inhibition at 1 mM, IC50 is 0.1 mM Canavalia ensiformis (2R,3R,4S)-2-[([(1S)-2-hydroxy-1-phenylethyl]amino)methyl]pyrrolidine-3,4-diol
0.11
-
 88% inhibition at 1 mM, IC50 is 0.11 mM Canavalia ensiformis (2R,3R,4S)-2-[([(1R,2S)-2-hydroxy-1,2-diphenylethyl]amino)methyl]pyrrolidine-3,4-diol
0.128
-
 84% inhibition at 1 mM, IC50 is 0.128 mM Canavalia ensiformis (2R,3R,4S)-2-[([(1S,2R)-2-hydroxy-1,2-diphenylethyl]amino)methyl]pyrrolidine-3,4-diol