Pyrrolidine Derivatives as New Inhibitors of ?-Mannosidases and Growth Inhibitors of Human Cancer Cells
New pyrrolidine-3,4-diol derivatives were prepared from D-(?)- and L-(+)-phenylglycinol and tested for their ability to inhibit 25 commercial glycosidases. The influence of the substitution of the lateral side chain and of the pyrrolidine ring on the enzyme inhibition was evaluated. (2R,3R...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
2006-04-01
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| Series: | CHIMIA |
| Subjects: | |
| Online Access: | https://chimia.ch/chimia/article/view/4144 |
| _version_ | 1828097757974364160 |
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| author | Hélène Fiaux Catherine Schütz Pierre Vogel Lucienne Juillerat-Jeanneret Sandrine Gerber-Lemaire |
| author_facet | Hélène Fiaux Catherine Schütz Pierre Vogel Lucienne Juillerat-Jeanneret Sandrine Gerber-Lemaire |
| author_sort | Hélène Fiaux |
| collection | DOAJ |
| description |
New pyrrolidine-3,4-diol derivatives were prepared from D-(?)- and L-(+)-phenylglycinol and tested for their ability to inhibit 25 commercial glycosidases. The influence of the substitution of the lateral side chain and of the pyrrolidine ring on the enzyme inhibition was evaluated.
(2R,3R,4S)-2-({[(1R)-2-Hydroxy-1-phenylethyl]amino} methyl)pyrrolidine-3,4-diol was a potent and selective inhibitor of ?-mannosidase from jack bean. This compound was derivatized into lipophilic esters in order to allow its internalization by human cancer
cells. In particular, the 4-bromobenzoate derivative demonstrated promising inhibition of glioblastoma and melanoma cells whereas it was less effective on healthy human fibroblasts.
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| first_indexed | 2024-04-11T07:52:02Z |
| format | Article |
| id | doaj.art-d785327409b4441e9b0cdb56e2ab9b45 |
| institution | Directory Open Access Journal |
| issn | 0009-4293 2673-2424 |
| language | deu |
| last_indexed | 2024-04-11T07:52:02Z |
| publishDate | 2006-04-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj.art-d785327409b4441e9b0cdb56e2ab9b452022-12-22T04:36:03ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24242006-04-0160410.2533/000942906777674930Pyrrolidine Derivatives as New Inhibitors of ?-Mannosidases and Growth Inhibitors of Human Cancer CellsHélène FiauxCatherine SchützPierre VogelLucienne Juillerat-JeanneretSandrine Gerber-Lemaire New pyrrolidine-3,4-diol derivatives were prepared from D-(?)- and L-(+)-phenylglycinol and tested for their ability to inhibit 25 commercial glycosidases. The influence of the substitution of the lateral side chain and of the pyrrolidine ring on the enzyme inhibition was evaluated. (2R,3R,4S)-2-({[(1R)-2-Hydroxy-1-phenylethyl]amino} methyl)pyrrolidine-3,4-diol was a potent and selective inhibitor of ?-mannosidase from jack bean. This compound was derivatized into lipophilic esters in order to allow its internalization by human cancer cells. In particular, the 4-bromobenzoate derivative demonstrated promising inhibition of glioblastoma and melanoma cells whereas it was less effective on healthy human fibroblasts. https://chimia.ch/chimia/article/view/4144GlioblastomaGrowth inhibitionAlpha-mannosidase inhibitorMelanomaPyrrolidine derivatives |
| spellingShingle | Hélène Fiaux Catherine Schütz Pierre Vogel Lucienne Juillerat-Jeanneret Sandrine Gerber-Lemaire Pyrrolidine Derivatives as New Inhibitors of ?-Mannosidases and Growth Inhibitors of Human Cancer Cells CHIMIA Glioblastoma Growth inhibition Alpha-mannosidase inhibitor Melanoma Pyrrolidine derivatives |
| title | Pyrrolidine Derivatives as New Inhibitors of ?-Mannosidases and Growth Inhibitors of Human Cancer Cells |
| title_full | Pyrrolidine Derivatives as New Inhibitors of ?-Mannosidases and Growth Inhibitors of Human Cancer Cells |
| title_fullStr | Pyrrolidine Derivatives as New Inhibitors of ?-Mannosidases and Growth Inhibitors of Human Cancer Cells |
| title_full_unstemmed | Pyrrolidine Derivatives as New Inhibitors of ?-Mannosidases and Growth Inhibitors of Human Cancer Cells |
| title_short | Pyrrolidine Derivatives as New Inhibitors of ?-Mannosidases and Growth Inhibitors of Human Cancer Cells |
| title_sort | pyrrolidine derivatives as new inhibitors of mannosidases and growth inhibitors of human cancer cells |
| topic | Glioblastoma Growth inhibition Alpha-mannosidase inhibitor Melanoma Pyrrolidine derivatives |
| url | https://chimia.ch/chimia/article/view/4144 |
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