{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T13:49:12Z","timestamp":1790689752545,"version":"4.1.0"},"reference-count":55,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2019,1,19]],"date-time":"2019-01-19T00:00:00Z","timestamp":1547856000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Vaincre les Maladies Lysosomales","award":["Design of new polypharmacophoric dendrimers for an innovative dual therapeutic strategy for Gaucher disease"],"award-info":[{"award-number":["Design of new polypharmacophoric dendrimers for an innovative dual therapeutic strategy for Gaucher disease"]}]},{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ShingoDR"],"award-info":[{"award-number":["ShingoDR"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of simple C-alkyl pyrrolidines already known as cytotoxic inhibitors of ceramide glucosylation in melanoma cells can be converted into their corresponding 6-membered analogues by means of a simple ring expansion. This study illustrated how an isomerisation from iminosugar pyrrolidine toward piperidine could invert their targeting from glucosylceramide (GlcCer) formation toward GlcCer hydrolysis. Thus, we found that the 5-membered ring derivatives did not inhibit the hydrolysis reaction of GlcCer catalysed by lysosomal \u03b2-glucocerebrosidase (GBA). On the other hand, the ring-expanded C-alkyl piperidine isomers, non-cytotoxic and inactive regarding ceramide glucosylation, revealed to be potent inhibitors of GBA. A molecular docking study showed that the positions of the piperidine ring of the compound 6b and its analogous 2-O-heptyl DIX 8 were similar to that of isofagomine. Furthermore, compound 6b promoted mutant GBA enhancements over 3-fold equivalent to that of the related O-Hept DIX 8 belonging to one of the most potent iminosugar-based pharmacological chaperone series reported to date.<\/jats:p>","DOI":"10.3390\/molecules24020354","type":"journal-article","created":{"date-parts":[[2019,1,22]],"date-time":"2019-01-22T03:08:22Z","timestamp":1548126502000},"page":"354","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Selective Targeting of the Interconversion between Glucosylceramide and Ceramide by Scaffold Tailoring of Iminosugar Inhibitors"],"prefix":"10.3390","volume":"24","author":[{"given":"C\u00e9cile","family":"Baudoin-Dehoux","sequence":"first","affiliation":[{"name":"Laboratoire de Synth\u00e8se et Physico-Chimie de Mol\u00e9cules d\u2019Int\u00e9r\u00eat Biologique (SPCMIB), Universit\u00e9 Paul Sabatier-Toulouse III\/ CNRS (UMR5068), 118 route de Narbonne, F-31062 Toulouse, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tessa","family":"Castellan","sequence":"additional","affiliation":[{"name":"Laboratoire de Synth\u00e8se et Physico-Chimie de Mol\u00e9cules d\u2019Int\u00e9r\u00eat Biologique (SPCMIB), Universit\u00e9 Paul Sabatier-Toulouse III\/ CNRS (UMR5068), 118 route de Narbonne, F-31062 Toulouse, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5491-8165","authenticated-orcid":false,"given":"Fr\u00e9d\u00e9ric","family":"Rodriguez","sequence":"additional","affiliation":[{"name":"Laboratoire de Synth\u00e8se et Physico-Chimie de Mol\u00e9cules d\u2019Int\u00e9r\u00eat Biologique (SPCMIB), Universit\u00e9 Paul Sabatier-Toulouse III\/ CNRS (UMR5068), 118 route de Narbonne, F-31062 Toulouse, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arnaud","family":"Rives","sequence":"additional","affiliation":[{"name":"Laboratoire de Synth\u00e8se et Physico-Chimie de Mol\u00e9cules d\u2019Int\u00e9r\u00eat Biologique (SPCMIB), Universit\u00e9 Paul Sabatier-Toulouse III\/ CNRS (UMR5068), 118 route de Narbonne, F-31062 Toulouse, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fabien","family":"Stauffert","sequence":"additional","affiliation":[{"name":"Laboratoire d\u2019Innovation Mol\u00e9culaire et Application (LIMA). Universit\u00e9 de Strasbourg, Universit\u00e9 de Haute-Alsace, CNRS (UMR 7042), Equipe Synth\u00e8se Organique et Mol\u00e9cules Bioactives (SYBIO), Ecole Europ\u00e9enne de Chimie, Polym\u00e8res et Mat\u00e9riaux, 25 rue Becquerel, 67000 Strasbourg, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Virginie","family":"Garcia","sequence":"additional","affiliation":[{"name":"Institut National de la Sant\u00e9 et de la Recherche M\u00e9dicale (INSERM) UMR1037, Centre de Recherches en Canc\u00e9rologie de Toulouse (CRCT), Universit\u00e9 Paul Sabatier, Laboratoire de Biochimie M\u00e9tabolique, Institut F\u00e9d\u00e9ratif de Biologie, CHU Purpan, F-31059 Toulouse, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thierry","family":"Levade","sequence":"additional","affiliation":[{"name":"Institut National de la Sant\u00e9 et de la Recherche M\u00e9dicale (INSERM) UMR1037, Centre de Recherches en Canc\u00e9rologie de Toulouse (CRCT), Universit\u00e9 Paul Sabatier, Laboratoire de Biochimie M\u00e9tabolique, Institut F\u00e9d\u00e9ratif de Biologie, CHU Purpan, F-31059 Toulouse, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Philippe","family":"Compain","sequence":"additional","affiliation":[{"name":"Laboratoire d\u2019Innovation Mol\u00e9culaire et Application (LIMA). Universit\u00e9 de Strasbourg, Universit\u00e9 de Haute-Alsace, CNRS (UMR 7042), Equipe Synth\u00e8se Organique et Mol\u00e9cules Bioactives (SYBIO), Ecole Europ\u00e9enne de Chimie, Polym\u00e8res et Mat\u00e9riaux, 25 rue Becquerel, 67000 Strasbourg, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yves","family":"G\u00e9nisson","sequence":"additional","affiliation":[{"name":"Laboratoire de Synth\u00e8se et Physico-Chimie de Mol\u00e9cules d\u2019Int\u00e9r\u00eat Biologique (SPCMIB), Universit\u00e9 Paul Sabatier-Toulouse III\/ CNRS (UMR5068), 118 route de Narbonne, F-31062 Toulouse, France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,1,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"6387","DOI":"10.1021\/cr2002917","article-title":"Sphingolipid and Glycosphingolipid Metabolic Pathways in the Era of Sphingolipidomics","volume":"111","author":"Merrill","year":"2011","journal-title":"Chem. 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