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Título: | Thiol-ene "click" synthesis and pharmacological evaluation of c-glycoside sp2-iminosugar glycolipids |
Autor: | Sánchez-Fernández, Elena M. CSIC ORCID; García-Moreno, M. Isabel; García-Hernández, Raquel CSIC ORCID; Padrón, José M.; García Fernández, José Manuel CSIC ORCID; Gamarro, Francisco; Ortiz Mellet, Carmen | Palabras clave: | Sp2-Iminosugars C-glycosides Glycolipids Glycomimetics Glycosidase inhibitors Leishmaniasis Cancer |
Fecha de publicación: | 8-ago-2019 | Editor: | Multidisciplinary Digital Publishing Institute | Citación: | Molecules 24(16): 2882 (2019) | Resumen: | The unique stereoelectronic properties of sp2-iminosugars enable their participation in glycosylation reactions, thereby behaving as true carbohydrate chemical mimics. Among sp2-iminosugar conjugates, the sp2-iminosugar glycolipids (sp2-IGLs) have shown a variety of interesting pharmacological properties ranging from glycosidase inhibition to antiproliferative, antiparasitic, and anti-inflammatory activities. Developing strategies compatible with molecular diversity-oriented strategies for structure–activity relationship studies was therefore highly wanted. Here we show that a reaction sequence consisting in stereoselective C-allylation followed by thiol-ene “click” coupling provides a very convenient access to α-C-glycoside sp2-IGLs. Both the glycone moiety and the aglycone tail can be modified by using sp2-iminosugar precursors with different configurational profiles (d-gluco or d-galacto in this work) and varied thiols, as well as by oxidation of the sulfide adducts (to the corresponding sulfones in this work). A series of derivatives was prepared in this manner and their glycosidase inhibitory, antiproliferative and antileishmanial activities were evaluated in different settings. The results confirm that the inhibition of glycosidases, particularly α-glucosidase, and the antitumor/leishmanicidal activities are unrelated. The data are also consistent with the two later activities arising from the ability of the sp2-IGLs to interfere in the immune system response in a cell line and cell context dependent manner. | Versión del editor: | https://doi.org/10.3390/molecules24162882 | URI: | http://hdl.handle.net/10261/188973 | DOI: | 10.3390/molecules24162882 |
Aparece en las colecciones: | (IPBLN) Artículos (IIQ) Artículos |
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