dc.creator | Sánchez Fernández, Elena Matilde | es |
dc.creator | García Moreno, M. Isabel | es |
dc.creator | García Hernández, Raquel | es |
dc.creator | Padrón, José M. | es |
dc.creator | García Fernández, José Manuel | es |
dc.creator | Gamarro, Francisco | es |
dc.creator | Ortiz Mellet, Carmen | es |
dc.date.accessioned | 2019-10-16T09:43:27Z | |
dc.date.available | 2019-10-16T09:43:27Z | |
dc.date.issued | 2019 | |
dc.identifier.citation | Sánchez Fernández, E.M., García Moreno, M.I., García Hernández, R., Padrón, J.M., García Fernández, J.M., Gamarro, F. y Ortiz Mellet, C. (2019). Thiol-ene "Click" Synthesis and Pharmacological Evaluation of C-Glycoside sp2-Iminosugar Glycolipids. Molecules, 24 (16), 2882. | |
dc.identifier.issn | 1420-3049 | es |
dc.identifier.uri | https://hdl.handle.net/11441/89697 | |
dc.description.abstract | 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. | es |
dc.description.sponsorship | España, MINECO RTI2018-093940-B-I00 and SAF2016-76083-R | es |
dc.description.sponsorship | España, Ministerio de Ciencia, Innovación y Universidades RTI2018-097210-B-I00 to FG | es |
dc.description.sponsorship | Unión Europea, FEDER PGC2018-094503-B-C22 | es |
dc.format | application/pdf | es |
dc.language.iso | eng | es |
dc.publisher | MDPI | es |
dc.relation.ispartof | Molecules, 24 (16), 2882. | |
dc.rights | Attribution-NonCommercial-NoDerivatives 4.0 Internacional | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ | * |
dc.subject | sp2-Iminosugars | es |
dc.subject | C-glycosides | es |
dc.subject | glycosidase inhibitors | es |
dc.subject | Leishmaniasis | es |
dc.subject | cancer | es |
dc.title | Thiol-ene "Click" Synthesis and Pharmacological Evaluation of C-Glycoside sp2-Iminosugar Glycolipids | es |
dc.type | info:eu-repo/semantics/article | es |
dcterms.identifier | https://ror.org/03yxnpp24 | |
dc.type.version | info:eu-repo/semantics/publishedVersion | es |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | es |
dc.contributor.affiliation | Universidad de Sevilla. Departamento de Química orgánica | es |
dc.relation.projectID | RTI2018-093940-B-I00 and SAF2016-76083-R | es |
dc.relation.projectID | RTI2018-097210-B-I00 to FG | es |
dc.relation.projectID | PGC2018-094503-B-C22 | es |
dc.relation.publisherversion | http://dx.doi.org/10.3390/molecules24162882 | es |
dc.identifier.doi | 10.3390/molecules24162882 | es |
idus.format.extent | 21 p. | es |
dc.journaltitle | Molecules | es |
dc.publication.volumen | 24 | es |
dc.publication.issue | 16 | es |
dc.publication.initialPage | 2882 | es |