RT journal article
T1 Synthesis of sp(2)-Iminosugar Selenoglycolipids as Multitarget Drug Candidates with Antiproliferative, Leishmanicidal and Anti-Inflammatory Properties
A1 Sánchez-Fernández, Elena M.
A1 García-Hernández, Raquel
A1 Gamarro, Francisco
A1 Arroba Espinosa, Ana Isabel
A1 Aguilar Diosdado, Manuel
A1 Padrón, José M.
A1 García-Fernández, José M.
A1 Ortiz Mellet, Carmen
A2 Medicina
K1 seleno-sp2-iminoglycolipids
K1 multitarget
K1 immunomodulation
K1 cancer
K1 Leishmania
K1 inflammation
AB sp2-Iminosugar glycolipids (sp2-IGLs) represent a consolidated family of glycoconjugatemimetics encompassing a monosaccharide-like glycone moiety with a pseudoamide-type nitrogenreplacing the endocyclic oxygen atom of carbohydrates and an axially-oriented lipid chain anchoredat the pseudoanomeric position. The combination of these structural features makes them promisingcandidates for the treatment of a variety of conditions, spanning from cancer and inflammatory disordersto parasite infections. The exacerbated anomeric effect associated to the putative sp2-hybridizedN-atom imparts chemical and enzymatic stability to sp2-IGLs and warrants total  -anomeric stereoselectivityin the key glycoconjugation step. A variety of O-, N-, C- and S-pseudoglycosides, differingin glycone configurational patterns and lipid nature, have been previously prepared and evaluated.Here we expand the chemical space of sp2-IGLs by reporting the synthesis of  -D-gluco-configuredanalogs with a bicyclic (5N,6O-oxomethylidene)nojirimycin (ONJ) core incorporating selenium at theglycosidic position. Structure–activity relationship studies in three different scenarios, namely cancer,Leishmaniasis and inflammation, convey that the therapeutic potential of the sp2-IGLs is highlydependent, not only on the length of the lipid chain (linear aliphatic C12 vs. C8), but also on thenature of the glycosidic atom (nitrogen vs. sulfur vs. selenium). The ensemble of results highlightsthe  -dodecylseleno-ONJ-glycoside as a promising multitarget drug candidate.
PB MDPI
SN 1420-3049
YR 2021
FD 2021-12
LK http://hdl.handle.net/10498/26448
UL http://hdl.handle.net/10498/26448
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 13-nov-2026