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Synthesis, Binding Properties, and Differences in Cell Uptake of G-Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates

AutorArévalo-Ruiz, Matilde; Doria, Filippo; Belmonte-Reche, Efres; De Rache, Aurore; Campos-Salinas, Jenny; Lucas, Ricardo ; Falomir, Eva; Carda, Miguel; Pérez-Victoria, J. M.; Mergny, Jean-Louis; Freccero, Mauro; Morales, Juan Carlos
Fecha de publicación16-ene-2017
EditorJohn Wiley & Sons
CitaciónChemistry - A European Journal
ResumenThe G-quadruplexes (G4s) are currently being explored as therapeutic targets in cancer and other pathologies. Six carbohydrate naphthalene diimide conjugates (carb-NDIs) have been synthesized as G4 ligands to investigate their potential selectivity in G4 binding and cell penetration. Carb-NDIs have shown certain selectivity for G4 structures against DNA duplexes, but different sugar moieties do not induce a preference for a specific G4 topology. Interestingly, when monosaccharides were attached through a short ethylene linker to the NDI scaffold, their cellular uptake was two- to threefold more efficient than that when the sugar was directly attached through its anomeric position. Moreover, a correlation between more efficient cell uptake of these carb-NDIs and their higher toxicity in cancerous cell lines has been observed. Carb-NDIs seem to be mainly translocated into cancer cells through glucose transporters (GLUT), of which GLUT4 plays a major role.
Versión del editorhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201604886/abstract
URIhttp://hdl.handle.net/10261/159375
DOI10.1002/chem.201604886
ISSN0947-6539
E-ISSN1521-3765
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