Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 9, Pages 2157-2164Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604886
Keywords
cancer; carbohydrates; glycoconjugates; G-quadruplexes; structure-activity relationships
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Funding
- Spanish Ministerio de Economia y Competitividad [CTQ2012-35360, CTQ2015-64275-P, SAF2016-80228-R]
- Junta de Andalucia [BIO1786]
- Worldwide Cancer Research Foundation [16-0290]
- Italian Association for Cancer Research [IG2013-14708]
- Agence Nationale de la Recherche (ANR Quarpdiem) [ANR-12-BSV8-0008-01]
- EU
- Ministerio de Educacion
- ANRS
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The 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.
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