Synthesis, Binding Properties, and Differences in Cell Uptake of G-Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates
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Other documents of the author: Arevalo-Ruiz, Matilde; Doria, Filippo; Belmonte Reche, Efres; De Rache, Aurore; Campos-Salinas, Jenny; Lucas, Ricardo; Falomir, Eva; Carda, Miguel; Pérez-Victoria, José María; Mergny, Jean-Louis
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comunitat-uji-handle2:10234/7053
comunitat-uji-handle3:10234/8639
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http://dx.doi.org/10.1002/chem.201604886 |
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Title
Synthesis, Binding Properties, and Differences in Cell Uptake of G-Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide ConjugatesAuthor (s)
Date
2017-02-10Publisher
WileyISSN
0947-6539; 1521-3765Bibliographic citation
ARÉVALO‐RUIZ, Matilde, et al. Synthesis, Binding Properties, and Differences in Cell Uptake of G‐Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates. Chemistry-A European Journal, 2017, vol. 23, no 9, p. 2157-2164.Type
info:eu-repo/semantics/articlePublisher version
http://onlinelibrary.wiley.com/doi/10.1002/chem.201604886/fullVersion
info:eu-repo/semantics/publishedVersionSubject
Abstract
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 ... [+]
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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Chemistry-A European Journal, 2017, vol. 23, no 9, p. 2157-2164Investigation project
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-BSV8-0008-01Rights
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