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Synthesis, Binding Properties, and Differences in Cell Uptake of G-Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates
dc.contributor.author | Arevalo-Ruiz, Matilde | |
dc.contributor.author | Doria, Filippo | |
dc.contributor.author | Belmonte Reche, Efres | |
dc.contributor.author | De Rache, Aurore | |
dc.contributor.author | Campos-Salinas, Jenny | |
dc.contributor.author | Lucas, Ricardo | |
dc.contributor.author | Falomir, Eva | |
dc.contributor.author | Carda, Miguel | |
dc.contributor.author | Pérez-Victoria, José María | |
dc.contributor.author | Mergny, Jean-Louis | |
dc.date.accessioned | 2017-12-14T08:37:06Z | |
dc.date.available | 2017-12-14T08:37:06Z | |
dc.date.issued | 2017-02-10 | |
dc.identifier.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. | ca_CA |
dc.identifier.issn | 0947-6539 | |
dc.identifier.issn | 1521-3765 | |
dc.identifier.uri | http://hdl.handle.net/10234/170910 | |
dc.description.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 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. | ca_CA |
dc.format.extent | 8 p. | ca_CA |
dc.format.mimetype | application/pdf | ca_CA |
dc.language.iso | eng | ca_CA |
dc.publisher | Wiley | ca_CA |
dc.relation.isPartOf | Chemistry-A European Journal, 2017, vol. 23, no 9, p. 2157-2164 | ca_CA |
dc.rights | Copyright © John Wiley & Sons, Inc. All Rights Reserved | ca_CA |
dc.rights.uri | http://rightsstatements.org/vocab/InC/1.0/ | * |
dc.subject | cancer | ca_CA |
dc.subject | carbohydrates | ca_CA |
dc.subject | glycoconjugates | ca_CA |
dc.subject | G-quadruplexes | ca_CA |
dc.subject | structure-activity relationships | ca_CA |
dc.title | Synthesis, Binding Properties, and Differences in Cell Uptake of G-Quadruplex Ligands Based on Carbohydrate Naphthalene Diimide Conjugates | ca_CA |
dc.type | info:eu-repo/semantics/article | ca_CA |
dc.identifier.doi | http://dx.doi.org/10.1002/chem.201604886 | |
dc.relation.projectID | 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 | ca_CA |
dc.rights.accessRights | info:eu-repo/semantics/restrictedAccess | ca_CA |
dc.relation.publisherVersion | http://onlinelibrary.wiley.com/doi/10.1002/chem.201604886/full | ca_CA |
dc.contributor.funder | M.A.R. thanks the Ministerio de Educacion for a FPU predoctoral fellowship. A.D.R. is the recipient of an ANRS postdoctoral fellowship. We also thank Aurore Guedin for helpful advice. | ca_CA |
dc.type.version | info:eu-repo/semantics/publishedVersion | ca_CA |
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