Design and synthesis of a multivalent fluorescent folate-calix[4]arene conjugate: cancer cell penetration and intracellular localization (Articolo in rivista)

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Label
  • Design and synthesis of a multivalent fluorescent folate-calix[4]arene conjugate: cancer cell penetration and intracellular localization (Articolo in rivista) (literal)
Anno
  • 2015-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1039/c4ob02333a (literal)
Alternative label
  • Grazia Maria Letizia Consoli, Giuseppe Granata, Giorgia Fragassi, Mauro Grossi, Michele Sallese, Corrada Geraci (2015)
    Design and synthesis of a multivalent fluorescent folate-calix[4]arene conjugate: cancer cell penetration and intracellular localization
    in Organic & biomolecular chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Grazia Maria Letizia Consoli, Giuseppe Granata, Giorgia Fragassi, Mauro Grossi, Michele Sallese, Corrada Geraci (literal)
Pagina inizio
  • 3298 (literal)
Pagina fine
  • 3307 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 13 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 10 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Istituto di Chimica Biomolecolare, C.N.R., Via Paolo Gaifami 18, Catania, Italy Unit of Genomic Approaches to Membrane Traffic, Fondazione Mario Negri Sud, Via Nazionale 8/A, S. Maria Imbaro (CH), Italy (literal)
Titolo
  • Design and synthesis of a multivalent fluorescent folate-calix[4]arene conjugate: cancer cell penetration and intracellular localization (literal)
Abstract
  • A novel fluorescently labeled folate conjugate in which four folic acid units are covalently conjugated with a 7-nitro-benzofurazan fluorophore by means of a calix[4]arene platform was synthesized by using a Cucatalyzed azide-alkyne cycloaddition reaction (click chemistry). The synthesized construct (FA-C4-NBD) was characterized by mass spectrometry, NMR and fluorescence spectroscopy. Confocal fluorescence microscopy experiments were carried out to evaluate the cell penetration ability of FA-C4-NBD on normal and cancer cells. The cellular uptake of FA-C4-NBD proceeds via folate receptor-mediated endocytosis. FA-C4-NBD is internalized into HeLa cancer cells which express high levels of folate receptors, whereas the uptake into fibroblast NIH3T3 cells which have very low expression levels of folate receptors is negligible. The involvement of the folate receptor was corroborated by competition tests with free folic acid. Co-localization analysis with different organelle markers indicated that FA-C4-NBD is not eliminated by recycling towards the outside of the cell, but accumulates intracellularly in the endo-lysosomal system. (literal)
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