Probing the Use of Triphenyl Phosphonium Cation for Mitochondrial Nucleoside Delivery.

Mathis Guiraud, Lamiaa M A Ali, Emma Gabrieli-Magot, Laure Lichon, Morgane Daurat, David Egron, Magali Gary-Bobo, Suzanne Peyrottes
Author Information
  1. Mathis Guiraud: Team Nucleosides & Phosphorylated Effectors, IBMM, Pole Balard Recherche, University of Montpellier, CNRS, ENSCM, 34293 Montpellier, France.
  2. Lamiaa M A Ali: Team Glyco & Nanovectors for Therapeutic Targeting, IBMM, Pole Balard Recherche, University of Montpellier, CNRS, ENSCM, 34293 Montpellier, France.
  3. Emma Gabrieli-Magot: Team Glyco & Nanovectors for Therapeutic Targeting, IBMM, Pole Balard Recherche, University of Montpellier, CNRS, ENSCM, 34293 Montpellier, France.
  4. Laure Lichon: Team Glyco & Nanovectors for Therapeutic Targeting, IBMM, Pole Balard Recherche, University of Montpellier, CNRS, ENSCM, 34293 Montpellier, France.
  5. Morgane Daurat: NanoMedSyn, 34090 Montpellier, France.
  6. David Egron: Team Nucleosides & Phosphorylated Effectors, IBMM, Pole Balard Recherche, University of Montpellier, CNRS, ENSCM, 34293 Montpellier, France.
  7. Magali Gary-Bobo: Team Glyco & Nanovectors for Therapeutic Targeting, IBMM, Pole Balard Recherche, University of Montpellier, CNRS, ENSCM, 34293 Montpellier, France.
  8. Suzanne Peyrottes: Team Nucleosides & Phosphorylated Effectors, IBMM, Pole Balard Recherche, University of Montpellier, CNRS, ENSCM, 34293 Montpellier, France. ORCID

Abstract

Herein, we report the design, the synthesis, and the study of novel triphenyl phosphonium-based nucleoside conjugates. 2'-Deoxycytidine was chosen as nucleosidic cargo, as it allows the introduction of fluorescein on the exocyclic amine of the nucleobase and grafting of the vector was envisaged through the formation of a biolabile ester bond with the hydroxyl function at the 5'-position. Compound was identified as a potential nucleoside prodrug, showing ability to be internalized efficiently into cells and to be co-localized with mitochondria.

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