title: Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines.
abstract: The synthesis of ω-di-(trideuteromethyl)-trisnorsqualenic acid has been achieved from natural squalene. The synthesis features the use of a Shapiro reaction of acetone-d 6 trisylhydrazone as a key step to implement the terminal isopropylidene-d 6 moiety. The obtained squalenic acid-d 6 has been coupled to gemcitabine to provide the deuterated analogue of squalenoyl gemcitabine, a powerful anticancer agent endowed with self-assembling properties. The Raman spectra of both deuterated and non-deuterated squalenoyl gemcitabine nanoparticles displayed significant Raman scattering signals. They revealed no differences except from the deuterium peak patterns in the silent spectral region of cells. This paves the way for label-free intracellular trafficking studies of squalenoyl nanomedicines.
authors: Institut Galien (UMR CNRS 8612) Faculté de Pharmacie, Université Paris-Sud, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France.
authors: Eric
authors: E
authors: Buchy
authors: Department of Drug Delivery, Helmholtz Centre for Infection Research and Helmholtz Institute for Pharmaceutical Research Saarland, Campus E8.1, 66123 Saarbruecken, Germany; Biopharmaceutics and Pharmaceutical Technology, Saarland University, Campus A 4.1, 66123 Saarbruecken, Germany.
authors: Branko
authors: B
authors: Vukosavljevic
authors: Department of Drug Delivery, Helmholtz Centre for Infection Research and Helmholtz Institute for Pharmaceutical Research Saarland, Campus E8.1, 66123 Saarbruecken, Germany; Biopharmaceutics and Pharmaceutical Technology, Saarland University, Campus A 4.1, 66123 Saarbruecken, Germany.
authors: Maike
authors: M
authors: Windbergs
authors: Institut Galien (UMR CNRS 8612) Faculté de Pharmacie, Université Paris-Sud, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France.
authors: Dunja
authors: D
authors: Sobot
authors: BIOCIS (UMR CNRS 8076) Faculté de Pharmacie, Université Paris-Sud, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France.
authors: Camille
authors: C
authors: Dejean
authors: Institut Galien (UMR CNRS 8612) Faculté de Pharmacie, Université Paris-Sud, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France.
authors: Simona
authors: S
authors: Mura
authors: Institut Galien (UMR CNRS 8612) Faculté de Pharmacie, Université Paris-Sud, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France.
authors: Patrick
authors: P
authors: Couvreur
authors: Institut Galien (UMR CNRS 8612) Faculté de Pharmacie, Université Paris-Sud, 5, rue Jean-Baptiste Clément, 92296 Châtenay-Malabry, France.
authors: Didier
authors: D
authors: Desmaële
keywords: Raman spectroscopy; Shapiro reaction; deuterium labelling; nanomedicine; squalene