Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines
| Autor: | Branko Vukosavljevic, Didier Desmaële, Camille Dejean, Dunja Sobot, Patrick Couvreur, Maike Windbergs, Simona Mura, Eric Buchy |
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| Přispěvatelé: | Helmholtz-Institut für Pharmazeutische Forschung Saarland, Universitätscampus E8.1,56123 Saarbrücken, Germany. |
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
Confocal
Nanoparticle 02 engineering and technology squalene 010402 general chemistry 01 natural sciences Full Research Paper lcsh:QD241-441 symbols.namesake Nuclear magnetic resonance lcsh:Organic chemistry Shapiro reaction Microscopy Moiety lcsh:Science Chemistry Organic Chemistry 021001 nanoscience & nanotechnology Combinatorial chemistry nanomedicine 0104 chemical sciences deuterium labelling Raman spectroscopy symbols Nanomedicine lcsh:Q 0210 nano-technology Raman scattering |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 1127-1135 (2016) Beilstein Journal of Organic Chemistry |
| ISSN: | 1860-5397 |
| Popis: | 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-d6 trisylhydrazone as a key step to implement the terminal isopropylidene-d6 moiety. The obtained squalenic acid-d6 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. |
| Databáze: | OpenAIRE |
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