Ultrabright Green-Emitting Nanoemulsions Based on Natural Lipids-BODIPY Conjugates

Xinyue Wang (1, 2) , Sophie Bou (3) , Andrey S Klymchenko (4) , Nicolas Anton (1, 2) , Mayeul Collot (4)

1 CAMB - Conception et application de molécules bioactives
2 NanoRegMed - Nanomédecine Régénérative
3 LBP - Laboratoire de Bioimagerie et Pathologies
4 LBP - Laboratoire de Biophotonique et Pharmacologie - UMR 7213

Nanoemulsions (NEs) are water-dispersed oil droplets that constitute stealth biocompatible nanomaterials. NEs can reach an impressive degree of fluorescent brightness owing to their oily core that can encapsulate a large number of fluorophores on the condition the latter are sufficiently hydrophobic and oil-soluble. BODIPYs are among the brightest green emitting fluorophores and as neutral molecules possess high lipophilicity. Herein, we synthesized three different natural lipid-BODIPY conjugates by esterification of an acidic BODIPY by natural lipids, namely: α-tocopherol (vitamin E), cholesterol, and stearyl alcohol. The new BODIPY conjugates were characterized in solvents and oils before being encapsulated in NEs at various concentrations. The physical (size, stability over time, leakage) and photophysical properties (absorption and emission wavelength, brightness, photostability) are reported and showed that the nature of the lipid anchor and the nature of the oil used for emulsification greatly influence the properties of the bright NEs.

Mots clés: nanoemulsions; BODIPY; fluorescence; brightness; fluorescence correlation spectroscopy

Domaines: Chimie organique

Xinyue Wang, Sophie Bou, Andrey S Klymchenko, Nicolas Anton, Mayeul Collot. Ultrabright Green-Emitting Nanoemulsions Based on Natural Lipids-BODIPY Conjugates. Nanomaterials, 2021, 11 (3), pp.826. ⟨10.3390/nano11030826⟩. ⟨hal-03309018⟩