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

Overview

Journal Nanomaterials (Basel)

Date 2021 Apr 3

PMID 33807096

Citations 4

Authors

Xinyue Wang

Sophie Bou

Andrey S Klymchenko

Nicolas Anton

Mayeul Collot

Affiliations

Soon will be listed here.

Abstract

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.

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References

Li Z, Mintzer E, Bittman R . First synthesis of free cholesterol-BODIPY conjugates. J Org Chem. 2006; 71(4):1718-21. DOI: 10.1021/jo052029x. View

de Vaugelade S, Nicol E, Vujovic S, Bourcier S, Pirnay S, Bouchonnet S . UV-vis degradation of α-tocopherol in a model system and in a cosmetic emulsion-Structural elucidation of photoproducts and toxicological consequences. J Chromatogr A. 2017; 1517:126-133. DOI: 10.1016/j.chroma.2017.08.015. View

Collot M, Schild J, Fam K, Bouchaala R, Klymchenko A . Stealth and Bright Monomolecular Fluorescent Organic Nanoparticles Based on Folded Amphiphilic Polymer. ACS Nano. 2020; 14(10):13924-13937. DOI: 10.1021/acsnano.0c06348. View

Khan A, Mudassir J, Mohtar N, Darwis Y . Advanced drug delivery to the lymphatic system: lipid-based nanoformulations. Int J Nanomedicine. 2013; 8:2733-44. PMC: 3732201. DOI: 10.2147/IJN.S41521. View

Mandal B, Bhattacharjee H, Mittal N, Sah H, Balabathula P, Thoma L . Core-shell-type lipid-polymer hybrid nanoparticles as a drug delivery platform. Nanomedicine. 2012; 9(4):474-91. DOI: 10.1016/j.nano.2012.11.010. View

Attia M, Anton N, Chiper M, Akasov R, Anton H, Messaddeq N . Biodistribution of X-ray iodinated contrast agent in nano-emulsions is controlled by the chemical nature of the oily core. ACS Nano. 2014; 8(10):10537-50. DOI: 10.1021/nn503973z. View

Bouchaala R, Mercier L, Andreiuk B, Mely Y, Vandamme T, Anton N . Integrity of lipid nanocarriers in bloodstream and tumor quantified by near-infrared ratiometric FRET imaging in living mice. J Control Release. 2016; 236:57-67. PMC: 4968657. DOI: 10.1016/j.jconrel.2016.06.027. View

Anton N, Vandamme T . The universality of low-energy nano-emulsification. Int J Pharm. 2009; 377(1-2):142-7. DOI: 10.1016/j.ijpharm.2009.05.014. View

Jurkiewicz B, Bissett D, Buettner G . Effect of topically applied tocopherol on ultraviolet radiation-mediated free radical damage in skin. J Invest Dermatol. 1995; 104(4):484-8. DOI: 10.1111/1523-1747.ep12605921. View

10.

Wang Z, Hong X, Zong S, Tang C, Cui Y, Zheng Q . BODIPY-doped silica nanoparticles with reduced dye leakage and enhanced singlet oxygen generation. Sci Rep. 2015; 5:12602. PMC: 4515827. DOI: 10.1038/srep12602. View

11.

Kilin V, Anton H, Anton N, Steed E, Vermot J, Vandamme T . Counterion-enhanced cyanine dye loading into lipid nano-droplets for single-particle tracking in zebrafish. Biomaterials. 2014; 35(18):4950-7. DOI: 10.1016/j.biomaterials.2014.02.053. View

12.

Bou S, Wang X, Anton N, Klymchenko A, Collot M . Near infrared fluorogenic probe as a prodrug model for evaluating cargo release by nanoemulsions. J Mater Chem B. 2020; 8(27):5938-5944. DOI: 10.1039/d0tb00783h. View

13.

Yao M, Xiao H, McClements D . Delivery of lipophilic bioactives: assembly, disassembly, and reassembly of lipid nanoparticles. Annu Rev Food Sci Technol. 2013; 5:53-81. DOI: 10.1146/annurev-food-072913-100350. View

14.

Klymchenko A, Roger E, Anton N, Anton H, Shulov I, Vermot J . Highly lipophilic fluorescent dyes in nano-emulsions: towards bright non-leaking nano-droplets. RSC Adv. 2017; 2(31):11876-11886. PMC: 5726488. DOI: 10.1039/C2RA21544F. View

15.

Attia M, Dieng S, Collot M, Klymchenko A, Bouillot C, Serra C . Functionalizing Nanoemulsions with Carboxylates: Impact on the Biodistribution and Pharmacokinetics in Mice. Macromol Biosci. 2017; 17(7). DOI: 10.1002/mabi.201600471. View

16.

Collot M, Boutant E, Lehmann M, Klymchenko A . BODIPY with Tuned Amphiphilicity as a Fluorogenic Plasma Membrane Probe. Bioconjug Chem. 2018; 30(1):192-199. DOI: 10.1021/acs.bioconjchem.8b00828. View

17.

Ulrich G, Ziessel R, Harriman A . The chemistry of fluorescent bodipy dyes: versatility unsurpassed. Angew Chem Int Ed Engl. 2007; 47(7):1184-201. DOI: 10.1002/anie.200702070. View

18.

Operti M, Dolen Y, Keulen J, van Dinther E, Figdor C, Tagit O . Microfluidics-Assisted Size Tuning and Biological Evaluation of PLGA Particles. Pharmaceutics. 2019; 11(11). PMC: 6921086. DOI: 10.3390/pharmaceutics11110590. View

19.

Bou S, Wang X, Anton N, Bouchaala R, Klymchenko A, Collot M . Lipid-core/polymer-shell hybrid nanoparticles: synthesis and characterization by fluorescence labeling and electrophoresis. Soft Matter. 2020; 16(17):4173-4181. DOI: 10.1039/d0sm00077a. View

20.

Wang X, Anton N, Ashokkumar P, Anton H, Fam T, Vandamme T . Optimizing the Fluorescence Properties of Nanoemulsions for Single Particle Tracking in Live Cells. ACS Appl Mater Interfaces. 2019; 11(14):13079-13090. DOI: 10.1021/acsami.8b22297. View