Bulky Barbiturates as Non-toxic Ionic Dye Insulators for Enhanced Emission in Polymeric Nanoparticles

Bohdan Andreiuk , Ilya O Aparin , Andreas Reisch , Andrey S Klymchenko (1)

1 LBP - Laboratoire de Bioimagerie et Pathologies

Bulky hydrophobic counterions (weakly coordinating anions) can insulate ionic dyes against aggregation-caused quenching (ACQ) and enable preparation of highly fluorescent dye-loaded nanoparticles (NPs) for bioimaging, biosensing and light harvesting. Here, we introduce a family of hydrophobic anions based on fluorinated C-acyl barbiturates with delocalized negative charge and bulky non-polar groups. Similarly to fluorinated tetraphenylborates, these barbiturates prevent ACQ of cationic dye alkyl rhodamine B inside polymer NPs made of biodegradable poly(lacticco-glycolic acid) (PLGA). Their efficiency to prevent ACQ increases for analogues with higher acidity and bulkiness. Their structure controls dye-dye communication, yielding bright NPs with on/off switching or stable emission. They enhance dye encapsulation inside NPs, allowing intracellular imaging without dye leakage. Compared to fluorinated tetraphenylborates known as cytotoxic transmembrane ion transporters, the barbiturates display a significantly lower cytotoxicity. These chemically available and versatile barbiturate derivatives are promising counterion scaffolds for preparation of bright non-toxic fluorescent nanomaterials.

Mots clés: nanoparticles; fluorescence; dyes/pigments; bulky hydrophobic anions; aggregation

Domaines: Chimie

Bohdan Andreiuk, Ilya O Aparin, Andreas Reisch, Andrey S Klymchenko. Bulky Barbiturates as Non-toxic Ionic Dye Insulators for Enhanced Emission in Polymeric Nanoparticles. Chemistry - A European Journal, 2021, ⟨10.1002/chem.202101986⟩. ⟨hal-03284795⟩