New red-emitting conjugated polyelectrolyte: stabilization by interaction with biomolecules and potential use as drug carriers and bioimaging probes

Abstract

The design and development of fluorescent conjugated polyelectrolytes (CPEs) emitting in the red region of the visible spectrum is at present of great interest for bioimaging studies. However, despite the wide variety of CPEs available, stable bright redemitters remain scarce due to their low solubility and instability in aqueous media, consequently limiting their applications. In this work, we have synthesized and characterized a new red-emitting cationic conjugated polyelectrolyte copoly-{[9,9-bis(6′- N,N,N-trimethylammonium)hexyl]-2,7-(fluorene)-alt-1,4-(naphtho[2,3c]-1,2,5-thiadiazole)} bromide (HTMA-PFNT), based on the incorporation of naphtha[2,3c][1,2,5] thiadiazole on fluorene backbone to increase the bathochromic emission, extending the conjugation length in the polymer backbone. Water stabilization was achieved by binding the polyelectrolyte to two different biological systems which are currently used as nanocarriers: human serum albumin (HSA) and lipid vesicles. Using both systems, stable nanostructures of different composition were obtained and their properties were characterized. The properties of the protein-based nanoparticles are consistent with polyelectrolyte aggregates covered with HSA molecules, while the liposome system is composed of lipid vesicles coated with polyelectrolyte chains partially inserted in the bilayer. Both protein and vesicle structural integrity were not affected after their interaction with HTMA-PFNT, as well as the carrier properties, allowing for the binding and transport of ligands. In addition, the nanoparticles displayed the ability of labeling the cell membrane of living cells. All these results extend the potential applications of these novel multifunctional nanoparticles as therapeutic carriers and bioimaging probes.