Physicochemical Properties of a New PEGylated Polybenzofulvene Brush for Drug Encapsulation

Abstract

A new polymer brush was synthesized by spontaneous polymerization of benzofulvene macromonomer 6-MOEG-9-T-BF3k bearing a nona(ethylene glycol) side chain linked to the 3-phenylindene scaffold by means of a triazole heterocycle. The polymer structure was studied by SEC-MALS, NMR spectroscopy, and MALDI-TOF MS techniques, and the results supported the role of oligomeric initiatory species in the spontaneous polymerization of polybenzofulvene derivatives. The aggregation features of high molecular weight poly-6-MOEG-9-T-BF3k-FE were investigated by pyrene fluorescence analysis, dynamic light scattering studies, and transmission electron microscopy, which suggested a tendency towards the formation of spherical objects showing dimensions in the range of 20–200 nm. Moreover, poly-6-MOEG-9-T-BF3k-FE showed an interesting cytocompatibility in the whole concentration range tested that, besides its aggregation features, makes this polybenzofulvene brush a good polymer candidate for nanoencapsulation and delivery of drug molecules. Finally, the photo-physical features of poly-6-MOEG-9-T-BF3k-FE could allow the biodistribution of the resulting drug delivery systems to be monitored by fluorescence microscopy techniques.

Design, Synthesis and Characterization of a Visible‐Light‐Sensitive Molecular Switch and Its PEGylation Towards a Self‐Assembling Molecule

“…In the present paper, we report a novel HBDI‐like homologue photoswitch capable of functioning in both the E ‐to‐ Z and Z ‐to‐ E directions via visible and UV light, respectively. More specifically, 1 features an extended conjugation due to a 3‐phenylindene‐2‐carboxylate scaffold, the structure at the basis of the polybenzofulvene monomeric unit (Figure 1C) [52–65] . We also show that the obtained LDMS 1 can be easily functionalized with a clickable azide group (compound 2 ) for the insertion of the photoswitch in more complex synthetic and/or biological structures via azide‐alkyne click reactions.…”

“…More specifically, 1 features an extended conjugation due to a 3phenylindene-2-carboxylate scaffold, the structure at the basis of the polybenzofulvene monomeric unit (Figure 1C). [52][53][54][55][56][57][58][59][60][61][62][63][64][65] We also show that the obtained LDMS 1 can be easily functionalized with a clickable azide group (compound 2) for the insertion of the photoswitch in more complex synthetic and/or biological structures via azide-alkyne click reactions. In fact, we report that methyl-end-capped nona(ethylene glycol) (NEG) side chain, an amphiphilic solubilizing group, [66] can be successfully conjugated with 2 in a preliminary effort to obtain an amphiphilic LDMS capable of self-assembling in nanometric micelles in water solution and operated by visible light (Figure 1D).…”