Micellar Nanocarriers from Dendritic Macromolecules Containing Fluorescent Coumarin Moieties.

Alberto Concellón,Pilar Romero,Silvia Hernández-Ainsa,María San Anselmo,Mercedes Marcos,José Luis Serrano

doi:10.3390/polym12122872

Abstract

The design of efficient drug-delivery vehicles remains a big challenge in materials science. Herein, we describe a novel class of amphiphilic hybrid dendrimers that consist of a poly(amidoamine) (PAMAM) dendritic core functionalized with bisMPA dendrons bearing cholesterol and coumarin moieties. Their self-assembly behavior both in bulk and in water was investigated. All dendrimers exhibited smectic A or hexagonal columnar liquid crystal organizations, depending on the generation of the dendrimer. In water, these dendrimers self-assembled to form stable spherical micelles that could encapsulate Nile Red, a hydrophobic model compound. The cell viability in vitro of the micelles was studied in HeLa cell line, and proved to be non-toxic up to 72 h of incubation. Therefore, these spherical micelles allow the encapsulation of hydrophobic molecules, and at the same time provided fluorescent traceability due to the presence of coumarin units in their chemical structure, demonstrating the potential of these dendrimers as nanocarriers for drug-delivery applications.

Highlights

The preparation of polymeric drug nanocarriers is a stimulating topic of research in chemistry, biology and materials science [1,2,3]
The mixture was ultrasonicated for 5 min, THF was slowly evaporated at room the PAMAM dendrimer in the stoichiometry necessary to functionalize all terminal amine groups temperature, and the sample was dried under vacuum at 40 ◦ C until the weight remained constant
Fourier transform infra-red (FTIR) and nuclear magnetic resonance (NMR) data are consistent with covalent analogues were synthesized by coupling of theThe formation of ionic interactions(PAMAMn–cov–ChCou) between PAMAM dendrimers and Ac–ChCou

Summary

Introduction

The preparation of polymeric drug nanocarriers is a stimulating topic of research in chemistry, biology and materials science [1,2,3]. Amphiphilic Janus dendrimers have demonstrated facile self-assembly in aqueous media to form stable polymeric nanocarriers [15] These systems are generally prepared by coupling two antagonistic. These amphiphilic self-assemble wateramphiphilic generating unimolecular micelles that dendritic surrounded bydendrimers an hydrophilic shell [18].inThese dendrimers self-assemble can load hydrophobic drugs and potentially be internalized into cells duedrugs to their diameters in water generating unimolecular micelles that can load hydrophobic andsmall potentially be We report theirwe synthesis, thermal properties, and properties, morphological or 64 terminal groups,respectively) Report their synthesis, thermal and aggregation study in water ofstudy thesein amphiphilic dendrimers. These dendrimers were dendrimers designed as morphological aggregation water of these amphiphilic Since these polymeric drug carriers, their cytotoxicity in vitro well as their to encapsulate.

Synthesis andDiscussion

Synthesis and Characterization of Dendrimers

Absorption and Emission Properties of the Self-Assemblies

Cytotoxicity and Celullar Uptake of the Self-Assemblies

Conclusions