Carbosilane Dendritic Amphiphiles from Cholesterol or Vitamin E for Micelle Formation
Gabriel Mencia,
Sergio Algar,
Tania Lozano-Cruz,
Mª Ángeles Muñoz-Fernández,
Elizabeth R. Gillies,
Jesús Cano,
Mercedes Valiente,
Rafael Gómez
Affiliations
Gabriel Mencia
Department of Organic and Inorganic Chemistry, Research Institute in Chemistry “Andrés M. Del Río” (IQAR), University of Alcalá, 28805 Madrid, Spain
Sergio Algar
Department of Organic and Inorganic Chemistry, Research Institute in Chemistry “Andrés M. Del Río” (IQAR), University of Alcalá, 28805 Madrid, Spain
Tania Lozano-Cruz
Department of Organic and Inorganic Chemistry, Research Institute in Chemistry “Andrés M. Del Río” (IQAR), University of Alcalá, 28805 Madrid, Spain
Mª Ángeles Muñoz-Fernández
Networking Research Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), 28029 Madrid, Spain
Elizabeth R. Gillies
Department of Chemistry and Chemical and Biochemical Engineering, School of Biomedical Engineering, University of Western Ontario, London, ON N6G1Z1, Canada
Jesús Cano
Department of Organic and Inorganic Chemistry, Research Institute in Chemistry “Andrés M. Del Río” (IQAR), University of Alcalá, 28805 Madrid, Spain
Mercedes Valiente
Department of Analytical Chemistry, Physical Chemistry and Chemical Engineering, Research Institute in Chemistry “Andrés M. Del Río” (IQAR), University of Alcalá, 28805 Madrid, Spain
Rafael Gómez
Department of Organic and Inorganic Chemistry, Research Institute in Chemistry “Andrés M. Del Río” (IQAR), University of Alcalá, 28805 Madrid, Spain
Cationic dendritic amphiphiles were prepared through the linkage of interesting hydrophobic molecules such as cholesterol or vitamin E to the focal point of carbosilane dendrons. These new dendritic systems self-assembled in saline, producing micellar aggregates with hydrodynamic diameters ranging from 6.5 to 9.2 nm, and critical micelle concentrations of approximately 5 and 10 μM for second- and third-generation systems, respectively. The assemblies were able to encapsulate drugs of different charges (anionic, neutral, and cationic). Surprisingly, a 92% encapsulation efficiency for diclofenac was achieved in micelles prepared from second-generation dendrons. Toxicity measurements on peripheral blood mononuclear cells indicated different behavior depending on the generation, corresponding to the micellar regime. In contrast to the third-generation system, the second-generation system was non-toxic up to 20 μM, opening a window for its use in a micellar regimen, thereby operating as a drug delivery system for different biomedical applications.
