Here, we present a modular synthesis as well as physicochemical and biological evaluation of a new series of amphiphilic dendrons carrying triphenylphosphonium groups at their periphery. Within the series, the size and mutual balance of lipophilic and hydrophilic domains are systematically varied, changing the dendron shape from cylindrical to conical. In physiological solution, the dendrons exhibit very low critical micelle concentrations (2.6-4.9 μM) and form stable and uniform micelles 6-12 nm in diameter, depending on dendron shape; the results correlate well with molecular dynamics simulations. The compounds show relatively high cytotoxicity (IC50 1.2-21.0 μM) associated with micelle formation and inversely related to the size of assembled particles. Depending on their shape, the dendrons show promising results in terms of dendriplex formation and antibacterial activity. In addition to simple amphiphilic dendrons, a fluorescently labeled analogue was also prepared and utilized as an additive visualizing the dendron's cellular uptake.

• MeSH
• Anti-Bacterial Agents pharmacology   chemistry   chemical synthesis   MeSH
• Dendrimers * chemistry   chemical synthesis   pharmacology   MeSH
• Hydrophobic and Hydrophilic Interactions MeSH
• Humans MeSH
• Micelles * MeSH
• Organophosphorus Compounds * chemistry   MeSH
• Surface-Active Agents chemistry   chemical synthesis   pharmacology   MeSH
• Silanes chemistry   MeSH
• Molecular Dynamics Simulation MeSH
• Check Tag
• Humans MeSH
• Publication type
• Journal Article MeSH
• Names of Substances
• Anti-Bacterial Agents MeSH
• carbosilane MeSH Browser
• Dendrimers * MeSH
• Micelles * MeSH
• Organophosphorus Compounds * MeSH
• Surface-Active Agents MeSH
• Silanes MeSH