New amphiphilic carbosilane dendrons with pH-dependent behaviour based on the presence of carboxylate (propionate or succinate) groups at their peripheries and a fatty acid at the focal point were developed. In the presence of salts, they were able to form micelles with critical aggregation concentrations increasing with increasing dendron generation. Their thermodynamic parameters were calculated from surface tension measurements and their diameters at different pHs were measured by dynamic light scattering. These micelles were stable at basic pH but degraded under acidic conditions. No significant differences were found for the propionate and succinate based dendron micelles at basic or acidic pH, but the succinate dendron assemblies were more stable at neutral pH. The properties of these systems as drug nano-carriers were studied using both hydrophilic and hydrophobic molecules, and the drug loading varied with the structure and charge of the drug. In addition, due to the presence of multiple negative charges, the dendrons exhibited anti-HIV activity. Higher generation dendrons with more peripheral carboxylates that were not assembled into micelles were more active than micelles composed of lower generation dendrons having fewer peripheral carboxylates.