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This study summarizes the synthesis, characterization, and evaluation of a library of biocompatible self‐assembling Janus dendrimers (JDs) and their resulting nanostructures possessing either a cationic (NH₃⁺), anionic (COO⁻), or neutral (OH) surface. Strategically designed for applications in therapeutic delivery, the dendrimers are comprised of a polyamidoamine (PAMAM) dendron as the hydrophilic portion and fatty acid (FA) functionalized dendrons as the hydrophobic portion. The physicochemical characterization and in vitro cell viability of amphiphilic JDs were performed. Microscopy (TEM) and dynamic light scattering (DLS) analysis indicate the size (i. e., diameters) of spherical nanoaggregates ranging from 40 to 100 nm with zeta‐potential values ranging from −17.9 to +58.7 mV with respect to the terminal functional group of the JD employed. Furthermore, these systems exhibited spherical …