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Non-aqueous dispersions (NAD) with two types of polymeric nanoparticles (NPs), such as hydrophobic poly(ε-caprolactone) (PCL) and hydrophilic cross-linked poly(vinylpyrrolidone) (PNVP), were synthesized in the present study starting from monomer-in-silicone oil (PDMS) polymerizable non-aqueous emulsions stabilized with the same tailor-made PDMS-based block copolymer. These NPs were loaded with CCisplatin, an antitumoral model drug, directly from the emulsion polymerization step, and it was observed that the presence of the drug leads only to a slight increase of the NPs size, from 120 to 150 nm. The drug release kinetics was evaluated at 37 °C in phosphate buffer at pH = 7.4 and it appeared that the drug release rate from the hydrophilic cross-linked PNVP-based NPs is higher than that from the hydrophobic PCL-based NPs. Moreover, haemolysis tests revealed the fact that these two types of NPs have a good compatibility with the blood. Furthermore, for both the free and drug-loaded NPs, the in vitro cytotoxicity and apoptosis was studied on two types of cancer cell lines, such as MCF-7 (breast cancer cell line) and A-375 (skin cancer cell line). Both types of NPs had no cytotoxic effect but, at a concentration of 500 μg/mL, presented an apoptotic effect similar to that of the free drug.