In this study, Pickering emulsions of dodecane and medium chain triglyceride (MCT) oils were stabilized by simply alkylated-dextran nanoparticles. Our findings show that very little of these bio-friendly nanoparticles is necessary to stabilize Pickering emulsions while providing a high time stability (more than a year at 37 °C). As dextran is known to be cleavable by dextranase enzyme, hydrolysis of the nanoparticles in the presence of dextranase could be achieved. This allowed performing on-demand destabilization of Pickering emulsions. Furthermore, two different fluorescent probes were loaded into the stabilizing particles and the oil droplets respectively, providing a proof of concept for co-encapsulation of actives in advanced delivery applications. Additionally, to a conventional fluorescence probe, quinine, an antimalarial drug was also encapsulated into the nanoparticles.