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Gemcitabine is a nucleoside analogue, used in various carcinomas such as non small cell lung cancer, pancreatic cancer, ovarian cancer and breast cancer. The major setbacks to the conventional therapy with gemcitabine include its short half-life and highly hydrophilic nature. The objectives of this investigation were to synthesize lipophilic derivative of gemcitabine, evaluate the physiochemical properties, entrapment efficiency, in vitro release, cytotoxicity, and cellular uptake of nanoparticulate formulations containing gemcitabine and stearoyl gemcitabine. We successfully prepared a formulation providing dual protection of gemcitabine against chemical decomposition from plasma catabolism and improve metabolic stability, first by covalently linking the amino group of gemcitabine to a long fatty chain, and then by encapsulating this lipophilic derivative in the formulations. PLGA nanoparticles can act as carriers for both lipophilic and hydrophilic drugs.