Using cyclooctaglycine and Se8 ring model for cyclic peptide (CP) and selenium nanoparticle (SeNP), fifteen noncovalent configurations for the functionalization of gemcitabine (GCB) anticancer drug on cyclic peptide-selenium nanoparticle (CPSeNP) have been studied. In addition to the solvation and binding energies, quantum molecular descriptors were also investigated at M06-2X/6-31G**. According to the large negative values of binding energies, the noncovalent structures (CPSeNP/GCB1-15) exhibit significant energetic stability. The solvation energies demonstrated that solubility of GCB and SeNP increases which is a major factor in any anticancer drug delivery system. The important role of intermolecular hydrogen bonds and Se-X interactions in CPSeNPs was revealed by atoms in molecules (AIM) analysis (X = O, N, C, F, H). Se-X interactions in all configurations are weak interactions. The configurations in which GCB drug is placed parallel to the carrier and interacts simultaneously with CP and SeNP are more stable (more negative energy) than those in which GCB interacts with only CP or SeNP.