Chirality is a fundamental phenomenon in biological systems, since most of the biomolecules and biological components and species are chiral and therefore recognize and respond differently depending on the enantiomer present. With increasing research into the use of nanomaterials for biomedical purposes, it is essential to understand the role that chirality of nanoparticles plays at the cellular level. Here, the chiral cysteine functionalization of mesoporous silica nanoparticles has been shown to broadly affect its interaction with U87 MG human glioblastoma cell, healthy human fibroblast (GM08680) and methicillin-resistant S. aureus bacteria. We believe that this research is important to further advancement of nano-biotechnology.