Chirality, known as mirror asymmetry, is a geometrical property of biological and nonbiological forms of matter. At nanoscale, building blocks of life, including proteins, nucleic acids, glycans, and lipids, are dominated by chiral enantiomers. As such, chiral nanostructures are of extraordinary significance in a variety of important biological events, such as cell uptake and tissue transport. However, there is a significant gap in our understanding of how the chirality of nanostructures selectively mediates the interaction with other chiral objects in living systems. This fundamental knowledge opens up numerous potential applications in health and environment, including asymmetric biocatalysis, enantiomeric separation, chiral sensing, and drug formulations. My lab designs and develops engineered chiral nanomaterials to regulate chiral nanoscale interactions at biointerfaces and in tumor microenvironments. We  take an interdisciplinary approach combining experiment, computational simulation, and three-dimensional (3D) culture models to establish a theoretical and experimental framework to support the rationale design of chiral nanomaterials and their assemblies, with control over the materials’ transport and uptake. Collectively, these fundamental studies and developed experimental tools will provide knowledge and engineering tools that can be used in cancer therapeutic and diagnostic strategies using chiral nanomaterials, including drug/gene loading into therapeutic exosomes.