A supramolecular enantioselective transfer amino acid@pillar[5]arene bio-interface for effective tumour cell suppression

Abstract

Chirality is a fundamental feature of living organisms, playing an essential role in biological and physiological processes that are closely related to the fate of cancer cells. It is challenging to design a simple and improved chiral artificial system to induce tumor cells' behavior based on their chirality selectively. Accordingly, we designed and fabricated pillar[5]arene silica surfaces through a click reaction, and further self-assembled a chiral functional unit onto these silica surfaces driven by dynamic host–guest interaction, which exhibited chiral transfer properties with a magnifying effect. Moreover, the cancer cells exhibit chiral-dependent adherent ability on these chiral interfaces; the L-film showed a positive effect on cancer cell adherent ability, while the D-substrate showed a negative impact on cancer cell growth. The chiral transfer surface induced by arginine, lysine, and histidine enantiomers demonstrated a significant chirality difference in cancer cells' viability, with discrimination ratios (K_L/K_D) of 1.87, 1.85, and 2.91, respectively. Furthermore, Annexin V-FITC/PI apoptosis analysis by flow cytometry demonstrates that the chiral-dependent decrease in viability results from an apoptotic pathway. Based on this finding, we believe that our research will accelerate the chiral material engineering process, provide new insights into interpreting chiral phenomena in nature, and further promote the applications of the chiral effect in medicine, oncotherapy, and related fields.