N-Acetylneuraminic
acid (Neu5Ac), one of the abundant
types of sialic acid, is an emerging anticancer agent owing to its
ability to target selectins in the plasma membrane of cancer cells.
Considering the functionality of Neu5Ac, obtaining novel Neu5Ac-conjugated
materials with a selective and an enhanced antitumor activity has
remained a challenge. Herein, we report the supramolecular materials
of three novel amphiphiles composed of Neu5Ac as a hydrophilic segment
and pyrene or adamantane as a hydrophobic segment. The synthetic amphiphiles 1, 2, and 3 self-assembled into
ribbons, vesicles, and irregular aggregates in an aqueous solution,
respectively. Among the materials, vesicles of amphiphile 2 showed the most substantial selectivity toward cancer cells, followed
by cell death due to the production of reactive oxygen species by
the pyrene group. The dual advantage of Neu5Ac-selectivity and the
pyrene-cytotoxicity of vesicles of amphiphile 2 can provide
a strategy for effective anticancer materials.