Here,
we report photoinitiated polymerization-induced self-assembly
(photo-PISA) mediated by Rose Bengal methacrylate (RBMA) to reproducibly
construct nanoparticles in one pot, on a large scale, for photodynamic
therapy (PDT). In this work, we take advantage of the multifunctionality
of RBMA by applying the monomer as a photocatalyst for self-catalyzed
PISA, a singlet oxygen (1O2) generator for PDT,
and a fluorophore for imaging. Covalent incorporation of Rose Bengal
(RB) into nanostructures by the polymerizable methacrylate moiety
permitted quantitative and controlled loading. When activated by visible
light in aqueous solution, the RB within the cores of micelles yielded 1O2 more efficiently than free RB. Post-PISA modification
of the RB-loaded nanocarriers with a DNA aptamer enhanced internalization
by HCT116 cells and significantly inhibited tumor cell proliferation
when exposed to yellow light. Such aptamer-labeled nanoparticles,
prepared for PDT, extend the practical biomedical applications of
PISA and are potential candidates for clinical cancer treatment.