Complexation-induced nanoarchitectonics of sulfonate cailx[4]resorcinol substituted at the upper rim by N-methyl-d-glucamine fragments: Morphological transition and in vitro anticancer activity

Abstract

Complexes of various nitrogen-containing ligands with transition metals are known for their anticancer activity. At the same time, the shape of aggregates of these complexes can have a significant effect on cytotoxicity and selectivity of action in tumor cells, however, this issue has received insufficient attention in the literature. In this work, the selective binding ability of sulfonate calix[4]resorcinol functionalized at the upper rim by N-methyl-D-glucamine fragments towards copper (II) ion (Cu2+) was demonstrated. N-methyl-D-glucamine calix[4]resorcinol weakly interacts with Zn2+, but effectively binds Cu2+ with the formation of a 2:1 complex. The complexation of calix[4]resorcinol with copper leads to a significant change in the shape of aggregates from rounded to rod-like particles, which is confirmed by TEM images. The rod-like aggregates of calix[4]resorcinol–copper(II) showed a pronounced cytotoxic effect against HuTu 80 cell line, while not affecting Chang liver cells.