Supramolecular
systems (macromolecules), such as calix[n]arenes
(SCn), cyclodextrins (CDs), and cucurbiturils (CBs),
are promising vehicles for anticancer drugs. In this work, guest–host
complexes of carboplatin, a second-generation platinum-based anticancer
drug, and p-4-sulfocalix[n]arenes (n = 4 and 6; PS4 and PS6, respectively) were prepared and studied
using 1H NMR, UV, Job’s plot analysis, HPLC, and
density-functional theory calculations. The experimental and the computational
studies suggest the formation of 1:1 complexes between carboplatin
and each of PS4 and PS6. The stability constants of the formed complexes
were estimated to be 5.3 × 104 M–1 and 9.8 × 104 M–1, which correspond
to free energy of complexation of −6.40 and −6.81 kcal
mol–1, in the case of PS4 and PS6, respectively.
The interaction free energy depends on the different inclusion modes
of carboplatin in the host cavities. UV–vis findings and atoms
in molecules analysis showed that hydrogen bond interactions stabilize
the host–guest complexes without the full inclusion in the
host cavity. The in vitro anticancer study revealed that both complexes
exhibited stronger anticancer activities against breast adenocarcinoma
cells (MCF-7) and lung cancer cells (A-549) compared to free carboplatin,
preluding to their potential use in cancer therapy.