The addition of specific chemical groups in a macrocycle
structure influences its functional properties and, consequently,
can provide new possibilities, among which are aggregation properties,
water solubility, biocompatibility, stimuli response, biological activity,
etc. Herein, we report synthesis of new resorcin[4]arene with N-methyl-d-glucamine groups on the upper rim and
n-decyl chains on the lower rim, an investigation of its self-assembly
behavior in aqueous media, and its use as a building block for the
formation of drug nanocontainer. N-methyl-d-glucamine fragments in the resorcin[4]arene structure promote higher
stability in solutions, simplification of self-aggregation, and increased
biological activity. Antimicrobial and hemolytic activity assessment
revealed that this resorcin[4]arene obtained is nontoxic. The study
of cell penetration was carried out with both free and encapsulated
doxorubicin (DOX). Surprisingly, DOX-loaded macrocycle aggregates
are more efficient in causing apoptosis in human cancer cell line.
Conceivably, this knowledge will help in the rational design of DOX
combination for novel drug-administration strategies in cancer treatment.