Issue 41, 2022

Novel cytotoxic 1,10-phenanthroline–triterpenoid amphiphiles with supramolecular characteristics capable of coordinating 64Cu(ii) labels

Abstract

1,10-Phenanthroline was decorated with triterpenoid-based substituents bearing additional spermine units to form amphiphilic molecules. The synthetic procedure designed for the new phenanthroline–triterpenoid amphiphiles is described in detail. Besides 1,10-phenanthroline, all target structures bear 1,4-disubstituted 1,2,3-triazole rings. The target compounds self-assembled into either helical-like or sheet-like nanostructures, depending on the structure of the target molecule, either based on betulinic acid or oleanolic acid, and on the way of binding spermine subunits to the rest of the molecules. They also proved their ability to coordinate 64Cu(II) ions. Finally, the target compounds showed cytotoxicity that was partly dependent on the formation of nanostructures.

Graphical abstract: Novel cytotoxic 1,10-phenanthroline–triterpenoid amphiphiles with supramolecular characteristics capable of coordinating 64Cu(ii) labels

Supplementary files

Article information

Article type
Paper
Submitted
30 Jun 2022
Accepted
29 Sep 2022
First published
05 Oct 2022

Org. Biomol. Chem., 2022,20, 8157-8163

Novel cytotoxic 1,10-phenanthroline–triterpenoid amphiphiles with supramolecular characteristics capable of coordinating 64Cu(II) labels

U. Bildziukevich, Z. Özdemir, D. Šaman, M. Vlk, M. Šlouf, L. Rárová and Z. Wimmer, Org. Biomol. Chem., 2022, 20, 8157 DOI: 10.1039/D2OB01172G

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