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

0563219 - ÚEB 2023 RIV GB eng J - Journal Article
Bildziukevich, Uladzimir - Özdemir, Zülal - Šaman, David - Vlk, M. - Šlouf, Miroslav - Rárová, L. - Wimmer, Zdeněk
Novel cytotoxic 1,10-phenanthroline-triterpenoid amphiphiles with supramolecular characteristics capable of coordinating Cu-64(ii) labels.
Organic & Biomolecular Chemistry. Roč. 20, č. 41 (2022), s. 8157-8163. ISSN 1477-0520. E-ISSN 1477-0539
R&D Projects: GA MPO(CZ) FV10599; GA TA ČR(CZ) TN01000008
Grant - others:Czech Academy of Sciences(CZ) L200381952
Institutional support: RVO:61389030 ; RVO:61388963 ; RVO:61389013
Keywords : BETULINIC ACID * CHELATORS * SQUALAMINE
OECD category: Organic chemistry; Polymer science (UMCH-V)
Impact factor: 3.2, year: 2022
Method of publishing: Limited access
https://doi.org/10.1039/d2ob01172g

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 Cu-64(ii) ions. Finally, the target compounds showed cytotoxicity that was partly dependent on the formation of nanostructures.
Permanent Link: https://hdl.handle.net/11104/0335255