| Autor: |
Tuktarov AR; Institute of Petrochemistry and Catalysis of RAS (IPC RAS), Prospect Octyabrya, 141, 450075 Ufa, Russian Federation. tuktarovar@gmail.com Dzhemilev@mail.ru., Khuzina LL; Institute of Petrochemistry and Catalysis of RAS (IPC RAS), Prospect Octyabrya, 141, 450075 Ufa, Russian Federation. tuktarovar@gmail.com Dzhemilev@mail.ru., Sadretdinova ZR; Institute of Petrochemistry and Catalysis of RAS (IPC RAS), Prospect Octyabrya, 141, 450075 Ufa, Russian Federation. tuktarovar@gmail.com Dzhemilev@mail.ru., Makarova EK; Institute of Petrochemistry and Catalysis of RAS (IPC RAS), Prospect Octyabrya, 141, 450075 Ufa, Russian Federation. tuktarovar@gmail.com Dzhemilev@mail.ru., Dzhemileva LU; Institute of Petrochemistry and Catalysis of RAS (IPC RAS), Prospect Octyabrya, 141, 450075 Ufa, Russian Federation. tuktarovar@gmail.com Dzhemilev@mail.ru., D'yakonov VA; Institute of Petrochemistry and Catalysis of RAS (IPC RAS), Prospect Octyabrya, 141, 450075 Ufa, Russian Federation. tuktarovar@gmail.com Dzhemilev@mail.ru., Dzhemilev UM; Institute of Petrochemistry and Catalysis of RAS (IPC RAS), Prospect Octyabrya, 141, 450075 Ufa, Russian Federation. tuktarovar@gmail.com Dzhemilev@mail.ru. |
| Abstrakt: |
Previously unreported macrodiolides containing a 1Z,5Z-diene fragment in the structure have been synthesized with high yields and stereoselectivity by our research group, using the intermolecular esterification of malonic acid with α,ω-diols containing bis-methylene-separated Z-double bonds, catalyzed by Hf(OTf)4 hafnium triflate. Under Bingel-Hirsch conditions, the synthesized macrodiolides were chemically bonded with a C60 fullerene to produce the corresponding methanofullerenes. The cytotoxic activity of macrodiolides and methanofullerenes in relation to Jurkat, K562, U937, HL60 tumor cell lines and normal fibroblasts was studied. Covalent binding of macrodiolides to the C60 fullerene molecule was found to significantly increase the cytotoxic effect (from 5 to 170 times) of the hybrid molecule as compared to the initial macrodiolide. Moreover, the synthesized hybrid molecules initiate apoptosis by uncoupling oxidation and phosphorylation of the mitochondrial membrane of tumor cells. |
