The Bingel-Hirsch reaction is a universal key to the synthesis of hybrid molecules based on C60 fullerene and 5Z,9Z-dienoic acids - potential antitumor drugs.

The data obtained by the author in the field of chemistry of carbon clusters, namely, the chemical binding of C₆₀ fullerene with 5Z,9Z-dienoic acids by nucleophilic addition to the carbon cluster of α halocarbanions generated in situ from their malonic acid esters are summarized. Based on ethyl, benzyl, acetylene and triazole esters of malonic acid containing 5Z,9Z-dienoic acids and C₆₀ fullerene, new hybrid methanofullerenes were synthesized under the conditions of the Bingel-Hirsch reaction. The synthesized methanofullerenes exhibit high cytotoxic activity towards tumor cells of the Jurkat, K562, U937, HL60 lines, and it has also been established that they are effective inducers of apoptosis, exerting a phase-specific cytotoxic effect on the cell cycle of tumor cells.

Next, by the method of intermolecular esterification of malonic acid with α,ω-diols, in the presence of hafnium triflate Hf(OTf)4, previously undescribed macrodiolides containing a 1Z,5Z-diene fragment in the structure were synthesized in high yields and stereoselectivity.Under the conditions of the Bingel-Hirsch reaction, chemical binding of the synthesized macrodiolides with C₆₀ fullerene was carried out to obtain the corresponding methanofullerenes. The cytotoxic activity of macrodiolides and methanofullerenes in relation to tumor cell lines Jurkat, K562, U937, HL60 and normal fibroblasts was studied. It was found that the cytotoxicity of the hybrid molecule is higher compared to the original macrodiolide (from 5 to 170 times). In addition, the synthesized hybrid molecules initiate apoptosis by uncoupling oxidation and phosphorylation of the mitochondrial membrane of tumor cells.