Display options
Cite
Tuktarov AR, Khuzina LL, Sadretdinova ZR, et al. Synthesis and cytotoxic activity of unsaturated macrolides and their hybrid molecules with a C. Org Biomol Chem. 2021;19(8):1847-1853doi: 10.1039/d1ob00023c.
Tuktarov, A. R., Khuzina, L. L., Sadretdinova, Z. R., Makarova, E. K., Dzhemileva, L. U., D'yakonov, V. A., & Dzhemilev, U. M. (2021). Synthesis and cytotoxic activity of unsaturated macrolides and their hybrid molecules with a C. Organic & biomolecular chemistry, 19(8), 1847-1853. https://doi.org/10.1039/d1ob00023c
Tuktarov, Airat R, et al. "Synthesis and cytotoxic activity of unsaturated macrolides and their hybrid molecules with a C." Organic & biomolecular chemistry vol. 19,8 (2021): 1847-1853. doi: https://doi.org/10.1039/d1ob00023c
Tuktarov AR, Khuzina LL, Sadretdinova ZR, Makarova EK, Dzhemileva LU, D'yakonov VA, Dzhemilev UM. Synthesis and cytotoxic activity of unsaturated macrolides and their hybrid molecules with a C. Org Biomol Chem. 2021 Mar 04;19(8):1847-1853. doi: 10.1039/d1ob00023c. PMID: 33565546.
Copy Download .nbib Format: NLM
Share it on

Org Biomol Chem. 2021 Mar 04;19(8):1847-1853. doi: 10.1039/d1ob00023c.

Synthesis and cytotoxic activity of unsaturated macrolides and their hybrid molecules with a C.

Organic & biomolecular chemistry

Airat R Tuktarov, Liliya L Khuzina, Zarema R Sadretdinova, Elina Kh Makarova, Lilya U Dzhemileva, Vladimir A D'yakonov, Usein M Dzhemilev

Affiliations

  1. Institute of Petrochemistry and Catalysis of RAS (IPC RAS), Prospect Octyabrya, 141, 450075 Ufa, Russian Federation. [email protected] [email protected].

PMID: 33565546 DOI: 10.1039/d1ob00023c

Abstract

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.

Publication Types