Synthesis of conjugates of (-)-cytisine derivatives with ferrocene-1-carbaldehyde and their cytotoxicity against HEK293, Jurkat, A549, MCF-7 and SH-SY5Y cells

TETRAHEDRON

卷:76

Article

Tsypysheva, Inna P.¹  Koval'skaya, Alena V.¹  Petrova, Polina R.¹  Lobov, Alexander N.¹  Erastov, Alexey S.¹  Zileeva, Zulfia R.²  Vakhitov, Vener A.²  Vakhitova, Yulia V.² 

[1] Russian Acad Sci, Ufa Fed Res Ctr, Ufa Chem Inst, 71 Prospect Oktyabrya, Ufa 450054, Russia

[2] Russian Acad Sci, Ufa Fed Res Ctr, Inst Biochem & Genet, Ufa, Russia

关键词: (-)-cytisine;    Ferrocene-carbaldehyde;    Cytotoxicity;    G2/M phase;   

DOI  :  10.1016/j.tet.2019.130902

来源: Elsevier

【 摘 要 】

First example of conjugation of quinolizidine alkaloids with ferrocene was presented. The cytotoxic properties of the obtained conjugates against cell lines HEK293, Jurkat, A549, MCF-7 and SH-SY5Y were studied. It was found, that conjugate 17 (having ferrocenyl methylene fragment and phenyl carboxamide moiety) produced a relatively higher cytotoxicity towards cancer Jurkat and SH-SY5Y cells with weak activity against non-cancerous HEK293 cells, suggesting the selectivity of this substance to inhibit certain tumor cells. The effect of leading compound 17 on cell cycle progression of HEK293, Jurkat, A549, MCF-7 and SH-SY5Y lines in a time-dependent fashion was studied. It was shown that hit-compound 17 caused a prominent arrest of MCF-7, Jurkat and A-549 cells in S phase along with a decrease of cells in G1 and a nearly total decline of cells in G2/M; the induction of apoptosis in HEK293 and SH-SY5Y cells was cell-cycle independent. (C) 2020 Elsevier Ltd. All rights reserved.

【 授权许可】

Free