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

Tetrahedron
2020.0

Abstract

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.

Knowledge Graph

Similar Paper

Synthesis of conjugates of (−)-cytisine derivatives with ferrocene-1-carbaldehyde and their cytotoxicity against HEK293, Jurkat, A549, MCF-7 and SH-SY5Y cells
Tetrahedron 2020.0
Synthesis of Several Cytisine Derivatives and their Cytotoxicities against A431, A375, and HCT 116 Tumor Cell Lines
Chemistry of Natural Compounds 2020.0
Synthesis and cytotoxicity of 2-phenylquinazolin-4(3H)-one derivatives
European Journal of Medicinal Chemistry 2011.0
3-Substituted 7-Phenyl-Pyrroloquinolinones Show Potent Cytotoxic Activity in Human Cancer Cell Lines
Journal of Medicinal Chemistry 2007.0
Sulfur and selenium derivatives of quinazoline and pyrido[2,3-d]pyrimidine: Synthesis and study of their potential cytotoxic activity in vitro
European Journal of Medicinal Chemistry 2012.0
Synthesis of substituted phenanthrene-9-benzimidazole conjugates: Cytotoxicity evaluation and apoptosis inducing studies
European Journal of Medicinal Chemistry 2017.0
Novel π‐Extended Quinazoline‐Ferrocene Conjugates: Synthesis, Structure, and Redox Behavior
European Journal of Organic Chemistry 2020.0
Azide-alkyne cycloaddition en route to novel 1H-1,2,3-triazole tethered isatin conjugates with in vitro cytotoxic evaluation
European Journal of Medicinal Chemistry 2012.0
Synthesis of 1,2,4-triazole-linked urea/thiourea conjugates as cytotoxic and apoptosis inducing agents
Bioorganic & Medicinal Chemistry Letters 2018.0
Synthesis and anticancer activity of some novel 5,6-fused hybrids of juglone based 1,4-naphthoquinones
European Journal of Medicinal Chemistry 2014.0