Mechanochemical synthesis and antiproliferative activity of novel ferrocene quinoline/quinolone hybrids

Author:

Maračić Silvija1ORCID,Jakopec Silvio1ORCID,Piškor Martina1ORCID,Leventić Marijana2ORCID,Lapić Jasmina3ORCID,Djaković Senka3ORCID,Cetina Mario4ORCID,Glavaš‐Obrovac Ljubica2ORCID,Raić‐Malić Silvana1ORCID

Affiliation:

1. Department of Organic Chemistry, Faculty of Chemical Engineering and Technology University of Zagreb Zagreb Croatia

2. Department of Medical Chemistry, Biochemistry and Clinical Chemistry, Faculty of Medicine Josip Juraj Strossmayer University of Osijek Osijek Croatia

3. Laboratory for Organic Chemistry, Faculty of Food Technology and Biotechnology University of Zagreb Zagreb Croatia

4. Faculty of Textile Technology, Department of Applied Chemistry University of Zagreb Zagreb Croatia

Abstract

The synthesis of novel 1,1′‐disubstituted ferrocene conjugates appended with N‐1 and O‐4 alkylated quinolone and quinoline was reported. The target compounds were synthesized employing a liquid‐assisted grinding (LAG) mechanochemical method in copper‐catalyzed azide‐alkyne cycloaddition (CuAAC) to obtain ferrocene−quinoline/quinolone hybrids (5a5d, 6a6d, 7a, 7b, 8a, and 8b) in higher yields and shorter reaction time compared to a conventional method, thus proving superiority of mechanochemistry versus conventional synthesis. Bis‐quinoline and bis‐quinolone ferrocene derivatives were evaluated for their antiproliferative effects on five selected tumor and two non‐tumor cell lines. Bis‐6‐methylquinolone–ferrocene conjugate 8b showed the best antiproliferative effect on T‐cell lymphoma (HuT78) cells (IC50 = 14.8 μM) and no cytotoxicity on both non‐tumor MDCK1 and BJ cells. Results obtained after mitochondrial membrane potential (∆Ψm) measurement using flow cytometry showed that compound 8b caused accumulation of HuT78 cells in subG0/G1 phase, disturbance of mitochondrial membrane potential, and apoptosis. The structure of the quinolone and ferrocene hybrid 8b can be further optimized to obtain candidates with better inhibitory effects on HuT78 cells.

Funder

Hrvatska Zaklada za Znanost

Publisher

Wiley

Subject

Inorganic Chemistry,General Chemistry

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