Synthesis, Characterisation and Cytotoxic Activity Evaluation of New Metalsalen Complexes Based on the 1,2-bicyclo[2.2.2]octane Bridge

Abstract

Diaminobicyclo[2.2.2]octane was used as starting material for the preparation, in solution or in a ball-mill, of a salen ligand. Five metal salen complexes were prepared in high yield and their cytotoxic activities were evaluated against HCT116 cell lines. Original manganese salen complex displayed the highest activity with a potency 16 fold higher than the one of cisplatin, demonstrating the benefit of the bridging backbone, compared to other salen systems. An alternative preparation route for this complex by mechanochemistry was also performed.<br>

Mechanosynthesis and Photophysics of Colour-tunable Photoluminescent Group 13 Metal Complexes with Sterically Demanding 3,5-di-tert-butyl Substituted Salen and Salophen Ligands

“…47,48,49 More recently, Lamaty et al achieved the mechanosynthesis of sterically demanding manganese complex with 1,2-bicyclo[2.2.2]octane bridge as cytotoxic agents. 50 Within the context of mechanochemically synthesised main group salen and salophen complexes is mainly unexplored. A previously reported example of mechanosynthesis consist of bromo-substituted salen and salophen complexes comprising aluminium and indium metal centres.…”

Multi-gram Mechanosynthesis of Salophen-Complex: A Comparative Analysis

“…These species, synthesized in the presence of sodium chloride as a salt additive, were produced in moderate to good yields (i.e., 62 to 98%) in the milligram scale (i.e.,, 9.8 to 129 mg). 48 Even though mechanosynthesis has demonstrated to have the potential to be a disruptive technology in industry, there are several aspects, however, that hinder its broader adoption. These issues include (i) the lack of comparable performance data between different synthetic methodologies, (ii) the impact of large scale production on environmental factors (e.g., E-factors), and (iii) the lack the need for new experimental designs at industrially relevant scale, among others.…”