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Synthesis, Anticancer and Antibacterial Activity of Salinomycin N-Benzyl Amides

Michał Antoszczak,E. Maj,A. Napiórkowska,J. Stefanska,E. AUGUSTYNOWICZ-KOPEĆ,J. Wietrzyk,J. Janczak,B. Brzeziński,Adam Huczyński

Published 2014 in Molecules

ABSTRACT

A series of 12 novel monosubstituted N-benzyl amides of salinomycin (SAL) was synthesized for the first time and characterized by NMR and FT-IR spectroscopic methods. Molecular structures of three salinomycin derivatives in the solid state were determined using single crystal X-ray method. All compounds obtained were screened for their antiproliferative activity against various human cancer cell lines as well as against the most problematic bacteria strains such as methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus epidermidis (MRSE), and Mycobacterium tuberculosis. Novel salinomycin derivatives exhibited potent anticancer activity against drug-resistant cell lines. Additionally, two N-benzyl amides of salinomycin revealed interesting antibacterial activity. The most active were N-benzyl amides of SAL substituted at -ortho position and the least anticancer active derivatives were those substituted at the -para position.

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