title: Synthesis, anticancer and antibacterial activity of salinomycin N-benzyl amides.
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.
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89 b, 61-614 Poznań, Poland. michant@amu.edu.pl.
authors.forename: Michał
authors.initials: M
authors.lastname: Antoszczak
authors.affiliation: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Rudolfa Weigla 12, 53-114 Wrocław, Poland. ewa.maj@iitd.pan.wroc.pl.
authors.forename: Ewa
authors.initials: E
authors.lastname: Maj
authors.affiliation: Department of Microbiology, Institute of Tuberculosis and Pulmonary Diseases, Płocka 26, 01-138 Warsaw, Poland. araceli@op.pl.
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Napiórkowska
authors.affiliation: Department of Pharmaceutical Microbiology, University of Warsaw, Oczki 3, 02-007 Warsaw, Poland. jstefanska@wum.edu.pl.
authors.forename: Joanna
authors.initials: J
authors.lastname: Stefańska
authors.affiliation: Department of Microbiology, Institute of Tuberculosis and Pulmonary Diseases, Płocka 26, 01-138 Warsaw, Poland. e.kopec@igichp.edu.pl.
authors.forename: Ewa
authors.initials: E
authors.lastname: Augustynowicz-Kopeć
authors.affiliation: Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Rudolfa Weigla 12, 53-114 Wrocław, Poland. wietrzyk@iitd.pan.wroc.pl.
authors.forename: Joanna
authors.initials: J
authors.lastname: Wietrzyk
authors.affiliation: Institute of Low Temperature and Structure Research, Polish Academy of Sciences, P.O. Box 1410, 50-950 Wrocław, Poland. J.Janczak@int.pan.wroc.pl.
authors.forename: Jan
authors.initials: J
authors.lastname: Janczak
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89 b, 61-614 Poznań, Poland. bbrzez@amu.edu.pl.
authors.forename: Bogumil
authors.initials: B
authors.lastname: Brzezinski
authors.affiliation: Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89 b, 61-614 Poznań, Poland. adhucz@amu.edu.pl.
authors.forename: Adam
authors.initials: A
authors.lastname: Huczyński
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000995:Antitubercular Agents / Q000494:pharmacology; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D006801:Humans; D006860:Hydrogen Bonding; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D066244:Proton Magnetic Resonance Spectroscopy; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D013212:Staphylococcus epidermidis / Q000187:drug effects; D013329:Structure-Activity Relationship; D000095662:Polyether Polyketides
chemical_list: D000577:Amides; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D000995:Antitubercular Agents; D011714:Pyrans; C010327:salinomycin; D000095662:Polyether Polyketides