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Copper( I ) (Pseudo)Halide Complexes with Neocuproine and Aminomethylphosphines Derived from Morpholine and Thiomorpholine – In Vitro Cytotoxic and Antimicrobial Activity and the Interactions with DNA and Serum Albumins
Author(s) -
Starosta Radosław,
Bykowska Aleksandra,
Kyzioł Agnieszka,
Płotek Michał,
Florek Magdalena,
Król Jarosław,
JeżowskaBojczuk Małgorzata
Publication year - 2013
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12187
Subject(s) - chemistry , morpholine , bovine serum albumin , quenching (fluorescence) , tris , in vitro , stereochemistry , antimicrobial , phenanthroline , medicinal chemistry , biochemistry , fluorescence , organic chemistry , quantum mechanics , physics
Herein, a series of C u I or C u NCS complexes with neocuproine (2,9‐dimethyl‐1,10‐phenanthroline: dmp) and two tris(aminomethyl)phosphines derived from morpholine ( P ( CH 2 N ( CH 2 CH 2 ) 2 O ) 3 ) or thiomorpholine ( P ( CH 2 N ( CH 2 CH 2 ) 2 S ) 3 ) were tested as cytotoxic agents in vitro towards mouse colon carcinoma ( CT 26) and human lung adenocarcinoma ( A 549). The studies showed that the complexes exhibit potential antitumor properties, displayed by IC 50 values below 10 μ m towards the tested cell lines, in the case of 4‐h incubation time with the examined compounds. Moreover, a high antimicrobial activity of all the complexes was observed against S taphylococcus aureus and C andida albicans with minimal inhibitory concentrations equal to 1–2 μg/mL. To gain insight into the molecular mechanism of biological activity of the complexes, we investigated also their interactions with plasmid DNA (p UC 18) and the human and bovine serum albumins. Gel electrophoresis experiments demonstrated that all the compounds were comparably efficient in DNA degradation process; however, luminescence quenching showed surprising dependence on the interactions strength of the used compounds with the albumins. Apart from exceptionally effective [ C uI(dmp) P ( CH 2 N ( CH 2 CH 2 ) 2 O ) 3 ], the complexes with P ( CH 2 N ( CH 2 CH 2 ) 2 O ) 3 quenched more strongly luminescence of bovine serum albumin, while the complexes with P ( CH 2 N ( CH 2 CH 2 ) 2 S ) 3 were more active in the quenching of human serum albumin luminescence.