Biological activity and structure dependent properties of cuprous iodide complexes with phenanthrolines and water soluble tris (aminomethyl) phosphanes

• Published in: Journal of inorganic biochemistry 2011-08, Vol.105 (8), p.1102-1108
• Main Authors: Starosta, Radosław, Stokowa, Kamila, Florek, Magdalena, Król, Jarosław, Chwiłkowska, Agnieszka, Kulbacka, Julita, Saczko, Jolanta, Skała, Jacek, Jeżowska-Bojczuk, Małgorzata
• Format: Article
• Language: English
• Subjects: Aminomethylphosphanes; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial, antifungal and anticancer activity; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Bovine serum albumin luminescence quenching; Candida albicans; Candida albicans - drug effects; Cell Line, Tumor; Copper - chemistry; Copper - pharmacology; Copper(I) complexes; Humans; Iodides - chemistry; Iodides - pharmacology; Ligands; pBluescsriptSK+ plasmid gel electrophoresis; Phenanthrolines - chemistry; Phenanthrolines - pharmacology; Phosphines - chemistry; Phosphines - pharmacology; Staphylococcus aureus; Staphylococcus aureus - drug effects; Structure-Activity Relationship; Water
• ISSN: 0162-0134; 1873-3344
• DOI: 10.1016/j.jinorgbio.2011.05.007

This paper presents the biological activity of copper(I) iodide complexes with 1,10-phenanthroline (phen) or 2,9-dimethyl-1,10-phenanthroline (dmp) and three tris (aminomethyl) phosphanes: P(CH 2N(CH 2CH 2) 2NCH 3) 3 ( 1), P(CH 2N(CH 2CH 2) 2O) 3 ( 2) and P (CH 2N(CH 3)CH 2CH 2OH) 3 ( 3). Crystallographic and DFT data indicate a significantly stronger binding ability of 3 in the complexes [CuI (phen) P (CH 2N (CH 3)CH 2CH 2OH) 3] ( 3P) and [CuI(dmp)P(CH 2N(CH 3)CH 2CH 2OH) 3] ( 3N) in comparison to the 1 or 2 ligands. Most probably, this is caused by the relatively small steric requirements of 3. The complexes with dmp exhibit a very high in vitro activity against the Staphylococcus aureus strain (MIC — minimal inhibitory concentration: 2.5–5 μg/mL) and Candida albicans diploid fungus (MIC: 1.25–2.5 μg/mL). All the tested complexes also show a strong in vitro antitumor activity against human ovarian carcinoma cell lines: MDAH 2774 (IC 50: 7–2 μM) and cisplatin-resistant SCOV 3 (IC 50: 3–2 μM). Interestingly, the complexes with dmp of higher biological activity more weakly interact with bovine serum albumin (BSA) and less efficiently cleave the pBluescriptSK+ plasmid. Copper(I) iodide complexes with phenanthrolines and tris(aminomethyl)phosphanes have a high in vitro antimicrobial and anticancer activity. Interestingly, the complexes with dmp (R′ = CH 3) having higher activity, more weakly interact with BSA and less efficiently cleave the pBluescriptSK+ plasmid. The activity depends also on the P Cu bond strength. [Display omitted] ► New copper(I) iodide complexes with diimines and P(CH 2N(Me)EtOH) 3 are described. ► X-ray structure of [CuI (phen)P(CH 2N(Me)EtOH) 3] is presented. ► CuI complexes with tris(aminomethyl)phosphanes have a high biological activity. ► Activity of the compounds correlates with their interactions with biomolecules. ► The plasmid cleavage and interactions with BSA depend on the molecular structures.