title: Redox behavior and biological properties of ferrocene bearing porphyrins.
abstract: In order to improve antimicrobial effects of previously studied meso-tetrakis(4-ferrocenylphenyl)porphyrin 1, we have modified its structure by replacing two trans-positioned ferrocenylphenyl moieties with methoxy methylene substituted tert-butylphenyl moieties. Newly synthesized 54,154-bis-(ferrocenyl)-104,204-bis-(tert-butyl)-102,106,202,206-tetrakis-(methoxy-methylene)-5,10,15,20-tetraphenylporphyrin 4 was chemically characterized in detail (by NMR, UV/Vis, IR, MALDI-TOF and ESI MS spectrometry, cyclic voltammetry, prediction of the relative lipophilicity as well as computational methods) and its biological effects were studied in terms of its antibacterial and antifungal activity (both with and without photoactivation), cytotoxicity, hemolysis and DNA cleavage. New ferrocene bearing porphyrin 4 has demonstrated a broader antimicrobial spectrum and modified effects on eukaryotic cells compared to 1. This was discussed in terms of its i) increased lipophilicity, while exhibiting lower toxicity, and ii) the redox potential of a two-electron process that is shifted to lower values, in comparison to ferrocene, thus, entering the physiologically available range and being activated towards redox interactions with biomolecules.
authors.affiliation: Department of Chemistry & Pharmacy, Friedrich-Alexander University Erlangen-Nuremberg, Egerlandstraße 1, D-91058 Erlangen, Germany.
authors.forename: Rainer
authors.initials: R
authors.lastname: Lippert
authors.affiliation: Computer Chemistry Center (CCC), Department of Chemistry & Pharmacy, Friedrich-Alexander University Erlangen-Nuremberg, Nägelsbachstraße 25, D-91052 Erlangen, Germany.
authors.forename: Tatyana E
authors.initials: TE
authors.lastname: Shubina
authors.affiliation: Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, 444a Vojvode Stepe, 11000 Belgrade, Serbia.
authors.forename: Sandra
authors.initials: S
authors.lastname: Vojnovic
authors.affiliation: Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, 444a Vojvode Stepe, 11000 Belgrade, Serbia.
authors.forename: Aleksandar
authors.initials: A
authors.lastname: Pavic
authors.affiliation: Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, 444a Vojvode Stepe, 11000 Belgrade, Serbia.
authors.forename: Jovana
authors.initials: J
authors.lastname: Veselinovic
authors.affiliation: Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, 444a Vojvode Stepe, 11000 Belgrade, Serbia.
authors.forename: Jasmina
authors.initials: J
authors.lastname: Nikodinovic-Runic
authors.affiliation: Institute of Molecular Genetics and Genetic Engineering, University of Belgrade, 444a Vojvode Stepe, 11000 Belgrade, Serbia.
authors.forename: Nada
authors.initials: N
authors.lastname: Stankovic
authors.affiliation: Department of Chemistry & Pharmacy, Friedrich-Alexander University Erlangen-Nuremberg, Egerlandstraße 1, D-91058 Erlangen, Germany. Electronic address: Ivana.Ivanovic@chemie.uni-erlangen.de.
authors.forename: Ivana
authors.initials: I
authors.lastname: Ivanović-Burmazović
mesh_terms: D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects*; D002175:Candida / Q000187:drug effects*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D005296:Ferrous Compounds / Q000737:chemistry*; D006801:Humans; D000075163:Metallocenes / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011166:Porphyrins / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D013194:Staining and Labeling
chemical_list: D000890:Anti-Infective Agents; D005296:Ferrous Compounds; D000075163:Metallocenes; D011166:Porphyrins; C004998:ferrocene
keywords: Antimicrobial; Cytotoxicity; Ferrocene; Porphyrin; Redox properties