title: The conjugates of ferrocene-1,1'-diamine and amino acids. A novel synthetic approach and conformational analysis.
abstract: A novel synthetic approach toward a poorly explored bioorganometallic consisting of ferrocene-1,1'-diamine bearing structurally and chirally diverse amino acid sequences is reported. Until now, ferrocene-1,1'-diamine was suitable for accommodating only identical amino acid sequences at its N-termini, leading to the symmetrically disubstituted homochiral products stabilized through a 14-membered intramolecular hydrogen-bonded ring as is seen in antiparallel β-sheet peptides. The key step of the novel synthetic pathway is the transformation of Ac-Ala-NH-Fn-COOH (5) (Fn = 1,1'-ferrocenylene) to orthogonally protected Ac-Ala-NH-Fn-NHBoc (7). The spectroscopic analysis (IR, NMR, CD) of the novel compounds, corroborated with DFT studies, suggests the interesting feature of the ferrocene-1,1'-diamine scaffold. The same hydrogen-bonding pattern, i.e. a 14-membered hydrogen-bonded ring, was determined both in solution and in the solid state, thus making them promising, yet simple scaffolds capable of mimicking β-sheet peptides. In vitro screening of potential anticancer activity in Hep G2 human liver carcinoma cells and Hs 578 T human breast cancer cells revealed a cytotoxic pattern for novel compounds (150-500 μM) with significantly decreased cell proliferation.
authors: Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, Zagreb, Croatia. lidija.barisic@pbf.hr.
authors: Monika
authors: M
authors: Kovačević
authors: Ivan
authors: I
authors: Kodrin
authors: Mario
authors: M
authors: Cetina
authors: Ivana
authors: I
authors: Kmetič
authors: Teuta
authors: T
authors: Murati
authors: Mojca Čakić
authors: MČ
authors: Semenčić
authors: Sunčica
authors: S
authors: Roca
authors: Lidija
authors: L
authors: Barišić
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D003959:Diamines / Q000737:chemistry*; D005296:Ferrous Compounds / Q000737:chemistry*; D056945:Hep G2 Cells; D006801:Humans; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D000075163:Metallocenes; D008968:Molecular Conformation; D010455:Peptides / Q000737:chemistry
chemical_list: D000596:Amino Acids; D000970:Antineoplastic Agents; D003959:Diamines; D005296:Ferrous Compounds; D000075163:Metallocenes; D010455:Peptides; C004998:ferrocene