NDLI: The conjugates of ferrocene-1,1′-diamine and amino acids. A novel synthetic approach and conformational analysis

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Semencic, Mojca Cakic Barisic, Lidija Kovacevic, Monika Roca, Suncica Cetina, Mario Kodrin, Ivan Murati, Teuta Kmetic, Ivana
Description	Author Affiliation: Kovacevic M ( Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, Zagreb, Croatia. lidija.barisic@pbf.hr.)
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––Fn–OH (5) (Fn = 1,1′-ferrocenylene) to orthogonally protected Ac–Ala––Fn–Boc (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.
ISSN	14779226
Issue Number	37
Volume Number	44
e-ISSN	13645447
Journal	Dalton Trans.
Language	English
Publisher	Royal Society of Chemistry
Publisher Date	2015-10-07
Publisher Place	Great Britain (UK)
Access Restriction	Subscribed
Subject Keyword	Amino Acids Chemistry Antineoplastic Agents Diamines Ferrous Compounds Chemical Synthesis Toxicity Cell Line, Tumor Cell Survival Drug Effects Crystallography, X-Ray Hep G2 Cells Humans Hydrogen Bonding Magnetic Resonance Spectroscopy Molecular Conformation Peptides Journal Article Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Inorganic Chemistry

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