Ferrocene Bioconjugates

Abstract

In this review we present our recent contribution to the field of bioorganometallic chemistry of ferrocene. Ferrocene conjugates with biomolecules have been synthesized and characterized using IR and NMR (1 H, 13 C, COSY, NOESY, HMBC) spectroscopy, ESI-MS and HRMS. The bioconjugates of ferrocene with resveratrol (2) and mannose (10, 11, 14 and 15) were biologically evaluated for their potential inhibitory effect on HepG2 cancer cells (2) and E. coli adherence to the bladder epithelium (10, 11, 14 and 15). The oxalamide-bridged ferrocene 17 was subjected to conformational analysis in solution and in the solid state, and tested for its gelation and cytotoxic activity.

Synthesis and Conformational Study of Monosubstituted Aminoferrocene‐Based Peptides Bearing Homo‐ and Heterochiral Pro‐Ala Sequences

“…[1][2][3] One group of ferrocene bioconjugates, namely, ferrocene peptides, came into focus because of their ability to mimic the secondary structures of proteins. [3][4][5][6][7][8][9] The distance of 3.3 Å between the two cyclopentadienyl (Cp) rings promotes intramolecular hydrogen bonding between two peptide chains attached to the rings of the ferrocene unit. [1,2] More recently, a series of mono-and disubstituted ferrocene peptide derivatives have shown self-assembly and gelation behaviour.…”

“…Studies of the conformational properties of disubstituted ferrocene peptides are much more common. The restricted rotation of ferrocene rings, induced by interchain constraints, gives rise to a helically chiral arrangement of the ferrocene core in conjugates of ferrocene-1,1′-dicarboxylic acid (Fcd), [4] 1′-aminoferrocene-1-carboxylic acid (Fca) [5][6][7] and 1,1′-diaminoferrocene (Fcda) [8] with natural amino acids and peptides ( Figure 1). The circular dichroism spectra of these derivatives are characterized by strong bands around the UV/Vis absorption maximum of the ferrocene chromophore (λ max ≈ 455 nm) as a result of an ordered conformation of the ferrocene scaffold.…”

Administration of ferrocene‐modified amino acids induces changes in synaptic transmission in the CA1 area of the hippocampus

“…Ferrocene‐based pyrazole‐containing amino acids were successfully prepared by Vukićević and co‐workers, and evaluated as promising antitumor agents . In a recent review, ferrocene conjugates with several natural amino acids were subjected to the detailed conformational and DFT analyses in order to determine the turn‐inducing potential of ferrocene scaffolds in the corresponding peptidomimetics …”

Biological Evaluation and Conformational Preferences of Ferrocene Dipeptides with Hydrophobic Amino Acids

“…Although many organic compounds and natural products with incorporated ferrocene units [29] have been investigated as potential drugs [30] due to the desirable properties of ferrocene (non-toxicity, stability, and lipophilicity), the literature on the bioactivity of 1,1 -disubstituted ferrocene peptides is very limited. To date, only a few studies on their biological activity have been performed, most of them carried out by our group to provide a guide for the development of potential drug candidates [6,[31][32][33]. Unfortunately, conjugates with the incorporated −NH−Fn−CO− template [Y-Fca-Pro-OMe (I, Y = Ac, Boc), Y-Pro-Fca-OMe (II, Y = Ac, Boc), and homo-and heterochiral Y-Pro-Ala-Fca-OMe (III, Y = Ac, Boc)] showed no or rather modest antiproliferative activity on MCF-7 and HeLa cell lines.…”