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Synthesis, Properties and Biological Evaluation of Ferrocene-Modified Peptides and Biomolecules

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Physical Chemistry and Chemical Physics".

Deadline for manuscript submissions: 15 July 2024 | Viewed by 508

Special Issue Editor


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Guest Editor
Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, University of Zagreb, Pierottijeva 6, 10000 Zagreb, Croatia
Interests: ferrocene bioconjugates; organometallic chemistry; conformational analysis; synthesis; peptidomimetics; bioactivity
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Special Issue Information

Dear Colleagues,

The bioorganometallic chemistry of ferrocene addresses the role of ferrocene in biological systems, focusing on the design and synthesis of ferrocene-containing peptides as models for the study of protein folding, and ferrocene conjugates with biomolecules used to diagnose and combat microbial infections.

The design and development of small molecules that mimic the secondary structures of recognition domains in protein-protein interactions have been the focus of scientific research over the past 40 years. Being structurally different from natural analogs, peptide and protein mimetics are characterized by higher conformational and proteolytic stability and generally better pharmacological properties compared to natural peptides and proteins. One of the approaches for designing peptidomimetics is based on the use of small, rigid molecular scaffolds such as ferrocene, which are capable of inducing highly ordered secondary structure elements when inserted into the unordered peptides.

Ferrocene is not only easy to modify, but is also characterized by stability, redox activity, and lipophilicity, which gives its conjugates with biomolecules significant biological potential. For example, the problems of ineffectiveness of tamoxifen against estrogen-independent cancer cells and microbial resistance to chloroquine have been successfully solved by derivatization with ferrocene to obtain the ferrocifen and ferroquine, which are considered the best-known bioorganometallic compounds.

Considering the beneficial effect that ferrocene may have on the molecular properties and biological activity of its conjugates with peptides and biomolecules, you are cordially invited to contribute to this Special Issue with your work.

Dr. Lidija Barišić
Guest Editor

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Published Papers (1 paper)

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Review

39 pages, 8508 KiB  
Review
Recent Advances in the Field of Amino Acid-Conjugated Aminoferrocenes—A Personal Perspective
by Mojca Čakić Semenčić, Monika Kovačević and Lidija Barišić
Int. J. Mol. Sci. 2024, 25(9), 4810; https://doi.org/10.3390/ijms25094810 - 28 Apr 2024
Viewed by 299
Abstract
The development of turn-based inhibitors of protein–protein interactions has attracted considerable attention in medicinal chemistry. Our group has synthesized a series of peptides derived from an amino-functionalized ferrocene to investigate their potential to mimic protein turn structures. Detailed DFT and spectroscopic studies (IR, [...] Read more.
The development of turn-based inhibitors of protein–protein interactions has attracted considerable attention in medicinal chemistry. Our group has synthesized a series of peptides derived from an amino-functionalized ferrocene to investigate their potential to mimic protein turn structures. Detailed DFT and spectroscopic studies (IR, NMR, CD) have shown that, for peptides, the backbone chirality and bulkiness of the amino acid side chains determine the hydrogen-bond pattern, allowing tuning of the size of the preferred hydrogen-bonded ring in turn-folded structures. However, their biological potential is more dependent on their lipophilicity. In addition, our pioneering work on the chiroptical properties of aminoferrocene-containing peptides enables the correlation of their geometry with the sign of the CD signal in the absorption region of the ferrocene chromophore. These studies have opened up the possibility of using aminoferrocene and its derivatives as chirooptical probes for the determination of various chirality elements, such as the central chirality of amino acids and the helicity of peptide sequences. Full article
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