Conjugates of 1'-Aminoferrocene-1-carboxylic Acid and Proline: Synthesis, Conformational Analysis and Biological Evaluation
Monika Kovačević,
Krešimir Molčanov,
Kristina Radošević,
Višnja Gaurina Srček,
Sunčica Roca,
Alan Čače,
Lidija Barišić
Affiliations
Monika Kovačević
Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia
Krešimir Molčanov
Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia
Kristina Radošević
Department of Biochemical Engineering, Laboratory for Cell Technology, Aplication and Biotransformation, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia
Višnja Gaurina Srček
Department of Biochemical Engineering, Laboratory for Cell Technology, Aplication and Biotransformation, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia
Sunčica Roca
NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia
Alan Čače
Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia
Lidija Barišić
Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia
Our previous studies showed that alteration of dipeptides Y-Fca-Ala-OMe (III) into Y-Ala-Fca-OMe (IV) (Y = Ac, Boc; Fca = 1'-aminoferrocene-1-carboxylic acid) significantly influenced their conformational space. The novel bioconjugates Y-Fca-Pro-OMe (1, Y = Ac; 2, Y = Boc) and Y-Pro-Fca-OMe (3, Y = Boc; 4, Y = Ac) have been prepared in order to investigate the influence of proline, a well-known turn-inducer, on the conformational properties of small organometallic peptides with an exchanged constituent amino acid sequences. For this purpose, peptides 1–4 were subjected to detailed spectroscopic analysis (IR, NMR, CD spectroscopy) in solution. The conformation of peptide 3 in the solid state was determined. Furthermore, the ability of the prepared conjugates to inhibit the growth of estrogen receptor-responsive MCF-7 mammary carcinoma cells and HeLa cervical carcinoma cells was tested.
