title: Conjugates of 1'-aminoferrocene-1-carboxylic acid and proline: synthesis, conformational analysis and biological evaluation.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia. mkovacevic@pbf.hr.
authors.forename: Monika
authors.initials: M
authors.lastname: Kovačević
authors.affiliation: Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia. Kresimir.Molcanov@irb.hr.
authors.forename: Krešimir
authors.initials: K
authors.lastname: Molčanov
authors.affiliation: Department of Biochemical Engineering, Laboratory for Cell Technology, Aplication and Biotransformation, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia. vgaurina@pbf.hr.
authors.forename: Kristina
authors.initials: K
authors.lastname: Radošević
authors.affiliation: Department of Biochemical Engineering, Laboratory for Cell Technology, Aplication and Biotransformation, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia. vgaurina@pbf.hr.
authors.forename: Višnja Gaurina
authors.initials: VG
authors.lastname: Srček
authors.affiliation: NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia. sroca@irb.hr.
authors.forename: Sunčica
authors.initials: S
authors.lastname: Roca
authors.affiliation: Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia.
authors.forename: Alan
authors.initials: A
authors.lastname: Cače
authors.affiliation: Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia. lbaris@pbf.hr.
authors.forename: Lidija
authors.initials: L
authors.lastname: Barišić
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D002264:Carboxylic Acids / Q000737:chemistry*; D002470:Cell Survival / Q000187:drug effects; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D005296:Ferrous Compounds / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D006860:Hydrogen Bonding; D020128:Inhibitory Concentration 50; D061986:MCF-7 Cells; D009842:Oligopeptides / Q000737:chemistry / Q000494:pharmacology*; D011392:Proline / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D017433:Protein Structure, Secondary
chemical_list: C504075:1'-aminoferrocene-1-carboxylic acid; D000970:Antineoplastic Agents; D002264:Carboxylic Acids; D005296:Ferrous Compounds; D009842:Oligopeptides; D011392:Proline