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Conjugates of 1'-aminoferrocene-1-carboxylic acid and proline : Synthesis, conformational analysis and biological evaluation

Kovačević, Monika; Molčanov, Krešimir; Radošević, Kristina; Gaurina Srček, Višnja; Roca, Sunčica; Čače, Alana; Barišić, Lidija (2014) Conjugates of 1'-aminoferrocene-1-carboxylic acid and proline : Synthesis, conformational analysis and biological evaluation. Molecules, 19 (8). pp. 12852-12880. ISSN 1420-3049

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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.

Item Type: Article
Uncontrolled Keywords: ferrocene; proline; peptidomimetic; intramolecular hydrogen bond; conformational analysis; X-ray crystallography; anticancer activity
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Physical Chemistry
NMR Center
Projects:
Project titleProject leaderProject codeProject type
Metalocenski biokonjugati, heterocikli i makromolekule-Veronika Kovač058-1191344-3122MZOS
Nekliničke metode ispitivanja tvari iz okoliša na stanicama sisavaca i riba-Višnja Gaurina-Srček058-0582184-2414MZOS
Protein-ligand međudjelovanja na atomnoj razini-Marija Luić098-1191344-2943MZOS
Depositing User: Krešimir Molčanov
Date Deposited: 14 Jul 2016 12:17
Last Modified: 14 Jul 2016 12:17
URI: http://fulir.irb.hr/id/eprint/2961
DOI: 10.3390/molecules190812852

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