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 | ||||||||||||||||
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| 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 |
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| Depositing User: | Krešimir Molčanov | ||||||||||||||||
| Date Deposited: | 14 Jul 2016 12:17 | ||||||||||||||||
| URI: | http://fulir.irb.hr/id/eprint/2961 | ||||||||||||||||
| DOI: | 10.3390/molecules190812852 |
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