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Molecules 2014, 19(8), 12852-12880; doi:10.3390/molecules190812852

Conjugates of 1'-Aminoferrocene-1-carboxylic Acid and Proline: Synthesis, Conformational Analysis and Biological Evaluation

1
Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia
2
Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia
3
Department of Biochemical Engineering, Laboratory for Cell Technology, Aplication and Biotransformation, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia
4
NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia
*
Authors to whom correspondence should be addressed.
Received: 1 July 2014 / Revised: 12 August 2014 / Accepted: 13 August 2014 / Published: 21 August 2014
(This article belongs to the Special Issue Intramolecular Hydrogen Bonding)
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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 14 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. View Full-Text
Keywords: ferrocene; proline; peptidomimetic; intramolecular hydrogen bond; conformational analysis; X-ray crystallography; anticancer activity ferrocene; proline; peptidomimetic; intramolecular hydrogen bond; conformational analysis; X-ray crystallography; anticancer activity
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MDPI and ACS Style

Kovačević, M.; Molčanov, K.; Radošević, K.; Srček, V.G.; Roca, S.; Čače, A.; Barišić, L. Conjugates of 1'-Aminoferrocene-1-carboxylic Acid and Proline: Synthesis, Conformational Analysis and Biological Evaluation. Molecules 2014, 19, 12852-12880.

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