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

Molecules

Monika Kovaპvić³  Krešimir Molლnov⁴  Kristina Radoᘞvić²  Višnja Gaurina Srპk²  Sunčica Roca¹  Alan ჊პ³ 

[1] NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia; E-Mail:;Department of Biochemical Engineering, Laboratory for Cell Technology, Aplication and Biotransformation, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia; E-Mail:;Department of Chemistry and Biochemistry, Faculty of Food Technology and Biotechnology, Pierottijeva 6, Zagreb 10000, Croatia; E-Mails:;Division of Physical Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, Zagreb 10000, Croatia; E-Mail:

关键词: ferrocene;    proline;    peptidomimetic;    intramolecular hydrogen bond;    conformational analysis;    X-ray crystallography;    anticancer activity;   

DOI  :  10.3390/molecules190812852

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
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