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

Autori
Kovačević, Monika ; Molčanov, Krešimir ; Radošević, Kristina ; Gaurina Srček, Višnja ; Roca, Sunčica ; Čače, Alana ; Barišić, Lidija

Izvornik
Molecules (1420-3049) 19 (2014), 8; 12852-12880

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
ferrocene ; proline ; peptidomimetic ; intramolecular hydrogen bond ; conformational analysis ; X-ray crystallography ; anticancer activity

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biotehnologija

POVEZANOST RADA