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

Molecules. 2014 Aug 21;19(8):12852-80. doi: 10.3390/molecules190812852.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Carboxylic Acids / chemistry*
  • Cell Survival / drug effects
  • Circular Dichroism
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Ferrous Compounds / chemistry*
  • HeLa Cells
  • Humans
  • Hydrogen Bonding
  • Inhibitory Concentration 50
  • MCF-7 Cells
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology*
  • Proline / analogs & derivatives*
  • Proline / chemical synthesis*
  • Proline / pharmacology
  • Protein Structure, Secondary

Substances

  • 1'-aminoferrocene-1-carboxylic acid
  • Antineoplastic Agents
  • Carboxylic Acids
  • Ferrous Compounds
  • Oligopeptides
  • Proline