New iron cyclopentadienyl complexes bearing different phosphane co-ligands: Structural factors vs. cytotoxicity

Adhan Pilon, Patrícia Gírio, Guilherme Nogueira, Fernando Avecilla, Harry Adams, Julia Lorenzo, M. Helena Garcia, Andreia Valente

Research output: Contribution to journalArticleResearchpeer-review

12 Citations (Scopus)

Abstract

© 2017 Elsevier B.V. A new family of piano stool iron-cyclopentadienyl compounds bearing different phosphane co-ligands has been synthesized. All the compounds, with the general structure [Fe(Cp)(CO)(PR 3 )(L)] n (PR 3 = triphenylphosphane, 4-(diphenylphosphino) benzoic acid or tris(4-fluorophenyl)phosphane; when L = I, n = 0; when L = 4-aminobenzonitrile, n = +1) were fully characterized by the usual analytical and spectroscopic techniques. Interestingly, compound [Fe(Cp)(CO)(PPh 3 )I] 1 crystalizes in the orthorhombic space group P2 1 2 1 2 1 and its crystal packing only contains one enantiomer, while compound [Fe(η 5 -Cp)(CO)(P(Ph-p-F) 3 )I] 3 crystalizes in the centrosymmetric space group Pbca presenting an important disorder in the structure, probably due to the presence of the two enatiomers in the crystal packing. All the compounds presented adequate stability in aqueous solution and they were tested against cervical HeLa human cancer cells. The cationic complexes bearing triphenylphosphane (4) or tris(4-fluorophenyl)phosphane (6) were found to be highly cytotoxic, causing cell death by apoptosis. The results point out that the electronic features of the new compounds might be related to their cytotoxic activity.
Original languageEnglish
Pages (from-to)34-42
JournalJournal of Organometallic Chemistry
Volume852
DOIs
Publication statusPublished - 1 Dec 2017

Keywords

  • Anticancer
  • Apoptosis
  • Electronic flow
  • Iron cyclopentadienyl

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