Curtin University Homepage
  • Library
  • Help
    • Admin

    espace - Curtin’s institutional repository

    JavaScript is disabled for your browser. Some features of this site may not work without it.
    View Item 
    • espace Home
    • espace
    • Curtin Research Publications
    • View Item
    • espace Home
    • espace
    • Curtin Research Publications
    • View Item

    Synthesis, reactivity and preliminary biological activity of iron(0) complexes with cyclopentadienone and amino-appended N-heterocyclic carbene ligands

    91825.pdf (496.3Kb)
    Access Status
    Open access
    Authors
    Cingolani, A.
    Zanotti, V.
    Zacchini, S.
    Massi, Max
    Simpson, Peter
    Maheshkumar Desai, N.
    Casari, I.
    Falasca, Marco
    Rigamonti, L.
    Mazzoni, R.
    Date
    2019
    Type
    Journal Article
    
    Metadata
    Show full item record
    Citation
    Cingolani, A. and Zanotti, V. and Zacchini, S. and Massi, M. and Simpson, P.V. and Maheshkumar Desai, N. and Casari, I. et al. 2019. Synthesis, reactivity and preliminary biological activity of iron(0) complexes with cyclopentadienone and amino-appended N-heterocyclic carbene ligands. Applied Organometallic Chemistry. 33 (4): ARTN e4779.
    Source Title
    Applied Organometallic Chemistry
    DOI
    10.1002/aoc.4779
    ISSN
    0268-2605
    Faculty
    Faculty of Science and Engineering
    Faculty of Health Sciences
    School
    School of Molecular and Life Sciences (MLS)
    Curtin Medical School
    Funding and Sponsorship
    http://purl.org/au-research/grants/arc/FT130100033
    URI
    http://hdl.handle.net/20.500.11937/92001
    Collection
    • Curtin Research Publications
    Abstract

    Neutral and cationic cyclopentadienone (CpO) N-heterocyclic carbene (NHC) bis-carbonyl iron(0) complexes bearing, appended to the NHC ligand, either a terminal amino group on the lateral chain, [Fe(η 4 -CpO)(CO) 2 (κC-NHC(CH 2 ) n NH 2 )] with n = 2 (2a) and 3 (2b), or a cationic NMe 3+ fragment, [Fe(η 4 -CpO)(CO) 2 (κC-NHC(CH 2 ) 2 NMe 3 )](I) (3), were prepared and characterized in terms of their structure, stability and reactivity. The photochemical properties of 2a and 2b were examined both in organic solvents and in water, revealing the photoactivated release of one CO ligand followed by the formation of the chelated complex [Fe(η 4 -CpO)(CO)(κ 2 C,N-NHC(CH 2 ) 2 NH 2 )] (4), whose molecular structure was confirmed by single crystal X-ray diffraction studies. This metallacyclization occurs only in the case of 2a, with the ethylene spacer between NHC ring and NH 2 group in the lateral chain, allowing the formation of a stable 6-membered ring. On the other hand, 2b undergoes decomposition upon irradiation. The reactivity in aqueous solutions revealed the chemical speciation of the complexes at different pH and especially under physiological conditions (phosphate buffer solution at pH 7.4 and 37 °C). The lack of data on the biological properties of iron(0) complexes prompted us to preliminarily investigate their cytotoxicity against model cancer cells (AsPC-1 and HPAF-II), along with a determination of their lipophilicity.

    Related items

    Showing items related by title, author, creator and subject.

    • Iron Formations: Their Origins and Implications for Ancient Seawater Chemistry
      Bekker, A.; Planavsky, N.; Rasmussen, Birger; Krapez, Bryan; Hofmann, A.; Slack, J.; Rouxel, O.; Konhauser, K. (2014)
      Iron formations are economically significant, iron- and silica-rich sedimentary rocks that are restricted to Precambrian successions. There are no known modern or Phanerozoic analogues for these deposits that are comparable ...
    • Cellular iron depletion stimulates the JNK and p38 MAPK signaling transduction pathways, dissociation of ASK1-thioredoxin, and activation of ASK1
      Yu, Yu; Richardson, D. (2011)
      The role of signaling pathways in the regulation of cellular iron metabolism is becoming increasingly recognized. Iron chelation is used for the treatment of iron overload but also as a potential strategy for cancer ...
    • Effect of iron corrosion on the fate of dosed copper to inhibit nitrification in chloraminated water distribution system
      Zhan, Weixi (2011)
      Nitrification has been acknowledged as one of the major barriers towards efficient chloramination in water supply distribution systems. Many water utilities employing monochloramine as the final disinfectant have been ...
    Advanced search

    Browse

    Communities & CollectionsIssue DateAuthorTitleSubjectDocument TypeThis CollectionIssue DateAuthorTitleSubjectDocument Type

    My Account

    Admin

    Statistics

    Most Popular ItemsStatistics by CountryMost Popular Authors

    Follow Curtin

    • 
    • 
    • 
    • 
    • 

    CRICOS Provider Code: 00301JABN: 99 143 842 569TEQSA: PRV12158

    Copyright | Disclaimer | Privacy statement | Accessibility

    Curtin would like to pay respect to the Aboriginal and Torres Strait Islander members of our community by acknowledging the traditional owners of the land on which the Perth campus is located, the Whadjuk people of the Nyungar Nation; and on our Kalgoorlie campus, the Wongutha people of the North-Eastern Goldfields.