Folic acid-conjugated europium complexes as luminescent probes for selective targeting of cancer cells

Silvio Quici, Alessandro Casoni, Francesca Foschi, Lidia Armelao, Gregorio Bottaro, Roberta Seraglia, Cristina Bolzati, Nicola Salvarese, Debora Carpanese, Antonio Rosato

Research output: Contribution to journalArticle

Abstract

We report the synthesis of three optical probes (Eu3+1, Eu3+2, and Eu3+3) having a luminescent Eu complex (signaling unit) bonded in different positions to folic acid (FA), the folate receptor (FR) targeting unit. The structures of the two regioisomers Eu3+1 and Eu3+2 were assigned by mass spectrometric experiments. The optical properties and stability of these probes were assessed in phosphate-buffered saline, cell culture medium, rat serum, and cellular lysate, and results indicated that they are chemically and photophysically stable. Cytotoxicity was studied with ovarian cancer cells having high (SKOV-3), intermediate (OVCAR-3), low (IGROV-1), or null (A2780) expression of FRs. The internalized probe, evaluated in SKOV-3, IGROV-1, and A2780 cells, was in the order Eu3+2 > Eu3+1 > Eu3+3. No internalization was observed for A2780 cells. Such results, together with those obtained in competition experiments of FA versus Eu3+2 and FA or Eu3+2 versus 3H-FA, indicate that internalization is receptor-mediated and that Eu3+2 shows high selectivity and specificity for FR.

Original languageEnglish
Pages (from-to)2003-2014
Number of pages12
JournalJournal of Medicinal Chemistry
Volume58
Issue number4
DOIs
Publication statusPublished - Feb 26 2015

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery
  • Medicine(all)

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  • Cite this

    Quici, S., Casoni, A., Foschi, F., Armelao, L., Bottaro, G., Seraglia, R., Bolzati, C., Salvarese, N., Carpanese, D., & Rosato, A. (2015). Folic acid-conjugated europium complexes as luminescent probes for selective targeting of cancer cells. Journal of Medicinal Chemistry, 58(4), 2003-2014. https://doi.org/10.1021/jm501945w