JBIC Journal of Biological Inorganic Chemistry

, Volume 18, Issue 7, pp 831–844 | Cite as

Synthesis, characterization, and biological studies of emissive rhenium–glutamine conjugates

  • Rachel Huang
  • Graeme Langille
  • Ravanjir K. Gill
  • Cindy Mei Jin Li
  • Yuji Mikata
  • May Q. Wong
  • Donald T. Yapp
  • Tim Storr
Original Paper

Abstract

Two new rhenium complexes containing pyridine–triazole (pyta) and quinoline–triazole (quinta) ligands with attached glutamine-targeting agents have been characterized and tested for uptake in the HT-29 human colon adenocarcinoma cell line. The glutamine moiety in Re(CO)3Br(pyta) (1) and Re(CO)3Br(quinta) (2) remains pendant in solution. Both complexes exhibit absorptions in the 300–400-nm range with metal-to-ligand charge transfer (MLCT) character, as predicted by time-dependent density functional theory calculations. Geometrical analysis by theoretical calculations provides information on the cationic complexes 1+ and 2+ resulting from aquo for halide ligand exchange under aqueous conditions. The emissive properties of both complexes were studied under aqueous conditions, and the measured quantum yields were 0.46 % for 1+ and 0.18 % for 2+. The large Stokes shifts and oxygen sensitivity of the emission suggest a 3MLCT process for both complexes. Cell studies in the HT-29 cell line demonstrate that both complexes are nontoxic over a large concentration range (0–1.4 mM). Preliminary uptake studies show that 2+, but not 1+, displays significant concentration-dependent uptake at 3 and 24 h.

Graphical abstract

Keywords

Cancer imaging Electronic structure Density functional theory Fluorescence 

Supplementary material

775_2013_1023_MOESM1_ESM.pdf (946 kb)
Supplementary material 1 (PDF 947 kb)

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Copyright information

© SBIC 2013

Authors and Affiliations

  • Rachel Huang
    • 1
  • Graeme Langille
    • 1
  • Ravanjir K. Gill
    • 2
  • Cindy Mei Jin Li
    • 1
  • Yuji Mikata
    • 3
  • May Q. Wong
    • 2
  • Donald T. Yapp
    • 2
  • Tim Storr
    • 1
  1. 1.Department of ChemistrySimon Fraser UniversityBurnabyCanada
  2. 2.The BC Cancer Agency Research CentreVancouverCanada
  3. 3.KYOUSEI Science CenterNara Women’s UniversityNaraJapan

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