Bis(o-methylserotonin)-containing iridium(III) and ruthenium(II) complexes as new cellular imaging dyes: synthesis, applications, and photophysical and computational studies

J Biol Inorg Chem. 2013 Aug;18(6):679-92. doi: 10.1007/s00775-013-1013-5. Epub 2013 Jun 22.

Abstract

We report the synthesis, characterization, and scope of a new versatile emissive molecular probe functionalized with a 1,10-phenanthroline moiety containing methylserotonin groups as binding sites for metal ion recognition. The synthesis, characterization, and evaluation of the in vitro imaging capability of the iridium(III) and ruthenium(II) complexes [Ir(ppy)2(N-N)](+) and [Ru(bpy)2(N-N)](2+), in which ppy is 2-phenylpyridine, bpy is 2,2'-bipyridine, and N-N is a 1,10-phenanthroline ligand functionalized with two methylserotonin groups to serve as binding sites for metal ion recognition, is reported. The uptake of these compounds by living freshwater fish (Carassius auratus) was studied by fluorescence microscopy, and the cytotoxicity of ligand N-N and [Ru(bpy)2(N-N)](2+) in this species was also investigated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Fluorescent Dyes / analysis
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacokinetics
  • Goldfish / metabolism
  • Iridium / chemistry*
  • Microscopy, Fluorescence
  • Models, Biological
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / analysis*
  • Organometallic Compounds / chemical synthesis
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / pharmacokinetics
  • Photochemical Processes
  • Quantum Theory
  • Ruthenium / chemistry*
  • Serotonin / analogs & derivatives*
  • Serotonin / chemistry
  • Tissue Distribution

Substances

  • Fluorescent Dyes
  • Organometallic Compounds
  • Serotonin
  • Iridium
  • Ruthenium