Deep-red fluorescent imaging probe for bacteria

Bioorg Med Chem Lett. 2012 Apr 15;22(8):2833-6. doi: 10.1016/j.bmcl.2012.02.078. Epub 2012 Mar 3.

Abstract

A versatile deep-red fluorescent imaging probe is described that is comprised of a bis(zinc(II)-dipicolylamine) targeting unit covalently attached to a pentamethine carbocyanine fluorophore with Cy5-like spectroscopic properties. A titration assay based on fluorescence resonance energy transfer is used to prove that the probe selectively associates with anionic vesicle membranes whose composition mimics bacterial cell membranes. Whole-body optical imaging experiments show that the probe associates with the surfaces of both Gram-positive and Gram-negative bacteria cells, and it can target the site of bacterial infection in a living mouse. In vivo accumulation at the infection site and subsequent clearance occurs more quickly than a structurally related near-infrared bis(zinc(II)-dipicolylamine) probe. The fact that the same deep-red probe molecule can be used for spectroscopic assays, cell microscopy, and in vivo imaging studies, is an important and attractive technical feature.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bacterial Infections / diagnosis
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / metabolism*
  • Luminescent Proteins / chemistry
  • Luminescent Proteins / metabolism
  • Mice
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry
  • Organometallic Compounds / metabolism*
  • Picolinic Acids / chemical synthesis*
  • Picolinic Acids / chemistry
  • Picolinic Acids / metabolism*
  • Red Fluorescent Protein
  • Solubility
  • Water / chemistry

Substances

  • Fluorescent Dyes
  • Luminescent Proteins
  • Organometallic Compounds
  • Picolinic Acids
  • bis-dipicolylamine-Zinc(II)
  • Water