Synthesis and assessment of a maleimide functionalized BF2 azadipyrromethene near-infrared fluorochrome

Chem Commun (Camb). 2015 Dec 4;51(93):16667-70. doi: 10.1039/c5cc06137g. Epub 2015 Oct 1.

Abstract

The first water soluble maleimide bearing NIR BF2-azadipyrromethene (NIR-AZA) fluorochrome has been synthesised which is capable of rapid thiol conjugations in water with peptides such as glutathione, the cell penetrating peptide (CPP) C(β-A)SKKKKTKV-NH2 and a thiol substituted cRGD. NIR fluorescence imaging showed rapid cellular delivery of the CPP conjugate and effective in vivo tumour localization for the cRGD conjugate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Aza Compounds / pharmacokinetics
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacokinetics
  • Glutathione / chemistry
  • Glutathione / pharmacokinetics
  • HeLa Cells
  • Humans
  • Infrared Rays*
  • Maleimides / chemistry*
  • Maleimides / pharmacokinetics
  • Mice
  • Molecular Structure
  • Neoplasms, Experimental / metabolism
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / pharmacokinetics
  • Porphobilinogen / analogs & derivatives*
  • Porphobilinogen / chemistry
  • Porphobilinogen / pharmacokinetics
  • Sulfhydryl Compounds / chemistry

Substances

  • Aza Compounds
  • Fluorescent Dyes
  • Maleimides
  • Peptides, Cyclic
  • Sulfhydryl Compounds
  • cyclic arginine-glycine-aspartic acid peptide
  • dipyrromethene
  • maleimide
  • Porphobilinogen
  • Glutathione