Simple one-pot preparation of water-soluble, cysteine-reactive cyanine and merocyanine dyes for biological imaging

Bioconjug Chem. 2007 Jul-Aug;18(4):1344-8. doi: 10.1021/bc060376n. Epub 2007 Jun 2.

Abstract

A simple one-pot-procedure for preparation of protein-reactive, water-soluble merocyanine and cyanine dyes has been developed. The 1-(3-ammoniopropyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate bromide (1) was used as a common starting intermediate. The method allows easy preparation of dyes with chloro- and iodoacetamide side chains for covalent attachment to cysteine. By placing a sulfonato group directly on the dye fluorophore system, dyes with high fluorescence quantum yields in water were generated. Both iodo- and chloroacetamido derivatives were shown to be useful in protein labeling. Less reactive chloroacetamides will be preferential for selective labeling of the most reactive cysteines.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carbocyanines / chemistry*
  • Carbocyanines / metabolism
  • Cysteine / chemistry
  • Diagnostic Imaging
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / metabolism
  • Green Fluorescent Proteins / metabolism
  • Mitogen-Activated Protein Kinase 1 / metabolism
  • Pyrimidinones / chemistry*
  • Pyrimidinones / metabolism
  • Recombinant Fusion Proteins / metabolism
  • Solubility
  • Water

Substances

  • Carbocyanines
  • Fluorescent Dyes
  • Pyrimidinones
  • Recombinant Fusion Proteins
  • enhanced green fluorescent protein
  • Water
  • Green Fluorescent Proteins
  • merocyanine dye
  • Mitogen-Activated Protein Kinase 1
  • Cysteine