Chemistry on Boranils: an entry to functionalized fluorescent dyes

Org Lett. 2012 Sep 21;14(18):4774-7. doi: 10.1021/ol3020573. Epub 2012 Sep 7.

Abstract

A Boranil fluorophore bearing a nitro-phenyl group has been selectively reduced to its anilino form and then successfully converted to amide, imine, urea, and thiourea derivatives which are fluorescent dyes. Its isolated isothiocyanate intermediate derivative was used in a model labeling experiment with Bovine Serum Albumin (BSA). The purified labeled-BSA exhibits strong luminescence (Φ(f) = 47%) in a phosphate buffer at pH = 7.4.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Hydrogen-Ion Concentration
  • Isothiocyanates
  • Molecular Structure
  • Serum Albumin, Bovine / chemistry
  • Thiourea / chemistry
  • Urea / chemistry

Substances

  • Boron Compounds
  • Fluorescent Dyes
  • Isothiocyanates
  • Serum Albumin, Bovine
  • isothiocyanic acid
  • Urea
  • Thiourea