Synthesis and spectral properties of cholesterol- and FTY720-containing boron dipyrromethene dyes

J Org Chem. 2007 Oct 26;72(22):8376-82. doi: 10.1021/jo701475q. Epub 2007 Oct 3.

Abstract

Two analogues (1, 2) of free cholesterol and one analogue (3) of the immunosuppressive sphingolipid FTY720 containing a boron dipyrromethene chromophore (BODIPY) were synthesized. The synthetic routes involved preparation of boron dipyrromethene moieties (5, 11), bearing a phenylethynyl group at different positions of the chromophore, and lipids (13, 20) bearing an azido group. The dye was tethered to the lipid via a 1,2,3-triazole in the linker by the click reaction. Analogues derived from 11 [in which an (E)-styrylethynyl moiety is bonded to C-5 of BODIPY] exhibited a marked red shift (approximately 70-80 nm) compared with those derived from 5 (in which a phenylethynyl moiety is bonded to C-8 of BODIPY).

Publication types

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

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Compounds / chemistry
  • Cholesterol / chemistry*
  • Fingolimod Hydrochloride
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Molecular Structure
  • Porphobilinogen / analogs & derivatives*
  • Porphobilinogen / chemical synthesis
  • Porphobilinogen / chemistry
  • Propylene Glycols / chemistry*
  • Spectrophotometry, Ultraviolet / methods
  • Sphingosine / analogs & derivatives*
  • Sphingosine / chemistry
  • Stereoisomerism

Substances

  • Boron Compounds
  • Fluorescent Dyes
  • Propylene Glycols
  • dipyrromethene
  • Porphobilinogen
  • Cholesterol
  • Fingolimod Hydrochloride
  • Sphingosine