Synthesis of conjugated spermine derivatives with 7-nitrobenzoxadiazole (NBD), rhodamine and bodipy as new fluorescent probes for the polyamine transport system

Bioorg Med Chem Lett. 2009 May 1;19(9):2474-7. doi: 10.1016/j.bmcl.2009.03.052. Epub 2009 Mar 18.

Abstract

The synthesis of a series of conjugated spermine derivatives with benzoxadiazole, phenylxanthene or bodipy fluorophores is described. These fluorescent probes were used to identify the activity of the polyamine transport system (PTS). N(1)-Methylspermine NBD conjugate 5 proved to have the optimal fluorescence characteristics and was used to show a selectivity for PTS-proficient CHO versus PTS-deficient CHO-MG cells. It can therefore be used as a tool for the selection of cells sensitive to cytotoxic compounds vectored through the PTS.

MeSH terms

  • Animals
  • Biological Transport
  • Boron Compounds / chemistry*
  • CHO Cells
  • Chemistry, Pharmaceutical / methods*
  • Cricetinae
  • Cricetulus
  • Drug Design
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacology*
  • Humans
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / pharmacology
  • Polyamines / chemistry
  • Rhodamines / chemistry*
  • Spermine / analogs & derivatives
  • Spermine / chemical synthesis*
  • Spermine / chemistry
  • Spermine / pharmacology

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • 7-nitrobenzoxadiazole
  • Boron Compounds
  • Fluorescent Dyes
  • Oxadiazoles
  • Polyamines
  • Rhodamines
  • alpha-methylspermine
  • 4-nitrobenzofurazan
  • Spermine