TMIO-PyrImid hybrids are profluorescent, site-directed spin labels for nucleic acids

Org Lett. 2014 Nov 7;16(21):5528-31. doi: 10.1021/ol502003a. Epub 2014 Oct 28.

Abstract

We report the synthesis of a new class of molecules which are hybrids of long-lived tetramethylisoindolinoxyl (TMIO) radicals and the pyrido[1,2-a]benzimidazole (PyrImid) scaffold. These compounds represent a new lead for noncovalently binding nucleic acid probes, as they interact with nucleic acids with previously unreported C (DNA) and C/U (RNA) complementarity, which can be detected by electron paramagnetic resonance (EPR) techniques. They also have promising properties for fluorimetric analysis, as their fluorescent spin-quenched derivatives exhibit a significant Stokes shift.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemistry*
  • DNA / chemistry*
  • Electron Spin Resonance Spectroscopy / methods*
  • Isoindoles / chemistry*
  • Molecular Structure
  • Nucleic Acids / chemistry*
  • Pyridines / chemistry*
  • RNA / chemistry*
  • Spin Labels / chemical synthesis*

Substances

  • Benzimidazoles
  • Isoindoles
  • Nucleic Acids
  • Pyridines
  • Spin Labels
  • RNA
  • DNA