Oligonucleotide labeling: synthesis of a new spin-labeled 2'-deoxyguanosine analogue

Nucleosides Nucleotides Nucleic Acids. 2000 Aug;19(8):1301-10. doi: 10.1080/15257770008033053.

Abstract

In order to achieve an EPR sensitive probe for DNA, 3-carboxy-Proxyl free radical was linked to O-6 of dG through a five-atoms-tether. The modified base was incorporated into a 30-mer ODN, then annealed to its complementary DNA strand. Hydrodynamic parameters show only a slight destabilization with respect to the equivalent unlabeled hybrid. EPR could monitor the hybrid formation showing a progressive enlargement of the upfield signal in passing from the labeled ss- to the ds-30-mer.

MeSH terms

  • Cyclic N-Oxides / chemistry*
  • DNA / analysis*
  • Deoxyguanosine / analogs & derivatives
  • Deoxyguanosine / chemical synthesis*
  • Deoxyguanosine / chemistry
  • Electron Spin Resonance Spectroscopy
  • Fluorescence Polarization
  • Free Radicals
  • Nucleic Acid Conformation
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry
  • Spectrophotometry, Ultraviolet
  • Spin Labels / chemical synthesis*

Substances

  • 5'-O-(4,4'-dimethoxytrityl)-O(6)-(3-(2,2,5,5-tetramethyl-1-pyrrolidinyloxy-3-carboxamido)propyl)deoxyguanosine-3'-(O-cyanoethyl-N,N-diisopropyl)phosphoramidite
  • Cyclic N-Oxides
  • Free Radicals
  • Organophosphorus Compounds
  • Spin Labels
  • 2,2,5,5-tetramethyl-1-pyrrolidinyloxy-3-carboxylic acid
  • DNA
  • Deoxyguanosine