5'-Porphyrin-oligonucleotide conjugates: neutral porphyrin-DNA interactions

Org Lett. 2005 Dec 8;7(25):5613-6. doi: 10.1021/ol0522992.

Abstract

[chemical reaction: see text]. Incorporation of hydrophilic tetraarylporphyrin phosphoramidites into the 5'-termimus of the DNA as well as noncharged porphyrin-DNA interactions have been studied. Porphyrin-modified oligonucleotides show lower melting temperatures than their unmodified analogues. Single-stranded DNA interacts more strongly with porphyrin and causes more intense chiral disturbance in the porphyrin environment than the corresponding double strand.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Base Composition
  • Base Sequence
  • Circular Dichroism
  • DNA / chemistry*
  • DNA / metabolism
  • Molecular Structure
  • Oligonucleotides / chemistry*
  • Organophosphorus Compounds / chemistry*
  • Porphyrins / chemistry*
  • Porphyrins / metabolism

Substances

  • Oligonucleotides
  • Organophosphorus Compounds
  • Porphyrins
  • phosphoramidite
  • DNA