Site-specific photomodification of DNA by porphyrin-oligonucleotide conjugates synthesized via a solid phase H-phosphonate approach

Bioconjug Chem. 1997 Jan-Feb;8(1):49-56. doi: 10.1021/bc960074t.

Abstract

meso-Tris(4-pyridyl)[[(omega-hydroxyhexamethylene)carbamoyl]phenyl ] porphyrin was converted to its H-phosphonate derivative and conjugated using solid phase synthesis with the 5'-hydroxyl group of deoxyribonucleotides d(TCTTCCCA) and d(T)12. These conjugates were transformed into their (N-methylpyridiniumyl)porphyrin analogs in the reaction with methyl iodide. A 532 nm laser beam was utilized to photoactivate both types of the conjugates in the presence of the target 22-mer and 16-mer oligonucleotides. Photoactivation of porphyrin-oligonucleotide conjugates resulted in site-specific DNA modification characterized by a main reaction site size of approximately 5 bases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • DNA / chemistry*
  • Densitometry
  • Electrophoresis, Capillary
  • Models, Chemical
  • Nucleic Acid Conformation
  • Oligonucleotides, Antisense / chemistry*
  • Organophosphonates / chemistry*
  • Photochemistry
  • Poly T / chemical synthesis
  • Porphyrins / chemistry*
  • Spectrophotometry, Ultraviolet

Substances

  • Oligonucleotides, Antisense
  • Organophosphonates
  • Porphyrins
  • Poly T
  • DNA