Site-specific photomodification of DNA by porphyrin-oligonucleotide conjugates synthesized via a solid phase H-phosphonate approach.
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.
Li
H
H
Department of Chemistry, University of Idaho, Moscow 83844, USA.
Fedorova
O S
OS
Trumble
W R
WR
Fletcher
T R
TR
Czuchajowski
L
L
D002851:Chromatography, High Pressure Liquid; D004247:DNA / Q000737:chemistry*; D003720:Densitometry; D019075:Electrophoresis, Capillary; D008956:Models, Chemical; D009690:Nucleic Acid Conformation; D016376:Oligonucleotides, Antisense / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D010777:Photochemistry; D011071:Poly T / Q000138:chemical synthesis; D011166:Porphyrins / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D016376:Oligonucleotides, Antisense; D063065:Organophosphonates; D011166:Porphyrins; D011071:Poly T; D004247:DNA