Photoinduced cleavage of DNA by bromofluoroacetophenone-pyrrolecarboxamide conjugates.
Bromofluoroacetophenone derivatives which produce fluorine substituted phenyl radicals that cleave DNA upon excitation were investigated as a novel photonuclease. Pyrrolecarboxamide-conjugated bromofluoroacetophenones; 4'-bromo-2'-fluoroacetophenone and 2'-bromo-4'-fluoroacetophenone were synthesized and their DNA cleaving activities and sequence selectivities were determined. Bromofluoroacetophenone-pyrrolecarboxamide conjugates were found to be effective DNA cleaving agents upon irradiation in concentration dependent manner based on plasma relaxation assay. The DNA cleaving activities of 2'-bromo-4'-fluoroacetophenone derivatives were larger than those of 4'-bromo-2'-fluoroacetophenone derivatives.
Department of Chemistry, Stanford University, CA 94305, USA.
Paul A
PA
Wender
Raok
R
Jeon
D000098:Acetophenones / Q000737:chemistry*; D001483:Base Sequence; D001665:Binding Sites; D004247:DNA / Q000737:chemistry* / Q000378:metabolism / Q000528:radiation effects; D004307:Dose-Response Relationship, Radiation; D005609:Free Radicals / Q000737:chemistry; D008027:Light; D010782:Photolysis; D011758:Pyrroles / Q000737:chemistry / Q000378:metabolism
D000098:Acetophenones; D005609:Free Radicals; D011758:Pyrroles; D004247:DNA