9-Acridinylpeptides and 9-acridinyl-4-nitrophenylsulfonylpeptides. Synthesis, binding to DNA, and photoinduced DNA cleavage.
The preparation of 6-(9-acridinylamino)hexanoic acid DHBT ester and N alpha-Fmoc-N epsilon-(4-nitrophenylsulfonyl)-L-lysine DHBT ester and their application in solid phase peptide synthesis are described. The 9-acridinylamino ligand was shown to confer high DNA affinity, probably by intercalation, to the resulting peptides. The 4-nitrophenylsulfamido ligand furthermore resulted in "photonuclease" activity of some of the modified peptides.
Karup
G
G
Bioorganic Group, H.C. Orsted Institute, Copenhagen, Denmark.
Meldal
M
M
Nielsen
P E
PE
Buchardt
O
O
D000166:Acridines / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D000595:Amino Acid Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D004247:DNA / Q000187:drug effects / Q000378:metabolism*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009578:Nitrobenzenes / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D010455:Peptides / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D010777:Photochemistry; D013450:Sulfones / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology
D000166:Acridines; D009578:Nitrobenzenes; D010455:Peptides; D013450:Sulfones; D004247:DNA