Novel synthesis of a tetra-acridinyl peptide as a new DNA polyintercalator.
Tetra-acridinyl peptide 2 was synthesized from Fmoc-Lys(Boc)-OH and Fmoc-Lys(Acr)-OH (1) with the peptide synthesizer. The CD measurement suggested that 2 forms a special organized structure by itself in buffered solution. Peptide 2 binds to double stranded DNA with a very large affinity constant, which is 10(3)-times larger than that of quinacrine. Spectrophotometric and hydrodynamic studies suggested that all of the acridinyl parts of 2 contribute to the intercalating interaction for the DNA binding. Our finding in this experiment demonstrates that polyintercalators such as 2 can be assembled quickly by the automated synthesizer.
Ueyama
H
H
Department of Applied Chemistry, Graduate School of Engineering, Kyushu University, Fukuoka 812-8581, Japan.
Waki
M
M
Takagi
M
M
Takenaka
S
S
D000166:Acridines / Q000737:chemistry; D000818:Animals; D001665:Binding Sites; D002417:Cattle; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry* / Q000187:drug effects; D066298:In Vitro Techniques; D007364:Intercalating Agents / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D007700:Kinetics; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013053:Spectrophotometry
D000166:Acridines; D007364:Intercalating Agents; D009842:Oligopeptides; D004247:DNA