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The Effect of an Amino‐Acid Bridge on Binding Affinity and Cleavage Efficiency of Pyrenyl‐Macrocyclic Polyamine Conjugates toward DNA
Author(s) -
Lu QiaoSen,
Huang Yu,
Li Jing,
Zhang ZhongWei,
Lin HongHui,
Yu XiaoQi
Publication year - 2009
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200800196
Subject(s) - cleavage (geology) , chemistry , dna , singlet oxygen , polyamine , radical , stereochemistry , biochemistry , oxygen , organic chemistry , geotechnical engineering , fracture (geology) , engineering
A series of pyrenyl‐macrocyclic polyamines 5a – 5c have been prepared and characterized. Their DNA‐cleavage properties were examined under physiological conditions. Without the presence of other additives, the DNA cleavage ability of 5a – 5c showed the order of 5c > 5a > 5b . Absorption and fluorescence experiments showed the binding affinity of 5a – 5c to DNA. The interactions of 5a – 5c with CT‐DNA indicated that the DNA binding ability followed an order according to their cleavage efficiency. All the results indicated that the structures of amino‐acid bridge in the ligands may affect the DNA binding and cleavage ability. The cleavage‐mechanism studies indicated that singlet oxygen and superoxide free radicals were involved in the catalytic DNA cleavage process.