The effect of an amino-acid bridge on binding affinity and cleavage efficiency of pyrenyl-macrocyclic polyamine conjugates toward DNA.
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.
Lu
Qiao-Sen
QS
Department of Chemistry, Key Laboratory of Green Chemistry and Technology (Ministry of Education), Sichuan University, Chengdu, PR China.
Huang
Yu
Y
Li
Jing
J
Zhang
Zhong-Wei
ZW
Lin
Hong-Hui
HH
Yu
Xiao-Qi
XQ
D000596:Amino Acids / Q000737:chemistry*; D000080027:Cyclams; D004247:DNA / Q000737:chemistry*; D053837:DNA Cleavage / Q000187:drug effects*; D004587:Electrophoresis, Agar Gel; D006571:Heterocyclic Compounds / Q000737:chemistry*; D011073:Polyamines / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
D000596:Amino Acids; D000080027:Cyclams; D006571:Heterocyclic Compounds; D011073:Polyamines; D011721:Pyrenes; D004247:DNA; C038072:cyclen