Synthesis, DNA binding and photocleavage study of novel anthracene-appended macrocyclic polyamines.
Two anthracene derivatives appended on cyclen (1,4,7,10-tetraazacyclododecane) moieties were synthesized and characterized. In these new compounds, the anthryl is used as a substitute for the nucleobases of classical PNA backbone, and the cyclen moiety appends on the terminal amino group. The interaction of the compounds with DNA was systematically investigated by absorption, fluorescence, and viscometric titration, DNA melting and gel electrophoresis experiments. From the absorption titration data, bis-anthryl compound can bind to CT DNA with K(b) = 1.21 x 10(5) M(-1) that is 121 times larger than that of mono-anthryl compound (K(b) = 1.00 x 10(3) M(-1)). Through the fluorescence titration data, compound shows distinct CG-selective DNA binding activity. DNA melting and viscometric titration experiments indicate that the binding mode of is a multiple binding mode that involves groove binding and partial intercalation. Compound also shows excellent DNA photocleavage ability, which is much more efficient than the mono-anthryl compound .
Huang
Yu
Y
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, PR China. xqyu@tfol.com.
Zhang
Yu
Y
Zhang
Ji
J
Zhang
Da-Wei
DW
Lu
Qiao-Sen
QS
Liu
Jun-Liang
JL
Chen
Shan-Yong
SY
Lin
Hong-Hui
HH
Yu
Xiao-Qi
XQ
D000873:Anthracenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D001665:Binding Sites; D000080027:Cyclams; D004247:DNA / Q000737:chemistry / Q000378:metabolism* / Q000528:radiation effects; D005453:Fluorescence; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D008027:Light; D009691:Nucleic Acid Denaturation; D055668:Photochemical Processes; D011073:Polyamines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D013053:Spectrophotometry; D017186:Titrimetry; D014783:Viscosity
D000873:Anthracenes; D000080027:Cyclams; D006571:Heterocyclic Compounds; D011073:Polyamines; D004247:DNA; C038072:cyclen; C034020:anthracene