title: Synthesis, DNA binding and photocleavage study of novel anthracene-appended macrocyclic polyamines.
abstract: 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 .
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, PR China. xqyu@tfol.com.
authors.forename: Yu
authors.initials: Y
authors.lastname: Huang
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhang
authors.forename: Ji
authors.initials: J
authors.lastname: Zhang
authors.forename: Da-Wei
authors.initials: DW
authors.lastname: Zhang
authors.forename: Qiao-Sen
authors.initials: QS
authors.lastname: Lu
authors.forename: Jun-Liang
authors.initials: JL
authors.lastname: Liu
authors.forename: Shan-Yong
authors.initials: SY
authors.lastname: Chen
authors.forename: Hong-Hui
authors.initials: HH
authors.lastname: Lin
authors.forename: Xiao-Qi
authors.initials: XQ
authors.lastname: Yu
mesh_terms: 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
chemical_list: D000873:Anthracenes; D000080027:Cyclams; D006571:Heterocyclic Compounds; D011073:Polyamines; D004247:DNA; C038072:cyclen; C034020:anthracene