title: Fluorescence-based affinity labeling of nucleobase by hydrogen-bond forming metal complex.
abstract: A new class of nucleobase-binding fluorescent ligand, ND-DOTA in which 2-amino-5,7-dimethyl-1.8-naphthyridine (ND) is conjugated with 1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid (DOTA) by an amide linker, was synthesized. On the basis of the experimental results obtained from the DNA melting analysis and fluorescent measurement, ND-DOTA-Tb (III) complex was found to strongly recognize cytosine (C) base opposite an abasic site in DNA duplexes. The binding of ND-DOTA-Tb (III) with C was accompanied by significant quenching of the fluorescence from the naphthyridine moiety (lambdamax, 435 nm), while the emission from the Tb based on lanthanoids energy-transfer luminescence (lambdamax, 550 nm) was relatively unaffected. Such a fluorescence response of ND-DOTA-Tb (III) is to be expected to develop the fluorescence-based affinity labelling of a nucleobase at the single-nucleotide segments in DNA duplexes.
authors.affiliation: Department of Materials Science, Graduate School of Pure and Applied Sciences, Center for Tsukuba Advanced Research Alliance (TARA), University of Tsukuba, 1-1-1 Ten-noudai, Tsukuba, Ibaraki 3058573, Japan.
authors.forename: Keitaro
authors.initials: K
authors.lastname: Yoshimoto
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Atsumi
authors.forename: Shingo
authors.initials: S
authors.lastname: Saito
authors.forename: Moriya
authors.initials: M
authors.lastname: Okuma
authors.forename: Mizuo
authors.initials: M
authors.lastname: Maeda
authors.forename: Yukio
authors.initials: Y
authors.lastname: Nagasaki
mesh_terms: D003596:Cytosine / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis / Q000737:chemistry*; D006860:Hydrogen Bonding; D009287:Naphthyridines / Q000138:chemical synthesis / Q000737:chemistry*; D009691:Nucleic Acid Denaturation; D013050:Spectrometry, Fluorescence; D013725:Terbium / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D006573:Heterocyclic Compounds, 1-Ring; C528374:N-(5,7-dimethyl-1,8-naphthyridin-2-yl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid-10-acetamide; D009287:Naphthyridines; D013725:Terbium; D003596:Cytosine; D004247:DNA