title: Ratiometric fluorescence detection of pyrimidine/purine transversion by using a 2-amino-1,8-naphthyridine derivative.
abstract: A new class of abasic site-binding fluorescence ligands, Naph-NBD in which 7-nitrobenzo-2-oxa-1,3-diazole (NBD) is connected to 2-amino-7-methyl-1,8-naphthyridine (Naph) by a propylene linker, is presented for the ratiometric assay for SNPs typing. In solutions buffered to pH 7.0 (I = 0.11 M, at 5 degrees C), Naph-NBD is found to selectively recognize pyrimidine bases over purine bases opposite the abasic site in DNA duplexes (K11/M(-1): T, 8.1 x 10(6); C, 2.5 x 10(6): G, 0.33 x 10(6); A, 0.27 x 10(6)). The binding of Naph-NBD is accompanied by significant quenching of the fluorescence from the naphthyridine moiety (lambda max, 409 nm), while the emission from the NBD (lamda max, 544 nm) is relatively unaffected. Such a fluorescence response of Naph-NBD allows the emission ratio detection of pyrimidine/purine transversion.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University, Japan.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Satake
authors.forename: Seiichi
authors.initials: S
authors.lastname: Nishizawa
authors.forename: Norio
authors.initials: N
authors.lastname: Teramae
mesh_terms: D020029:Base Pairing; D001665:Binding Sites; D002623:Chemistry Techniques, Analytical / Q000379:methods*; D004247:DNA / Q000737:chemistry; D005456:Fluorescent Dyes / Q000494:pharmacology; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008024:Ligands; D008856:Microscopy, Fluorescence / Q000379:methods*; D008956:Models, Chemical; D009287:Naphthyridines / Q000737:chemistry*; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry; D011687:Purines / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry; D013050:Spectrometry, Fluorescence; D013053:Spectrophotometry / Q000379:methods
chemical_list: C427025:2-amino-1,8-naphthyridine; D005456:Fluorescent Dyes; D008024:Ligands; D009287:Naphthyridines; D009692:Nucleic Acid Heteroduplexes; D011687:Purines; D011743:Pyrimidines; D004247:DNA