title: Fluorescent Sensing of Guanine and Guanosine Monophosphate with Conjugated Receptors Incorporating Aniline and Naphthyridine Moieties.
abstract: Ethyne-linked naphthyridine-aniline conjugated molecules are selective sensors of decylguanine in dichloromethane and guanosine monophosphate in water (Kass = 16,000 M(-1)). The 2-acetamido-1,8-naphthyridine moiety binds with guanine in a DAA-ADD triply hydrogen-bonded motif. The aniline moiety enhances an electron-donating effect, and the substituent is tuned to attain extra hydrogen bonds, π-π stacking, and electrostatic interactions. The proposed binding modes are supported by a Job plot, ESI-MS, (1)H NMR, UV-vis, and fluorescence spectral analyses.
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei 106, Taiwan.
authors.forename: Shao-Hung
authors.initials: SH
authors.lastname: Lu
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei 106, Taiwan.
authors.forename: Riping
authors.initials: R
authors.lastname: Phang
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei 106, Taiwan.|The Genomics Research Center, Academia Sinica , Taipei 115, Taiwan.
authors.forename: Jim-Min
authors.initials: JM
authors.lastname: Fang
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D005453:Fluorescence; D006147:Guanine / Q000737:chemistry*; D006157:Guanosine Monophosphate / Q000737:chemistry*; D006860:Hydrogen Bonding; D008279:Magnetic Resonance Imaging; D015394:Molecular Structure; D009287:Naphthyridines / Q000737:chemistry*
chemical_list: C000610793:2-acetamido-1,8-naphthyridine; D000081:Acetamides; D000814:Aniline Compounds; D009287:Naphthyridines; D006147:Guanine; D006157:Guanosine Monophosphate; C023650:aniline