Fluorescent Sensing of Guanine and Guanosine Monophosphate with Conjugated Receptors Incorporating Aniline and Naphthyridine Moieties

Ethyne-linked naphthyridine–aniline conjugated molecules are selective sensors of decylguanine in dichloromethane and guanosine monophosphate in water (K ass = 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 enhan...

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Veröffentlicht in:Organic letters 2016-04, Vol.18 (8), p.1724-1727
Hauptverfasser: Lu, Shao-Hung, Phang, Riping, Fang, Jim-Min
Format: Artikel
Sprache:eng
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Zusammenfassung:Ethyne-linked naphthyridine–aniline conjugated molecules are selective sensors of decylguanine in dichloromethane and guanosine monophosphate in water (K ass = 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, 1H NMR, UV–vis, and fluorescence spectral analyses.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00311