2016
DOI: 10.1021/acs.orglett.6b00311
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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, … Show more

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Cited by 21 publications
(19 citation statements)
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“…(a) Binding mode proposed by Fang et al for 8b with 9-alkylguanine and (b) revised binding mode based on the present work. Hydrogen bonds that play a key role in determining the guanine-binding strength are labeled (r1–3).…”
Section: Introductionmentioning
confidence: 84%
See 2 more Smart Citations
“…(a) Binding mode proposed by Fang et al for 8b with 9-alkylguanine and (b) revised binding mode based on the present work. Hydrogen bonds that play a key role in determining the guanine-binding strength are labeled (r1–3).…”
Section: Introductionmentioning
confidence: 84%
“…The desired DAA hydrogen-bonding pattern can be found in 2-acetamido-1,8-naphthyridine ( 1 , Figure ), derivatives of which were first utilized for guanine binding by Giese et al in the 1980s for hydrogen-bonding chromatography. Subsequently, derivatives of 1 have been exploited in a number of guanine-binding applications. For instance, Fang et al , developed a series of ethynyl bridged naphthyridine derivatives capable of high-yield fluorescence-based sensing, including sensors 2 and 3 (Figure ). These sensors, which form up to four hydrogen bonds with guanine, exhibit binding constants up to (9.1 ± 0.2) × 10 4 M –1 .…”
Section: Introductionmentioning
confidence: 99%
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“…For the detection of aromatic amines various analytical methods like gas chromatography-mass spectrometry (GC-MS), high performance liquid chromatography (HPLC), spectrophotometry, electrochemistry, Raman spectroscopy, ion mobility spectrometry, etc. have been used [7][8][9][10][11][12][13].…”
Section: Eintroductionmentioning
confidence: 99%
“…Hence, the desire for quick and effective determination of individual concentration of nucleobases or their ratio in DNA is important in getting a perspective into the fundamental mechanism of genetic information as well as the application in clinical diagnosis. Nowadays, various methods have been applied to evaluate these nitrogenous bases in biological system, such as fluorescence spectroscopy , surface enhanced Raman spectroscopy , chemiluminescence , etc. For simultaneous detection of four DNA bases, separation technique such as high performance liquid chromatography or electrophoresis was commonly coupled with other detection methods to reach the final goal, which was not convenient and time‐cost.…”
Section: Introductionmentioning
confidence: 99%