Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
Sensitive naked eye detection and quantification assay for nitrite by a fluorescence probe in various water resources
Graphical Abstract
Introduction
Nitrite (NO2−) is widely distributed in natural world and is one of the most widespread nitrogen compounds. Once reacts with proteins, nitrite ions are prone to form highly carcinogenic N-nitrosamines [1]. Excessive consumption of nitrites will lead to various diseases such as esophageal cancer and infant methemoglobinemia [[1], [2], [3]], etc. The maximum contaminant level (MCL) of nitrite, legislated by the U.S. Environmental Protection Agency (EPA), is 1 ppm (21.7 μM), and the analogous guideline value set by the World Health Organization (WHO) is 3 ppm [4,5]. Several methods have been reported for the detection of nitrite ions, including chromatography [[6], [7], [8]], electrochemical [[9], [10], [11], [12], [13], [14], [15], [16]] and spectroscopic methods [[17], [18], [19], [20], [21]]. Spectroscopic methods are the most widely used for nitrite determination due to the excellent limits of detection, facile method and can be used for visual on-site analysis. Griess Assay is undoubtedly the most common approach to detect nitrite which first developed in 1858 [22] and used till now. The assay typically relies on the diazotization of a suitable aromatic amine by acidified nitrite with the subsequent coupling reaction providing a highly coloured azo chromophore, from which the concentration of nitrite can be assessed [23]. Yang et al. designed a novel probe (NT555) for nitrite detection, which displays superior detection kinetics and sensitivity [24]. Ramaiah et al. developed a novel aza-BODIPY probe that selectively recognizes the nitrite ions through a distinct visual color change from bright blue to intense green with a sensitivity of 20 ppb [4]. Banerjee et al. reported a rhodamine based “turn-on” type fluorogenic probe which detects trace amount of nitrite ions in water as low as 4.6 ppb [25]. These probes have the analogous mechanism with Griess Assay. Almost all reported fluorescence probes for detection of nitrite ion have to satisfy the strong acid condition (pH = 0) [4,19,24] and some even required low temperature (0 °C) [25]. Recently, many nitrite sensors based nanoparticle probes have been reported [[26], [27], [28], [29], [30], [31], [32], [33]]. Most of them base on the nanoparticles modified with recognized groups to detect nitrite ions. Some of these methods have complicated procedure, expensive and may have extraordinary biotoxicity for human health [34].
The detection of NO2− by the Griess assay is a two-step process, including the initial addition of an aliquot of NO2− containing solution into an acidic solution of sulphanilamide to generate the electrophilic diazonium salt and subsequent addition of a naphthylethylenediamine solution to furnish an azo dye. It is a colorimetric assay with a detection limit of 2.5 μM and need strongly acidic media (pH = 0–1) [35]. Herein, we designed and synthesized a novel fluorescence probe (PyI) for the detection of nitrite ions by one-pot method and the detection of nitrite ions is a simple one-step process with a detection limit of 0.1 μM. Moreover, it can be used for sensitive visual detection of nitrite ions under the more mild condition with pH value from 2 to 5.
Section snippets
Materials
2,6-Pyridinedicarbonyl dichloride was purchased from J&K company (Beijing, China). 5-Aminoindole was obtained from Meryer company (Shanghai, China). 4-Dimethylaminopyridine (DMAP) was purchased from Aladdin company (Shanghai, China). 4-(2-hydroxyethyl)-1-piperazineethanesulfonicacid (HEPES) was purchased from Energy Chemical Technology (Shanghai, China) Co., Ltd. Anhydrous acetonitrile and triethylamine were pretreated with CaH2 and fractional distilled before use. Ultrapure water was produced
Characterization of the Probe PyI
PyI was easily synthesized via a facile one-step reaction with high yield (72%) shown in Fig. 1. The final product was unambiguously characterized on the basis of spectroscopic and analytical evidence (supplementary material, Figs. S1−S3).
X-ray Crystallography
Single-crystal X-ray diffraction analysis reveals that the PyI crystallizes in the monoclinic system space group P21/c (Table S1). The asymmetric unit contains one PyI and a methanol, as shown in Fig. 2. Hydrogen atom which located on acylamino nitrogen N(2)
Conclusion
In summary, we have developed a novel fluorescence probe PyI for the sensitive detection of nitrite ions in water by a direct and simple method. The Probe PyI can selectively detect nitrite ions by a distinct visual color change from colorless to pink with a detection limit of 0.1 μM. The probe PyI can be used for the detection of nitrite ions in the presence of other competing ions in natural water resources.
Acknowledgements
This work was financially supported by National Natural Science Foundation of China (No.21575055).
References (41)
- et al.
Enhanced electrocatalytic nitrite determination using poly(diallyldimethylammonium chloride)-coated Fe1.833(OH)0.5O2.5-decorated N-doped graphene ternary hierarchical nanocomposite
Sensors Actuators B Chem.
(2017) - et al.
A novel nitrite biosensor based on the direct electrochemistry of horseradish peroxidase immobilized on porous Co3O4 nanosheets and reduced graphene oxide composite modified electrode
Sensors Actuators B Chem.
(2017) - et al.
A highly sensitive and reductant-resistant fluorescent chemodosimeter for the rapid detection of nitroxyl
Sensors Actuators B Chem.
(2015) - et al.
Detection and determination of nitrate and nitrite—a review
Talanta
(2001) - et al.
A reaction based turn-on type fluorogenic and chromogenic probe for the detection of trace amount of nitrite in water
Talanta
(2012) - et al.
One-step, stabilizer-free and green synthesis of Cu nanoclusters as fluorescent probes for sensitive and selective detection of nitrite ions
Sensors Actuators B Chem.
(2016) The automatic determination of iodate- and total-iodine in seawater
Mar. Chem.
(1978)- et al.
The distribution of iodine in the earth's crust
Chem. Geol.
(1998) - et al.
Dietary nitrate and nitrite and the risk of thyroid cancer in the NIH-AARP diet and health study
Int. J. Cancer
(2011) - et al.
N. American Academy of Pediatrics Committee on, H. American Academy of Pediatrics Committee on Environmental, Infant methemoglobinemia: the role of dietary nitrate in food and water
Pediatrics
(2005)
A review of nitrates in drinking water: maternal exposure and adverse reproductive and developmental outcomes
Environ. Health Perspect.
Efficient reaction based colorimetric probe for sensitive detection, quantification, and on-site analysis of nitrite ions in natural water resources
Anal. Chem.
The chemical quality of self-supplied domestic well water in the United States
Ground Water Monitoring & Remediation
Determination of nitrite in waters by microplate fluorescence spectroscopy and HPLC with fluorescence detection
Anal. Chem.
Determination of nitrite, sulphate, bromide and nitrate in human serum by ion chromatography
Analyst
Determination of trace amounts of nitrite by derivatisation and gas chromatography
Analyst
Development of a novel nitrite electrochemical sensor by stepwise in situ formation of palladium and reduced graphene oxide nanocomposites
RSC Adv.
Electroanalytical sensing of nitrite at shallow recessed screen printed microelectrode arrays
Anal. Methods
Indirect measurement of nitric oxide production by monitoring nitrate and nitrite using microchip electrophoresis with electrochemical detection
Anal. Chem.
Porous cuprite films: facile solution deposition and their application for nitrite sensing
Analyst
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