Boeun Choi, Sooseong Lee, Hyejin Nam, Jae Jun Lee, Cheal Kim
{"title":"一种易于获取的荧光探针,用于通过亲核加成选择性氰化物检测:应用于环境水样,智能手机和真菌和植物的生物成像","authors":"Boeun Choi, Sooseong Lee, Hyejin Nam, Jae Jun Lee, Cheal Kim","doi":"10.1016/j.bioorg.2025.109014","DOIUrl":null,"url":null,"abstract":"<div><div>The monitoring of cyanide (CN<sup>−</sup>) is of great significance due to its extreme toxicity to both humans and the environment. In this study, we report a convenient fluorescent sensor <strong>HNIC</strong> ((<em>E</em>)-7-hydroxy-8-(((2-((7-nitrobenzo[<em>c</em>][1,2,5]oxadiazol-4-yl)amino)phenyl)imino)methyl)-2<em>H</em>-chromen-2-one) for detecting CN<sup>−</sup>. On addition of CN<sup>−</sup>, <strong>HNIC</strong> exhibited a blue fluorescence turn-on response in aqueous media. Moreover, <strong>HNIC</strong> could selectively monitor CN<sup>−</sup> over other interfering ions, with a detection limit of 4.43 μM. The reaction of CN<sup>−</sup> with <strong>HNIC</strong> was evaluated using Job plot at a 1:1 ratio. To elucidate the mechanism of the nucleophilic attack of CN<sup>−</sup> on <strong>HNIC</strong>, ESI-MS analysis, <sup>1</sup>H NMR titration, and DFT studies were employed. <strong>HNIC</strong> showed potential for quantifying CN<sup>−</sup> in environmental water samples (mineral, tap, river, and drinking water). Furthermore, a smartphone application utilizing <strong>HNIC</strong> successfully monitored CN<sup>−</sup> concentrations in environmental samples. Importantly, <strong>HNIC</strong> could track CN<sup>−</sup> through bio-imaging in fungi and plants, including white beech mushrooms, onions, and radish sprouts. Therefore, <strong>HNIC</strong> could be employed as a useful tool for detecting highly toxic CN<sup>−</sup> by triggering the fluorescent turn-on.</div></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":"165 ","pages":"Article 109014"},"PeriodicalIF":4.7000,"publicationDate":"2025-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"An easily accessible fluorometric probe for selective cyanide detection via nucleophilic addition: Applications to environmental water samples, smartphone, and bio-imaging of fungi and plants\",\"authors\":\"Boeun Choi, Sooseong Lee, Hyejin Nam, Jae Jun Lee, Cheal Kim\",\"doi\":\"10.1016/j.bioorg.2025.109014\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>The monitoring of cyanide (CN<sup>−</sup>) is of great significance due to its extreme toxicity to both humans and the environment. In this study, we report a convenient fluorescent sensor <strong>HNIC</strong> ((<em>E</em>)-7-hydroxy-8-(((2-((7-nitrobenzo[<em>c</em>][1,2,5]oxadiazol-4-yl)amino)phenyl)imino)methyl)-2<em>H</em>-chromen-2-one) for detecting CN<sup>−</sup>. On addition of CN<sup>−</sup>, <strong>HNIC</strong> exhibited a blue fluorescence turn-on response in aqueous media. Moreover, <strong>HNIC</strong> could selectively monitor CN<sup>−</sup> over other interfering ions, with a detection limit of 4.43 μM. The reaction of CN<sup>−</sup> with <strong>HNIC</strong> was evaluated using Job plot at a 1:1 ratio. To elucidate the mechanism of the nucleophilic attack of CN<sup>−</sup> on <strong>HNIC</strong>, ESI-MS analysis, <sup>1</sup>H NMR titration, and DFT studies were employed. <strong>HNIC</strong> showed potential for quantifying CN<sup>−</sup> in environmental water samples (mineral, tap, river, and drinking water). Furthermore, a smartphone application utilizing <strong>HNIC</strong> successfully monitored CN<sup>−</sup> concentrations in environmental samples. Importantly, <strong>HNIC</strong> could track CN<sup>−</sup> through bio-imaging in fungi and plants, including white beech mushrooms, onions, and radish sprouts. Therefore, <strong>HNIC</strong> could be employed as a useful tool for detecting highly toxic CN<sup>−</sup> by triggering the fluorescent turn-on.</div></div>\",\"PeriodicalId\":257,\"journal\":{\"name\":\"Bioorganic Chemistry\",\"volume\":\"165 \",\"pages\":\"Article 109014\"},\"PeriodicalIF\":4.7000,\"publicationDate\":\"2025-09-19\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bioorganic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0045206825008946\",\"RegionNum\":2,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioorganic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0045206825008946","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
An easily accessible fluorometric probe for selective cyanide detection via nucleophilic addition: Applications to environmental water samples, smartphone, and bio-imaging of fungi and plants
The monitoring of cyanide (CN−) is of great significance due to its extreme toxicity to both humans and the environment. In this study, we report a convenient fluorescent sensor HNIC ((E)-7-hydroxy-8-(((2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)phenyl)imino)methyl)-2H-chromen-2-one) for detecting CN−. On addition of CN−, HNIC exhibited a blue fluorescence turn-on response in aqueous media. Moreover, HNIC could selectively monitor CN− over other interfering ions, with a detection limit of 4.43 μM. The reaction of CN− with HNIC was evaluated using Job plot at a 1:1 ratio. To elucidate the mechanism of the nucleophilic attack of CN− on HNIC, ESI-MS analysis, 1H NMR titration, and DFT studies were employed. HNIC showed potential for quantifying CN− in environmental water samples (mineral, tap, river, and drinking water). Furthermore, a smartphone application utilizing HNIC successfully monitored CN− concentrations in environmental samples. Importantly, HNIC could track CN− through bio-imaging in fungi and plants, including white beech mushrooms, onions, and radish sprouts. Therefore, HNIC could be employed as a useful tool for detecting highly toxic CN− by triggering the fluorescent turn-on.
期刊介绍:
Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry.
For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature.
The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.