Preparation of D-NCCDs and its application in fluorescent/colorimetric dual-mode discrimination of glutamine enantiomers

IF 5.3 2区化学 Q1 CHEMISTRY, ANALYTICAL Microchimica Acta Pub Date : 2024-10-28 DOI:10.1007/s00604-024-06788-1

Xuan Liao, Cancan Lu, Yaning Duan, Cuiling Ren, Hongli Chen

{"title":"Preparation of D-NCCDs and its application in fluorescent/colorimetric dual-mode discrimination of glutamine enantiomers","authors":"Xuan Liao, Cancan Lu, Yaning Duan, Cuiling Ren, Hongli Chen","doi":"10.1007/s00604-024-06788-1","DOIUrl":null,"url":null,"abstract":"<div><p>A new type of carbon dots (D-NCCDs) was synthesized by 3, 5-diaminobenzoic acid, N,N-dimethyl-o-phenylenediamine, and D-cysteine. The morphology and structure of D-NCCDs were investigated by transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and FT-IR spectra, and the chirality was characterized by circular dichroism. In the presence of hydrogen peroxide, the fluorescence of D-NCCDs at 487 nm (<i>λ</i><sub>ex</sub> = 410 nm) showed great discrimination ability towards glutamine enantiomers. The ratio of fluorescence intensity (<i>F</i>/<i>F</i><sub>0</sub>) to the concentration of D-Gln showed good linearity in the range 0.5–10 mM, with a detection limits of 0.11 mM. Meanwhile, the color of the solution gradually changed from light yellow to yellow–brown. The UV–Vis absorption ratio (<i>A</i>/<i>A</i><sub>0</sub>) at 410 nm showed good linearity with the concentration of D-Gln in the range 0.5 to 20 mM; the detection limit is 7.7 μM. But the fluorescence and absorbance of D-NCCDs showed no significant change after the addition of L-glutamine. Thus, fluorescence and colorimetry dual-mode discrimination of glutamine enantiomers was achieved. The fluorescence enantioselectivity of Gln (<i>F</i><sub>L-Gln</sub>/<i>F</i><sub>D-Gln</sub>) is 1.62, and the colorimetric enantioselectivity of Gln (<i>A</i><sub>D-Gln</sub>/<i>A</i><sub>L-Gln</sub>) is 2.14. The chiral discrimination mechanism of D-NCCDs to Gln enantiomers was also investigated systematically. This work not only can discriminate glutamine enantiomers with high sensitivity and convenience, but also offers a new strategy for preparing new dual mode chiral nanoprobes.</p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":705,"journal":{"name":"Microchimica Acta","volume":"191 11","pages":""},"PeriodicalIF":5.3000,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Microchimica Acta","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s00604-024-06788-1","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ANALYTICAL","Score":null,"Total":0}

引用次数: 0

Abstract

A new type of carbon dots (D-NCCDs) was synthesized by 3, 5-diaminobenzoic acid, N,N-dimethyl-o-phenylenediamine, and D-cysteine. The morphology and structure of D-NCCDs were investigated by transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS), and FT-IR spectra, and the chirality was characterized by circular dichroism. In the presence of hydrogen peroxide, the fluorescence of D-NCCDs at 487 nm (λ_ex = 410 nm) showed great discrimination ability towards glutamine enantiomers. The ratio of fluorescence intensity (F/F₀) to the concentration of D-Gln showed good linearity in the range 0.5–10 mM, with a detection limits of 0.11 mM. Meanwhile, the color of the solution gradually changed from light yellow to yellow–brown. The UV–Vis absorption ratio (A/A₀) at 410 nm showed good linearity with the concentration of D-Gln in the range 0.5 to 20 mM; the detection limit is 7.7 μM. But the fluorescence and absorbance of D-NCCDs showed no significant change after the addition of L-glutamine. Thus, fluorescence and colorimetry dual-mode discrimination of glutamine enantiomers was achieved. The fluorescence enantioselectivity of Gln (F_L-Gln/F_D-Gln) is 1.62, and the colorimetric enantioselectivity of Gln (A_D-Gln/A_L-Gln) is 2.14. The chiral discrimination mechanism of D-NCCDs to Gln enantiomers was also investigated systematically. This work not only can discriminate glutamine enantiomers with high sensitivity and convenience, but also offers a new strategy for preparing new dual mode chiral nanoprobes.

Graphical Abstract

查看原文

微信好友朋友圈 QQ好友复制链接

本刊更多论文

制备 D-NCCD 及其在荧光/比色双模式谷氨酰胺对映体鉴别中的应用。

3，5-二氨基苯甲酸、N，N-二甲基邻苯二胺和D-半胱氨酸合成了一种新型碳点（D-NCCDs）。透射电子显微镜（TEM）、X 射线光电子能谱（XPS）和傅立叶变换红外光谱研究了 D-NCCDs 的形貌和结构，圆二色性表征了 D-NCCDs 的手性。在过氧化氢存在的条件下，D-NCCDs 在 487 nm（λex = 410 nm）处的荧光对谷氨酰胺对映体具有很强的鉴别能力。荧光强度（F/F0）与 D-Gln 浓度的比值在 0.5-10 mM 范围内呈良好的线性关系，检测限为 0.11 mM。同时，溶液的颜色由浅黄色逐渐变为黄褐色。在 410 nm 波长处的紫外可见吸收比（A/A0）与 D-Gln 的浓度在 0.5-20 mM 范围内呈良好的线性关系，检测限为 7.7 μM。但加入 L-谷氨酰胺后，D-NCCDs 的荧光和吸光度没有明显变化。因此，实现了对谷氨酰胺对映体的荧光和比色双模式鉴别。Gln 的荧光对映体选择性（FL-Gln/FD-Gln）为 1.62，而 Gln 的比色对映体选择性（AD-Gln/AL-Gln）为 2.14。此外，还系统研究了 D-NCCDs 对 Gln 对映体的手性鉴别机制。这项工作不仅能高灵敏、方便地鉴别谷氨酰胺对映体，而且为制备新型双模式手性纳米探针提供了一种新策略。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文去求助

来源期刊

Microchimica Acta 化学-分析化学

CiteScore

9.80

自引率

5.30%

发文量

410

审稿时长

2.7 months

期刊介绍： As a peer-reviewed journal for analytical sciences and technologies on the micro- and nanoscale, Microchimica Acta has established itself as a premier forum for truly novel approaches in chemical and biochemical analysis. Coverage includes methods and devices that provide expedient solutions to the most contemporary demands in this area. Examples are point-of-care technologies, wearable (bio)sensors, in-vivo-monitoring, micro/nanomotors and materials based on synthetic biology as well as biomedical imaging and targeting.