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一种用于检测pH值的“弱酸弱碱”型荧光探针：作用机制及在活细胞中的应用

A "weak acid and weak base" type fluorescent probe for sensing pH: mechanism and application in living cells.

作者信息

Jiao Chunpeng, Pang Jingxiang, Shen Li, Lu Wenjuan, Zhang Pingping, Liu Yuanyuan, Li Jing, Jia Xianhui, Wang Yanfeng

机构信息

School of Medicine and Life Sciences, University of Jinan-Shandong Academy of Medical Sciences Jinan 250200 Shandong China

Institute of Materia Medica, Shandong Academy of Medical Sciences Jinan 250062 Shandong China.

出版信息

RSC Adv. 2019 Jul 4;9(36):20982-20988. doi: 10.1039/c9ra03203g. eCollection 2019 Jul 1.

DOI:10.1039/c9ra03203g
PMID:35515522
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9066030/
Abstract

A simple pH fluorescent probe, -(6-morpholino-1, 3-dioxo-1-benzo[]isoquinolin-2(3)-yl) isonicotinamide (NDI), based on naphthalimide as the fluorophore and isonicotinic acid hydrazide as the reaction site was synthesized and characterized. It is useful for monitoring acidic and alkaline pH. The results of pH titration indicated that NDI exhibits obvious emission enhancement with a p of 4.50 and linear response to small pH fluctuations within the acidic range of 3.00-6.50. Interestingly, NDI also displayed strong pH-dependent characteristics with p 9.34 and linearly responded to an alkaline range of 8.30-10.50. The sensing response mechanism was confirmed by H NMR and ESI-MS spectroscopy. The mechanism of the optical responses of NDI toward pH was also determined by density functional theory (DFT) calculations. In addition, NDI displayed a highly selective and sensitive response to hydrogen ions and hydroxyl ions. The probe was successfully applied to image acidic and alkaline pH value fluctuations in HeLa cells and has lysosomal targeting ability.

摘要

合成并表征了一种基于萘二甲酰亚胺作为荧光团、异烟酸酰肼作为反应位点的简单pH荧光探针-(6-吗啉基-1,3-二氧代-1-苯并[]异喹啉-2(3)-基)异烟酰胺(NDI)。它可用于监测酸性和碱性pH值。pH滴定结果表明，NDI在pKa为4.50时表现出明显的发射增强，并且在3.00-6.50的酸性范围内对小的pH波动呈线性响应。有趣的是，NDI在pKa为9.34时也表现出强烈的pH依赖性特征，并在8.30-10.50的碱性范围内呈线性响应。通过1H NMR和ESI-MS光谱证实了传感响应机制。还通过密度泛函理论(DFT)计算确定了NDI对pH的光学响应机制。此外，NDI对氢离子和氢氧根离子表现出高度选择性和灵敏的响应。该探针已成功应用于成像HeLa细胞中酸性和碱性pH值的波动，并具有溶酶体靶向能力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/cfa6d56a0dd3/c9ra03203g-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/d8389e9f2c8e/c9ra03203g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/a535e95d325d/c9ra03203g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/2c7a363f3891/c9ra03203g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/aebcc0077781/c9ra03203g-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/6f18b008c074/c9ra03203g-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/6b9975e02bb1/c9ra03203g-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/c8bd444b9309/c9ra03203g-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/1ede125b4e3b/c9ra03203g-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/cfa6d56a0dd3/c9ra03203g-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/d8389e9f2c8e/c9ra03203g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/a535e95d325d/c9ra03203g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/2c7a363f3891/c9ra03203g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/aebcc0077781/c9ra03203g-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/6f18b008c074/c9ra03203g-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/6b9975e02bb1/c9ra03203g-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/c8bd444b9309/c9ra03203g-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/1ede125b4e3b/c9ra03203g-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6012/9066030/cfa6d56a0dd3/c9ra03203g-f8.jpg

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