Colorimetric/spectral dual-mode analysis of sensitive fluorescent probe based on 2,3,3-trimethyl-3H-benzo[e]indole detection of acid pH

Youfang Liu; Yingying Zhang; Jing Wang; Anquan Yang; Yanliang Zhao; Aying Zhou; Ranhua Xiong; Chaobo Huang

doi:10.1016/j.bioorg.2022.105792

Colorimetric/spectral dual-mode analysis of sensitive fluorescent probe based on 2,3,3-trimethyl-3H-benzo[e]indole detection of acid pH

Bioorg Chem. 2022 Jul:124:105792. doi: 10.1016/j.bioorg.2022.105792. Epub 2022 Apr 5.

Authors

Youfang Liu¹, Yingying Zhang², Jing Wang³, Anquan Yang³, Yanliang Zhao⁴, Aying Zhou¹, Ranhua Xiong⁵, Chaobo Huang⁶

Affiliations

¹ Joint Laboratory of Advanced Biomedical Materials (NFU-UGent), Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University (NFU), Nanjing 210037, China.
² Joint Laboratory of Advanced Biomedical Materials (NFU-UGent), Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University (NFU), Nanjing 210037, China. Electronic address: zhangyingying@njfu.edu.cn.
³ Zhejiang Osmum Group Co, Ltd, Huzhou 313000, China.
⁴ Institute of Molecular Sciences and Engineering, Institute of Frontier and Interdisciplinary Science, Shandong University, Qingdao 266235, China.
⁵ Joint Laboratory of Advanced Biomedical Materials (NFU-UGent), Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University (NFU), Nanjing 210037, China. Electronic address: ranhua.xiong@njfu.edu.cn.
⁶ Joint Laboratory of Advanced Biomedical Materials (NFU-UGent), Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University (NFU), Nanjing 210037, China. Electronic address: Chaobo.HUANG@njfu.edu.cn.

PMID: 35462233
DOI: 10.1016/j.bioorg.2022.105792

Abstract

Herein, a high-performance fluorescence probe, namely H4, based on intramolecular charge transfer (ICT) mechanism was developed. H4 could serve as fluorescent probe for detection acidic pH change in environment with outstanding sensitivity, short response time (<10 s), low hemolysis effect (<0.3%) and excellent photostability (>120 min). H4 exhibits a good linear relationship (R² = 0.9901, Y = 22.0409X-58.3397) characteristics in range of pH 2.2-7.4 with pK_a 4.3. In addition, the probe can be also made as fluorescent test sheets and further used as a portable sensor to enhance the screening speed to achieve detection of H⁺ in real-time. Further, H4 determined H⁺ in real food samples (milk, shrimps, and scallops) has excellent recoveries (98-105%), which making it of great potential use in food freshness evaluation. Initially, its favorable behavior for detecting H⁺ change is successfully illustrated in living onion tissues and zebrafish, which allows qualitative visualization of acid pH changes in in biological systems.

Keywords: Fluorescent probe; Intramolecular charge transfer; Living zebrafish; Onion tissues; pH.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Colorimetry*
Fluorescent Dyes* / chemistry
Hydrogen-Ion Concentration
Indoles
Zebrafish

Substances

Fluorescent Dyes
Indoles