N-quaternization of heterocyclic compound extended the emission to NIR with large Stokes shift and its application in constructing fluorescent probe
| Autor: | Xuezhao Shi, Haixia Zhang, Xiaoyan Liu, Lan Wu, Hong Gao, Yaya Wang, Can Gong, Syed Rizvi |
|---|---|
| Rok vydání: | 2022 |
| Předmět: |
chemistry.chemical_classification
Chemical Phenomena Chemistry Cellular imaging Optical Imaging Substituent Hydrogen Peroxide Photochemistry Small molecule Fluorescence Atomic and Molecular Physics and Optics Analytical Chemistry symbols.namesake chemistry.chemical_compound Wavelength Heterocyclic Compounds Heterocyclic compound Stokes shift symbols Instrumentation Spectroscopy Preclinical imaging Fluorescent Dyes |
| Zdroj: | Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 267:120566 |
| ISSN: | 1386-1425 |
| DOI: | 10.1016/j.saa.2021.120566 |
| Popis: | This is great significant to establish a method that extends the small molecules fluorescence emission wavelength to the near-infrared region (NIR) for in vivo imaging. Hence, we firstly reported a novel fluorogenic scaffold QOH that could extend its fluorescence wavelength from (λem = 555 nm) to NIR (λem = 720 nm) with a large Stokes shift (120 nm) by forming its N-quaternization product (QMOH). In addition, the effect of the introduction of substituent at different modification sites and the properties of substituent on the optical properties of QOH were fully discussed by theoretical calculation. To investigate the possibility of QOH as probe construction, the compound Q-SH and QM-R were synthesized and applied to detect H2S and H2O2 in vitro and in vivo, respectively. This study provided an efficient strategy to extend fluorescence emission to NIR and design fluorescence probes with large ratio variation for accurately imaging biomarkers in biological system. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect