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Published on: October 31, 2019
[1,3]Oxazine-based NIR molecular switches: Hydrochromic behavior, viscosity sensing, and targeted cell imaging
Peikun Xiao1, Jiaping Yu1, Ying Han1
1Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi, 435002, China.
Summary
Researchers developed novel near-infrared molecular switches using [1,3] oxazine. These switches enable precise intracellular imaging and show potential for Alzheimer's disease diagnosis.
Area of Science:
- Chemical Biology
- Molecular Imaging
- Biochemistry
Background:
- [1,3] oxazine derivatives exhibit distinct properties in ring-closed and ring-opened forms, offering potential for intracellular fluorescence imaging.
- Existing research on these molecular switches for biological applications is limited.
- Near-infrared (NIR) imaging offers advantages for deep tissue penetration and reduced background interference.
Purpose of the Study:
- To design and synthesize novel NIR molecular switches based on the [1,3] oxazine scaffold.
- To investigate the properties and intracellular sensing capabilities of these new molecular switches.
- To explore their potential applications in disease diagnosis, specifically Alzheimer's disease.
Main Methods:
- Synthesis of two NIR molecular switches, BOA-1 and BOA-2, utilizing the [1,3] oxazine core.
- Characterization of their photophysical properties, including hydrochromism and emission spectra.
- Evaluation of intracellular targeting, fluorescence activation in response to viscosity, and pKa determination in living cells.
Main Results:
- BOA-1 and BOA-2 demonstrated significant hydrochromic behavior with a 300 nm absorption red-shift.
- BOA-1 exhibited specific endoplasmic reticulum (ER) targeting and fluorescence activation in response to viscosity.
- BOA-1 showed two distinct emission peaks (230 nm separation) for quantitative ratiometric detection and low interference.
- BOA-1 displayed a pKa of 8.78, indicating its suitability for sensing in physiological environments.
Conclusions:
- The developed [1,3] oxazine-based NIR molecular switches offer a promising platform for intracellular fluorescence sensing.
- BOA-1 demonstrates potential for sensitive and selective detection of intracellular microenvironments, including viscosity.
- BOA-1 shows significant promise for early diagnosis and monitoring of Alzheimer's disease.
- This study pioneers the use of [1,3] oxazine derivatives for NIR fluorescent sensing in biological systems.
