Application of Near Infrared Aggregation-Induced Emission Fluorescence Probe with Benzopyranitrile in Viscosity Detection and Cell Imaging

doi:10.19894/j.issn.1000-0518.250116

Chinese Journal of Applied Chemistry ›› 2025, Vol. 42 ›› Issue (7): 971-981.DOI: 10.19894/j.issn.1000-0518.250116

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Application of Near Infrared Aggregation-Induced Emission Fluorescence Probe with Benzopyranitrile in Viscosity Detection and Cell Imaging

Zhen-Zhen MENG², Jin-Feng YANG¹^,²(), Yu-Kang YAN²

^1.Normal College，Shihezi University，Shihezi 832000，China
^2.College of Chemistry and Chemical Engineering，Shihezi University，Shihezi 832000，China

Received:2025-03-18 Accepted:2025-06-03 Published:2025-07-01 Online:2025-07-23
Contact: Jin-Feng YANG
About author:yangjinfeng@shzu.edu.cn
Supported by:
the National Natural Science Foundation of China(52273209);the High-level Scientific Research Initiation Project of Shihezi University(RCZX201936)

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Abstract

Abstract:

Viscosity in vivo is a necessary metabolic characteristic， and cell imaging and viscosity detection are crucial for a thorough understanding of physiological processes. In this study， a novel viscosity probe DCM-PD， was synthesized utilizing a Knoevevagel condensation reaction with 2-（2-methyl-4H-chromann-4-subunit） malonitrile and 1， 3-diphenyl-1H-pyrazole-4-formaldehyde as raw materials. The probe's chemical structure was validated by nuclear magnetic resonance spectroscopy （NMR） and high resolution mass spectrometry （HRMS）. The key properties of the probe， including solvent effects， aggregation-induced luminescence， and viscosity response， were systematically investigated through spectral testing. The molecular rotor was employed to accurately detect changes in cellular viscosity. The results showed that the probe DCM-PD exhibited excellent near-infrared emission characteristics， significant aggregation-induced emission （AIE） performance and large Stokes shift （245 nm）， which varied with the water-glycerol system （V∶V） The increase of glycerol volume fraction （φ（glycerol）） increased the fluorescence intensity at 660 nm by 10 times， and the two showed a good linear correlation （R²=0.9941）， which proved the feasibility of quantitative application of the probe in viscosity detection. The probe is simultaneously unaffected by metal ions， anions， amino acids， pH variations， and other potential interferences. It demonstrates exceptional selectivity in viscosity response， robust anti-interference capabilities， and remarkable light stability. After the probe was co-incubated with Nystatin induced HeLa cells for 30 min， the fluorescence brightness of the cells was significantly enhanced， indicating that DCM-PD had good biocompatibility and could be applied to the efficient detection of the changes in intracellular viscosity of HeLa induced by drugs， which laid a solid foundation for subsequent biomedical research and clinical diagnosis.

Key words: Viscosity response, Benzopyranonitrile, Aggregation-induced emission, Near-infrared fluorescent probe, Cell imaging

CLC Number:

O657.3

Zhen-Zhen MENG, Jin-Feng YANG, Yu-Kang YAN. Application of Near Infrared Aggregation-Induced Emission Fluorescence Probe with Benzopyranitrile in Viscosity Detection and Cell Imaging[J]. Chinese Journal of Applied Chemistry, 2025, 42(7): 971-981.

Figures/Tables 11

Fig.1 Schematic diagram of DCM-PD response viscosity of fluorescent probe

Fig.2 Synthetic route of fluorescence probe DCM-PD

Fig.3 （A） Solid DCM-PD， DCM and PD in sunlight and UV-light （365 nm）；（B） Fluorescence spectra of solid DCM， PD and DCM-PD （λex=450 nm）

Fig.4 （A） Ultraviolet absorption spectra of probe DCM-PD （10 μmol/L） in different solvents；（B） Fluorescence spectra of probe DCM-PD （10 μmol/L） in different solvents （λex=445 nm）； Illustration： fluorescence images of DCM-PD （10 μmol/L） irradiated by 365 nm ultraviolet light in different solvents

Fig.5 （A） UV absorption spectra of DCM-PD （10 μmol/L） in different φ（H2O）；（B） Fluorescence spectra of probe DCM-PD （10 μmol/L） in different φ（H2O）（λex=445 nm）；（C） Plot of the maximum fluorescence intensity versus the φ（H2O）， illustration： images of DCM-PD （10 μmol/L） in different φ（H2O） under ultraviolet light （365 nm）；（D） Dynamic light scattering （DLS） hydrodynamic diameter distribution of DCM-PD （10 μmol/L） in H2O （illustration： TEM image of the DCM-PD）

Fig.6 （A） Fluorescence spectra of probe DCM-PD （10 μmol/L） in different φ（glycerol） solution （λex=415 nm）；（B） Linear fitting curves of fluorescence intensity of probe DCM-PD （10 μmol/L） at 660 nm and the φ（glycerol） solution

Fig.7 （A） Stokes shift value of probe DCM-PD （10 μmol/L） in water；（B） Stokes shift value of probe DCM-PD （10 μmol/L） in glycerol

Fig.8 Fluorescence intensity of probe DCM-PD （10 μmol/L） and interference substance （1000 μmol/L） in water and glycerol （λex=415 nm）

Fig.9 （A） The relationship between the fluorescence intensity of probe DCM-PD （10 μmol/L） in glycerol and water with time；（B） Fluorescence intensity of probe DCM-PD （10 μmol/L） in PBS buffer solution at different pH

Fig.10 Cytotoxicity assays of probe DCM-PD with different concentrations （0~50 μmol/L） for HeLa cells

Fig.11 Fluorescence images of HeLa cells

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Application of Near Infrared Aggregation-Induced Emission Fluorescence Probe with Benzopyranitrile in Viscosity Detection and Cell Imaging

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