研究目的
To synthesize and characterize novel azaindole-substituted BODIPY dyes and investigate their fluorescent sensing capabilities for hydrogen sulfate anion, as well as evaluate their cytotoxicity against human leukemia K562 cell lines.
研究成果
The synthesized azaindole-BODIPY compounds 3 and 4 act as selective and sensitive turn-off fluorescent sensors for HSO4- anion, with compound 4 showing higher association constant and lower detection limit. Computational studies explained the positional effect of azaindole on electron distribution and sensing properties. Cytotoxicity assays indicated moderate inhibitory effects on K562 cells, not significantly altered by NaHSO4. These compounds are promising for applications in chemistry, biology, and medicine due to the harmful effects of bisulfate anion.
研究不足
The study is limited to in vitro conditions; cytotoxicity was only tested on K562 cell lines; sensor performance was evaluated in acetonitrile, which may not fully represent biological or environmental conditions; synthesis yields were low (22-28%); no in vivo studies were conducted.
1：Experimental Design and Method Selection:
The study involved the synthesis of azaindole-substituted BODIPY compounds using Knoevenagel reaction, structural characterization via MALDI-TOF MS, NMR, and elemental analysis, photophysical property investigation using UV-Vis and fluorescence spectroscopy, chemosensor studies with various anions, computational analysis using DFT, and cytotoxicity assays via MTT method.
2：Sample Selection and Data Sources:
Compounds 3 and 4 were synthesized from precursors; anions (I?, F?, SO4^2?, HPO4^2?, HSO4?, CH3COO?) were sourced as sodium salts; K562 cell lines were cultured.
3：List of Experimental Equipment and Materials:
Equipment included Shimadzu 2101 UV spectrophotometer, Varian Eclipse spectrofluorometer, Horiba-Jobin-Yvon-SPEX Fluorolog 3-2iHR instrument, Bruker Daltonics Microflex mass spectrometer, Thermo Finnigan Flash 1112 Instrument, Varian 500 MHz NMR spectrometer, Multiskan GO microplate spectrophotometer. Materials included silica gel, deuterated solvents, various chemicals from Merck and Sigma Aldrich.
4：Experimental Procedures and Operational Workflow:
Synthesis involved reflux with Dean-Stark apparatus, purification by column chromatography. Spectral measurements were done in acetonitrile; anion sensing involved adding anion solutions and recording spectra. Cytotoxicity assay involved cell culture, MTT treatment, and absorbance reading.
5：Data Analysis Methods:
Fluorescence quantum yields calculated using comparative method; association constants and detection limits determined from titration data; statistical analysis with GraphPad Prism; computational analysis with Gaussian 09.
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UV spectrophotometer
2101
Shimadzu
Recording electronic absorption spectra in the UV-visible region.
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mass spectrometer
Microflex
Bruker Daltonics
Acquiring mass spectra in linear modes.
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microplate spectrophotometer
Multiskan GO
Thermo Fisher Scientific
Reading microplates at 570 nm for cytotoxicity assay.
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spectrofluorometer
Eclipse
Varian
Recording fluorescence excitation and emission spectra.
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Fluorolog instrument
3-2iHR
Horiba-Jobin-Yvon-SPEX
Obtaining fluorescence lifetimes using time-correlated single photon counting.
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Elemental analyzer
Flash 1112
Thermo Finnigan
Obtaining elemental analyses.
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NMR spectrometer
500 MHz
Varian
Recording 1H and 13C NMR spectra.
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software
Gaussian 09
Gaussian
Performing computational calculations using DFT.
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software
GaussView
Gaussian
Visualization of computational structures.
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software
GraphPad Prism
GraphPad Software, Inc.
Statistical analysis of cytotoxicity data.
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