研究目的
Developing fluorescent markers for various bioobjects by synthesizing and characterizing novel BODIPY-conjugated amino acids.
研究成果
Three novel fluorescent amino acids – BODIPY conjugates were synthesized and characterized, showing good photophysical properties and water solubility. These bioconjugates are promising for bioimaging, biolabeling, drug delivery, and visualization of biological processes due to their bioavailability and affinity for biomolecules.
研究不足
The spectral properties of the conjugates in water were not investigated within the framework of the current study, and this is noted as an area for future work. The study focused on in vitro characterization, and further in vivo applications may require additional optimization.
1：Experimental Design and Method Selection:
The study involved the synthesis of BODIPY precursors and their conjugation with amino acids (lysine, methionine, tryptophan) via amino groups. Spectral properties were investigated using absorbance and fluorescence spectroscopy, and quantum chemical calculations were performed to interpret the results.
2：Sample Selection and Data Sources:
BODIPY precursors and DL-amino acids were obtained from commercial sources (Sigma-Aldrich, Merck Millipore, Reakhim). Solvents were dried before use.
3：List of Experimental Equipment and Materials:
Instruments included Bruker Avance III 500 NMR spectrometer, Bruker VERTEX 80v FTIR spectrometer, Shimadzu AXIMA Confidence MALDI TOF-TOF mass spectrometer, Solar SM 2203 spectrofluorometer, and standard quartz cuvettes. Materials included BODIPY precursors, amino acids, solvents (DMSO, DCM, CDCl3, D2O, H2O), and buffer solution components.
4：Experimental Procedures and Operational Workflow:
Synthesis of BODIPY precursors followed a literature procedure. Conjugation involved dissolving BODIPY precursor in DMSO and amino acid in buffer solution (pH
5：0), stirring in an ice bath for 12 h, washing with DCM, and removing solvents under reduced pressure. Characterization used NMR, IR, MALDI-TOF, absorbance, and fluorescence spectroscopy. Quantum chemical calculations used PC GAMESS v. 12 with B3LYP and CAM-B3LYP functionals. Data Analysis Methods:
Photophysical characteristics (quantum yields, lifetimes, rate constants) were calculated using standard equations and PhotochemCAD program. NMR and IR data were analyzed for structural confirmation. Quantum chemical calculations included geometry optimization and TDDFT analysis.
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NMR Spectrometer
Avance III 500
Bruker
Recording 1H and 11B nuclear magnetic resonance spectra for structural characterization of BODIPY precursors and conjugates.
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FTIR Spectrometer
VERTEX 80v
Bruker
Obtaining infrared spectra in the mid-infrared region to confirm functional groups and bond formation in BODIPY precursors and conjugates.
VERTEX 80 & 80v FT-IR Spectrometers
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MALDI TOF-TOF Mass Spectrometer
AXIMA Confidence
Shimadzu
Recording matrix-assisted laser desorption/ionization time of flight mass spectra to confirm molecular weights of synthesized compounds.
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Spectrofluorometer
SM 2203
Solar
Performing absorbance and fluorescence spectroscopy experiments to study spectral properties and photophysical characteristics of BODIPY compounds.
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Boron Trifluoride Diethyl Etherate
BF3·OEt2
Merck Millipore
Used as a reagent in the synthesis of BODIPY precursors.
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DL-Amino Acids
Reakhim
Used as starting materials for conjugation with BODIPY precursors to form bioconjugates.
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Dimethyl Sulfoxide
DMSO
Solvent for dissolving BODIPY precursor in conjugation reactions.
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Dichloromethane
DCM
Used for washing reaction mixtures to eliminate unreacted BODIPY precursor.
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Deuterated Chloroform
CDCl3
Solvent for NMR sample preparation of BODIPY precursors.
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Deuterated Water
D2O
Solvent component for NMR sample preparation of BODIPY conjugates.
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Tetramethylsilane
TMS
Internal reference for 1H NMR studies.
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Potassium Bromide
KBr
Used in pellet method for IR spectroscopy sample preparation.
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Rhodamine 6G
Used as a standard for fluorescence quantum yield determination.
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PhotochemCAD Program
Used for calculating fluorescence lifetimes and radiative rate constants based on spectral data.
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PC GAMESS Program
v. 12
Used for quantum chemical calculations including geometry optimization and TDDFT analysis of BODIPY conjugates.
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UCSF Chimera Program
Used for analysis and visualization of computational results.
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Chemcraft Program
1.8
Used for analysis and visualization of quantum chemistry computations.
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