BODIPY dye
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BODIPY dyes are a class of small-molecule fluorophores with strong ultraviolet absorption and sharp fluorescence emission peaks. BODIPY dyes can non-specifically label erythrocyte membranes, fail to inhibit the proliferation of Plasmodium falciparum, exhibit weak cytotoxicity against Chinese hamster ovary cells, and have extremely low hemolytic activity. BODIPY dyes serve as a universal scaffold for fluorescent compounds such as laser dyes and fluorescent probes, and can also be used to construct photoelectric and biophotonic molecular assembly units. BODIPY dyes are applicable to research related to live-cell imaging, fluorescent labeling of proteins and DNA, and various biological imaging assays.
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- CAS. Nr.: 945921-51-7
- Formel: C20H19BF2N2O2
- Molecular Weight:368.18
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Speicherung:
4°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Biologische Aktivität
Beschreibung
In Vitro
BODIPY dye improves its fluorescence efficiency through selective α-position chlorination of 8-methylphenyl-BODIPY and electron-withdrawing group functionalization on boron center[2].
BODIPY dye achieves bathochromic spectral shift toward far-red region and reaches maximum fluorescence quantum yield of 65 via extended conjugation with electron-withdrawing aryl substituents[2].
BODIPY dyes can be functionalized with meso-pyrene or 4-phenylphenol moieties respectively, enabling reversible fluorescent sensing of solvent polarity or environmental pH via ICT or PET processes[2].
BODIPY dyes induce chiral optical activities, including circular dichroism and circularly polarized luminescence. After forming helical bis-BODIPY via covalent linkage or combining with chiral binaphthol/vapol moieties, vapol-BODIPY acts as a highly efficient FRET-based antenna system[2].
BODIPY dye bearing iodine substituents generates high-content singlet oxygen under light irradiation[2].
BODIPY dye (5 μM; 15 min) non-specifically stains both Plasmodium falciparum strain W2-infected and uninfected human red blood cells[3].
BODIPY dye (100 nM; 24 h) does not alter the morphology of *Plasmodium falciparum* strain 3D7 in infected human red blood cells[3].
BODIPY dye exhibits no anti-plasmodial activity against *Plasmodium falciparum* strains W2 and HB3, shows moderate toxicity to CHO-K1 cells with an IC50 of 88 μM, and does not induce hemolysis in healthy human red blood cells even at concentrations as high as 100 μM[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only. Further protocols information, click here.
Chemical Information
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CAS. Nr. 945921-51-7
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Appearance Solid
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Molecular Weight 368.18
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Formel C20H19BF2N2O2
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SMILES
O=C(C1=CC=C(C2=C3C(C)=CC(C)=[N]3[B+3]([F-])([N-]4C(C)=CC(C)=C24)[F-])C=C1)[O-].[H+]
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Versand
Room temperature in continental US; may vary elsewhere.
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Speicherung
4°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Protokoll
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Cell Cytotoxicity Assay
Cytotoxicity assays are usually based on the assessment of cell membrane damage, which can also be indirectly detected by measuring cell viability. Detection methods include MTT assay, CKK-8 assay, LDH assay and ATP assay, etc.
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Mammalian live/dead viability and cytotoxicity staining
Live/dead viability and cytotoxicity staining assays are based on the simultaneous detection of intracellular esterase activity in metabolically active (viable) cells and membrane integrity loss in non-viable cells. In commonly used dual-staining approaches, membrane-permeant fluorogenic substrates are converted by intracellular esterases into fluorescent products in live cells, while impermeant DNA-binding dyes selectively enter cells with compromised plasma membranes and label nucleic acids in dead or dying cells, enabling discrimination between viable and non-viable populations by fluorescence microscopy or flow cytometry.
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Cell Viability Determination by MTT Colorimetric Assay
The following protocol uses the MTT colorimetric assay as a classic literature-established method for assessing cell viability/metabolic activity in cultured mammalian cells. MTT[3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] is reduced by metabolically active cells to a colored formazan product; the amount of formazan is quantified spectrophotometrically and provides an indirect measure of metabolically active viable cells. Importantly, MTT reduction reflects cellular oxidoreductase/metabolic activity rather than an absolute direct count of living cells, so changes in cellular metabolism can alter the signal independently of cell number.
Reinheit & Dokumentation
Verweise
[2]. Bañuelos J, et al. BODIPY Dye, the Most Versatile Fluorophore Ever?. Chemical record (New York, N.Y.). 2016 Feb;16(1):335-48. [Content Brief]
[3]. Rice DR, et al. Antiplasmodial activity of targeted zinc(II)-dipicolylamine complexes. Bioorganic & medicinal chemistry. 2017 May 15;25(10):2754-2760. [Content Brief]
Calculators
Konzentration (Stammlösung) × Volumen (Stammlösung) = Konzentration (Ziellösung) × Volumen (Ziellösung)
Keywords
- BODIPY dye
- 945921-51-7
- Fluorescent Dye
- Biochemical Assay Reagents
- Plasmodium falciparum
- CHO-K1 cells
- singlet oxygen generation
- bathochromic shift
- hypsochromic shift
- intramolecular charge transfer (ICT)
- F?rster resonance energy transfer (FRET)
- solid-state laser
- low cytotoxicity
- pH fluorescent sensor
- Inhibitor
- inhibitor
- inhibit