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• 939053-13-1 6-(9-diethylamino-5-oxo-5H-benzo[a]phenoxazin-2-ylethynyl)-2,3-bis(4-methoxybenzyl)-2,3-dihydrophthalazine-1,4-dione 

Relevant academic research and scientific papers

Artificial photosynthesis of methanol from carbon dioxide and water via a Nile red-embedded TiO2 photocathode

The conversion of carbon dioxide into useful chemicals is a prospective strategy for alleviating the greenhouse effect and the depletion of energy. Herein, we report an artificial photosynthetic system composed of a photoanode and a photocathode comprised of NRx@TiO2 functionalized with Nile red via covalent linkage or Pd/NRx@TiO2 with additional palladium nanoparticles. The new Nile red derivatives and organic-inorganic composite electrodes were steadily prepared and well characterized using NMR, HRMS, UV-vis, FTIR, TEM, XPS, XRD and SEM. Methanol and oxygen were the products that could be detected in the liquid and gas phase. The main active species in this artificial photosynthesis system were proven using EPR spectroscopy to be hydroxy radicals releasing O2 gas via H2O2. Moreover, the carbon source of methanol was validated using a 13CO2 labeling experiment; 18O2 was determined to come from H2O using GC-MS. The optimal photoelectrocatalytic CO2 reduction was carried out using Pd/NR2@TiO2 as the working electrode yielding methanol at a rate of 106 μM h?1 cm?2 with high light quantum efficiency (Φcell = 0.95).

BODIPY/Nile-Red-Based Efficient FRET Pair: Selective Assay of Endoplasmic Reticulum Membrane Fluidity

We synthesized a boron-dipyrromethene (BODIPY)/Nile Red hybrid probe capable of selectively recognizing fluidity changes in the endoplasmic reticulum (ER) membrane due to its preferential localization to the ER and strong energy transfer from BODIPY to the Nile Red moiety, emitting only in nonaqueous environments. ER membrane fluidity in HepG2 cells was markedly reduced by a cell model of metabolic syndrome.

Nile Red-Based GPCR Ligands as Ultrasensitive Probes of the Local Lipid Microenvironment of the Receptor

The local lipid microenvironment of transmembrane receptors is an essential factor in G protein coupled receptor (GPCR) signaling. However, tools are currently missing for studying endogenously expressed GPCRs in primary cells and tissues. Here, we introd

Single-molecule studies of diffusion by oligomer-bound dyes in organically modified sol-gel-derived silicate films

Single-molecule fluorescence spectroscopy is used to study dye diffusion within organically modified silicate (ORMOSIL) films. ORMOSIL films are prepared from sols containing tetraethoxysilane and isobutyltrimethoxysilane in 2:1 and 1:9 molar ratios. Nile

Sorption of vapors of aromatic compounds by cross-linked polymer particles containing luminophores: A spectroscopic study

Monodispersed core-shell particles 290-315 nm in diameter were prepared by seed emulsion copolymerization of styrene with divinylbenzene in the presence of luminophore-containing comonomers. The capability of the particles obtained to sorb toluene vapor was shown by solid-state 1H and 13C NMR spectroscopy.

Highly Functionalized β-Cyclodextrins by Solid-Supported Synthesis

Using covalent capture, a high yielding selective mono-functionalization of heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-β-CD with a 5-mercaptopentyl functional group has been achieved. Here, we demonstrate the immobilization of the mono-thiol functionaliz

Synthesis and optical properties of covalently bound Nile Red in mesoporous silica hybrids-comparison of dye distribution of materials prepared by facile grafting and by co-condensation routes

The fluorescence dye Nile Red (NR) can be covalently ligated to hexagonally ordered, mesoporous silica materials (MCM-41) via co-condensation and post grafting routes in order to investigate possible differences in the dye distributions. The obtained hybr

Switchable nile red-based probe for cholesterol and lipid order at the outer leaflet of biomembranes

Cholesterol and sphingomyelin form together a highly ordered membrane phase, which is believed to play important biological functions in plasma membranes of mammalian cells. Since sphingomyelin is present mainly at the outer leaflet of cell membranes, monitoring its lipid order requires molecular probes capable to bind specifically at this leaflet and exhibit negligibly slow flip-flop. In the present work, such a probe was developed by modifying the solvatochromic fluorescent dye Nile Red with an amphiphilic anchor group. To evaluate the flip-flop of the obtained probe (NR12S), we developed a methodology of reversible redox switching of its fluorescence at one leaflet using sodium dithionite. This method shows that NR12S, in contrast to parent Nile Red, binds exclusively the outer membrane leaflet of model lipid vesicles and living cells with negligible flip-flop in the time scale of hours. Moreover, the emission maximum of NR12S in model vesicles exhibits a significant blue shift in liquid ordered phase (sphingomyelin-cholesterol) as compared to liquid disordered phase (unsaturated phospholipids). As a consequence, these two phases could be clearly distinguished in NR12S-stained giant vesicles by fluorescence microscopy imaging of intensity ratio between the blue and red parts of the probe emission spectrum. Being added to living cells, NR12S binds predominantly, if not exclusively, their plasma membranes and shows an emission spectrum intermediate between those in liquid ordered and disordered phases of model membranes. Importantly, the emission color of NR12S correlates well with the cholesterol content in cell membranes, which allows monitoring the cholesterol depletion process with methyl-β-cyclodextrin by fluorescence spectroscopy and microscopy. The attractive photophysical and switching properties of NR12S, together with its selective outer leaflet staining and sensitivity to cholesterol and lipid order, make it a new powerful tool for studying model and cell membranes.

A Nile Red/BODIPY-based bimodal probe sensitive to changes in the micropolarity and microviscosity of the endoplasmic reticulum

We herein report a fluorescent bimodal probe (1) capable of determining ER viscosity and polarity changes using FLIM and fluorescence ratiometry, respectively; during ER stress caused by tunicamycin, the viscosity was increased from ca. 129.5 to 182.0 cP

Simultaneous in situ quantification of two cellular lipid pools using orthogonal fluorescent sensors

Lipids regulate a wide range of biological activities. Since their local concentrations are tightly controlled in a spatiotemporally specific manner, the simultaneous quantification of multiple lipids is essential for elucidation of the complex mechanisms of biological regulation. Here, we report a new method for the simultaneous in situ quantification of two lipid pools in mammalian cells using orthogonal fluorescent sensors. The sensors were prepared by incorporating two environmentally sensitive fluorophores with minimal spectral overlap separately into engineered lipid-binding proteins. Dual ratiometric analysis of imaging data allowed accurate, spatiotemporally resolved quantification of two different lipids on the same leaflet of the plasma membrane or a single lipid on two opposite leaflets of the plasma membrane of live mammalian cells. This new imaging technology should serve as a powerful tool for systems-level investigation of lipid-mediated cell signaling and regulation.