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Relevant academic research and scientific papers

A Ratiometric Two-Photon Fluorescent Probe for Tracking Lysosomal ATP: Direct In Cellulo Observation of Lysosomal Membrane Fusion Processes

Vesicles exchange their contents through membrane fusion processes, kiss-and-run and full-collapse fusion. Indirect observation of these fusion processes using artificial vesicles enhanced our understanding on the molecular mechanisms involved. Direct observation of the fusion processes in a real biological system, however, remains a challenge owing to many technical obstacles. We report a ratiometric two-photon probe offering real-time tracking of lysosomal ATP with quantitative information for the first time. By applying the probe to two-photon live-cell imaging, the lysosomal membrane fusion process in cells has been directly observed and the concentration of its content, lysosomal ATP, has been measured. Results show that the kiss-and-run process between lysosomes proceeds through repeated transient interactions with gradual content mixing, whereas the full-fusion process occurs at once. Furthermore, it is confirmed that both the fusion processes proceed with conservation of the content. Such a small-molecule probe exerts minimal disturbance and hence has potential for studying various biological processes associated with lysosomal ATP.

Fluorescent Labeling of Protein Using Blue-Emitting 8-Amino-BODIPY Derivatives

8-Amino-BODIPY (boron-dipyrromethane) dyes show bright blue fluorescence. Disclosed here are synthesis and characterization of the photophysical properties of a series of functionalized 8-Amino-BODIPY (BP1–4) for protein labeling. The compact structure and solvent-insensitive absorption property of the dye are desirable features for protein labeling. For the model protein, bovine serum albumin (BSA), the labeling proceeds under mild condition via amide bond formation or thiol-ene conjugation with maintaining the bright blue fluorescence. The chromatography and mass spectroscopy analysis clearly support the labeling of the BODIPY dye on the BSA. The protein labeling with blue-emitting BODIPY would be applicable for studying protein dynamics and fluorescence resonance energy transfer (FRET) with intrinsic biomolecules.

A Photoexcitation-Induced Twisted Intramolecular Charge Shuttle

Charge transfer and separation are important processes governing numerous chemical reactions. Fundamental understanding of these processes and the underlying mechanisms is critical for photochemistry. Herein, we report the discovery of a new charge-transfer and separation process, namely the twisted intramolecular charge shuttle (TICS). In TICS systems, the donor and acceptor moieties dynamically switch roles in the excited state because of an approximately 90° intramolecular rotation. TICS systems thus exhibit charge shuttling. TICSs exist in several chemical families of fluorophores (such as coumarin, BODIPY, and oxygen/carbon/silicon–rhodamine), and could be utilized to construct functional fluorescent probes (i.e., viscosity- or biomolecule-sensing probes). The discovery of the TICS process expands the current perspectives of charge-transfer processes and will inspire future applications.

Rapid and selective electrophilic trifluoromethylation of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) scaffold

This report deals with the rapid functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) scaffold by means of electrophilic trifluoromethylation. Subjecting dye 2 to the disclosed protocol led to the successful isolation of 3-trifluoromethylated derivative 9. Subsequent comparison of structural and electronic properties allowed for the characterization of changes imparted by the CF3 group. A diminution in the quantum yield [Φ F(2)MeOH = 0.15, Φ F(9)THF = 0.024] was accompanied by a larger Stokes shift [ΔS(2)MeOH = 12 nm, ΔS(9)THF = 54 nm], whereas the molar extinction coefficient at the global absorbance maximum remained largely unaffected [ε(2)MeOH = 40 × 103 M -1 cm-1, ε(9)THF = 30 × 103 M -1 cm-1]. A protocol for the rapid trifluoromethylation of the BODIPY scaffold, based on a mixture of 3,3-dimethyl-1-(trifluoromethyl)-3H-1λ3,2-benziodaoxole and iPrSH, is presented. The electronic and structural changes imparted by the CF3 moiety are studied by NMR and UV/Vis spectroscopy and X-ray crystallography.

Effect of solvent nature on spectral properties of blue-emitting meso-propargylamino-BODIPY

The spectral and luminescent properties of meso?propargylamino?boron (III) dipyrromethenate (BODIPY 1) were studied in a wide range of organic solvents of different polarities, electron- and proton-donating abilities. Effect of organic solvents on the properties of the BODIPY 1 spectral characteristics was analyzed in details. It was shown that the fluorescence of BODIPY 1 is characterized by a high sensitivity to the nature of the solvent. It was found that the complex, which emits in the blue-green region (433–486 nm), has a high quantum yield of fluorescence (~100%) in non-polar media (cyclohexane, benzene, toluene), while in proton- and especially electron donor media, sharp fluorescence quenching (2.2–31.2 times) of the dye is observed. For a better understanding of the spectral analysis results, a quantum-chemical analysis of the molecular structure, electronic structure, and spectral characteristics of BODIPY 1 was carried out. For the first time, it was shown that BODIPY 1 fluorescence quenching in proton and electron donor media is caused by the formation of a supramolecular dye complex due to specific interactions of solvent molecules with atoms of the meso?propargylamine group. Due to practically useful spectral properties, including the sensitivity of the fluorescence to the nature of the media, BODIPY 1 is recommended as a new effective fluorescent sensor of specific electron and proton donor molecules.

Hetaryl thioketones: Synthesis and selected reactions

A series of phenyl/hetaryl and bishetaryl thioketones have been prepared via oxygen/sulfur exchange of the corresponding ketones by treatment with Lawesson's reagent. The nonsymmetrical ketones were conveniently accessible via the reactions of lithiated f

A BODIPY-based reactive probe for ratiometric fluorescence sensing of mercury ions

A simple BODIPY derivative is demonstrated to fluorescently sense Hg 2+ in a ratiometric manner. The probe, an 8-methylthio-BODIPY, undergoes Hg2+-promoted hydrolysis to produce the corresponding 8-hydroxy-BODIPY, which conversion is accompanied with a large emission wavelength change. The probe can selectively detect Hg2+ over various other metal cations, with a detection limit of 1 ppb.

Modifiable hyperconjugation triple molten porphyrin dimer strong two-photon absorption material and preparation thereof

The invention relates to a modifiable hyperconjugation triple molten porphyrin dimer strong two-photon absorption material and preparation thereof. In two edge meso positions of a porphyrin dimer, oneof the two edge meso positions of the porphyrin dimer is provided with anilino, and the other of the two edge meso positions of the porphyrin dimer is provided with acetanilino. Compared with the prior art, the preparation method comprises the following steps: selectively modifying aniline groups on single porphyrin with vacancy at double meso sites in a unilateral manner, performing protection in advance, further separating out a symmetrical molten porphyrin dimer with two acetanilide groups through low-temperature oxidation and low-temperature extraction modes, and finally preparing a target compound with one anilino group and one acetanilino group through a unilateral deprotection reaction, namely the asymmetric triple molten porphyrin dimer TFP. The material not only has the strong TPA characteristic of the triple molten porphyrin dimer, but also is very easy to modify, provides possibility for preparing diversified nonlinear and other functional materials with a wider applicationrange, and has a good application prospect.

Triple molten porphyrin dimer covalent functionalized single-walled carbon nanotube nonlinear nano hybrid material and preparation method thereof

The invention relates to a triple molten porphyrin dimer covalent functionalized single-walled carbon nanotube non-linear nano hybrid material and a preparation method thereof. The non-linear nano hybrid material is formed by connecting a triple molten porphyrin dimer TFP to the surface of SWCNT through covalent bonds. Compared with the prior art, the organic-inorganic covalent functionalized nanofunctional material is prepared by connecting TFP to the surface of SWCNT through covalent bonds and the azo salt free radical addition reaction instead of simply and physically mixing the two different optical functional materials, and compared with a traditional material, the prepared material not only has enhanced nonlinear optical properties in the nanosecond visible light field, but also canconvert saturated absorption of a traditional material into anti-saturated absorption in the femtosecond near-infrared field, and has a very wide application prospect.

Boron Dipyrromethene (BODIPY) as Electron-Withdrawing Group in Asymmetric Copper-Catalyzed [3+2] Cycloadditions for the Synthesis of Pyrrolidine-Based Biological Sensors

In this work, we describe the use of Boron Dipyrromethene (BODIPY) as electron-withdrawing group for activation of double bonds in asymmetric copper-catalyzed [3+2] cycloaddition reactions with azomethine ylides. The reactions take place under smooth conditions and with high enantiomeric excess for a large number of different substituents, pointing out the high activation of the alkene by using a boron dipyrromethene as electron-withdrawing group. Experimental, theoretical studies and comparison with other common electron-withdrawing groups in asymmetric copper-catalyzed [3+2] cycloadditions show the reasons of the different reactivity of the boron dipyrromethene derivatives, which can be exploited as a useful activating group in asymmetric catalysis. Additional experiments show that the so obtained pyrrolidines can be employed as biocompatible biosensors, which can be located in the endosomal compartments and do not present toxicity in three cell lines. (Figure presented.).