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Jishan Wu, Minghui Chua, Taeyeon Kim, Zheng Long Lim, Tullimilli Y Gopalakrishna, Yong Ni, Jian Wei Xu, Dongho Kim
Two stable BODIPY-based antiaromatic macrocycles, Mc -Fur and Mc-Th, were synthesized via a one-pot Knoevenagel condensation reaction between a BODIPY precursor and furan-2,5-dicarboxaldehyde or thiophene-2,5-dicarboxaldehyde, respectively. 1H NMR characterization of the two macrocycles supported their large antiaromatic character. The oxidation properties of the two macrocycles were studied via electron spin resonance spectroscopy and UV-Vis absorption spectrophotometry, which suggested the formation of a stable mono-radical cation species on first oxidation followed by an aromatic dication species on the subsequent oxidation...
December 7, 2017: Chemistry: a European Journal
Judita Koreivienė
The staining of lipids in algae cells with BODIPY dyes is much less studied compared to Nile red; therefore, a complex of issues concerning staining details and fluorescence measurements still should be clarified for the species that vary in cell wall complexity. Nevertheless, some general guidelines could be given, and a preliminary protocol of the method is provided based on the existing data. The semiquantification of lipid could be reliable if the staining protocol will be developed and adapted for particular microalgae species...
December 8, 2017: Methods in Molecular Biology
Sarah M Greening, Katherine N Robertson, Alison Thompson
A series of synthetic analogs of the tripyrrolic natural product prodigiosin were complexed with boron trifluoride to generate the corresponding F-BODIPYs. The maximum wavelengths of absorption and emission of the pyrrolyldipyrrin F-BODIPYs were tuned through variation of the substituents about the pyrrolyldipyrrinato core. The limited variation of substituents on the C-ring did not significantly affect absorption and emission. However, variation of substituents on the B-ring and A-ring resulted in a corresponding red-shift in absorption and emission reaching maximum wavelengths of 600 nm...
December 8, 2017: Photochemical & Photobiological Sciences
Joshua K G Karlsson, Owen J Woodford, Heinz Mustroph, Anthony Harriman
Most quantitative fluorescence measurements report emission quantum yields by referring the integrated fluorescence profile to that of a well-known standard compound measured under carefully controlled conditions. This simple protocol works well provided an appropriate standard fluorophore is available and that the experimental conditions used for reference and unknown are closely comparable. Commercial fluorescence spectrophotometers tend to perform very well at wavelengths between 250 and 650 nm but are less responsive at longer wavelengths...
December 8, 2017: Photochemical & Photobiological Sciences
William J Peveler, Sacha Noimark, Hassan Al-Azawi, Gi Byoung Hwang, Colin R Crick, Elaine Allan, Joshua B Edel, Aleksandar P Ivanov, Alexander J MacRobert, Ivan P Parkin
The development of photo-activated antimicrobial surfaces that kill pathogens through the production of singlet oxygen has proved very effective in recent years, with applications in medical devices and hospital touch surfaces, to improve patient safety and well-being. However, many of these surfaces require a swell-encapsulation-shrink strategy to incorporate the photoactive agents in a polymer matrix, and this is resource intensive, given that only the surface fraction of the agent is active against bacteria...
December 6, 2017: ACS Applied Materials & Interfaces
Shuai Shao, Michael B Thomas, Kyu Hyung Park, Zoe Mahaffey, Dongho Kim, Francis D'Souza
Excitation transfer from 1BODIPY* to bisstyrylBODIPY followed by electron transfer to C60 leading to a charge separated state of appreciable lifetime in a supramolecularly assembled triad is demonstrated, as a mimic of the photosynthetic 'antenna-reaction centre'.
December 5, 2017: Chemical Communications: Chem Comm
Pierre D Harvey, Hu Lei, Paul-Ludovic Karsenti
The notoriously non-luminescent uncycled azophenine (Q) was harnessed with Bodipy and zinc(II)porphyrin antennas to probe its fluorescence properties, its ability to act as a singlet excited state energy acceptor and to mediate the transfer. Two near-IR emissions are depicted from time-resolved fluorescence spectroscopy, which are most likely due to the presence of tautomers of very similar calculated total energies (350 cm-1; DFT; B3LYP). The rates for energy transfer, kET(S1), for 1Bodipy*→Q are in the order of 1010-1011 s-1 and are surprisingly fast when considering the low absorptivity properties of the lowest energy charge transfer excited state of azophenine...
December 3, 2017: Chemphyschem: a European Journal of Chemical Physics and Physical Chemistry
Sebastian Requena, Olga Ponomarchuk, Marlius Castillo, Jonathan Rebik, Emmanuelle Brochiero, Julian Borejdo, Ignacy Gryczynski, Sergei V Dzyuba, Zygmunt Gryczynski, Ryszard Grygorczyk, Rafal Fudala
Abnormalities of mucus viscosity play a critical role in the pathogenesis of several respiratory diseases, including cystic fibrosis. Currently, there are no approaches to assess the rheological properties of mucin granule matrices in live cells. This is the first example of the use of a molecular rotor, a BODIPY dye, to quantitatively visualize the viscosity of intragranular mucin matrices in a large population of individual granules in differentiated primary bronchial epithelial cells using fluorescence lifetime imaging microscopy...
December 1, 2017: Scientific Reports
Alexandre Loukanov, Polina Mladenova, Svetlin Toshev, Hibiki Udono, Seiichiro Nakabayashi
The native shape and intracellular distribution of newly synthesized DNA was visualized by correlative (light and electron) microscopy in ice embedded whole cells of Escherichia coli. For that purpose, the commercially available modified nucleoside triphosphate named BODIPY® FL-14-dUTP was enzymatically incorporated in vivo into the genome of E. coli mutant K12 strain, which cannot synthesize thymine. The successful incorporation of this thymidine analogue was confirmed first by fluorescence microscope, where the cells were stained in the typical for bodipy green color...
November 27, 2017: Microscopy Research and Technique
Mitsuhiko Morisue, Shinya Nakano, Masaki Shimizu, Takashi Yumura
An antiparallel double-strand of a BODIPY-zinc-porphyrin dyad was assembled via geometrical complementarity of an unusual B-FZn coordination bonding interaction.
November 30, 2017: Chemical Communications: Chem Comm
E A Leushina, I A Usol'tsev, S I Bezzubov, A A Moiseeva, M V Terenina, A V Anisimov, I V Taydakov, A V Khoroshutin
8-Phenyl- and 8-(4-nitrophenyl)-BODIPYs with thien-2-ylthio- and (2,2'-dithien-5-yl)-thio-substitution at the 3,5-positions were synthesized. 2-Thienylthio derivatives were obtained using two different sequences, i.e., via nucleophilic substitution in the corresponding 1,9-dichlorodipyrromethenes, followed by BODIPY formation and via the same reaction using 3,5-dichloro-BODIPY dyes. The "dipyrromethene route" was observed to result in better overall yields. All the dyes were characterized by UV-Vis and fluorescence spectroscopy as well as cyclic voltammetry (CVA) studies...
November 30, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
Tomoya Kubota, Bobo Dang, Joao L Carvalho-de-Souza, Ana M Correa, Francisco Bezanilla
Voltage-gated sodium (Nav) channels play a key role in generating action potentials which leads to physiological signaling in excitable cells. The availability of probes for functional studies of mammalian Nav is limited. Here, by introducing two amino acid substitutions into the beta scorpion toxin Ts1, we have chemically synthesized a novel binder [S14R, W50Pra]Ts1 for Nav with high affinity, low dissociation rate and reduced toxicity while retaining the capability of conjugating Ts1 with molecules of interests for different applications...
November 27, 2017: Scientific Reports
John Christian Haught, Sancai Xie, Ben Circello, Cheryl S Tansky, Deepa Khambe, Yiping Sun, Yakang Lin, Koti Sreekrishna, Malgorzata Klukowska, Tom Huggins, Donald J White
PURPOSE: To study the reactivity of lipopolysaccharide (LPS) and lipoteichoic acid (LTA) with the cationically charged agents cetylpyridinium chloride, stannous fluoride, and the non-cationic agent triclosan. We also assessed the effect of these agents to inhibit LPS and LTA binding to cellular Toll-like Receptors (TLRs) in vitro. METHODS: The ability of these antimicrobials to bind with LPS and/or LTA was assessed in both the Limulus amebocyte lysate and BODIPY-TR-cadaverine dye assays...
December 2016: American Journal of Dentistry
Tom Huggins, John Christian Haught, Sancai Xie, Cheryl S Tansky, Malgorzata Klukowska, Melanie C Miner, Donald J White
PURPOSE: To apply quantitative Toll-like receptors (TLR) cell assays to compare lipopolysaccharides (LPSs) and lipoteichoic acids (LTAs) from different oral bacterial strains for potential pathogenicity in vitro. METHODS: The potency of LPS and LTA from different bacteria on activation of TLR reporter genes in HEK-tlr cell lines was examined. P. gingivalis LPS mix, P. gingivalis 1690 LPS, P. gingivalis 1435/50 LPS, E. coli LPS (E. coli K12), B. subtilis LTA, S. aureus LTA, E...
December 2016: American Journal of Dentistry
Yogesh Gawale, Lydia Rhyman, Mohamed I Elzagheid, Ponnadurai Ramasami, Nagaiyan Sekar
Density functional theory and time-dependent density functional theory computations were used to understand the electronic and photophysical parameters of NIR β-thiophene-fused BF2-azadipyrromethene dyes. The computed data are in good agreement with those obtained experimentally and they provide insights into the origin of red shifted optical spectra compared to the parent aza-BODIPY, low Stokes shift, non-linear optical responses and quantitative description of the singlet-triplet energy gap. The resultant decrease in the HOMO - LUMO energy gap is responsible for the red shift...
November 21, 2017: Journal of Fluorescence
Amit Kumar Mandal, James R Diers, Dariusz M Niedzwiedzki, Gongfang Hu, Rui Liu, Eric J Alexy, Jonathan S Lindsey, David F Bocian, Dewey Holten
Three sets of tetrapyrrole-chromophore arrays have been examined that exhibit panchromatic absorption across large portions of the near-ultraviolet (NUV) to near-infrared (NIR) spectrum along with favorable excited-state properties for use in solar-energy conversion. The arrays vary the tetrapyrrole (porphyrin, chlorin, bacteriochlorin), chromophore (boron-dipyrrin, perylene, terrylene), and attachment sites (meso-position, β-pyrrole position). In all, seven dyads, one triad, and nine benchmarks in toluene and benzonitrile were studied using steady-state and time-resolved absorption and fluorescence spectroscopy...
November 21, 2017: Journal of the American Chemical Society
Deyan Gong, Shi-Chong Han, Anam Iqbal, Jing Qian, Ting Cao, Wei Liu, Wei-Sheng Liu, Wenwu Qin, Huichen Guo
Two fluorescent, m-nitrophenol-substituted difluoroboron dipyrromethene dyes have been designed by nucleophilic substitution reaction of 3,5-dichloro-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY). Non-symmetric and symmetric probes i.e. BODIPY 1 (with one nitrophenol group at the position 3) and BODIPY 2 (with two nitrophenol groups at the positions 3 and 5) were applied to ratiometric fluorescent glutathione detection. The detection is based on the two-step nucleophilic aromatic substitution of the nitrophenol groups of the probes by glutathione in buffer solution containing CTAB...
November 21, 2017: Analytical Chemistry
Sandro Jurinovich, Lorenzo Cupellini, Ciro A Guido, Benedetta Mennucci
We introduce EXcitonic Analysis Tool (EXAT), a program able to compute optical spectra of large excitonic systems directly from the output of quantum mechanical calculations performed with the popular Gaussian 16 package. The software is able to combine in an excitonic scheme the single-chromophore properties and exciton couplings to simulate energies, coefficients, and excitonic spectra (UV-vis, CD, and LD). The effect of the environment can also be included using a Polarizable Continuum Model. EXAT also presents a simple graphical user interface, which shows on-screen both site and exciton properties...
November 19, 2017: Journal of Computational Chemistry
Kang Yuan, Xiang Wang, Soren K Mellerup, Igor Kozin, Suning Wang
New spiro-BODIPYs with a diaryl chelate unit have been obtained. Crystal structural analysis reveals that the spiro-structures facilitate J-stacking involving the BODIPY core in the solid state. The new BODIPYs form J-aggregates in methanol-water solvent mixture and are brightly emissive in the solid state. The diaryl chelate unit has a significant impact on J-aggregates and fluorescence of BODIPYs.
November 16, 2017: Journal of Organic Chemistry
Xiaomei Dai, Xuelei Chen, Yu Zhao, Yunjian Yu, Xiaosong Wei, Xinge Zhang, Chaoxing Li
A multitude of serious chronic infections involved in bacterial biofilms that are difficult to eradicate. Here, a water-soluble galactose functionalized cationic 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based photodynamic therapy agent was synthesized for selectively eliminating the bacterial biofilm. These conjugates can capture bacteria to form aggregations through electrostatic interaction and then generate a large number of reactive oxygen species (ROS) under visible light irradiation to kill the bacteria without the emergence of bacterial resistance...
November 15, 2017: Biomacromolecules
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