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https://www.readbyqxmd.com/read/28106194/connectivity-pattern-modifies-excited-state-relaxation-dynamics-of-fluorophore-photoswitch-molecular-dyads
#1
F Schweighöfer, J Moreno, S Bobone, S Chiantia, A Herrmann, S Hecht, J Wachtveitl
In order to modulate the emission of BODIPY fluorophores, they were connected to a diarylethene (DAE) photoswitch via phenylene-ethynylene linkers of different lengths and orientations. The latter allowed for modulation of the electronic coupling in the prepared four BODIPY-DAE dyads, which were compared also to appropriate BODIPY and DAE model compounds by steady state as well as time-resolved spectroscopies. In their open isomers, all dyads show comparable luminescence behavior indicative of an unperturbed BODIPY fluorophore...
January 20, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28104574/synthesis-photodynamic-activity-and-quantitative-structure-activity-relationship-modelling-of-a-series-of-bodipys
#2
Enrico Caruso, Marzia Gariboldi, Alessandro Sangion, Paola Gramatica, Stefano Banfi
Here we report the synthesis of eleven new BODIPYs (14-24) characterized by the presence of an aromatic ring on the 8 (meso) position and of iodine atoms on the pyrrolic 2,6 positions. These molecules, together with twelve BODIPYs already reported by us (1-12), represent a large panel of BODIPYs showing different atoms or groups as substituent of the aromatic moiety. Two physico-chemical features ((1)O2 generation rate and lipophilicity), which can play a fundamental role in the outcome as photosensitizers, have been studied...
January 10, 2017: Journal of Photochemistry and Photobiology. B, Biology
https://www.readbyqxmd.com/read/28101544/tetrathienyl-functionalized-red-and-nir-absorbing-bodipy-dyes-appending-various-peripheral-substituents
#3
Ping Liu, Feng Gao, Lina Zhou, Yu Chen, Zhijian Chen
A series of boron-dipyrromethene dyes (BODIPYs) 4a-g with different thienyl moieties at 2,3,5,6-positions of the BODIPY core were synthesized by the Stille cross-coupling reaction. The new compounds were characterized by (1)H NMR, (13)C NMR, HRMS, and IR spectroscopy. The single crystal structure of compound 4e was obtained by X-ray crystallography. The optical and electrochemical properties of these dyes were studied by UV/Vis spectroscopy, fluorescence spectroscopy, and cyclic voltammetry. The DFT calculation of the frontier molecular orbitals of these dyes corroborates the observed effects of peripheral substituents on the optical and redox properties...
January 19, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28099171/an-approach-to-estimate-spatial-distribution-of-analyte-within-cells-using-spectrally-resolved-fluorescence-microscopy
#4
Dharmendar Kumar Sharma, Mir Irfanullah, Santanu Kumar Basu, Sheri Madhu, Suman De, Sameer Jadhav, Mangalampalli Ravikanth, Arindam Chowdhury
While fluorescence microscopy has become an essential tool amongst chemists and biologists for the detection of various analyte within cellular environments, non-uniform spatial distribution of sensors within cells often restricts extraction of reliable information on relative abundance of analytes in different subcellular regions. As an alternative to existing sensing methodologies such as ratiometric or FRET imaging, where relative proportion of analyte with respect to the sensor can be obtained within cells, we propose a methodology using spectrally-resolved fluorescence microscopy, via which both the relative abundance of sensor as well as their relative proportion with respect to the analyte can be simultaneously extracted for local subcellular regions...
January 18, 2017: Methods and Applications in Fluorescence
https://www.readbyqxmd.com/read/28098320/versatile-tissue-lasers-based-on-high-q-fabry-p%C3%A3-rot-microcavities
#5
Yu-Cheng Chen, Qiushu Chen, Tingting Zhang, Wenjie Wang, Xudong Fan
Biolasers are an emerging technology for next generation biochemical detection and clinical applications. Progress has recently been made to achieve lasing from biomolecules and single living cells. Tissues, which consist of cells embedded in an extracellular matrix, mimic more closely the actual complex biological environment in a living body and therefore are of more practical significance. Here, we developed a highly versatile tissue laser platform, in which tissues stained with fluorophores are sandwiched in a high-Q Fabry-Pérot microcavity...
January 18, 2017: Lab on a Chip
https://www.readbyqxmd.com/read/28080031/a-new-approach-to-sensitize-antitumor-monofunctional-platinum-ii-complexes-via-short-time-photo-irradiation
#6
Xuling Xue, Chengcheng Zhu, Huachao Chen, Yang Bai, Xiangchao Shi, Yang Jiao, Zhongyan Chen, Yupeng Miao, Weijiang He, Zijian Guo
Sensitizing the antitumor activity of monofunctional Pt(II) complexes is a reliable approach to developing antitumor agents different from the classic Pt-based drugs. Considering the poor intracellular accumulation of monofunctional Pt(II) complexes, in this study, the photosensitizing monofunctional Pt(II) complex Pt-BA was derived from a weak BODIPY (boron-dipyrromethene)-derived photosensitizer BA, with the purpose to improve its antitumor cytotoxicity via enhancing its intracellular accumulation with a short time photo-irradiation...
December 6, 2016: Inorganic Chemistry
https://www.readbyqxmd.com/read/28079223/ultrafast-energy-and-electron-transfers-in-structurally-well-addressable-bodipy-porphyrin-fullerene-polyads
#7
Di Gao, Shawkat M Aly, Paul-Ludovic Karsenti, Gessie Brisard, Pierre D Harvey
Two electron transfer polyads built upon [C60]-[ZnP]-[BODIPY] (1) and [ZnP]-[ZnP](-[BODIPY])(-[C60]) (2), where [C60] = N-methyl-2-phenyl-3,4-fulleropyrrolidine, [BODIPY] = boron dipyrromethane, and [ZnP] = zinc(ii) porphyrin, were synthesized along with their corresponding energy transfer polyads [ZnP]-[BODIPY] (1a) and [ZnP]-[ZnP]-[BODIPY] (2a) as well as relevant models. These polyads were studied using cyclic voltammetry, DFT computations, steady state and time-resolved fluorescence spectroscopy, and fs transient absorption spectroscopy...
January 12, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28078885/an-ambipolar-bodipy-derivative-for-a-white-exciplex-oled-and-cholesteric-liquid-crystal-laser-towards-multi-functional-devices
#8
Marian Chapran, Enrico Angioni, Neil John Findlay, Benjamin Breig, Vladyslav Cherpak, Pavlo Stakhira, Tell Tuttle, Dmytro Volyniuk, Juozas Vidas Grazulevicius, Yuriy A Nastishin, Oleg D Lavrentovich, Peter John Skabara
A new interface engineering method is demonstrated for the preparation of an efficient white organic light emitting diode (WOLED) by embedding an ultra-thin layer of the novel ambipolar red emissive compound 4,4-di-fluoro-2,6-di(4-hexylthiopen-2-yl)-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene (bThBODIPY) in the exciplex formation region. The compound shows a hole and electron mobility of 3.3 × 10-4 cm2 V-1 s-1 and 2 × 10-4 cm2 V-1 s-1, respectively at electric fields higher than 5.3 × 105 V cm-1...
January 12, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28078077/a-novel-method-for-the-quantification-of-fatty-infiltration-in-skeletal-muscle
#9
Nicole K Biltz, Gretchen A Meyer
BACKGROUND: Fatty infiltration of the skeletal muscle is a common but poorly understood feature of many myopathies. It is best described in human muscle, where non-invasive imaging techniques and representative histology have been optimized to view and quantify infiltrating fat. However, human studies are limited in their ability to identify cellular and molecular mechanisms regulating fatty infiltration, a likely prerequisite to developing targeted interventions. As mechanistic investigations move to small animals, studies may benefit from new or adapted imaging tools optimized for high resolution and whole muscle quantification...
2017: Skeletal Muscle
https://www.readbyqxmd.com/read/28073372/a-novel-method-for-the-quantification-of-fatty-infiltration-in-skeletal-muscle
#10
Nicole K Biltz, Gretchen A Meyer
BACKGROUND: Fatty infiltration of the skeletal muscle is a common but poorly understood feature of many myopathies. It is best described in human muscle, where non-invasive imaging techniques and representative histology have been optimized to view and quantify infiltrating fat. However, human studies are limited in their ability to identify cellular and molecular mechanisms regulating fatty infiltration, a likely prerequisite to developing targeted interventions. As mechanistic investigations move to small animals, studies may benefit from new or adapted imaging tools optimized for high resolution and whole muscle quantification...
January 10, 2017: Skeletal Muscle
https://www.readbyqxmd.com/read/28064068/the-naphthoate-modifying-cu-2-detective-bodipy-sensors-with-the-fluorescent-on-off-performance-unaffected-by-molecular-configuration
#11
Yuting Chen, Luyang Zhao, Jianzhuang Jiang
Two new boron-dipyrromethenes decorated with 8-hydroxyquinoline-naphthoate moiety, namely 4,4-difluoro-8-(5-(8-hydroxyquinoline-naphthoate))-3,5-dimethyl-4-bora-3a,4a-diaza-s-indacene (8-HQ-N-DMe-Bodipy) (1) and 4,4-difluoro-8-(5-(8-hydroxyquinoline-naphthoate))-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene (8-HQ-N-TMe-Bodipy) (2) have been synthesized. Single crystal X-ray diffraction analysis discloses the very much similar steric arrangement of 8-hydroxyquinoline-naphthoate moiety in these two compounds as revealed by the close torsion angle of C-C-O-C bridge, 174...
December 21, 2016: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
https://www.readbyqxmd.com/read/28064042/influence-of-aglycone-structures-on-n-glycan-processing-reactions-in-the-endoplasmic-reticulum
#12
Kiichiro Totani, Kenta Yamaya, Makoto Hirano, Yukishige Ito
Glycoprotein N-linked oligosaccharides in the endoplasmic reticulum function as tags to regulate glycoprotein folding, sorting, secretion and degradation. Since the N-glycan structure of a glycoprotein should reflect the folding state, N-glycan processing may be affected by the aglycone state. In this study, we examined the influence of aglycone structures on N-glycan processing using synthetic substrates. We prepared (Glc1)Man9GlcNAc2 linked to hydrophobic BODIPY-dye with a systematic series of different linker lengths...
December 29, 2016: Carbohydrate Research
https://www.readbyqxmd.com/read/28058418/halogen-atom-effect-on-the-photophysical-properties-of-substituted-aza-bodipy-derivatives
#13
B C De Simone, G Mazzone, J Pirillo, N Russo, E Sicilia
The influence of halogen atom substitution (Br and I), in different amounts and positions in an aza-BODIPY skeleton, on the photophysical properties of some aza-BODIPY derivatives has been investigated by using density functional theory and its time-dependent extension. The heavy atom effect on excitation energies, singlet-triplet energy gaps and spin-orbit matrix elements has been considered. The maximum absorption within the therapeutic window has been confirmed for all the aza-BODIPY derivatives. The feasible intersystem spin crossing pathways for the population of the lowest triplet state, that will depend on the values of the spin-orbit matrix elements, the energy gap as well as the orbital composition of the involved states have been found to most likely involve the S1 and T1 or T2 states...
January 18, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28055199/observation-of-the-strong-electronic-coupling-in-near-infrared-absorbing-tetraferrocene-aza-dipyrromethene-and-aza-bodipy-with-direct-ferrocene-%C3%AE-and-ferrocene-%C3%AE-pyrrole-bonds-toward-molecular-machinery-with-four-bit-information-storage-capacity
#14
Yuriy V Zatsikha, Cole D Holstrom, Kullapa Chanawanno, Allen J Osinski, Christopher J Ziegler, Victor N Nemykin
The 1,3,7,9-tetraferrocenylazadipyrromethene (3) and the corresponding 1,3,5,7-tetraferrocene aza-BODIPY (4) were prepared via three and four synthetic steps, respectively, starting from ferrocenecarbaldehyde using the chalcone-type synthetic methodology. The novel tetra-iron compounds have ferrocene groups directly attached to both the α- and the β-pyrrolic positions, and the shortest Fe-Fe distance determined by X-ray crystallography for 3 was found to be ∼6.98 Å. These new compounds were characterized by UV-vis, nuclear magnetic resonance, and high-resolution electrospray ionization mass spectrometry methods, while metal-metal couplings in these systems were probed by electro- and spectroelectrochemistry, chemical oxidations, and Mössbauer spectroscopy...
January 5, 2017: Inorganic Chemistry
https://www.readbyqxmd.com/read/28054075/zwitterionic-bodipys-with-large-stokes-shift-small-molecular-biomarkers-for-live-cells
#15
Adiki Raja Sekhar, Santhosh Kumar Sariki, R V Ramana Reddy, Alakesh Bisai, Pushpendra Kumar Sahu, Raghuvir S Tomar, Jeyaraman Sankar
The two first examples of zwitterionic BODIPYs have been synthesized via a simple SN-Ar methodology. The molecules exhibit excellent optical behavior, such as a large Stokes shift in solution and therefore a very intense emission, and can thus avoid self-quenching. The zwitterionic nature of the molecules was unambiguously elucidated using single crystal XRD studies. The electronic conjugation was investigated by NMR, DFT (NICS (0)) and XRD analysis. Due to their inherent ionic nature, their enhanced solubility in aqueous conditions was exploited for their utility in bio-imaging and cell viability studies...
January 5, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28052673/-clickable-nanogels-via-thermally-driven-self-assembly-of-polymers-facile-access-to-targeted-imaging-platforms-using-thiol-maleimide-conjugation
#16
Bugra Aktan, Laura Chambre, Rana Sanyal, Amitav Sanyal
Mutlifunctionalizable nanogels are fabricated using thermally driven self-assembly and crosslinking of reactive thermoresponsive copolymers. Nanogels thus fabricated can be easily conjugated with various appropriately functionalized small molecules and/or ligands to tailor them for various applications in delivery and imaging. In this study, poly (ethylene glycol) methacrylate based maleimide bearing copolymer was crosslinked with a dithiol-based crosslinker to synthesize nanogels. Due to lower critical solution temperature around 55 oC in aqueous media, these copolymers assemble into nano-sized aggregates when heated to this temperature, and are crosslinked using the thiol-maleimide conjugation...
January 4, 2017: Biomacromolecules
https://www.readbyqxmd.com/read/28049591/bodipy-17%C3%AE-ethynylestradiol-conjugates-synthesis-fluorescence-properties-and-receptor-binding-affinities
#17
Samira Osati, Hasrat Ali, Fernanda Marques, Michel Paquette, Simon Beaudoin, Brigitte Guerin, Jeffrey V Leyton, Johan E van Lier
In vivo imaging of estrogen receptor (ER) densities in human breast cancer is a potential tool to stage disease, guide treatment protocols and follow-up on treatment outcome. Both positron emission tomography (PET) and fluorescence imaging have received ample attention to detect ligand-ER interaction. In this study we prepared BODIPY-estradiol conjugates using 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) as fluorescent probe and estradiol derivatives as ligand and established their relative binding affinity (RBA) for the ERα...
December 25, 2016: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28045179/heck-functionalization-of-an-asymmetric-aza-bodipy-core-synthesis-of-far-red-infrared-probes-for-bioimaging-applications
#18
Stefano Parisotto, Beatrice Lace, Emma Artuso, Chiara Lombardi, Annamaria Deagostino, Roberto Scudu, Claudio Garino, Claudio Medana, Cristina Prandi
As part of our ongoing work on the synthesis of a new class of plant hormones named Strigolactones (SLs) and their analogues, we became interested in tracing bioactive molecules with red emitting BODIPY fluorophores in order to unravel signaling and distribution of SLs in plants. In this paper we report on an unprecedented Heck functionalization of azadipyrromethenes (aza-DIPY) which allows for the introduction of suitable functional groups to convert aza-BODIPY in bioconjugate complexes useful for untangling biological processes...
January 3, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28045176/second-order-nonlinear-polarizability-of-ferrocene-bodipy-donor-acceptor-adducts-quantifying-charge-redistribution-in-the-excited-state
#19
Navdeep Kaur, Nick Van Steerteghem, Priya Singla, Paramjit Kaur, Koen Clays, Kamaljit Singh
A series of dyads and triads using ferrocene (Fc) as the donor and 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) as the acceptor, linked either directly or through an N-phenylmethanimine or ethynylbenzene linker have been synthesized. While the former (directly linked) dyads were prepared through acid catalyzed condensation of pyrrole with ferrocenecarboxaldehye or 1,1'-ferrocenedicarboxaldehyde followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), the latter two sets (imine and alkyne linked) of dyads were obtained through Schiff base condensation or Sonogashira coupling reactions, respectively...
January 3, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
https://www.readbyqxmd.com/read/28038998/activation-of-ampk-by-berberine-induces-hepatic-lipid-accumulation-by-upregulation-of-fatty-acid-translocase-cd36-in-mice
#20
You-Jin Choi, Kang-Yo Lee, Seung-Hwan Jung, Hyung Sik Kim, Gayong Shim, Mi-Gyeong Kim, Yu-Kyoung Oh, Seon-Hee Oh, Dae Won Jun, Byung-Hoon Lee
Emerging evidence has shown that berberine has a protective effect against metabolic syndrome such as obesity and type II diabetes mellitus by activating AMP-activated protein kinase (AMPK). AMPK induces CD36 trafficking to the sarcolemma for fatty acid uptake and oxidation in contracting muscle. However, little is known about the effects of AMPK on CD36 regulation in the liver. We investigated whether AMPK activation by berberine affects CD36 expression and fatty acid uptake in hepatocytes and whether it is linked to hepatic lipid accumulation...
December 28, 2016: Toxicology and Applied Pharmacology
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