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https://www.readbyqxmd.com/read/28724190/testing-limits-of-bophy-platform-preparation-characterization-and-theoretical-modeling-of-bophys-bophys-with-electron-withdrawing-groups-at-b-pyrrolic-and-bridging-positions
#1
Victor N Nemykin, Yuriy V Zatsikha, Dion B Nemez, Rebecca L Davis, Simarpreet Singh, David E Herbert, Alex J King, Christopher J Ziegler
Several BOPHY derivatives with and without ferrocene fragments and with electron-withdrawing carbethoxy groups appended to the -pyrrolic positions have been prepared and characterized by NMR, UV-Vis-NIR, APCI MS, and fluorescence spectroscopy as well as X-ray crystallography. The redox properties of new BOPHYs were probed by electrochemical (CV and DPV) and spectroelectrochemical methods. In attempt for the preparation of the BOPHY derivatives with cyano group at bridging position using similar to recently communicated BODIPY cyanation approach (Chem...
July 19, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28722041/ultrafast-dynamics-and-solvent-dependent-deactivation-kinetics-of-bodipy-molecular-rotors
#2
Tomislav Suhina, Saeed Amirjalayer, Sander Woutersen, Daniel Bonn, Albert M Brouwer
Molecular rotors based on meso-substituted boron-dipyrromethane (BODIPY) are widely recognized fluorescent viscosity sensors. The viscosity dependence of their fluorescence arises from an efficient excited-state deactivation process that can only occur when molecular-scale motion is not hindered. Here, we use visible and IR pump-probe spectroscopies combined with TD-DFT calculations to show that this fluorescence deactivation takes place through a fast and irreversible process which does not involve intermediate electronic states...
July 19, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28721419/highly-fluorescent-hyperbranched-bodipy-based-conjugated-polymer-dots-for-cellular-imaging
#3
Rongxin Du, Shuang Cui, Zezhou Sun, Ming Liu, Yong Zhang, Qiong Wu, Changfeng Wu, Fengyun Guo, Liancheng Zhao
The first hyperbranched BODIPY-based conjugated polymer dots (Pdots) were reported. The Pdots showed quantum yields of as high as 22%, which is 40% higher than their linear counterparts. The Pdots were successfully applied in cell-labelling applications. These results demonstrated that hyperbranched polymers are a very promising material for biological imaging and applications.
July 19, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28718466/exploring-viscosity-polarity-and-temperature-sensitivity-of-bodipy-based-molecular-rotors
#4
Aurimas Vyšniauskas, Ismael López-Duarte, Nicolas Duchemin, Thanh-Truc Vu, Yilei Wu, Ekaterina M Budynina, Yulia A Volkova, Eduardo Peña Cabrera, Diana E Ramírez-Ornelas, Marina K Kuimova
Microviscosity is a key parameter controlling the rate of diffusion and reactions on the microscale. One of the most convenient tools for measuring microviscosity is by fluorescent viscosity sensors termed 'molecular rotors'. BODIPY-based molecular rotors in particular proved extremely useful in combination with fluorescence lifetime imaging microscopy, for providing quantitative viscosity maps of living cells as well as measuring dynamic changes in viscosity over time. In this work, we investigate several new BODIPY-based molecular rotors with the aim of improving on the current viscosity sensing capabilities and understanding how the structure of the fluorophore is related to its function...
July 18, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28703788/preparation-of-a-trp-bodipy-fluorogenic-amino-acid-to-label-peptides-for-enhanced-live-cell-fluorescence-imaging
#5
Lorena Mendive-Tapia, Ramon Subiros-Funosas, Can Zhao, Fernando Albericio, Nick D Read, Rodolfo Lavilla, Marc Vendrell
Fluorescent peptides are valuable tools for live-cell imaging because of the high specificity of peptide sequences for their biomolecular targets. When preparing fluorescent versions of peptides, labels must be introduced at appropriate positions in the sequences to provide suitable reporters while avoiding any impairment of the molecular recognition properties of the peptides. This protocol describes the preparation of the tryptophan (Trp)-based fluorogenic amino acid Fmoc-Trp(C2-BODIPY)-OH and its incorporation into peptides for live-cell fluorescence imaging-an approach that is applicable to most peptide sequences...
August 2017: Nature Protocols
https://www.readbyqxmd.com/read/28702554/in-vitro-and-in-vivo-trackable-titanocene-based-complexes-using-optical-imaging-or-spect
#6
Océane Florès, Audrey Trommenschlager, Souheila Amor, Fernanda Marques, Francisco Silva, Lurdes Gano, Franck Denat, Maria Paula Cabral Campello, Christine Goze, Ewen Bodio, Pierre Le Gendre
A novel Ti/(111)In-heterometallic radiotheranostic along with non-radioactive Ti/In, Ti/Lu, and Ti/Y analogues has been reported, thanks to the design of a challenging synthesis of the first titanocene-DOTA ligand. The corresponding titanocene-BODIPY complex was developed for in vitro tracking by optical imaging. The different complexes were characterized and their antiproliferative properties were evaluated on three cancer cell lines (A2780, B16F1, and PC3). As a proof of concept, initial studies in healthy mice were performed with a Ti/(111)In derivative to obtain information about its uptake, its biodistribution, and its excretion...
July 12, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
https://www.readbyqxmd.com/read/28700900/nanoparticles-administered-intrapericardially-enhance-payload-myocardial-distribution-and-retention
#7
Victor Segura-Ibarra, Francisca E Cara, Suhong Wu, David A Iruegas-Nunez, Sufen Wang, Mauro Ferrari, Arturas Ziemys, Miguel Valderrabano, Elvin Blanco
Pharmacological therapies for cardiovascular diseases are limited by short-term pharmacokinetics and extra-cardiac adverse effects. Improving delivery selectivity specifically to the heart, wherein therapeutic drug levels can be maintained over time, is highly desirable. Nanoparticle (NP)-based pericardial drug delivery could provide a strategy to concentrate therapeutics within a unique, cardiac-restricted compartment to allow sustained drug penetration into the myocardium. Our objective was to explore the kinetics of myocardial penetration and retention after pericardial NP drug delivery...
July 9, 2017: Journal of Controlled Release: Official Journal of the Controlled Release Society
https://www.readbyqxmd.com/read/28696681/optical-ph-sensor-covering-the-range-from-ph-0-14-compatible-with-mobile-device-readout-and-based-on-a-set-of-rationally-designed-indicator-dyes
#8
Raúl Gotor, Pichandi Ashokkumar, Mandy Hecht, Karin Keil, Knut Rurack
In this work, a family of pH-responsive fluorescent probes has been designed in a rational manner with the aid of quantum chemistry tools, covering the entire pH range from 0-14. Relying on the boron-dipyrromethene (BODIPY) core, all the probes as well as selected reference dyes display very similar spectroscopic properties with ON-OFF fluorescence switching responses, facilitating optical readout in simple devices used for detection and analysis. Embedding of the probes and references dyes into hydrogel spots on a plastic strip yielded a test strip that reversibly indicates pH with a considerably small uncertainty of ca...
July 11, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28696443/a-facile-synthesis-of-novel-near-infrared-pyrrolopyrrole-aza-bodipy-luminogens-with-aggregation-enhanced-emission-characteristics
#9
Lanqing Li, Lingyun Wang, Hao Tang, Derong Cao
Here we report the facile synthesis of two triphenylethylene-modified pyrrolopyrrole aza-BODIPY dyes with an aggregation-enhanced emission feature. NIR-emitting nanoparticles with remarkable photostability properties and applications in bioimaging were generated due to their good dispersity in water and biocompatibility.
July 11, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28681566/design-and-synthesis-of-the-bodipy-bsa-complex-for-biological-applications
#10
Mani Vedamalai, Iti Gupta
A quinoxaline-functionalized styryl-BODIPY derivative (S1) was synthesized by microwave-assisted Knoevenagel condensation. It exhibited fluorescence enhancement upon micro-encapsulation into the hydrophobic cavity of bovine serum albumin (BSA). The S1-BSA complex was characterized systematically using ultraviolet (UV)-visible absorption, fluorescence emission, kinetics, circular dichroism and time-resolved lifetime measurements. The binding nature of BSA towards S1 was strong, and was found to be stable over a period of days...
July 6, 2017: Luminescence: the Journal of Biological and Chemical Luminescence
https://www.readbyqxmd.com/read/28678301/diphenylacrylonitrile-connected-bodipy-dyes-fluorescence-enhancement-based-on-dark-and-aie-resonance-energy-transfer
#11
Liangbin Lin, Xiaoru Lin, Hongyu Guo, Fafu Yang
This study focuses on the construction of novel diphenylacrylonitrile-connected BODIPY dyes with high fluorescence in both solution and an aggregated state by combining DRET and FRET processes in a single donor-acceptor system. The first BODIPY derivatives with one, two, or three AIE-active diphenylacrylonitrile groups were designed and synthesized in moderate yields. Strong fluorescence emissions were observed in the THF solution under excitation at the absorption wavelength of non-emissive diphenylacrylonitrile chromophores, implying the existence of the DRET process between the dark diphenylacrylonitrile donor and the emissive BODIPY acceptor...
July 19, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28675038/boron-dipyridylmethene-dipyr-dyes-shedding-light-on-pyridine-based-chromophores
#12
Jessica H Golden, John W Facendola, Daniel Sylvinson M R, Cecilia Quintana Baez, Peter I Djurovich, Mark E Thompson
Boron dipyrromethene (BODIPY) derivatives have found widespread utility as chromophores in fluorescent applications, but little is known about the photophysical properties of pyridine-based BODIPY analogues, dipyridylmethene dyes. Indeed, it has been reported that boron difluoride dipyridylmethene (DIPYR) is nonemissive, and that derivatives of DIPYR have modest, if any, luminescence. In this report, we explore this little-touched area of chemical space and investigate the photophysical properties of three simple DIPYR dyes: boron dipyridylmethene, boron diquinolylmethene, and boron diisoquinolylmethene...
July 11, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28654288/a-general-strategy-toward-highly-fluorogenic-bioprobes-emitting-across-the-visible-spectrum
#13
Haoliang Chen, Xiujing He, Meihui Su, Wenhao Zhai, Hao Zhang, Changhua Li
A general approach toward highly fluorogenic probes across the visible spectrum for various analytes offers significant potential for engineering a wide range of bioprobes with diverse sensing and imaging functions. Here we show a facile and general strategy by introducing a new fluorogenic mechanism in boron dipyrromethene (BODIPY) dyes, based on the principle of stimuli-triggered dramatic reduction in the electron-withdrawing capabilities of the meso-substituents of BODIPYs. The fluorogenic mechanism has been demonstrated to be applicable in variable BODIPYs with emission maxima ranging from green to far red (509, 585, and 660 nm), and the synthetic strategy allows to access a panel of highly fluorogenic bioprobes for various biomolecules and enzymes (H2O2, H2S, and protease) via introducing specific triggering motifs...
June 27, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28654213/novel-alkoxy-substituted-dipyrromethenes-and-near-ir-bodipy-dyes-preparation-and-photophysical-properties
#14
Hans-Ulrich Reissig, Stefan Schoder, Scheghajeh Kord Daoroun Kalai
Starting from 3-alkoxy-2-aryl-substituted pyrroles and aromatic aldehydes, a collection of new dipyrromethenes was prepared. Under the standard conditions of Treibs, these were converted into the corresponding boron dipyrromethenes (BODIPYs). Compounds of this type with alkoxy groups at C-3 position of both pyrrole subunits are new and hence the photophysical properties of this collection of novel dipyrromethenes and BODIPY dyes were investigated. The dipyrromethenes show absorption maxima up to 596 nm and emissions of up to 677 nm...
June 27, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28653831/detoxification-of-a-sulfur-mustard-simulant-using-a-bodipy-functionalized-zirconium-based-metal-organic-framework
#15
Ahmet Atilgan, Timur Islamoglu, Ashlee J Howarth, Joseph T Hupp, Omar K Farha
Effective detoxification of chemical warfare agents is a global necessity. As a powerful photosensitizer, a halogenated BODIPY ligand is postsynthetically appended to the Zr6 nodes of the metal-organic framework (MOF), NU-1000, to enhance singlet oxygen generation from the MOF. The BODIPY/MOF material is then used as a heterogeneous photocatalyst to produce singlet oxygen under green LED irradiation. The singlet oxygen selectively detoxifies the sulfur mustard simulant, 2-chloroethyl ethyl sulfide (CEES), to the less toxic sulfoxide derivative (2-chloroethyl ethyl sulfoxide, CEESO) with a half-life of approximately 2 min...
July 17, 2017: ACS Applied Materials & Interfaces
https://www.readbyqxmd.com/read/28650096/n-bridged-annulated-bodipys-synthesis-of-highly-fluorescent-blue-shifted-dyes
#16
Hua Lu, Yanping Wu, John Mack, XuQiong Xiao, Zhifang Li, Zhen Shen
A series of novel BODIPY dyes has been prepared through the introduction of an N-bridged annulated meso-phenyl ring at one of the belta-positions of the BODIPY core. An unusual blue shift of the main spectral bands is observed,since the fusion of a meso-substituent results in a marked relative destabilization of the LUMO. The greater rigidity of the ring-fused structure leads to very high fluorescence quantum yields. The position of the main spectral bands can be fine-tuned by introducing electron withdrawing and donating groups onto the meso-phenyl ring...
June 26, 2017: Chemistry, An Asian Journal
https://www.readbyqxmd.com/read/28648076/asymmetric-dipyrrin-and-f-bodipys-conjugated-to-terminal-alkynes-and-alkenes
#17
Carlotta Figliola, Katherine N Robertson, Sarah Greening, Alison Thompson
An asymmetric meso-H dipyrrin featuring a conjugated terminal alkyne substituent was converted to its corresponding difluoro boron complex, and the extent of π-conjugation was extended using Sonogashira cross-coupling. Treatment of the alkyne-substituted dipyrrin with BF3·OEt2 and NEt3 revealed the reactivity of the conjugated terminal alkyne toward Lewis-activated electrophilic substitution and led to the isolation of F-BODIPYs bearing terminal bromovinyl and enol substituents.
June 24, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28648044/dendrons-and-multiarm-polymers-with-thiol-exchangeable-cores-a-reversible-conjugation-platform-for-delivery
#18
Ozgul Gok, Pelin Erturk, Burcu Sumer Bolu, Tugce Nihal Gevrek, Rana Sanyal, Amitav Sanyal
Disulfide exchange reaction has emerged as a powerful tool for reversible conjugation of proteins, peptides and thiol containing molecules to polymeric supports. In particular, the pyridyl disulfide group provides an efficient handle for the site-specific conjugation of therapeutic peptides and proteins bearing cysteine moieties. In this study, novel biodegradable dendritic platforms containing a pyridyl disulfide unit at their focal point were designed. Presence of hydroxyl groups at the periphery of these dendrons allows their elaboration to multivalent initiators that yield poly(ethylene glycol) based multiarm star polymers via controlled radical polymerization...
July 6, 2017: Biomacromolecules
https://www.readbyqxmd.com/read/28639661/ferrocene-bodipymerocyanine-dyads-new-nir-absorbing-platforms-with-optical-properties-susceptible-to-protonation
#19
Yuriy V Zatsikha, Natalia O Didukh, Dion Nemez, Adrien C Schlachter, Paul-Ludovic Karsenti, Yuriy P Kovtun, Pierre D Harvey, Victor N Nemykin
Ferrocene-BODIPYmerocyanine dyads 5 and 6 were prepared and characterized by a variety of spectroscopic, electrochemical, and theoretical methods. Experimental and theoretical data on these NIR absorbing compounds are suggestive of unusual susceptibility (for BODIPY chromophores) of the delocalized π-system in 5 and 6 to protonation and low-potential oxidation of their π-systems.
July 4, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28636039/a-convenient-method-for-multicolour-labelling-of-proteins-with-bodipy-fluorophores-via-tyrosine-residues
#20
Miffy H Y Cheng, Huguette Savoie, Francesca Bryden, Ross W Boyle
Fluorescence is an essential imaging modality for labelling and visualising cells and sub-cellular structures. Multicolour labelling is especially challenging due to differences in physicochemical and photophysical behaviour of structurally unrelated fluorophores in the heterogeneous environments found in sub-cellular compartments. Herein, we report the conjugation of three azide-bearing BODIPYs with similar core structures but widely different emission wavelengths (green, red and NIR) to tyrosine residues of a model globular protein (BSA) via a common linking methodology...
June 21, 2017: Photochemical & Photobiological Sciences
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