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Elena A Makarova, Yuriy V Zatsikha, Kelly M E Newman, Vinod K Paidi, Valeria A Beletsky, Johan van Lierop, Evgeny A Lukyanets, Victor N Nemykin
An unprecedented stable neutral radical nickel(II) complex of 3,5-bis(dimedonyl)azadiisoindomethene (1) was prepared by the direct reaction between 1,3-diiminoisoindoline and dimedone. A new radical complex 1 has an intense and narrow absorption at 1008 nm and can be reduced to a less stable anionic [1](-) with a typical aza(dibenzo)boron dipyrromethene (aza-BODIPY) UV-vis spectrum. Complex 1, along with two other colored condensation reaction products 2 and 3, was characterized by spectroscopy and X-ray crystallography, while the paramagnetic nature of 1 was probed by EPR and SQUID methods...
May 19, 2017: Inorganic Chemistry
Zhijia Wang, Jianzhang Zhao, Antonio Barbon, Antonio Toffoletti, Yan Liu, Yonglin An, Liang Xu, Ahmet Karatay, Halime Gul Yaglioglu, Elif Akhuseyin Yildiz, Mustafa Hayvali
A long-lived triplet excited state of the well-known fluorophore borondipyrromethene (Bodipy) was observed for the first time via efficient radical-enhanced intersystem crossing (EISC). The triplet state has been obtained in two dyads prepared by linking Bodipy to a nitroxide radical, 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) with two different length spacers. The photophysical properties were studied with steady-state and time-resolved transient optical spectroscopies, and electron spin resonance (cw-ESR and TR-ESR)...
May 19, 2017: Journal of the American Chemical Society
Adam Meares, Andrius Satraitis, Joshua Akhigbe, Nithya Santhanam, Subramani Swaminathan, Melanie Ehudin, Marcin Ptaszek
BODIPY-hydroporphyrin energy transfer arrays allow for development of family of fluorophores featuring a common excitation band at 500 nm, tunable excitation band in deep red/near-infrared window, and tunable emission. Their biomedical applications are contingent upon retaining their optical properties in aqueous environment. Amphiphilic arrays containing PEG-substituted BODIPY and chlorins or bacteriochlorins were prepared and their optical and fluorescence properties were determined in organic solvents and aqueous surfactants...
May 18, 2017: Journal of Organic Chemistry
Nicolai Stuhr-Hansen, Charikleia-Despoina Vagianou, Ola Blixt
The glycocalyx cover membrane surfaces of all living cells. These complex archtechtures render their interaction mechanisms on the membrane surface difficult to study. Artificial cell-sized membranes with selected and defined glycosylation patterns may serve as a minimalistic approach to systematically study cell surface glycan interactions. Here we developed a facile general synthetic procedure for the synthesis of BODIPY-labelled cholesterylated glycopeptides, which can coat cell-size giant unilamellar vesicles (GUVs)...
May 17, 2017: Chemistry: a European Journal
Yong Ni, Ravi Kumar Kannadorai, Sidney W-K Yu, Young-Tae Chang, Jishan Wu
A series of push-pull type meso-ester substituted BODIPY dyes 1-4 with intense near-infrared absorption, largely enhanced photoacoustic (PA) activity and excellent photo-stability were synthesized. The impact of the electronic structure on the PA activity was also discussed. Moreover, the in vitro and in vivo PA imaging were investigated, which suggested a passive targeting capacity in the tumor site.
May 17, 2017: Organic & Biomolecular Chemistry
Nerea Epelde-Elezcano, Ruth Prieto-Montero, Virginia Martínez-Martínez, María J Ortiz, Alejandro Prieto-Castañeda, Eduardo Peña-Cabrera, José L Belmonte-Vázquez, Iñigo López-Arbeloa, Ross Brown, Sylvie Lacombe
A modified Stöber method is used to synthesize spherical core-shell silica nanoparticles (NPs) with an external surface functionalized by amino groups and with an average size around 50 nm. Fluorescent dyes and photosensitizers of singlet oxygen were fixed, either separately or conjointly, respectively in the core or in the shell. Rhodamines were encapsulated in the core with relatively high fluorescence quantum yields (Φfl ≥ 0.3), allowing fluorescence tracking of the particles. Various photosensitizers of singlet oxygen (PS) were covalenty coupled to the shell, allowing singlet oxygen production...
May 15, 2017: Physical Chemistry Chemical Physics: PCCP
Kepeng Lei, Mingtai Sun, Libo Du, Xiaojie Zhang, Huan Yu, Suhua Wang, Tasawar Hayat, Ahmed Alsaedi
The sensitive and selective fluorescence probe for hydroxyl radical analysis is of significance because hydroxyl radical plays key roles in many physiological and pathological processes. In this work, a novel organic fluorescence molecular probe OHP for hydroxyl radical is synthesized by a two-step route. The probe employs 4-bora-3a,4a-diaza-s-indacene (difluoroboron dipyrromethene, BODIPY) as the fluorophore and possesses relatively high fluorescence quantum yields (77.14%). Hydroxyl radical can rapidly react with the probe and quench the fluorescence in a good linear relationship (R(2)=0...
August 1, 2017: Talanta
Tesla Yudhistira, Sandip V Mulay, Kyungjin Lee, Youngsam Kim, Hee-Sung Park, David G Churchill
The role of fluorescent molecules in diagnosis, treatments as well as in biomedical research has great current medicinal significance; related research continues to reveal new practical systems with enhanced features for interfacing of substituted molecules with biological systems. As part of an effort to better understand chalcogenide systems, a new dithiomaleimide BODIPY (BDP-NGM) probe has been designed, synthesized and characterized. The fluorescence of BDP-NGM was quenched by the incorporation of [3,4-bis(phenylthio)] on the maleimide-4-phenyl moiety which is in turn placed at the meso-position of the BODIPY system...
May 11, 2017: Chemistry, An Asian Journal
E Avellanal-Zaballa, G Durán-Sampedro, A Prieto-Castañeda, A R Agarrabeitia, I García-Moreno, I López-Arbeloa, J Bañuelos, M J Ortiz
We report the synthesis of novel multichromophoric organic architectures, where perylene red is decorated with BODIPY and/or hydroxycoumarin dyes acting as light harvesters and energy donors. The computationally-aided photophysical study of these molecular assemblies reveals a broadband absorption which, regardless of the excitation wavelength, leads solely to a bright red-edge emission from perylene bisimide after efficient intramolecular energy transfer hops. The increase of the absorbance of these molecular antennas at key pumping wavelengths enhances the laser action of the commercial perylene red...
May 24, 2017: Physical Chemistry Chemical Physics: PCCP
Andrea Zampetti, Alessandro Minotto, Benedetta Maria Squeo, Vasilis G Gregoriou, Sybille Allard, Ullrich Scherf, Christos L Chochos, Franco Cacialli
We take advantage of a recent breakthrough in the synthesis of α,β-unfunctionalised 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) moieties, which we symmetrically conjugate with oligothienyls in an unexpectedly stable form, and produce a "metal-free" A-D-A (acceptor-donor-acceptor) oligomer emitting in the near-infrared (NIR) thanks to delocalisation of the BODIPY low-lying lowest unoccupied molecular orbital (LUMO) over the oligothienyl moieties, as confirmed by density functional theory (DFT). We are able to retain a PL efficiency of 20% in the solid state (vs...
May 9, 2017: Scientific Reports
Francis D'Souza, Prabhat Gautam, Rajneesh Misra, Michael Thomas
A series of triphenylamine (TPA) substituted BODIPYs 1-3 have been newly designed and synthesized by the Pd catalysed Sonogashira cross-coupling and [2+2] cycloaddition-retroelectrocyclization reaction in good yields. This procedure yielded highly electron deficient tetracyanobutadiene (TCBD) or dicyanoquinodimethane (DCNQ) electron acceptor units centrally located at the TPA-BODIPY system. As a consequence, significant perturbation of the photonic and electronic properties were observed. The triads 2 and 3 showed red-shifted absorption in addition to a strong charge transfer type absorption in the case of 3...
May 9, 2017: Chemistry: a European Journal
Muhammed Üçüncü, Erman Karakuş, Eylem Kurulgan Demirci, Melike Sayar, Suay Dartar, Mustafa Emrullahoğlu
Upon complexation with Au(I), a photoinactive BODIPY derivative was transformed into a highly photoactive triplet sensitizer. Along with high efficiency in singlet oxygen generation (ΦΔ = 0.84), the new BODIPY-Au(I) skeleton showed excellent photocytotoxic activity against cancer cell lines (EC50 = 2.5 nM).
May 9, 2017: Organic Letters
Samira Osati, Hasrat Ali, Brigitte Guerin, Johan E van Lier
To develop receptor based fluorescence ligands for imaging breast and prostate cancer, a series of estrogen-, testosterone- and 19-nortestosterone conjugates linked to BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) or aza-BODIPY, were prepared. Their synthesis involves attachment of iodo derivatives of differently substituted BODIPY and aza-BODIPY analogs to the C17α-position of the steroid moieties using either the Sonogashira coupling or Click reaction. The UV-Vis absorption spectra of the conjugates range from 500 to 710nm with fluorescence emission properties ranging from 520 to 700nm, facilitating observations in living cells and tissues...
May 5, 2017: Steroids
Mehmet Yilmaz, Mustafa Erkartal, Mehmet Özdemir, Unal Sen, Hakan Usta, Gokhan Demirel
The design and development of three-dimensional (3D) nanostructures with high surface-enhanced Raman scattering (SERS) performances have attracted considerable attention in the fields of chemistry, biology and materials science. Nevertheless, electrospraying of organic small molecules on low-cost flexible substrates has never been studied to realize large-scale SERS-active platforms. Here, we report the facile, efficient, and low-cost fabrication of stable and reproducible Au-coated electrosprayed organic semiconductor films (Au@BDY-4T-BDY) on flexible regular aluminum foil at large scale (5 cm × 5 cm) for practical SERS and catalytic applications...
May 8, 2017: ACS Applied Materials & Interfaces
Sabrina Nickel, Mohammed Ali Selo, Juliane Fallack, Caoimhe G Clerkin, Hanno Huwer, Nicole Schneider-Daum, Claus-Michael Lehr, Carsten Ehrhardt
PURPOSE: Breast cancer resistance protein (BCRP/ABCG2) has previously been identified with high expression levels in human lung. The subcellular localisation and functional activity of the transporter in lung epithelia, however, remains poorly investigated. The aim of this project was to study BCRP expression and activity in freshly isolated human alveolar epithelial type 2 (AT2) and type 1-like (AT1-like) cells in primary culture, and to compare these findings with data obtained from the NCI-H441 cell line...
May 3, 2017: Pharmaceutical Research
Pengfei Xu, Jiao Li, Jin Liu, Jing Wang, Zekai Wu, Xiaotian Zhang, Yonggong Zhai
Lipid-filled mature adipocytes are important for the study of lipid metabolism and in the development of obesity, but whether they are capable of reproliferation is still controversial. Here, we monitored lipid droplet dynamics and adipocyte reproliferation in live, differentiated 3T3-L1 cells using a phase-contrast microscope in real time. Phase-contrast microscopy achieves a similar visual effect in situ to that obtained using traditional dyes such as Oil Red O and BODIPY in vitro. Using this method, we captured the process that lipid droplets use for dynamic fusion in living cells...
May 2017: FEBS Open Bio
César Ray, Laura Díaz-Casado, Edurne Avellanal, Jorge Bañuelos, Luis Cerdán, Inmaculada García-Moreno, Florencio Moreno, Beatriz L Maroto, Iñigo López-Arbeloa, Santiago de la Moya Cerero
N-BODIPYs (diaminoboron dipyrromethenes) are unveiled as a new family of BODIPY dyes with huge technological potential. Their synthetic access is accomplished from a judicious design focused on stabilizing the involved diaminoboron chelate. Once stabilized, achieved N-BODIPYs retain the effective photophysical behavior exhibited by other boron-substituted BODIPYs, such as the O-BODIPYs. However, key bonding features of nitrogen, when compared with oxygen (enhanced bond valence and different bond directionality) open up new possibilities for functionalizing BODIPYs, allowing the increase of the number of pendant moieties (from two in O-BODIPYs, up to four in N-BODIPYs) near the chromophore and, therefore, a smarter photophysics modulation...
May 3, 2017: Chemistry: a European Journal
Bangshao Yin, Taeyeon Kim, Mingbo Zhou, Weiming Huang, Dongho Kim, Jianxin Song
Cyclic and acyclic azobenzene bridged porphyrin-dipyrrin derivatives were successfully prepared via Suzuki-Miyaura coupling reaction of α,α'-diborylated dipyrromethane with bromoazophenyl porphyrin or reaction of borylated porphyrin with dibromoazophenyl dipyrrin, and the corresponding porphyrin-Bodipy derivatives were obtained by subsequent boron complexation. The cyclic porphyrin-dipyrrin compound 3Ni was confirmed by X-ray diffraction. The low fluorescence quantum yields of azobenzene bridged porphyrin-Bodipy can be ascribed to the presence of the intramolecular charge transfer state...
May 3, 2017: Organic Letters
Deirdre Fahy, Marwa N M E Sanad, Kerstin Duscha, Madison Lyons, Fuquan Liu, Peter Bozhkov, Hans-Henning Kunz, Jianping Hu, H Ekkehard Neuhaus, Patrick G Steel, Andrei Smertenko
No abstract text is available yet for this article.
May 3, 2017: Scientific Reports
Lei Shi, Fumiya Ito, Yue Wang, Yasumasa Okazaki, Hiromasa Tanaka, Masaaki Mizuno, Masaru Hori, Tasuku Hirayama, Hideko Nagasawa, Des R Richardson, Shinya Toyokuni
Non-thermal plasma (NTP) is a potential new therapeutic modality for cancer. However, its mechanism of action remains unclear. Herein, we studied the effect of NTP on mesothelioma cells and fibroblasts to understand its anti-proliferative efficacy. Interestingly, NTP demonstrated greater selective anti-proliferative activity against mesothelioma cells relative to fibroblasts than cisplatin, which is used for mesothelioma treatment. The anti-proliferative effect of NTP was enhanced by pre-incubation with the cellular iron donor, ferric ammonium citrate (FAC), and inhibited by iron chelation using desferrioxamine (DFO)...
May 2, 2017: Free Radical Biology & Medicine
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