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Ek Raj Thapaliya, Yang Zhang, Pravat Dhakal, Adrienne S Brown, James N Wilson, Kevin Collins, Françisco M Raymo
Seven macromolecular constructs incorporating multiple borondipyrromethene (BODIPY) fluorophores along a common poly(methacrylate) backbone with decyl and oligo(ethylene glycol) side chains were synthesized. The hydrophilic oligo(ethylene glycol) components impose solubility in aqueous environment on the overall assembly. The hydrophobic decyl chains insulate effectively the fluorophores from each other to prevent detrimental interchromophoric interactions and preserve their photophysical properties. As a result, the brightness of these multicomponent assemblies is approximately three times greater than that of a model BODIPY monomer...
April 21, 2017: Bioconjugate Chemistry
Tomoya Sameshima, Ikuo Miyahisa, Seiji Yamasaki, Mika Gotou, Toshitake Kobayashi, Junichi Sakamoto
In a high-throughput screening (HTS) process, the chemical reactivity of test samples should be carefully examined because such reactive compounds may lead to false-positive results and adverse effects in vivo. Among all natural amino acids, the thiol side chain in cysteine has the highest nucleophilicity; thus, assessment of intrinsic thiol group reactivity in the HTS processes is expected to accelerate drug discovery. In general, kchem (M(-1)s(-1)), the secondary reaction rate constant of a compound to thiol, can be evaluated via time course measurements of thiol-compound adducts using liquid chromatography-mass spectroscopy; this requires time-consuming and labor-intensive procedures...
April 1, 2017: SLAS Discovery
Ning Zhao, Tyrslai Williams, Zehua Zhou, Frank R Fronczek, Martha Sibrian-Vazquez, Seetharama Jois, M Graca Henriques Vicente
Regioselective functionalization of 2,3,5,6,8-pentachloro-BODIPY 1 produced unsymmetric BODIPY 5, bearing an isothiocyanate group suitable for conjugation, in only four steps. The X-ray structure of 5 reveals a nearly planar BODIPY core with aryl dihedral angles in the range 47.4° - 62.9°. Conjugation of 5 to two EGFR-targeting pegylated peptides, 3PEG-LARLLT (6) and 3PEG-GYHWYGYTPQNVI (7), under mild conditions (30 min at room temperature), afforded BODIPY conjugates 8 and 9 in 50-80% isolated yields. These conjugates show red-shifted absorption and emission spectra compared with 5, in the near-IR region, and were evaluated as potential fluorescence imaging agents for EGRF over-expressing cells...
April 17, 2017: Bioconjugate Chemistry
Mikhail A Filatov, Safakath Karuthedath, Pavel M Polestshuk, Huguette Savoie, Keith J Flanagan, Cindy Sy, Elisabeth Sitte, Maxime Telitchko, Frédéric Laquai, Ross W Boyle, Mathias O Senge
Heavy atom-free BODIPY-anthracene dyads (BADs) upon photoexcitation generate locally excited triplet excited states by way of photoinduced electron transfer (PeT), followed by recombination of the resulting charge-separated states (CSS). Subsequent quenching of the triplet states by molecular oxygen produces singlet oxygen ((1)O2), which reacts with the anthracene moiety yielding highly fluorescent species. The steric demand of the alkyl substituents in the BODIPY subunit defines the site of (1)O2 addition...
April 13, 2017: Journal of the American Chemical Society
Ewelina Warzych, Piotr Pawlak, Marcin Pszczola, Adam Cieslak, Zofia E Madeja, Dorota Lechniak
Among many factors, lipid metabolism within the follicular environment emerges as an important indicator of oocyte quality. In the literature a crucial significance is described concerning follicular fluid (FF) composition as well as messenger RNA (mRNA) expression in follicular cells. The aim of this study was to describe the relationship between oocyte, FF and follicular cells with regard to lipid metabolism. The set of data originating from individual follicles comprised: lipid droplets (LD) number in oocytes (BODIPY staining), mRNA expression of seven genes in cumulus and granulosa cells (SCD, FADS2, ELOVL2, ELOVL5, GLUT1, GLUT3, GLUT8; real time polymerase chain reaction) and fatty acid (FA) composition in FF (gas chromatography)...
April 12, 2017: Animal Science Journal, Nihon Chikusan Gakkaihō
Yuanlin Zhang, Aidong Peng, Xiaoke Jie, Yanlin Lv, Xuefei Wang, Zhiyuan Tian
A new type of phosgene probe with a limit of detection down to 0.12 nM, response time of less than 1.5 s, and high selectivity over other similarly reactive toxic chemicals was developed using ethylenediamine as the recognition moiety and 8-substituted BODIPY unit as the fluorescence signaling component. The probe undergoes sequential phosgene-mediated nucleophilic substitution reaction and intramolecular cyclization reaction with high rate, yielding a product with the intramolecular charge transfer (ICT) process from amine to the BODIPY core significantly inhibited...
April 17, 2017: ACS Applied Materials & Interfaces
Boris Le Guennic, Giovanni Scalmani, Michael J Frisch, Adèle D Laurent, Denis Jacquemin
Using a computational approach combining Time-Dependent Density Functional Theory (TD-DFT) and second-order Coupled Cluster (CC2) approaches, we investigate the spectral properties of a large panel of BOIMPY dyes. BOIMPY derivatives constitute a new class of fluorophores that appeared only very recently [Angew. Chem. Int. Ed., 2016, 55, 13340-13344] and display intriguing properties. First, we show that theory is able to reproduce experimental 0-0 energies with reasonable accuracy, and more importantly excellent consistency (R = 0...
April 19, 2017: Physical Chemistry Chemical Physics: PCCP
Elif Şenkuytu, Esra Tanrıverdi Eçik
No abstract text is available yet for this article.
April 1, 2017: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Lukas J Patalag, Jan A Ulrichs, Peter G Jones, Daniel B Werz
A novel entry to meso-decorated BODIPY motifs on the basis of an unusual aldol-type addition with diethyl ketomalonate is reported. The evolving β-hydroxyl group can be optionally eliminated, which suppresses the fluorescence of the BODIPY core by attachment of a π-electronically coupled methylidene malonate unit. This unit serves as a versatile, highly electrophilic acceptor platform for various nucleophilic additions. Corresponding products benefit from a fully restored fluorescence.
April 7, 2017: Organic Letters
Gajendra Gupta, Abhishek Das, Kyoung Chul Park, Artur Tron, Hyunuk Kim, Junyoung Mun, Nripendranath Mandal, Ki-Whan Chi, Chang Yeon Lee
Four new palladium metal supramolecules with triangular/square architectures derived from boron dipyrromethane (BODIPY) ligands were synthesized by self-assembly and fully characterized by (1)H and (31)P NMR, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction. These supramolecules were more cytotoxic to brain cancer (glioblastoma) cells than to normal lung fibroblasts. Their cytotoxicity to the glioblastoma cells was higher than that of a benchmark metal-based chemotherapy drug, cisplatin...
April 6, 2017: Inorganic Chemistry
Adriana Pietropaolo, Sicheng Tang, Françisco M Raymo
We reconstructed the free-energy landscape for supramolecular nanoparticles of amphiphilic methacrylated-based co-polymers. Their self-assembly in aqueous solution and encapsulation of borondipyrromethene (BODIPY) derivatives were enforced through atomistic free-energy simulations. The BODIPY binding modes detected in each of the free-energy basins were validated through a comparison of theoretical absorption spectra, calculated at the TD-DFT level, to their experimental counterparts. The nanoparticle distribution is controlled within a thermodynamic regime, with free-energy barriers approaching 8 kcal mol(-1), enabling the existence of different-sized nanoparticles in aqueous solution at room temperature...
April 6, 2017: Nanoscale
Zhijian Chen, Yong Liu, Wolfgang Wagner, Vladimir Stepanenko, Xiangkui Ren, Soichiro Ogi, Frank Würthner
A new amphiphilic BF2 -azadipyrromethene (aza-BODIPY) dye 1 has been synthesized using a Cu(I) -catalyzed "click" reaction. For this dye, two self-assembly pathways that lead to different type of J-aggregates with distinct near-infrared optical properties have been discovered. The metastable off-pathway product displays a broad, structureless absorption band while the thermodynamically stable on-pathway aggregate exhibits the characteristic spectral features of a J-aggregate, that is, red-shifted intense absorption band with significantly narrowed linewidth...
March 29, 2017: Angewandte Chemie
Fang Miao, Zheng Long Lim, Pan Hu, Shaoqiang Dong, Qingbiao Qi, Xiaojie Zhang, Jishan Wu
Two BODIPY-substituted anthroxyl radicals were investigated. The one with two ethyl substituents (2Et-BO-An-O) is sensitive to air and silica gel due to the lack of sufficient kinetic blocking, while another one with four methyl substituents (4Me-BO-An-O) shows high stability. The structure of the latter was fully characterized by X-ray crystallographic analysis and electron-spin resonance spectra. 4Me-BO-An-O was subjected to react with various reactive oxygen/nitrogen species (ROS/RNS) and selective fluorescence turn-on detection of a hydroxyl radical was achieved, validating the concept of "using stable radicals to detect ROS/RNS"...
April 11, 2017: Organic & Biomolecular Chemistry
Mingming Zhang, Manik Lal Saha, Ming Wang, Zhixuan Zhou, Bo Song, Chenjie Lu, Xuzhou Yan, Xiaopeng Li, Feihe Huang, Shouchun Yin, Peter J Stang
The syntheses, characterization, and emission properties of three tetragonal prismatic cages, 4a-4c, constructed from eight 90° Pt(II) acceptors, four linear dipyridyl ligands, and two tetraphenylethene (TPE)-based sodium benzoate ligands, are described. These cages are emissive in dilute solutions due to the metal-coordination-induced partial restriction of intramolecular rotation of their TPE units, while the dipyridyl moieties, which act as the pillars as well as the solvents, strongly influence these emissions...
March 31, 2017: Journal of the American Chemical Society
Wuyu Mao, Lingying Xia, Hexin Xie
Antibiotic resistance has become a major challenge to public health worldwide. This crisis is further aggravated by the increasing emergence of bacterial resistance to carbapenems, typically considered as the antibiotics of last resort, which is mainly due to the production of carbapenem-hydrolyzing carbapenemases in bacteria. Herein, the carbapenem-based fluorogenic probe CB-1 with an unprecedented enamine-BODIPY switch is developed for the detection of carbapenemase activity. This reagent is remarkably specific towards carbapenemases over other prevalent β-lactamases...
March 23, 2017: Angewandte Chemie
Nicolas Leclerc, Ibrahim Bulut, Quentin Huaulmé, Antoine Mirloup, Patricia Chávez, Sadiara Fall, Anne Hébraud, Stéphane Méry, Benoit Heinrich, Thomas Heiser, Patrick Lévêque
Boron dipyrromethene (Bodipy) are known to be efficient photon harvesting chromophores. However, their study as active materials in bulk heterojunction (BHJ) solar cells is still scarce. In this paper, we developed new synthetic ways to design original Bodipy-based dumbbell-shape molecules, including a first 2,3,5,6-tetravinyl aromatic Bodipy molecule. We demonstrated that high fill factors can be obtained in BHJ solar cells when blended with a fullerene derivative, leading to a new Bodipy-based record power conversion efficiency of 5...
March 21, 2017: ChemSusChem
Shumin Yang, Ting Li, Aipin Zhang, Rufei Gao, Chuan Peng, Lulu Liu, Qingfeng Cheng, Mei Mei, Ying Song, Xiaojiao Xiang, Chaodong Wu, Xiaoqiu Xiao, Qifu Li
Context: Accumulating evidence suggests that bisphenol A (BPA) exposure is associated with nonalcoholic fatty liver disease. Disruption of autophagy causes lipid accumulation in hepatocytes. Whether and how BPA regulates autophagy remains to be explored. Objective: We investigated the effect of BPA on autophagy in hepatocytes and examined the influence of BPA-regulated autophagy on hepatic lipid accumulation. Design: Male CD1 mice were treated with BPA for eight weeks, followed by histological and biochemical evaluation of liver lipids and autophagy...
February 21, 2017: Endocrinology
Dumitru Sirbu, Andrew C Benniston, Anthony Harriman
Tin(IV) catalysis allows isolation of a boron dipyrromethene derivative bearing a solitary strap around the boron center. The conditions favor internal cyclization without contamination by side products and provide high yields of product in good purity. A phenolate-based strap imposes chirality and causes geometrical distortion of the dipyrrin. Relatively strong fluorescence is observed for single crystals, evaporated films, and adsorbed layers. Single-crystal absorption and emission spectra resemble those observed from solution with contributions from a dimer...
April 7, 2017: Organic Letters
Lijing Yang, Brett Drew, Ravi Shekar Yalagala, Rameez Chaviwala, Razvan Simionescu, Alan J Lough, Hongbin Yan
In the title compound (3-amino-4,4-diphenyl-BODIPY), C28H32BN3, the central six-membered ring has a flattened sofa conformation, with one of the N atoms deviating by 0.142 (4) Å from the mean plane of the other five atoms, which have an r.m.s. deviation of 0.015 Å. The dihedral angle between the two essentially planar outer five-membered rings is 8.0 (2)°. In the crystal, mol-ecules are linked via weak N-H⋯π inter-actions, forming chains along [010]. The com-pound displays solvent-dependent behaviours in both NMR and fluorescence spectroscopy...
March 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
Hui He, Shuangshuang Ji, Yang He, Aijun Zhu, Yelin Zou, Yibin Deng, Hengte Ke, Hong Yang, Youliang Zhao, Zhengqing Guo, Huabing Chen
Photoconversion tunability of fluorophore dye is of great interest in cancer nanomedicine such as fluorescence imaging, photodynamic therapy (PDT), and photothermal therapy (PTT). Herein, this paper reports wavelength-dependent photoconversional polymeric vesicles of boron dipyrromethene (Bodipy) fluorophore for either PDT under 660 nm irradiation or PTT under 785 nm irradiation. After being assembled within polymeric vesicles at a high drug loading, Bodipy molecules aggregate in the conformations of both J-type and H-type, thereby causing red-shifted absorption into near-infrared region, ultralow radiative transition, and ideal resistance to photobleaching...
March 15, 2017: Advanced Materials
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