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Nagaiyan Sekar, Ramaiah D, Yogesh Gawale, Adarsh N, Joseph J, M Pramanik, S K Kalva
Four novel N-ethylcarbazole linked aza-BODIPY dyes (8a-b and 9a-b) were synthesized and characterized. The presence of N-ethylcarbazole moiety shifts their absorption and fluorescence spectra to the near-infrared region, ca. 650-730 nm, of electromagnetic spectra. These dyes possess strong molar absorptivity in the range of 3-4 x 104 M-1cm-1 with low fluorescence quantum yields. The triplet excited state as well as singlet oxygen generation of these dyes were enhanced upon iodination at the core position. The core iodinated dyes 9a-b showed excellent triplet quantum yield of ca...
February 22, 2017: Chemistry: a European Journal
M Hassan Pervaiz, Sridevi Durga, Abed Janoudi, Kevin Berger, George S Abela
BACKGROUND: PET/CTA was used to evaluate the effect of cholesterol crystal emboli (CCE) on muscle injury. Cholesterol crystals (CCs) released during plaque rupture travel downstream and lodge in muscle triggering inflammation and tissue injury. METHODS: Thigh muscles in three groups of rabbits (n = 22) were studied after intra-arterial injection of CCs, Group I (n = 10); polystyrene microspheres, Group II (n = 5); or normal saline, Group III (n = 7). After 48 hours, muscle inflammation and injury were measured by fluorodeoxy-glucose uptake using PET/CTA, serum tissue factor (TF), and creatinine phosphokinase (CPK)...
February 21, 2017: Journal of Nuclear Cardiology: Official Publication of the American Society of Nuclear Cardiology
Mina Raeisolsadati Oskouei, Albert M Brouwer
Two fluorescent derivatives of 2-amino-3-carbonitrile-4H-chromene were synthesized by means of a fluorogenic Michael addition of dimedone to dicyano alkene labeled BODIPY derivatives. Different organocatalysts were used in different conditions to obtain compounds 3 and 4 in good yield (up to 65% and 85%) and moderate enantiomeric excess (51% and 41% ee, respectively). This work provides the first example of an enantioselective organocatalytic conversion combined with fluorogenesis.
February 21, 2017: Journal of Fluorescence
Bingbing Cheng, Venugopal Bandi, Shuai Yu, Francis D'Souza, Kytai T Nguyen, Yi Hong, Liping Tang, Baohong Yuan
Highly environment-sensitive fluorophores have been desired for many biomedical applications. Because of the noninvasive operation, high sensitivity, and high specificity to the microenvironment change, they can be used as excellent probes for fluorescence sensing/imaging, cell tracking/imaging, molecular imaging for cancer, and so on (i.e., polarity, viscosity, temperature, or pH measurement). In this work, investigations of the switching mechanism of a recently reported near-infrared environment-sensitive fluorophore, ADP(CA)₂, were conducted...
February 11, 2017: International Journal of Molecular Sciences
Deyan Gong, Xiangtao Zhu, Yuejun Tian, Shi-Chong Han, Min Deng, Anam Iqbal, Weisheng Liu, Wenwu Qin, Huichen Guo
Herein a phenylselenium-substituted BODIPY (1) fluorescent turn-off sensor was developed for the purpose to achieve excellent selectivity and sensitivity for H2S detection based on the substitution reaction of the phenylselenide group at the 3-position with H2S. The excess addition of hydrogen sulfide promoted further substitution of the phenylselenide group at the 5-position of the probe and was accompanied by a further decrease in fluorescence emission intensity. Sensor 1 demonstrated remarkable performance with 49-fold red color fluorescence intensity decrease at longer excitation wavelength, a low detection limit (0...
February 7, 2017: Analytical Chemistry
Maciej Modzel, Frederik W Lund, Daniel Wüstner
Cellular cholesterol homeostasis relies on precise control of the sterol content of organelle membranes. Obtaining insight into cholesterol trafficking pathways and kinetics by live-cell imaging relies on two conditions. First, one needs to develop suitable analogs that resemble cholesterol as closely as possible with respect to their biophysical and biochemical properties. Second, the cholesterol analogs should have good fluorescence properties. This interferes, however, often with the first requirement, such that the imaging instrumentation must be optimized to collect photons from suboptimal fluorophores, but good cholesterol mimics, such as the intrinsically fluorescent sterols, cholestatrienol (CTL) or dehydroergosterol (DHE)...
2017: Methods in Molecular Biology
Tomoya Kubota, Thomas Durek, Bobo Dang, Rocio K Finol-Urdaneta, David J Craik, Stephen B H Kent, Robert J French, Francisco Bezanilla, Ana M Correa
Voltage-gated sodium channels (Navs) play crucial roles in excitable cells. Although vertebrate Nav function has been extensively studied, the detailed structural basis for voltage-dependent gating mechanisms remain obscure. We have assessed the structural changes of the Nav voltage sensor domain using lanthanide-based resonance energy transfer (LRET) between the rat skeletal muscle voltage-gated sodium channel (Nav1.4) and fluorescently labeled Nav1.4-targeting toxins. We generated donor constructs with genetically encoded lanthanide-binding tags (LBTs) inserted at the extracellular end of the S4 segment of each domain (with a single LBT per construct)...
February 15, 2017: Proceedings of the National Academy of Sciences of the United States of America
Cloé Azarias, Roberto Russo, Lorenzo Cupellini, Benedetta Mennucci, Denis Jacquemin
The excitation energy transfer (EET) allowing the concentration of the energy has been investigated in several multi-BODIPY architectures with the help of an approach coupling time dependent density functional theory to an implicit solvation scheme, the polarizable continuum model. We have first considered several strategies to compute the electronic coupling in a dyad varying the size of the donor/acceptor units, the bridge, the geometries and conformations. We have next studied the electronic coupling in three different architectures for which the EET rate constants have been experimentally measured both from luminescence and transient absorption data and from Förster theory...
February 15, 2017: Physical Chemistry Chemical Physics: PCCP
Anyanee Kamkaew, Nanyan Fu, Weibo Cai, Kevin Burgess
Actively targeting probe 1b, an unsymmetrical bivalent dipeptide mimic, selectively bound melanoma over healthy skin tissue in histological samples from patients and Sinclair swine. Modifications to 1b gave agents 2-4 that contain a near-IR aza-BODIPY fluor. Contrary to our expectations, symmetrical probe 3 gave the highest melanoma-to-healthy skin selectivity in histochemistry and experiments with live cells; this was surprising because 2, not 3, is unsymmetrical like the original lead 1. Optical imaging of 3 in a mouse melanoma model failed to show tumor accumulation in vivo, but the probe did selectively accumulate in the tumor (some in lung and less in the liver) as proven by analysis of the organs post mortem...
February 9, 2017: ACS Medicinal Chemistry Letters
Anna I Arkhypchuk, Andreas Orthaber, K Eszter Borbas
We present the synthesis and characterization of meso-ferrocenyl-substituted hydroporphyrins (chlorins) and 1,1'-linked chlorin dimers. The dipyrromethane chlorin precursors were also transformed into Fc-substituted BODIPYs and 1,1'-ferrocenyl-linked BODIPY dimers. The chlorin dimers were studied by 1D and 2D NMR experiments and DFT calculations, which showed that their solution structures were dependent on the central metal. Monomeric and dimeric Ni(II) chlorins had similar (1)H NMR spectra. Monomeric and dimeric free base, Zn(II), and Pd(II) chlorins, on the other hand, showed significantly more different spectra...
February 10, 2017: Inorganic Chemistry
Verónica S Mary, Silvina L Arias, Santiago N Otaiza, Pilar A Velez, Héctor R Rubinstein, Martín G Theumer
Human oral exposure to aflatoxin B1 (AFB1 ) and fumonisin B1 (FB1 ) is associated with increased hepatocellular carcinoma. Although evidence suggested interactive AFB1 -FB1 hepatotoxicity, the underlying mechanisms remain mostly unidentified. This work was aimed at evaluating the possible AFB1 -FB1 interplay to induce genetic and cell cycle toxicities in BRL-3A rat hepatocytes, reactive oxygen species (ROS) involvement, and the AFB1 metabolizing pathways cytochrome P450 (CYP) and arachidonic acid (ArAc) metabolism as ROS contributors...
February 9, 2017: Environmental Toxicology
Anna M Christianson, François P Gabbaï
We describe the synthesis of a BODIPY dye substituted with a Lewis acidic antimony(v) moiety. This compound, which has been fully characterized, shows a high affinity for small anions including fluoride and cyanide, the complexation of which elicits a fluorescence turn-on response.
February 9, 2017: Chemical Communications: Chem Comm
Taisuke Katoh, Masato Yoshikawa, Takeshi Yamamoto, Ryosuke Arai, Noriyuki Nii, Yoshihide Tomata, Shinkichi Suzuki, Ryoukichi Koyama, Nobuyuki Negoro, Takatoshi Yogo
We describe a methodology for quick development of fluorescent probes with the desired potency for the target of interest by using a method of parallel synthesis, termed as Parallel Fluorescent Probe Synthesis (Parallel-FPS). BODIPY FL propionic acid 1 is a widely used fluorophore, but it is difficult to prepare a large amount of 1, which hinders its use in parallel synthesis. Optimization of a synthetic scheme enabled us to obtain 50g of 1 in one batch. With this large quantity of 1 in hand, we performed Parallel-FPS of BODIPY FL-labeled ligands for estrogen related receptor-α (ERRα)...
January 28, 2017: Bioorganic & Medicinal Chemistry Letters
Sheng-Yong Li, Zuo-Bang Sun, Cui-Hua Zhao
Triarylboranes have attracted significantly increasing research interest as a remarkable class of photoelectronic π-electron materials. Because of the presence of vacant p orbital on the B center, the boryl group is a very unique electron acceptor that exhibits not only electron-accepting ability through p-π* conjugation but also high Lewis acidity to coordinate with Lewis bases and steric bulk arising from the aryl substituent on the B center to get enough kinetic stability. Thus, the incorporation of a trivalent B element into π-conjugated systems is an efficient strategy to tune the electronic and stereo structures and thus the photoelectronic properties of π-electron systems...
February 6, 2017: Inorganic Chemistry
Nerea Epelde-Elezcano, Eduardo Palao, Hegoi Manzano, Alejandro Prieto-Castañeda, Antonia R Agarrabeitia, Andrea Tabero, Angeles Villanueva, Santiago de la Moya, Iñigo López-Arbeloa, Virginia Martinez-Martinez, Maria J Ortiz
The synthesis, photophysical characterization and modelling of a new library of halogen-free photosensitizers (PS) based on orthogonal BODIPY dimers are reported. Herein we establish key structural factors to enhance singlet oxygen generation by judiciously chosen the substitution patterns attending to key electronic effects and synthetic accessibility factors. The photosensization mechanism of orthogonal BODIPY dimers is demonstrated to be strongly related to their intrinsic intramolecular charge transfer (ICT) character by SOCT-ISC (spin-orbit charge-transfer intersystem crossing) mechanism...
February 6, 2017: Chemistry: a European Journal
Jing Xu, Wenxu Liu, Yanfang Geng, Ke Deng, Chuanlang Zhan, Qingdao Zeng
In this article, a donor-acceptor H-T-BO/C70 system was studied by a STM/STS method on the molecular level. STM results revealed that H-T-BO, a BODIPY-based derivative, can form a semi-closed molecular network at the 1-phenyloctane/HOPG interface. After introducing C70 fullerene molecules into the network, two kinds of self-assembled nanoarrays were observed by STM. Density functional theory has been utilized to reveal the formation mechanism of the molecular nanoarrays. Scanning Tunneling Spectroscopy (STS) measurements were performed to investigate the electronic properties of H-T-BO/C70 systems...
February 2, 2017: Nanoscale
Sunting Xuan, Ning Zhao, Xiangyi Ke, Zehua Zhou, Frank R Fronczek, Karl M Kadish, Kevin Malcolm Smith, M Graca Henriques Vicente
A series of push-pull BODIPYs bearing multiple electron-donating and electron-acceptor groups were synthesized regioselectively from 2,3,5,6,8-pentachloro-BODIPY, and characterized by NMR spectroscopy, HRMS and X-ray crystallography. The influence of the push-pull substituents on the spectroscopic and electrochemical properties of BODIPYs was investigated. Bathochromic shifts were observed for both absorbance (up to 37 nm) and emission (up to 60 nm) in different solvents upon introduction of the push-pull moieties...
February 2, 2017: Journal of Organic Chemistry
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
Plant peroxisomes maintain a plethora of key life processes including fatty acid β-oxidation, photorespiration, synthesis of hormones, and homeostasis of reactive oxygen species (ROS). Abundance of peroxisomes in cells is dynamic; however mechanisms controlling peroxisome proliferation remain poorly understood because measuring peroxisome abundance is technically challenging. Counting peroxisomes in individual cells of complex organs by electron or fluorescence microscopy is expensive and time consuming. Here we present a simple technique for quantifying peroxisome abundance using the small probe Nitro-BODIPY, which in vivo fluoresces selectively inside peroxisomes...
February 1, 2017: Scientific Reports
Hai-Juan Lv, Xiao-Tai Zhang, Shu Wang, Guo-Wen Xing
Two BODIPY-carbazole dye based fluorescent probes BCA and BCAS were designed, synthesized and encapsulated by liposomes to obtain fluorescent nanoparticles BCA-FNP and BCAS-FNP. The fluorescence imaging showed that BCA-FNP was membrane-permeable and capable of localizing lysosomes in living cells.
January 31, 2017: Analyst
Mark Van der Auweraer, Hui Chong, Eduard Fron, Zhen Liu, Stijn Boodts, Joice Thomas, Jeremy N Harvey, Johan Hofkens, Wim Dehaen, Mario Smet
A novel palladium-catalyzed direct C(sp³)-H arylation of the methyl group at the 8-position of BODIPY by bromoarenes was established. A deprotonative cross-coupling process is supposed to be involved in the reaction. This approach allowed us to attach electron donating/withdrawing, halogen substituted aryls and a heteroaryl with a yield running from 55 to 99%. Novel pH sensors, which showed in the absence of acid the occurrence of photo-induced electron transfer, were synthesized by attaching dimethylaniline to the methyl at the C8-position of BODIPY...
January 30, 2017: Chemistry: a European Journal
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