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Po-Yu Ho, Michael F Mark, Yi Wang, Sze-Chun Yiu, Wai-Hong Yu, Cheuk-Lam Ho, David W McCamant, Richard Eisenberg, Shuping Huang
Three molecular photosensitizers (PSs) with carboxylic acid anchors for attachment to platinized titanium dioxide nanoparticles were studied for light-driven hydrogen production from a fully aqueous medium with ascorbic acid (AA) as the sacrificial electron donor. Two zinc(II) porphyrin (ZnP) based PSs (ZnP-dyad and YD2-o-C8) were used to examine the effect of panchromatic sensitization in promoting photocatalytic H2 generation. A dyad molecular design was used to construct the Bodipy-conjugated ZnP PS (ZnP-dyad) and another one was featured with an electron-donating diarylamino moiety (YD2-o-C8)...
June 19, 2018: ChemSusChem
Minkyu Kyeong, Jinho Lee, Kwanghee Lee, Sukwon Hong
Recently perovskite solar cells (PSCs) have emerged as an excellent photovoltaic device owing to the outstanding power conversion efficiency (PCE). Nevertheless, device instability remains a critical issue in this field. To overcome device instability without deteriorating PCE, dopant-free hole transporting materials (HTMs) is needed to separate the air-sensitive perovskite layer from extrinsic factors which induce its degradation. Herein we developed novel conjugate polymers of benzo[1,2-b:4,5-b']dithiophene (BDT) and 4,4-difluoro-4-bora-3a,4a-diaza- s-indacene (BODIPY) for use as HTMs without dopants...
June 19, 2018: ACS Applied Materials & Interfaces
E J van Rooden, M Kohsiek, R Kreekel, A C M van Esbroeck, A M C H van den Nieuwendijk, A P A Janssen, R J B H N van den Berg, H S Overkleeft, M van der Stelt
Diacylglycerol lipases (DAGL) are responsible for the biosynthesis of the endocannabinoid 2-arachidonoylglycerol. The fluorescent activity-based probes DH379 and HT-01 have been previously shown to label DAGLs and to cross-react with the serine hydrolase ABHD6. Here, we report the synthesis and characterization of two new quenched activity-based probes 1 and 2, the design of which was based on the structures of DH379 and HT-01, respectively. Probe 1 contains a BODIPY-FL and a 2,4-dinitroaniline moiety as a fluorophore-quencher pair, whereas probe 2 employs a Cy5-fluorophore and a cAB40-quencher...
June 14, 2018: Chemistry, An Asian Journal
Jingtuo Zhang, Soo Jung Yang, Federico Gonzalez, Jiaying Yang, Yumiao Zhang, Maomao He, Nilabh Shastri, Niren Murthy
ERAAP is an intracellular amino-peptidase that plays a central role in determining the repertoire of peptides displayed by cells by MHC class I molecules, and dysfunctions in ERAAP are linked to a variety of diseases. There is therefore great interest in developing probes that can image ERAAP in cells. In this report we present a fluorescent probe, termed Ep, that can image ERAAP activity in live cells. Ep is composed of a 10 amino acid ERAAP substrate that has a donor quencher pair conjugated to it, composed of BODIPY and dinitro-toluene...
June 13, 2018: Chemical Communications: Chem Comm
Yunjie Xiao, Qian Zhang, Yanyan Wang, Bin Wang, Fengnan Sun, Ziyu Han, Yaqing Feng, Haitao Yang, Shuxian Meng, Zefang Wang
Low water solubility and poor selectivity are two fundamental limitations that compromise applications of near-infrared (NIR) fluorescent probes. Methods: Here, a simple strategy that can resolve these problems simultaneously was developed by using a novel hybrid protein named RGD-HFBI that is produced by fusion of hydrophobin HFBI and arginine-glycine-aspartic acid (RGD) peptide. This unique hybrid protein inherits self-assembly and targeting functions from HFBI and RGD peptide respectively. Results: Boron-dipyrromethene (BODIPY) used as a model NIR dye can be efficiently dispersed in the RGD-HFBI solution by simple mixing and sonication for 30 min...
2018: Theranostics
Hiroaki Tabe, Kei Sukenobe, Toru Kondo, Atsunori Sakurai, Minako Maruo, Akari Shimauchi, Mitsuharu Hirano, Shin-Nosuke Uno, Mako Kamiya, Yasuteru Urano, Michio Matsushita, Satoru Fujiyoshi
We prepared a pair of visible-absorbing donor dye and near-infrared fluorescing acceptor dye. The donor and the acceptor were covalently linked close enough for Förster resonance energy transfer to occur. Under cryogenic conditions at 1.7 K, we ob-served the fluorescence excitation spectra of the individual pairs in a water matrix. We tested one Rhodamine, two Bodipy, and one Carbopyronine derivatives as the donor. Among these donors, Bodipy derivatives show the narrowest spectral width of the individuals with respect to the ensemble width...
June 11, 2018: Journal of Physical Chemistry. B
Ioanna K Sideri, Errika Voutyritsa, Christoforos G Kokotos
Photocatalysis, the use of light to promote organic transformations, is a field of catalysis that has received limited attention despite existing for over 100 years. With the revolution of photoredox catalysis in 2008, the rebirth or awakening of the field of photoorganocatalysis has brought new ideas and reactions to organic synthesis. This review will focus on the sudden outburst of literature regarding the use of small organic molecules as photocatalysts after 2013. In particular, it will focus on acridinium salts, benzophenones, pyrylium salts, thioxanthone derivatives, phenylglyoxylic acid, BODIPYs, flavin derivatives, and classes of organic molecules as catalysts for the photocatalytic generation of C-C and C-X bonds...
June 11, 2018: Organic & Biomolecular Chemistry
Wei Wang, Mélanie Lorion, Oscar Martinazzoli, Lutz Ackermann
Late-stage BODIPY diversification of structurally complex amino acids and peptides was accomplished by racemization-free palladium-catalyzed C(sp3)-H activation. Thus, transformative fluorescence modification proved viable by triazole-assisted C(sp3)-H arylation in a chemo- and site-selective fashion, providing modular access to novel BODIPY peptide sensors.
June 8, 2018: Angewandte Chemie
Zhengye Gu, Heyong Cheng, Xi Shen, Tian He, Kezhi Jiang, Huayu Qiu, Qian Zhang, Shouchun Yin
A BODIPY-based colorimetric and fluorescent chemosensor 1 anchored with dipyridylamino (DPA) receptor has been designed, synthesized and characterized. It exhibited a simultaneous sensitive recognition for Cu2+ , Hg2+ and Pb2+ ions. With the addition of these three kinds of metal ions into 1 in CH3 CN, its initial absorption maximum displayed obvious blue shifts, and the color changes of the solution could be clearly observed by naked eyes. Besides, the fluorescence intensity was significantly enhanced accompanied with the appearance of new emission peaks at 587 nm for Pb2+ and Hg2+ ions and 545 nm for Cu2+ ions...
May 30, 2018: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Maodie Wang, M Graça H Vicente, Deanna Mason, Petia Bobadova-Parvanova
Boron-dipyrromethene (BODIPY) dyes have been extensively investigated in recent years for a variety of bioanalytical and bioimaging applications. The success of these applications relies on the stability of BODIPYs, particularly under acidic conditions. In this work, the stability of a series of 4,4'-disubstituted BODIPYs (-F, -CN, -Ph, -Me, -OMe) toward addition of excess trifluoroacetic acid (TFA) was studied systematically and comprehensively through 11 B and 1 H NMR, UV-vis, fluorescence, thin layer chromatography, mass spectrometry, and infrared...
May 31, 2018: ACS Omega
Jin Wen, Bowen Han, Zdeněk Havlas, Josef Michl
The previously reported (Duman et al., J. Org. Chem. 2012, 77, 4516) calculated state energies of monomeric difluoroborondipyrromethene (BODIPY) and its axial dimer would suggest that these dyes are promising candidates for singlet fission, and that the dimer was computed to have an unusual low-lying doubly excited state. We find that these results were affected by the use of an imbalanced active space in multireference calculations and are not correct. Multi-state complete-active-space second-order perturbation theory (MS-CASPT2/cc-pVDZ) calculations using an [8,8] (8 electrons in 8 orbitals) active space for the monomer and a [16,16] active space for the dimer reproduce quite well the observed excitation energies of the S1 states of both, and yield T1 excitation energies well in excess of half of the S1 excitation energies...
June 6, 2018: Journal of Chemical Theory and Computation
Hongwei Kang, YuBing Si, Yuxiu Liu, Xiaofan Zhang, Weiwei Zhang, Yi Zhao, Baocheng Yang, Yaxuan Liu, Zhongyi Liu
Singlet oxygen is the key elements for photodynamic therapy. In this paper, six novel distyryl-BODIPY compounds were synthesized and investigated in detail to fully evaluate their photophysical/chemistry characteristics. Specially, the singlet oxygen 1O2 quantum yield of compounds 2 and 4 each bearing two bromine atoms in their skeleton revealed the position effect of heavy atom for 1O2 production. The 1O2 quantum yield of 4, which was brominated at 2/6 position of BODIPY skeleton, was much higher than that of compound 2, brominated at styryl group with a long distance towards BODIPY core...
June 5, 2018: Journal of Physical Chemistry. A
Yayu Chen, Jianzhi Liu, Meiru Song, Lizhi Jiang, Lin Liu, Yichang Liu, Gang Fu, Jinping Xue, Jian-Yong Liu, Mingdong Huang, Jinyu Li
Photodynamic therapy (PDT) is a noninvasive and effective approach in clinical cancer treatments. Boron-dipyrromethene (BODIPY)-based derivatives have emerged as novel and promising photosensitizers (PSs) in PDT, attributed to their strong near-infrared singlet oxygen luminescence emissions and high photostabilities. However, the binding mechanism of BODIPY derivatives to proteins, key for their therapeutic and biomedical applications is still poorly understood. Here, we investigated the molecular interactions of two 2, 6-diiodo-BODIPY derivatives with human serum albumin (HSA) using combined experimental and computational techniques...
May 29, 2018: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Lorenzo Sansalone, Sicheng Tang, Jaume Garcia-Amorós, Yang Zhang, Santi Nonell, James D Baker, Burjor Captain, Françisco M Raymo
A mechanism to photoactivate far-red/near-infrared fluorescence with infinite contrast and under mild visible illumination was designed around the photophysical properties of borondipyrromethene (BODIPY) dyes and the photochemical behavior of oxazine heterocycles. Specifically, the photoinduced and irreversible cleavage of an oxazine ring with a laser line at 405 nm extends the electronic conjugation of a BODIPY chromophore over a 3H-indole auxochrome with a 2-(4-methoxyphenyl)ethenyl substituent in position 5...
June 4, 2018: ACS Sensors
Jinhua Gao, Yuanfang Tao, Nannan Wang, Jinling He, Jian Zhang, Weili Zhao
Cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) are interconnected and play essential roles in many biological processes. It is significant importance to detect these thiols for investigating their functions in cells and disease diagnosis. In this work, we have designed and synthesized two novel BODIPY-based turn-on fluorescent probes (BDP-Ph and BDP-R-Ph) carrying 4-methoxythiophenol moiety at meso position as good leaving group for highly selective detection of Cys and Hcy. Furthermore, the probes have been successfully applied to detect intracellular Cys and Hcy by fluorescent imaging in living cells...
May 29, 2018: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Honorine Lebraud, Richard Noble, Nicole Phillips, Keisha Hearn, Juan Castro, Yan Zhao, David R Newell, John Lunec, Steve Wedge, Tom D Heightman
MDM2 is a key negative regulator of the p53 tumour suppressor. Direct binding of MDM2 to p53, represses the protein's transcriptional activity and induces its polyubiquitination, targeting it for degradation by the proteasome. Consequently, small molecule inhibitors that antagonise MDM2-p53 binding, such as RG7388, have progressed into clinical development aiming to reactivate p53 function in TP53 wild-type tumours. Here, we describe the design, synthesis and biological evaluation of a trans-cyclooctene tagged derivative of RG7388, RG7388-TCO, which showed high cellular potency and specificity for MDM2...
May 31, 2018: Bioconjugate Chemistry
Ryo Arai, Sayo Soda, Tomoko Okutomi, Hiroko Morita, Fumito Ohmi, Tomoe Funakoshi, Akihiro Takemasa, Yoshiki Ishii
We studied the subsets of peripheral blood dendritic cells (DCs) and lipid accumulation in DCs to investigate the involvement of DCs in the decreased anticancer immunity of advanced lung cancer patients. We analyzed the population of DC subsets in peripheral blood using flow cytometry. We then determined lipid accumulation in the DCs using BODIPY 650/665, a fluorophore with an affinity for lipids. Compared with healthy controls, the number of DCs in the peripheral blood of treatment-naive cancer patients was significantly reduced...
2018: Journal of Immunology Research
Dhruval J Joshi, Meesook Jun, Lijing Yang, Alan J Lough, Hongbin Yan
The treatment of non-fully substituted 4,4-di-fluoro-4-bora-3a,4a-di-aza- s -indacene (BODIPY) with cupric nitrate leads to the introduction of a nitro group at different positions of the BODIPY core, depending on the substitution pattern. This methodology complements the treatment of fully substituted BODIPY with cupric nitrate that was previously reported. The crystal structures of 4,4-di-fluoro-1,3,5,7,8-penta-methyl-2-nitro-4-bora-3a,4a-di-aza- s -indacene, C14 H16 BF2 N3 O2 ( 5a ) 4,4-di-fluoro-3-nitro-8-phenyl-4-bora-3a,4a-di-aza- s -indacene, C15 H10 BF2 N3 O2 (5b ) and 3-chloro-6-ethyl-5,7,8-trimethyl-2-nitro-4,4-diphenyl-4-bora-3a,4a-di-aza- s -indacene, C26 H25 BClN3 O2 ( 5d ) are presented...
February 1, 2018: Acta Crystallographica. Section E, Crystallographic Communications
Chin Siang Kue, Shie Yin Ng, Siew Hui Voon, Anyanee Kamkaew, Lip Yong Chung, Lik Voon Kiew, Hong Boon Lee
BODIPYs are photosensitizers activatable by light to generate highly reactive singlet oxygen (1O2) from molecular oxygen, leading to tissue damage in the photoirradiated region. Despite their extraordinary photophysical characteristics, they are not featured in clinical photodynamic therapy. This review discusses the recent advances in the design and/or modifications of BODIPYs since 2013, to improve their potential in photodynamic cancer therapy and related areas.
May 30, 2018: Photochemical & Photobiological Sciences
Chun Tian, Jinyun Niu, Xuerui Wei, Yujie Xu, Lifen Zhang, Zhenping Cheng, Xiulin Zhu
The performance of functional polymer nanomaterials is a vigorously discussed topic in polymer science. We devoted ourselves to investigating polymer nanomaterials based on near-infrared (NIR) fluorescence imaging and polymer prodrug in this study. Aza-boron dipyrromethene (BODIPY) is an important organic dye, having characteristics such as environmental resistance, light resistance, high molar extinction coefficient, and fluorescence quantum yield. We incorporated it into our target monomer, which can be polymerized without changing its parent structure in a polar solvent and copolymerized with water-soluble monomer to improve the solubility of the dye in an aqueous solution...
May 23, 2018: Nanoscale
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