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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.
June 22, 2017: Chemical Communications: Chem Comm
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
Ruyong Jiang, Xiuguang Yang, Di Wu
The direct C-H activation of electron-deficient aza-BODIPYs has been effectively achieved via a concise and inexpensive Cu(ii)-promoted oxidative C-H/C-H coupling approach. The resulting indole-aza-BODIPY 6b covers a broad spectrum of 429-900 nm with a FWHM of 294 nm in solution and covers a UV-vis-NIR region up to 1100 nm in film.
June 20, 2017: Organic & Biomolecular Chemistry
Mizuho Tsuchiya, Ryota Sakamoto, Masaki Shimada, Yoshinori Yamanoi, Yohei Hattori, Kunihisa Sugimoto, Eiji Nishibori, Hiroshi Nishihara
Imine-linked BODIPY oligomers show fluorescence quantum yields of up to 0.93. The azine linker may mediate π-conjugation that extends over six BODIPY units with redshifts up to 125 nm. BODIPYs are immobilized on silica gel through heterogeneous imine-bond formation, being fluorescent and robust.
June 20, 2017: Chemical Communications: Chem Comm
Sunit Kumar, Kishor Gulab Thorat, Mangalampalli Ravikanth
The azaBODIPYs containing one and two formyl functional groups on the 1, 7-aryl groups present at the azaBODIPY core were synthesized over sequence of steps and characterized by mass, NMR, absorption and electrochemical techniques. The mono-formylated and di-formylated azaBODIPYs are very useful synthons to prepare wide variety of new fluorescent compounds. The mono- and di-formylated azaBODIPYs were treated with pyrrole under mild acidic conditions followed by column chromatographic purification to afford azaBODIPYs appended with one and two dipyrromethanyl groups...
June 19, 2017: Journal of Organic Chemistry
Yuzuru Kubohara, Haruhisa Kikuchi, Van Hai Nguyen, Hidekazu Kuwayama, Yoshiteru Oshima
Differentiation-inducing factor-1 [1-(3,5-dichloro-2,6-dihydroxy-4-methoxyphenyl)hexan-1-one (DIF-1)] is an important regulator of cell differentiation and chemotaxis in the development of the cellular slime mold Dictyostelium discoideum However, the entire signaling pathways downstream of DIF-1 remain to be elucidated. To characterize DIF-1 and its potential receptor(s), we synthesized two fluorescent derivatives of DIF-1, boron-dipyrromethene (BODIPY)-conjugated DIF-1 (DIF-1-BODIPY) and nitrobenzoxadiazole (NBD)-conjugated DIF-1 (DIF-1-NBD), and investigated their biological activities and cellular localization...
June 15, 2017: Biology Open
Sohini Bose, Anh H Ngo, Loi H Do
In the present work, we show for the first time that the conversion of aldehydes to alcohols can be achieved using "unprotected" iridium transfer hydrogenation catalysts inside living cells. The reactions were observed in real time by confocal fluorescence microscopy using a Bodipy fluorogenic substrate. We propose that the reduced cofactor nicotinamide adenine dinucleotide (NADH) is a possible hydride source inside the cell based on studies using pyruvate as a cellular redox modulator. We expect that this biocompatible reductive chemistry will be broadly useful to practitioners working at the interface of chemistry and the life sciences...
June 22, 2017: Journal of the American Chemical Society
R Srinivasa Rao, Anirban Bagui, G Hanumantha Rao, Vinay Gupta, Surya Prakash Singh
A novel boron dipyrromethene based dye, coded as BODIPY-DTF, decorated with dithiafulvalene wings has been developed for solar cell application. A very high efficiency of 7.2% has been achieved, which is the highest reported value so far for BODIPY based donors. A remarkable value of about 88.1% of external quantum efficiency has also been observed at 371 nm.
June 22, 2017: Chemical Communications: Chem Comm
Masahiro Ono, Hiroyuki Watanabe, Yuki Ikehata, Ning Ding, Masashi Yoshimura, Kohei Sano, Hideo Saji
In molecular imaging research, the development of multimodal imaging probes has recently attracted much attention. In the present study, we prepared radioiodinated BODIPY and applied it as a nuclear and optical dual functional labeling agent for proteins and peptides. We designed and synthesized [(125)I]BODIPY with a N-hydroxysuccinimide (NHS) ester, and evaluated its utility as a nuclear and fluorescent dual labeling agent for proteins and peptides. In the radioiodination reaction of BODIPY-NHS with [(125)I]NaI, [(125)I]BODIPY-NHS was obtained at a 48% radiochemical yield...
June 13, 2017: Scientific Reports
Richard J Karpowicz, Conor M Haney, Tiberiu S Mihaila, Raizel M Sandler, E James Petersson, Virginia M-Y Lee
Direct cell-to-cell transmission of proteopathic alpha-synuclein (α-syn) aggregates is thought to underlie the progression of neurodegenerative synucleinopathies. However, the specific intracellular processes governing this transmission remain unclear because currently-available model systems are limited. For example, in cell culture models of α-syn-seeded aggregation, it is difficult to discern intracellular from extracellular exogenously applied α-syn seed species. Herein, we employed fluorescently labeled α-syn preformed fibrils (pffs) in conjunction with the membrane-impermeable fluorescence quencher trypan blue to selectively image internalized α-syn seeds in cultured primary neurons and to quantitatively characterize the concentration dependence, time course, and inhibition of pff uptake...
June 13, 2017: Journal of Biological Chemistry
Francis D'Souza, Shuai Shao, Habtom Gobeze, Paul Karr
BF2-chelaed dipyrromethene, BODIPY, was functionalized to carry two stryryl crown ether tails and a secondary electron donor at the meso-position. Using a 'two-point' self-assembly strategy, a bis-alkyl ammonium functionalized fullerene, C60 was allowed to self-assemble the crown ether voids of BODIPY to obtain multi-modular donor-acceptor conjugates. As a consequence of the two-point binding, the 1:1 stoichiometric complexes formed yielded complexes of higher stability in which fluorescence of BODIPY was found to be quenched suggesting occurrence of excited state processes...
June 13, 2017: Chemistry, An Asian Journal
Abdallah Mound, Vesela Lozanova, Céline Warnon, Maryse Hermant, Julie Robic, Christelle Guere, Katell Vie, Catherine Lambert de Rouvroit, Donatienne Tyteca, Florence Debacq-Chainiaux, Yves Poumay
Membrane lipid raft model has long been debated, but recently the concept of lipid submicrometric domains has emerged to characterize larger (micrometric) and more stable lipid membrane domains. Such domains organize signaling platforms involved in normal or pathological conditions. In this study, adhering human keratinocytes were investigated for their ability to organize such specialized lipid domains. Successful fluorescent probing of lipid domains, by either inserting exogenous sphingomyelin (BODIPY-SM) or using detoxified fragments of lysenin and theta toxins fused to mCherry, allowed specific, sensitive and quantitative detection of sphingomyelin and cholesterol and demonstrated for the first time submicrometric organization of lipid domains in living keratinocytes...
June 5, 2017: Biochimica et Biophysica Acta
Okta Suryani, Yuta Higashino, Jacob Yan Mulyana, Masayoshi Kaneko, Takayuki Hoshi, Koichiro Shigaki, Yuji Kubo
Dye-sensitized photoelectrochemical cells (DSPECs) composed of a new near-infrared BODIPY dye D1 that is co-deposited with a ruthenium water oxidation catalyst C1 have been fabricated. The devices at pH 7.2 showed an excellent Faradaic efficiency of H2 production (65.8%) that was 5.4 times larger than that of a triphenylamine photosensitizer D2 and C1-coadsorbed cell.
June 9, 2017: Chemical Communications: Chem Comm
Audrey Trommenschlager, Florian Chotard, Benoît Bertrand, Souheila Amor, Lucile Dondaine, Michel Picquet, Philippe Richard, Ali Bettaïeb, Pierre Le Gendre, Catherine Paul, Christine Goze, Ewen Bodio
Two new gold(i)-BODIPY-imidazole based trackable therapeutic bimetallic complexes have been synthesized and fully characterized. They display strong antiproliferative properties on several types of cancers including colon, breast, and prostate and one of them presents a significant anti-inflammatory effect. Additionally, the two compounds could be visualised in vitro by confocal microscopy in the submicromolar range.
June 8, 2017: Dalton Transactions: An International Journal of Inorganic Chemistry
Ling Huang, Zhanjun Li, Yang Zhao, Jinyi Yang, Yucheng Yang, Aarushi Iris Pendharkar, Yuanwei Zhang, Sharon Kelmar, Liyong Chen, Wenting Wu, Jianzhang Zhao, Gang Han
Photodynamic therapy (PDT) is an important cancer treatment modality due to its minimally invasive nature. However, the efficiency of existing PDT drug molecules in the deep-tissue-penetrable near-infrared (NIR) region has been the major hurdle that has hindered further development and clinical usage of PDT. Thus, herein a strategy is presented to utilize a resonance energy transfer (RET) mechanism to construct a novel dyad photosensitizer which is able to dramatically boost NIR photon utility and enhance singlet oxygen generation...
June 6, 2017: Advanced Materials
Bernhard J Müller, Tanja Rappitsch, Christoph Staudinger, Christian Rüschitz, Sergey M Borisov, Ingo Klimant
A new fluorescent sensor for Na(+) is presented. The sensor relies on a Na(+) selective fluoroionophore based on a bright red-emitting BODIPY chromophore. The fluorescence of the fluoroionophore is enhanced upon binding of Na(+)-ions to the highly selective aza-crown ether receptor due to reduction of the photoinduced electron transfer (PET) quenching. Solid state sensing materials were prepared by physically embedding the fluoroionophore into water-swellable biocompatible polymer matrices (polyurethane hydrogels), thus enabling continuous measurements of aqueous samples...
June 16, 2017: Analytical Chemistry
Zhikuan Zhou, Jianping Zhou, Lizhi Gai, Aihua Yuan, Zhen Shen
Naphtho[b]-fused BODIPYs have been facilely synthesized via Suzuki-Miyaura-Knoevenagel reaction between mono-iodo-BODIPY or 2,6-diiodo-BODIPY with (2-formylphenyl)boronic acid. This one-pot reaction represents a very straightforward approach for tuning the absorption and emission of BODIPYs in the red visible/NIR range.
June 21, 2017: Chemical Communications: Chem Comm
Bo Qiu, M Celeste Simon
Lipid droplets (LDs) are ubiquitous, dynamic organelles and function as a storage depot for neutral lipids, including triglycerides and cholesterol esters (Walther and Farese, 2012). The movement of lipid species into and out of LDs impacts a variety of cellular processes, such as energy homeostasis, lipid-based signaling, and membrane homeostasis (Greenberg et al., 2011). For example, neutral lipid storage is enhanced upon increased synthesis or uptake of lipid species. On the other hand, extracellular signals can enhance the release of lipid species packaged within neutral LDs...
September 5, 2016: Bio-protocol
Yuriy S Marfin, Alexey V Solomonov, Alexander S Timin, Evgeniy V Rumyantsev
The group of fluorophores on boron dipyrrin platform (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, also known as BODIPY) has attracted much attention in the field of molecular sensorics, including sensing of biomolecules and bioprocesses. Structural diversity of existing BODIPY with ample opportunities of directed modification of compounds makes this class of fluorophores attractive for medical and biological purposes. The recent progress in the design and functionalization of BODIPY allows to use them for modification of drug micro- and nanocarriers in order to improve their therapeutic effect in cancer treatment...
May 31, 2017: Current Medicinal Chemistry
Xiaojun Li
In this work, we reported the geometrical structures, electronic and spectral properties of the carborane-containing BODIPYs complexes using the density functional theory calculations. In two structures, the calculated main bond lengths and bond angels of structural framework are consistent with X-ray experiment, and the two BODIPYs complexes are thermodynamically and kinetically stable. The strongest DOS band is mainly dominated by the BB and BH σ-bonds of carborane fragment, whereas the π-type MOs on the pyrromethene fragment contribute to the high-energy DOS bands...
May 23, 2017: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
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