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Talita B Gontijo, Rossimiriam P de Freitas, Flavio S Emery, Leandro F Pedrosa, José B Vieira Neto, Bruno C Cavalcanti, Claudia Pessoa, Aaron King, Fabio de Moliner, Marc Vendrell, Eufrânio N da Silva Júnior
Fluorescent quinone-based BODIPY hybrids were synthesised and characterised by NMR analysis and mass spectrometry. We measured their cytotoxic activity against cancer and normal cell lines, performed mechanistic studies by lipid peroxidation and determination of reduced (GSH) and oxidized (GSSG) glutathione, and imaged their subcellular localisation by confocal microscopy. Cell imaging experiments indicated that nor-β-lapachone-based BODIPY derivatives might preferentially localise in the lysosomes of cancer cells...
August 4, 2017: Bioorganic & Medicinal Chemistry Letters
Andreas Paulus, Marco Maenen, Natascha Drude, Emmani B M Nascimento, Wouter D van Marken Lichtenbelt, Felix M Mottaghy, Matthias Bauwens
BACKGROUND: Brown adipose tissue research is in the focus in the field of endocrinology. We designed a dual-modal fluorescent/PET fatty acid based tracer on commercially available Bodipy-C16, which can be synthesized to its corresponding triglyceride and which combines the benefits of fluorescent and PET imaging. METHODS: Bodipy-C16 was coupled to 1,3-diolein resulting in Bodipy-triglyceride. Bodipy-C16 and Bodipy-triglyceride compounds were radiolabeled with 18F using an 18F/19F exchange reaction to yield a dual-modal imaging molecule...
2017: PloS One
Aisling Byrne, Jaco Jacobs, Christopher S Burke, Aaron Martin, Andreas Heise, Tia E Keyes
A new approach for the fabrication of luminescent ratiometric sensing nanosensors is described using core-shell nanoparticles in which the probe and reference are spatially separated into the shell and core of the nanostructure respectively. The isolation of the reference in the core of the particle ensures a stable emission reference signal unaffected by the external environment. The core shell structure was prepared by engineering structurally well-defined Ru-conjugated block copolymers which acted as emulsifiers in the miniemulsion polymerisation of BODIPY loaded styrene nanoparticles...
August 16, 2017: Analyst
Zhijia Wang, Jianzhang Zhao
Bodipy-anthracene dyads with two chromophores assuming orthogonal geometry to enhance the spin-orbital charge-transfer intersystem crossing (SOCT-ISC) were prepared. The photosensitizers show strong absorption of visible light, efficient triplet-state formation (quantum yield 90%), and a long-lived triplet state (85 μs). The dipole moment orientation exerts significant effect on the ISC efficiency. It is also the first time that photosensitizers based on SOCT-ISC were used for triplet-triplet annihilation upconversion...
August 15, 2017: Organic Letters
Praseetha E Kesavan, Raghu Nath Behera, Shigeki Mori, Iti Gupta
Carbazole and p-anisyl substituted BODIPY dyes with a cyanoacetic acid anchoring group have been prepared and their spectral, electrochemical properties and photosensitizing potential in DSSC have been evaluated. X-ray structure of N-phenylcarbazole substituted BODIPY revealed lower torsion angle between BODIPY plane and carbazole plane, suggesting increased communication between the two units. DFT studies indicated effective electronic interactions between the BODIPY unit and carbazole substituents. The N-butylcarbazole and N-phenylcarbazole substituted BODIPYs showed anodic shifts in their reduction potentials, indicating facile reduction process...
August 14, 2017: Journal of Fluorescence
Jessica Harris, Lizhi Gai, Gugu Kubheka, John Mack, Tebello Nyokong, Zhen Shen
The optical limiting properties of a series of near infrared absorbing 3,5-dithienylenevinylene BODIPY dyes (1-3) that contain donor and acceptor moieties in their π-conjugation systems were studied by using the z-scan technique at 532 nm in the nanosecond pulse range. A strong reverse saturable absorption RSA response was observed when the compounds are embedded into poly(bisphenol carbonate A) polymer thin films, which demonstrates that BODIPY dyes with this type of structure are suitable for use in optical limiting applications...
August 14, 2017: Chemistry: a European Journal
Alexey A Pakhomov, Igor E Deyev, Natalia M Ratnikova, Stepan P Chumakov, Veronika B Mironiuk, Yuriy N Kononevich, Aziz M Muzafarov, Vladimir I Martynov
In nonpolar solvents, hydrophobic organic fluorophores often show bright fluorescence, whereas in polar media, they usually suffer from aggregation-caused quenching (ACQ). Here, we harnessed this solvatochromic behavior of a 1,3,5,7-tetramethyl-BODIPY derivative for cell staining and applied it to live-cell imaging and flow cytometry. As opposed to commercially available dyes, this BODIPY derivative showed excellent contrast immediately after staining and did not require any wash-off.
August 1, 2017: BioTechniques
Chihiro Maeda, Keiji Nagahata, Tadashi Ema
Carbazole-based BODIPYs 1-6 with several different substituents at the boron atom site were synthesized. These dyes fluoresced in the solid state, and 3a with phenylethynyl groups exhibited a red-shifted and broad fluorescence spectrum, which suggested an excimer emission. Its derivatives 3b-n were synthesized, and the relationship between the solid-state emission and crystal packing was investigated. The X-ray crystal structures revealed cofacial dimers that might form excimers. From the structural optimization results, we found that the introduction of mesityl groups hindered intermolecular access and led to reduced interactions between the dimers...
August 11, 2017: Organic & Biomolecular Chemistry
Kaustabh Kumar Maiti, Adarsh Nagappanpillai, Ramya A N, Ramaiah Danaboyina
Development of novel Raman reporters attracted immense attention in diagnostic research based on surface enhanced Raman scattering (SERS) techniques, a well established modality for ultrsensitive detection through molecular fingerprinting and imaging. Herein, for the first time, we report an unique and efficient Raman active features of the selected aza-BODIPY dyes 1-6. These distinctive attribute could be extended at the molecular level detection through SERS. Among the newly revealed Raman reporters, the amino substituted derivative, 4, showed significantly high signal intensity at very low concentrations (0...
August 10, 2017: Chemistry: a European Journal
Mehrdad Ghashghaeinia, Mauro Carlos Wesseling, Elena Ramos, Polina Petkova-Kirova, Sabrina Waibel, Elisabeth Lang, Rosi Bissinger, Kossai Alzoubi, Baerbel Edelmann, Zohreh Hosseinzadeh, Peter Dreischer, Azam Shahvaroughi-Farahani, Ulrich Mrowietz, Martin Köberle, Lars Kaestner, Ingolf Bernhardt, Antonio Martínez-Ruiz, Thomas Wieder, Florian Lang
BACKGROUND AND PURPOSE: The high potency antipsychotic drug trifluoperazine (10-[3-(4-methyl-1-piperazinyl)-propyl]-2-(trifluoromethyl)-(10)H-phenothiazine dihydrochloride; TFP) may either counteract or promote suicidal cell death or apoptosis. Similar to apoptosis, erythrocytes may enter eryptosis, characterized by phosphatidylserine exposure at the cell surface and cell shrinkage. Eryptosis can be stimulated by an increase in cytoplasmic Ca2+ concentration ([Ca2+]i) and inhibited by nitric oxide (NO)...
August 9, 2017: Cellular Physiology and Biochemistry
Yaxiong Wei, Miaomiao Zhou, Qiaohui Zhou, Xiaoguo Zhou, Shilin Liu, Song Zhang, Bing Zhang
Three new triplet photosensitizers consisting of a bodipy derivative and C60 moieties were synthesized for triplet-triplet annihilation upconversion of perylene. With the extension of the π-conjugated structure of the bodipy derivative, the three photosensitizers exhibited different absorption wavelengths, e.g. 517 nm for B-2, 532 nm for B-4, and 557 nm for B-6. The steady-state and transient absorption, steady-state fluorescence, and upconverted fluorescence emission were investigated to reveal step-by-step the dynamic processes of the above systems...
August 9, 2017: Physical Chemistry Chemical Physics: PCCP
Juan Tang, Yanfei Zhang, Hao-Yan Yin, Guoheng Xu, Jun-Long Zhang
Designing two-photon probes for precise labelling lipid droplet (LD) and monitoring LD dynamics in adipocytes is of great significance to understand LD homeostasis. We herein report that a luminescent metal complex LD-TPZn can specifically image LDs in adipose cells and tissue using one- or two-photon fluorescence microscopy. Importantly, LD-TPZn exhibited higher specificity to LD than commercial Nile Red and Bodipy 493/503, probably due to different cellular uptake pathways, clathrin-mediated endocytosis and non-selectively passive diffusion, respectively...
August 4, 2017: Chemistry, An Asian Journal
J N Louvet, C Carrion, T Stalder, M Alrhmoun, M Casellas, O Potier, M N Pons, C Dagot
Antibiotics-bacteria interactions depend on antibiotic concentration at the scale of bacteria. This study investigates how vancomycin penetrates into activated sludge flocs and can be sorbed on the bacteria and extracellular polymeric substances (EPS). The 3D structure of flocs was imaged using EPS autofluorescence. The green fluorescent BODIPY(®) FL vancomycin was introduced in a microscopic chamber containing activated sludge and penetration of vancomycin into the flocs by diffusion was observed using time-lapse microscopy...
July 26, 2017: Water Research
Jianxin Song, Lei Xu, Bin Wen, Gakhyun Kim, Taeyeon Kim, Fei Cheng, Mingbo Zhou, Ling Xu, Takayuki Tanaka, Atsuhiro Osuka, Dongho Kim, Bangshao Yin
A powerful and concise synthetic protocol of directly linked porphyrin-BODIPY hybrids has been demonstrated, which consists of condensation of directly linked meso-pyrroyl NiII-porphyrin with arylaldehyde, oxidation with p-chloranil, and complexation with BF3*Et2O. Synthesized hybrids include porphyrin dimer 6Ni, trimers 8Ni, 9Ni, tetramer 12Ni, pentamer 16Ni, hexamer 13Ni, and nonamers 17Ni and 18Ni. The structures of 6Ni, 9Ni and 12Ni were unambiguously confirmed by X-ray diffraction analysis. Some NiII-porphyrins were effectively converted to the corresponding ZnII-porphryins...
August 2, 2017: Angewandte Chemie
Leonardo W T Barros, Thiago A S Cardoso, Angela Bihlmeier, Danny Wagner, Dominik K Kölmel, Anna Hörner, Stefan Bräse, Carlos H Brito Cruz, Lazaro A Padilha
We report on the two-photon absorption spectra of a series of 2,6-disubstituted BODIPY dyes. Depending on the substituents, we observe increasing two-photon absorption cross sections with values up to 350 GM compared to 70 GM in the unsubstituted dye. Quantum chemical calculations are performed to assign the absorption bands and to understand the factors controlling the size of the two-photon absorption cross section. Both the maximum of the two-photon absorption band as well as the red-shift of the whole spectrum correlate with the ability of the substituents to extend the π-electron system of the dye...
August 16, 2017: Physical Chemistry Chemical Physics: PCCP
Feihong Deng, Yuan Fang, Zhiyong Shen, Wei Gong, Tao Liu, Jing Wen, Wanling Zhang, Xianjun Zhu, Hui Zhong, Tong Wang, Fachao Zhi, Biao Nie
Endoscopic treatment for early colorectal cancer closely correlates with patient prognosis. However, endoscopic differentiation between carcinomas and non-neoplastic lesions remains difficult. Here, we topically stained colorectal neoplasms with a fatty acid analogue (BODIPY-FA) and quantified the fluorescent signals using confocal laser endomicroscopy (CLE) and fluorescence microscopy. We also analyzed protein expression in colorectal cancer tissues. We found that expression of fatty acid synthase was elevated, while the expression of fatty acid transporters was reduced in colorectal cancer...
July 24, 2017: Oncotarget
Chin-Ti Chen, Shih-Chieh Yeh, Li-Jing Wang, Hong-Ming Yang, Yu-Huei Dai, Ru-Jong Jeng, Chiao-Wen Lin
Including MPBTCA, which is a literature known compound, seven BODIPY dyes have been characterization by varied physical methods, such as UV-visible absorption spectroscopy, low energy photo-electron spectroscopy (AC-2), HOMO-LUMO DFT/TDDFT calculation. All seven BODIPY dyes have absorption max around 535-545 nm, which is significantly longer than 499 nm of 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indacene (PM 546). Having structural variation on donor group, acceptor group, donor -spacer, acceptor -spacer, and the substituent on boron, some BODIPY dyes exhibit small extinction coefficient or spectral integral in solution (MPCtBTCA, MPBT-pyO, MPBTT-pyO, MTBTCA), broadening absorption spectral profile (MTBTCA), weak intramolecular charge transfer characteristics (MPBT-pyO, MPBTT-pyO, MTBTCA), too low LUMO energy level (PPBTCA), insufficient dye-uptake by TiO2 FTO (MPBT-pyO, MPBTT-pyO, MTBTCA)...
August 1, 2017: Chemistry: a European Journal
Andrew J Musser, Prakash P Neelakandan, Johannes M Richter, Hirotaka Mori, Richard H Friend, Jonathan R Nitschke
We have prepared a series of M(II)4L6 tetrahedral cages containing one or the other of two distinct BODIPY moieties, as well as mixed cages that contain both BODIPY chromophores. The photophysical properties of these cages and their fullerene-encapsulated adducts were studied in depth. Upon cage formation, the charge-transfer character exhibited by the bis(aminophenyl)-BODIPY subcomponents disappeared. Strong excitonic interactions were instead observed between at least two BODIPY chromophores along the edges of the cages, arising from the electronic delocalization through the metal centers...
August 15, 2017: Journal of the American Chemical Society
Jian Yin, Quan Zhang, Ying Cai, Qiu-Yan Li, Lin-Na Hao, Zheng Ma, Xiao-Jun Wang
The targeted delivery of a photosensitizer (PS) with appropriate carriers represents an attractive means of selectively delivering cargo to target tissues or subcellular compartments for photodynamic therapy (PDT). Herein, we report a three-arm distyryl BODIPY derivative conjugated with mannose units (denoted by BTM) that can co-assemble with Tween 80 to form nanomicelles (BTM-NMs) for targeted PDT. MDA-MB-231 breast cancer cells recognized and specifically internalized BTM-NMs via mannose receptor-mediated endocytosis with preferential accumulation in the lysosomes...
July 28, 2017: Chemistry: a European Journal
Liu Xingang, W U Min, L I Suying, Li Zhongbao, H U Qinglian, Zhou Jun, Tang Guping
Objective: To design and synthesize photosensitizers with different substituents and to identify its physicochemical characteritics and photodynamic effect on cancer cells. Methods: Two kinds of BODIPY photosensitizers BPOI and BPCI were synthesized through condensation reaction between aldehyde and reactive hydrogen of pyrrole, followed with electrophilic substitution reaction. Physicochemical properties were characterized by (1)H NMR, FT-IR and UV-visible absorption spectra and fluorescence emission spectra...
March 25, 2017: Zhejiang da Xue Xue Bao. Yi Xue Ban, Journal of Zhejiang University. Medical Sciences
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