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Giorgio Mirri, Daniël C Schoenmakers, Paul H J Kouwer, Peter Veranič, Igor Muševič, Bogdan Štefane
Fluorescent materials are widely used in biological and material applications as probes for imaging or sensing; however, their customization is usually complicated without the support of an organic chemistry laboratory. Here, we present a straightforward method for the customization of BODIPY cores, which are among the most commonly used fluorescent probes. The method is based on the formation of a new C-C bond through Friedel-Crafts electrophilic aromatic substitution carried out at room temperature. The method presented can be used to obtain completely customized fluorescent materials in one or two steps from commercially available compounds...
October 2016: ChemistryOpen
Talita B Gontijo, Rossimiriam P de Freitas, Guilherme F de Lima, Lucas C D de Rezende, Leandro F Pedrosa, Thaissa L Silva, Marilia O F Goulart, Bruno C Cavalcanti, Claudia Pessoa, Marina P Bruno, José R Corrêa, Flavio S Emery, Eufrânio N da Silva Júnior
For the first time, a fluorescent lapachone-based BODIPY was synthesised and characterised by NMR and mass spectrometry. Computational and electrochemical aspects, as well as cytotoxic activity and subcellular localisation, were studied. Confocal microscopy experiments indicated that the probe was a specific mitochondria-staining agent. These in-detail analyses were useful in understanding the cytotoxic effects and mechanism of action of this novel hybrid compound. This molecule constitutes a promising prototype owing to its potential biological activities and the new strategies aimed at mechanistic investigations in cells and in vivo, and opens up an interesting avenue of research...
October 24, 2016: Chemical Communications: Chem Comm
Wen-Jing Shi, Pui-Chi Lo, Shirui Zhao, Roy C H Wong, Qiong Wang, Wing-Ping Fong, Dennis K P Ng
An efficient ferrocenyl BODIPY based dark quencher has been developed and employed to construct a FRET-based fluorescent probe that contains a biotin moiety as a potential directing ligand for cancer cells and a glutathione-cleavable disulfide linker connecting the quencher and a distyryl BODIPY fluorophore. This molecular probe is deactivated in the native form through FRET followed by intramolecular charge transfer due to the ferrocenyl unit. However, upon interaction with glutathione in phosphate buffered saline and inside cancer cells, the fluorescence emission is significantly increased due to detachment of the fluorophore from the quencher...
October 24, 2016: Dalton Transactions: An International Journal of Inorganic Chemistry
Yun Wang, Jinchen Xia, Juan Han, Xu Bao, Yuanyuan Li, Xu Tang, Liang Ni, Lei Wang, Mengmeng Gao
Hypochlorite serves as a powerful antimicrobial agent in human immune system, the detection of which is of great significance. Herein a novel fluorescent probe based on BODIPY dye and diaminomaleonitrile has been synthesized and characterized to sense hypochlorite. The fluorescence of the system is dramatically enhanced by ClO(-) due to the removal of C=N isomerization effect in physiological pH condition. The complete reaction only needs a few seconds, which enables the probe to facilitate real-time detection...
December 1, 2016: Talanta
Hao Zhu, Jiangli Fan, Huiying Mu, Tao Zhu, Zhen Zhang, Jianjun Du, Xiaojun Peng
Polarity-sensitive fluorescent probes are powerful chemical tools for studying biomolecular structures and activities both in vitro and in vivo. However, the lack of "off-on" polarity-sensing probes has limited the accurate monitoring of biological processes that involve an increase in local hydrophilicity. Here, we design and synthesize a series of "off-on" polarity-sensitive fluorescent probes BP series consisting of the difluoroboron dippyomethene (BODIPY) fluorophore connected to a quaternary ammonium moiety via different carbon linkers...
October 21, 2016: Scientific Reports
Jin Li, Qian Zhang, Jian Yin, Changjiang Yu, Kai Cheng, Yun Wei, Erhong Hao, Lijuan Jiao
Prodiginines, as a family of bacterial alkaloids, possess a number of interesting biological activities. New, concise synthetic routes for the facile preparation of both synthetic and natural prodiginines in good yields have been developed, which use BODIPY functionalization reactions, such as condensation, nucleophilic substitution, and BF2 deprotection. This new metal-free synthetic method opens the door toward a wide variety of C-ring functionalized prodiginines, including those that are not possible to obtain through current synthetic methods, for their advanced biological activities...
October 21, 2016: Organic Letters
Boran Lee, Byung Gyu Park, Wansang Cho, Ho Yong Lee, András Olasz, Chun-Hsing Chen, Seung Bum Park, Dongwhan Lee
A series of air-stable boron complexes 1-5 were prepared by using N-aryl iminopyrrolide ligands. Designed as minimalist structural mimics of the privileged BODIPY motif, these new BOIMPY (BOron complexes of IMinoPYrrolide ligands) fluorophores feature low molecular symmetry that promotes emission from CT-type excited states with large Stokes shifts and little self-quenching. Through comparative studies on the homologous set of compounds 1-4, we have confirmed that a delicate interplay between conformational twisting and donor-acceptor interaction dictates the mechanism of de-excitation, which responds sensitively to solvent polarity as well as protonation states...
October 18, 2016: Chemistry: a European Journal
Maximiliano L Agazzi, M Belén Ballatore, Eugenia Reynoso, Ezequiel D Quiroga, Edgardo N Durantini
Two cationic BODIPYs 3 and 4 were synthesized by acid-catalyzed condensation of the corresponding pyrrole and benzaldehyde, followed by complexation with boron and methylation. Compound 3 contains methyl at the 1,3,5 and 7 positions of the s-indacene ring and a N,N,N-trimethylamino group attached to the phenylene unit, while 4 is not substituted by methyl groups and the cationic group is bound by an aliphatic spacer. UV-visible absorption spectra of these BODIPYs show an intense band at ∼500 nm in solvents of different polarities and n-heptane/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles...
October 3, 2016: European Journal of Medicinal Chemistry
Herbert Plenio, Oliver Halter, Roman Vasiuta, Israel Fernandez
Five different highly fluorescent Bodipy-tagged NHC-gold halide complexes were synthesized. The substitution of the halogeno ligand by 4-substituted aryl thiolates leads to a decrease in the brightness of the complexes. This decrease depends on the electronic nature of the thiols, being most pronounced with highly electron rich thiols (4-R= NMe2). The brightness of the gold-thiolates also depends on the distance between the sulfur atom and the Bodipy moiety. The systematic variation of the electron density of [(NHC-Bodipy)Au(SC6H4R)] (via different R groups) enables the systematic variation of the fluorescence brightness of an appended Bodipy fluorophore...
October 11, 2016: Chemistry: a European Journal
Junji Uchida, Takashi Nakamura, Masaki Yamamura, Gento Yamaguchi, Tatsuya Nabeshima
The effectiveness of a m-phenylene linker, which has rigidity as well as rotational flexibility, is presented to produce a series of variously shaped macrocyclic oligomers of dipyrrins and BODIPYs, whose structures were revealed by X-ray crystallography and (1)H NMR analysis. Although the chemical structures of the repeating units are the same for dipyrrin/BODIPY oligomers, their absorbance and emission properties changed significantly depending on the size and shape of the macrocycles.
October 10, 2016: Organic Letters
Xiaoqing Wang, Qingsong Liu, Fen Qi, Lin Li, Hai-Dong Yu, Zhipeng Liu, Wei Huang
A new family of BODIPY analogues (BDB1-8) derived from benzothiazole-pyrimidine-based bidentate ligands was synthesized and fully characterized. The photophysical properties of these boron complexes were measured both in solution and solid-state. These new luminophores exhibited intense fluorescence with high quantum yields ranging from 0.27 to 0.79, and moderate Stokes shifts ranging from 660 to 2120 cm(-1) in solution. Due to the existence of strong intermolecular interactions, BDB1-8 showed quenched fluorescence with low quantum yields ranging from 0...
October 7, 2016: Dalton Transactions: An International Journal of Inorganic Chemistry
Zafar Mahmood, Jianzhang Zhao
Fluorescent molecular probes based on photo-induced electron transfer (PET) are well-known for which fluorescence is efficiently tuned OFF/ON by a PET process. Now we demonstrate that the triplet excited state of the probes is unable to be quenched by PET, which is in stark contrast to the singlet excited state (fluorescence). This conclusion was proved by the preparation of a fluorescent molecular probe BDP-DPA, which shows enhanced fluorescence upon addition of a Zn(ii) salt. With fluorescence spectroscopy, nanosecond transient absorption spectroscopy and electrochemical studies, we found that the triplet excited state of BDP-DPA was not quenched by any PET process, although the singlet excited state (fluorescence) of BDP-DPA was quenched...
September 29, 2016: Photochemical & Photobiological Sciences
Stephanie Karmann, Stéphanie Follonier, Monica Bassas-Galia, Sven Panke, Manfred Zinn
Poly(3-hydroxyalkanoates) (PHAs) are bio-based and biodegradable polyesters which have been considered as a promising alternative to petrol-based plastics. Its bacterial production is a dynamic process in which intracellular polymerization and depolymerization are closely linked and depend on the availability of carbon substrates and other nutrients. These dynamics require a fast and quantitative method to determine the optimal harvest-time of PHA containing cells or to adjust carbon supply. In principle, flow cytometry (FCM) is an ideal tool that suits these requirements and, in addition, provides data on the PHA content of different cell populations...
October 6, 2016: Journal of Microbiological Methods
Yaroslav Faletrov, Anna Brzostek, Renata Plocinska, Jarosław Dziadek, Elena Rudaya, Irina Edimecheva, Vladimir Shkumatov
Fluorescent steroids BODIPY-cholesterol (BPCh) and 7-nitrobenzoxadiazole-4-amino-(NBD)-labeled 22-NBD-chelesterol (22NC) as well as synthesized 20-(NBD)-pregn-5-en-3β-ol (20NP) were found to undergo bioconversions by Mycobacterium tuberculosis H37Rv and M. smegmatis mc(2) 155. The major fluorescent products were determined to be 4-en-3-one derivatives of the compounds. Degradation of NBD fluorophore was also detected in the cases of 22NC and 20NP, but neither NBD degradation nor steroidal part modification were observed for the synthesized 3-(NBD)-cholestane...
October 5, 2016: Steroids
Shrikant S Thakare, Goutam Chakraborty, Parvathi Krishnakumar, Alok K Ray, Dilip Kumar Maity, Haridas Pal, Nagaiyan Sekar
Supramolecular host-guest interaction of neutral and cationic (protonated) forms of two BODIPY-benzimidazole (mono-benzimidazole and di-benzimidazole) conjugate dyes with the macrocyclic host Cucurbit[7]uril (CB7) has been investigated using photophysical and DFT studies. Expectedly, cationic forms of the dyes show exceptionally stronger binding than that of the neutral forms with CB7, which can be ascribed to strong ion-dipole interaction between the positive charge of the dye and highly polarizable carbonyl portals of the host...
October 7, 2016: Journal of Physical Chemistry. B
Marina Laine, Nuno A Barbosa, Robert Wieczorek, Mikhail Ya Melnikov, Aleksander Filarowski
A number of fluorescent dyes based on BODIPY (4,4'-difluoro-4-bora-3a,4a-diaza-s-indacene) have been studied theoretically. This paper presents the results of calculations of these BODIPY dyes in their ground and excited states, performed using DFT and TD-DFT methods, respectively. The influences of N,N-dimethylaminobenzyl, ortho-fluorophenol, and methyl substituents as well as the solvent polarity on the positions of the absorption and emission bands of the dyes were analyzed. The computational data obtained in this work were compared to the corresponding experimental data...
November 2016: Journal of Molecular Modeling
Lan Yang, Ya-Jian Ji, Jia-Fu Yin, Yongquan Wu, Haiming Fan, Yi Zhang, Gui-Chao Kuang
Three novel amphiphilic BODIPY derivatives were prepared and their photophysical properties in THF/water mixtures with varying fractions of water were investigated. BDP-1 could self-assemble into different vesicle architectures in aqueous solution, while BDP-2 and BDP-3 with more hydrophilic abilities formed spherical and worm-like micelles. The BODIPY derivatives could be absorbed by HeLa cells and showed no apparent toxicity during the course of the test. In particular, unlike traditional amines or morpholinyl functionalized lysosome fluorescent probes, BDP-1 nanovesicles without targeted groups exhibit red emission and show effective lysosome biological imaging...
September 26, 2016: Soft Matter
Tugba Ozdemir, Jose Luis Bila, Fazli Sozmen, Leyla T Yildirim, Engin U Akkaya
Orthogonally linked BODIPY units show exceptional intersystem crossing efficiencies. We now report orthogonal BODIPY trimers with strong absorption in the visible region and high singlet oxygen generation capability. The X-ray diffraction structure confirms that the two peripheral BODIPY units are at a perpendicular angle to the core structure.
October 7, 2016: Organic Letters
Xin-Dong Jiang, Shuang Li, Boris Le Guennic, Denis Jacquemin, Daniel Escudero, Linjiu Xiao
Isometrically dibromated thienyl-containing aza-BODIPYs CDB-1 and BDB-2 with potential use as photosensitizers (PSs) were successfully prepared and their photophysical properties were fully characterized. Singlet oxygen generation experiments were also performed. In this regard, PS CDB-1 was found to be more effective and had about two-fold rate enhancement compared to PS BDB-2. DFT and TD-DFT calculations helped to provide insights into the distinct intersystem crossing (ISC) processes observed for CDB-1 and BDB-2...
September 21, 2016: Physical Chemistry Chemical Physics: PCCP
E Palao, T Slanina, P Klán
Seven new 2-chalcogen- or 2,6-dichalcogen- (S, Se, Te) BODIPY derivatives were synthesized in good to excellent yields (55-95%) by a Pd-catalyzed C-heteroatom Stille cross-coupling reaction, overcoming the limitations of SNAr. The fluorophores show interesting tunable optical properties associated with the formation of a twisted intramolecular charge transfer excited state and competing intersystem crossing.
September 29, 2016: Chemical Communications: Chem Comm
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