Journal articles: 'BODIPY based zwitterionic molecules'

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Sutradhar, Tanushree, and Anirban Misra. "The role of π-linkers and electron acceptors in tuning the nonlinear optical properties of BODIPY-based zwitterionic molecules." RSC Advances 10, no. 66 (2020): 40300–40309. http://dx.doi.org/10.1039/d0ra02193h.

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Das, Sarasija, Sudipto Dey, Sanujit Patra, Arindam Bera, Totan Ghosh, Bibin Prasad, Kapil Dev Sayala, Krishnendu Maji, Anjan Bedi, and Sashi Debnath. "BODIPY-Based Molecules for Biomedical Applications." Biomolecules 13, no. 12 (November 30, 2023): 1723. http://dx.doi.org/10.3390/biom13121723.

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BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) derivatives have attracted attention as probes in applications like imaging and sensing due to their unique properties like (1) strong absorption and emission in the visible and near-infrared regions of the electromagnetic spectrum, (2) strong fluorescence and (3) supreme photostability. They have also been employed in areas like photodynamic therapy. Over the last decade, BODIPY-based molecules have even emerged as candidates for cancer treatments. Cancer remains a significant health issue world-wide, necessitating a continuing search for novel therapeutic options. BODIPY is a flexible fluorophore with distinct photophysical characteristics and is a fascinating drug development platform. This review provides a comprehensive overview of the most recent breakthroughs in BODIPY-based small molecules for cancer or disease detection and therapy, including their functional potential.

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Gayathri, Thumuganti, Ravulakollu Srinivasa Rao, Vinay Gupta, and Surya Prakash Singh. "Panchromatic aza-Bodipy based π-conjugates." New Journal of Chemistry 45, no. 17 (2021): 7792–98. http://dx.doi.org/10.1039/d1nj00847a.

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Squeo, Benedetta Maria, Lucia Ganzer, Tersilla Virgili, and Mariacecilia Pasini. "BODIPY-Based Molecules, a Platform for Photonic and Solar Cells." Molecules 26, no. 1 (December 31, 2020): 153. http://dx.doi.org/10.3390/molecules26010153.

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The 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY)-based molecules have emerged as interesting material for optoelectronic applications. The facile structural modification of BODIPY core provides an opportunity to fine-tune its photophysical and optoelectronic properties thanks to the presence of eight reactive sites which allows for the developing of a large number of functionalized derivatives for various applications. This review will focus on BODIPY application as solid-state active material in solar cells and in photonic devices. It has been divided into two sections dedicated to the two different applications. This review provides a concise and precise description of the experimental results, their interpretation as well as the conclusions that can be drawn. The main current research outcomes are summarized to guide the readers towards the full exploitation of the use of this material in optoelectronic applications.

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Gupta, Monika, Soumyaditya Mula, Mrityunjay Tyagi, Tapan K. Ghanty, Sushant Murudkar, Alok K. Ray, and Subrata Chattopadhyay. "Rational Design of Boradiazaindacene (BODIPY)-Based Functional Molecules." Chemistry - A European Journal 19, no. 52 (November 28, 2013): 17766–72. http://dx.doi.org/10.1002/chem.201302359.

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Ma, Guanglong, Weifeng Lin, Zhen Wang, Juan Zhang, Haofeng Qian, Liangbo Xu, Zhefan Yuan, and Shengfu Chen. "Development of polypeptide-based zwitterionic amphiphilic micelles for nanodrug delivery." Journal of Materials Chemistry B 4, no. 31 (2016): 5256–64. http://dx.doi.org/10.1039/c6tb01144f.

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Rybczynski, Patryk, and Anna Kaczmarek-Kȩdziera. "BODIPY dimers: structure, interaction, and absorption spectrum." Structural Chemistry 32, no. 3 (March 26, 2021): 953–65. http://dx.doi.org/10.1007/s11224-021-01759-1.

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AbstractThe object of the present study are BODIPY molecules obtained previously by Piskorz et al. (Dyes Pigm. 178:108322, 2020) for their antimicrobial activity. Structural analysis of the BODIPY dimers is presented in context of the aggregation influence on the photophysical properties. The thorough investigation of the nature of intermolecular interaction in the representative BODIPY dimers is provided together with the decomposition of the interaction energy into the components of well-defined origin according to SAPT procedure. For the model BODIPY systems the careful examination of the interaction nature for the dimer structure based on experimental crystal study as well as fully optimized is given. The tendencies observed in the model dimers are further on investigated for two pairs of BODIPY systems designed for biomedical application. The analyzed molecules are shown to maximize the mutual interaction by the optimization of the stacking dispersion contacts between the aromatic rings of the molecules, therefore producing stable dimers. The estimation of SAPT0 interaction energy components confirms the dominating dispersion character arising from mutual BODIPY core contacts. The influence of the dimerization process on the photophysical properties of the systems studied theoretically depends to the high extend on the dimerization mode and is significant for parallel and antiparallel dispersion-governed dimers.

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Sabari, P., Rima Sengupta, B. Umasekhar, and Mangalampalli Ravikanth. "Meso-pyrrolyl BODIPY based colorimetric optical sensor for Cu2+ ions." Journal of Porphyrins and Phthalocyanines 24, no. 09 (August 28, 2020): 1121–28. http://dx.doi.org/10.1142/s1088424620500261.

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A simple meso-pyrrolyl BODIPY-Schiff base conjugate was synthesized by reacting ([Formula: see text]-formylpyrrolyl) BODIPY with 2-aminophenol in ethanol at reflux followed by recrystallization from CH2Cl2/petroleum ether, affording the conjugate in 72% yield. The conjugate was thoroughly characterized by HR-MS, 1D and 2D NMR and X-ray crystallographic techniques. The X-ray structure of the meso-pyrrolyl BODIPY-Schiff base conjugate revealed that the meso-pyrrole and the phenyl substituents were deviated by an angle of [Formula: see text] and [Formula: see text], respectively, from the plane of the BF2-dipyrrin core. The absorption spectrum of the conjugate was similar to the ([Formula: see text]-formylpyrrolyl) BODIPY with a strong absorption band at 508 nm, whereas the fluorescence of the ([Formula: see text]-formylpyrrolyl) BODIPY was completely quenched in the BODIPY-Schiff base conjugate. Furthermore, cation sensing studies revealed that the conjugate has a specific sensing ability for the Cu(II) ion even in the presence of the other metal ions, as verified by the visual, absorption and mass spectral studies. The DFT optimized structure revealed that the Cu(II) ion was bound to pyrrolic nitrogen, imine nitrogen, phenolic oxygen and two water molecules in a distorted square pyramidal fashion. TD-DFT studies accounted well for the absorption spectra of the BODIPY-Schiff base conjugate and its Cu[Formula: see text] bound complex.

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Demirel Topel, Seda, and Mustafa İlker Beyaz. "Fluorescence quenching-based bodipy-boronic acid linked viologen dual system for potential glucose sensing applications." Sensor Review 42, no. 1 (October 28, 2021): 62–69. http://dx.doi.org/10.1108/sr-03-2021-0088.

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Purpose The purpose of this study is to develop a non-enzymatic based glucose-sensing platform composed of Bodipy-BBV dual system which can be monitored by a photodetector under the blue LED excitation. Design/methodology/approach The sensor has been developed from a dual system including a fluorescent dye, an aldehyde derivative of boron dipyrromethene (Bodipy) and a quencher, orto-boronic acid linked viologen (o-BBV) where their combination resulted in a ratiometric fluorescence quenching in ethanol: PBS (1:1, pH:7.4) solution under UV light excitation. By glucose addition, o-BBV has been released from the Bodipy and binded to cis-diol groups of glucose, thereby fluorescence emission of Bodipy has been regained. Furthermore, a setup consisting of a light emitting diode (LED) and a photodiode (PD) was used to prove electrical detection of glucose without the need for expensive and bulky optical equipment, enabling the development of a miniaturized and low-cost glucose-sensing platform. Findings The fluorescence intensity of the Bodipy derivative in the solution (2 × 10−6 M) was diminished by 93% in the presence of o-BBV solution (5 × 10−3 M). Upon the glucose addition, 81% of the Bodipy fluorescence intensity has been recovered after introduction of 30 mM of glucose, where the ratio of o-BBV/Bodipy was 35:1. A linear response between 10 and 30 mM glucose concentration was obtained, which covers the biologically significant range. A high correlation between the photodiode current and Bodipy fluorescence intensity was achieved. Originality/value Even though Bodipy molecules are known with their superior optical properties and applied to the fluorescence-based detection of glucose, to the best of the authors’ knowledge, no work has been reported on Bodipy-BBV dual system to detect glucose molecules as a non-enzymatic based method. This design enables the dye and the quencher to independently coexist in the solution, allowing for tuning of their individual concentrations to optimize the glucose sensitivity. Furthermore, an electrical light detection scheme consisting of a LED and a photodiode has been implemented to eliminate the bulky optical equipment from the measurement setup and further this work for the development of a compact and inexpensive sensor. The results presented here demonstrate the feasibility of this system for the development of a novel glucose sensor.

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Nisanci, Bilal, Sinem Sahinoglu, Esra Tuner, Mustafa Arik, İbrahim Kani, Arif Dastan, and Özgür Altan Bozdemir. "Synthesis of an F-BODIPY [2]catenane using the chemistry of bis(dipyrrinato)metal complexes." Chemical Communications 53, no. 92 (2017): 12418–21. http://dx.doi.org/10.1039/c7cc07021g.

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Jang, Yoon Jeong, Olga G. Tsay, Dhiraj P. Murale, Jeong A. Jeong, Aviv Segev, and David G. Churchill. "Novel and selective detection of Tabun mimics." Chem. Commun. 50, no. 56 (2014): 7531–34. http://dx.doi.org/10.1039/c4cc02689f.

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12

Díaz-Norambuena, Carolina, Edurne Avellanal-Zaballa, Alejandro Prieto-Castañeda, Jorge Bañuelos, Santiago de la Moya, Antonia R. Agarrabeitia, and María J. Ortiz. "Formylation as a Chemical Tool to Modulate the Performance of Photosensitizers Based on Boron Dipyrromethene Dimers." International Journal of Molecular Sciences 24, no. 14 (July 23, 2023): 11837. http://dx.doi.org/10.3390/ijms241411837.

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Heavy-atom-free photosensitizers are envisioned as the next generation of photoactive molecules for photo-theragnosis. In this approach, and after suitable irradiation, a single molecular scaffold is able to visualize and kill tumour cells by fluorescence signalling and photodynamic therapy (PDT), respectively, with minimal side effects. In this regard, BODIPY-based orthogonal dimers have irrupted as suitable candidates for this aim. Herein, we analyse the photophysical properties of a set of formyl-functionalized BODIPY dimers to ascertain their suitability as fluorescent photosensitizers. The conducted computationally aided spectroscopic study determined that the fluorescence/singlet oxygen generation dual performance of these valuable BODIPY dimers not only depends on the BODIPY-BODIPY linkage and the steric hindrance around it, but also can be modulated by proper formyl functionalization at specific chromophoric positions. Thus, we propose regioselective formylation as an effective tool to modulate such a delicate photonic balance in BODIPY-based dimeric photosensitizers. The taming of the excited-state dynamics, in particular intramolecular charge transfer as the key underlying process mediating fluorescence deactivation vs. intersystem crossing increasing, could serve to increase fluorescence for brighter bioimaging, enhance the generation of singlet oxygen for killing activity, or balance both for photo-theragnosis.

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Koczorowski, Tomasz, Arleta Glowacka-Sobotta, Stepan Sysak, Dariusz T. Mlynarczyk, Roman Lesyk, Tomasz Goslinski, and Lukasz Sobotta. "BODIPY-Based Nanomaterials—Sensing and Biomedical Applications." Applied Sciences 12, no. 15 (August 3, 2022): 7815. http://dx.doi.org/10.3390/app12157815.

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Cancerous diseases are rightfully considered among the most lethal, which have a consistently negative effect when considering official statistics in regular health reports around the globe. Nowadays, metallic nanoparticles can be potentially applied in medicine as active pharmaceuticals, adjustable carriers, or distinctive enhancers of physicochemical properties if combined with other drugs. Boron dipyrromethene (BODIPY) molecules have been considered for future applications in theranostics in the oncology field, thus expanding the potential of conceivable applicability. Hence, taking into account positive practical features of both metal-based nanostructures and BODIPY derivatives, the present study aims to gather recent results connected to BODIPY-conjugated metallic nanoparticles. This is with respect to their expediency in the diagnosis and treatment of tumor ailments as well as in sensing of heavy metals. To fulfill the designated objectives, multiple research documents were analyzed concerning the latest discoveries within the scope of BODIPY-based nanomaterials with particular emphasis on their utilization for diagnostical sensing as well as cancer diagnostics and therapy. In addition, collected examples of mentioned conjugates were presented in order to draw the attention of the scientific community to their practical applications, elucidate the topic in a consistent manner, and inspire fellow researchers for new findings.

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Wang, Xinyue, Sophie Bou, Andrey S. Klymchenko, Nicolas Anton, and Mayeul Collot. "Ultrabright Green-Emitting Nanoemulsions Based on Natural Lipids-BODIPY Conjugates." Nanomaterials 11, no. 3 (March 23, 2021): 826. http://dx.doi.org/10.3390/nano11030826.

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Nanoemulsions (NEs) are water-dispersed oil droplets that constitute stealth biocompatible nanomaterials. NEs can reach an impressive degree of fluorescent brightness owing to their oily core that can encapsulate a large number of fluorophores on the condition the latter are sufficiently hydrophobic and oil-soluble. BODIPYs are among the brightest green emitting fluorophores and as neutral molecules possess high lipophilicity. Herein, we synthesized three different natural lipid-BODIPY conjugates by esterification of an acidic BODIPY by natural lipids, namely: α-tocopherol (vitamin E), cholesterol, and stearyl alcohol. The new BODIPY conjugates were characterized in solvents and oils before being encapsulated in NEs at various concentrations. The physical (size, stability over time, leakage) and photophysical properties (absorption and emission wavelength, brightness, photostability) are reported and showed that the nature of the lipid anchor and the nature of the oil used for emulsification greatly influence the properties of the bright NEs.

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Zhou, Jinfeng, Lizhi Gai, Zhikuan Zhou, John Mack, Kejing Xu, Jianzhang Zhao, Hailin Qiu, Kin Shing Chan, and Zhen Shen. "Highly efficient near IR photosensitizers based-on Ir–C bonded porphyrin-aza-BODIPY conjugates." RSC Advances 6, no. 76 (2016): 72115–20. http://dx.doi.org/10.1039/c6ra10131c.

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Novel orthogonally arranged Ir(iii) porphyrin-aza-BODIPY conjugates exhibit strong absorbance in the near infrared region and have unusually high singlet oxygen quantum yields, since they act as unique molecules rather than as dyads.

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Kalyagin, Alexander, Lubov Antina, Alexander Ksenofontov, Elena Antina, and Mikhail Berezin. "Solvent-Dependent Fluorescence Properties of CH2-bis(BODIPY)s." International Journal of Molecular Sciences 23, no. 22 (November 19, 2022): 14402. http://dx.doi.org/10.3390/ijms232214402.

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Biocompatible luminophores based on organic dyes, which have fluorescence characteristics that are highly sensitive to the properties of the solvating medium, are of particular interest as highly sensitive, selective, and easy-to-use analytical agents. We found that BODIPY dimers (2,2′-, 2,3′-3,3′-CH2-bis(BODIPY) (1–3)) demonstrate fluorescence characteristics with a high sensitivity to the presence of polar solvents. The intense fluorescence of 1–3 in nonpolar/low-polarity solvents is dramatically quenched in polar media (acetone, DMF, and DMSO). It has been established that the main reason for CH2-bis(BODIPY) fluorescence quenching is the specific solvation of dyes by electron-donating molecules (Solv) with the formation of stable supramolecular CH2-bis(BODIPY)·2Solv structures. Using steady-state absorption and fluorescence spectroscopy, time-resolved fluorescence spectroscopy, and computational modeling, the formation mechanism, composition, and structure of CH2-bis(BODIPY)·2Solv supramolecular complexes have been substantiated, and their stability has been evaluated. The results show the promise of developing fluorescent probes based on CH2-bis(BODIPY)s for detecting toxic N/O-containing compounds in solutions.

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Bujaroska, Biljana, Kiro Stojanoski, and Ljupco Pejov. "On the differential hydration of various forms of glycine in diluted aqueous solutions: a Monte Carlo study." Macedonian Journal of Chemistry and Chemical Engineering 31, no. 2 (December 20, 2012): 295. http://dx.doi.org/10.20450/mjcce.2012.11.

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Rigid-body Monte Carlo simulations were carried out to study the differential hydration of zwitterionic and neutral forms of glycine in water. To account for the solute polarization by the rather polar liquid environment, initial geometries were chosen as minima on the MP2/aug-cc-pVTZ potential energy surfaces of neutral and zwitterionic glycine continuously solvated by water, implementing the polarizable continuum model (PCM) within the integral equation formalism (IEFPCM). The dynamically changing hydrogen bonding network between the solute and solvent molecules was analyzed imposing distance, energy and angular distribution-based criteria. It was found that, on average, the zwitterionic form of glycine acts as an acceptor of 4.53 hydrogen bonds, while it plays the role of a proton donor in (on average) 2.73 hydrogen bonds with the solvent water molecules. In particular, we have found out that 2.73 solvent water molecules are involved in hydrogen bonding interaction with the ammonium group, acting as proton-acceptors. This is in excellent agreement with the recent experimental neutron diffraction studies, which have indicated that 3.0 water molecules reside in the vicinity of the NH3+ group of aqueous zwitterionic glycine. Neutral form of aqueous glycine, on the other hand, on average donates protons in 1.63 hydrogen bonds with the solvent water molecules, while at the same time it accepts 2.53 hydrogen bonds from the solvent molecules. The greater charge polarization in the zwitterionic form thus makes it much more exposed to hydrogen bonding interaction in polar medium such as water, which is certainly the main reason of the larger stability of this form of glycine in condensed media.

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Andreozzi, Patrizia, Lorenza Tamberi, Elisamaria Tasca, Gina Elena Giacomazzo, Marta Martinez, Mirko Severi, Marco Marradi, et al. "The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY." Beilstein Journal of Organic Chemistry 16 (September 11, 2020): 2272–81. http://dx.doi.org/10.3762/bjoc.16.188.

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Mechanochemistry is an emerging and reliable alternative to conventional solution (batch) synthesis of complex molecules under green and solvent-free conditions. In this regard, we report here on the conjugation of a dextran polysaccharide with a fluorescent probe, a phenylboronic acid (PBA)-functionalized boron dipyrromethene (BODIPY) applying the ball milling approach. The ball milling formation of boron esters between PBA BODIPY and dextran proved to be more efficient in terms of reaction time, amount of reactants, and labelling degree compared to the corresponding solution-based synthetic route. PBA-BODIPY dextran assembles into nanoparticles of around 200 nm by hydrophobic interactions. The resulting PBA-BODIPY dextran nanoparticles retain an apolar interior as proved by pyrene fluorescence, suitable for the encapsulation of hydrophobic drugs with high biocompatibility while remaining fluorescent.

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ZHAI, Y., and Y. L. ZHAO. "A SELF-CONSISTENT-CHARGE DENSITY-FUNCTIONAL TIGHT-BINDING THEORY BASED MOLECULAR DYNAMICS SIMULATION OF A ZWITTERIONIC GLYCINE IN AN EXPLICIT WATER ENVIRONMENT." Journal of Theoretical and Computational Chemistry 12, no. 04 (June 2013): 1350019. http://dx.doi.org/10.1142/s0219633613500193.

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A zwitterionic glycine (zGLY) is adopted as an example to study the impact of water environment (310 H2O molecules) on the molecular structure and energetics using a self-consistent-charge density-functional tight-binding theory based molecular dynamics (SCC-DFTB/MD) method. It is found that maximal eight hydrogen bonds could be formed simultaneously between eight water molecules and the zGLY. The ability of the COO- terminal to adsorb water molecules is stronger than the [Formula: see text] terminal with respect to hydrogen bonding with more water molecules and exhibits lower adiabatic adsorption energies. The zGLY's intramolecular hydrogen bond appeared unpredictably, without involving any proton transfer and generally helpful for enhancing the system stability. Water molecules play an important role to stabilize the zwitterionic amino acids and restrain the proton migration from the [Formula: see text] to the COO− group. Our results show that the SCC-DFTB/MD method could successfully describe geometry dynamical evolutions and energetics of biomolecules in a nanoscale simulation with the presence of a large number of water molecules. Our study not only verified the feasibility of a QM level methodology for describing the aqueous states of biochemical molecules, but also gave a clear evidence for the impact of water environment on amino acids.

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Peng, Xiao Jun. "Fluorescence Chemosensors Based on Intramolecular Charge Transfer and Intramolecular Energy Transfer." Advanced Materials Research 441 (January 2012): 783. http://dx.doi.org/10.4028/www.scientific.net/amr.441.783.

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Ratiometric fluorescent sensors which based on ICT mechanism permit signal rationing to detect target molecules by measuring the ratio of fluorescence intensities at two different wavelengths, which are autoemitted by sensors upon binding objects. The autoreferential function of relative changes of two fluorescence intensities may avoid the influences of many nontarget factors in the changes of monofluorescence intensity. Therefore, the design of ratiometric fluorescent sensors is of great current interest. Generally, Cd2+ and Zn2+ havevery similar chemical properties, so the discrimination of them is very difficult.In sensor 1, we chose boradiazaindacene (BODIPY) as the fluorophore because it absorbs and emits in the visible region with high quantum yield, large extinction coefficient and good photo-stability,and N, N-bis(pyridin-2-ylmethyl)benzenamine as Cd2+ receptor. A vinyl group between the receptor and BODIPY fluorophore can induce red-shifts in absorption and fluorescence spectra. When Cd2+ is added into the aqueous solution of 1, owing to the reduction of the electron-donating character of the receptor, the photophysical properties of BODIPY will consequently be changed. In fact, 1 can distinguish Cd2+ from Zn2+ and especially can be used in both general fluorescence microscopy and ratiometric fluorescence microscopy.

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Guseva, Galina B., Elena V. Antina, Mikhail B. Berezin, Liliya E. Nikitina, Ilmir R. Gilfanov, Roman S. Pavelyev, Svetlana A. Lisovskaya, et al. "Novel BODIPY Conjugates with Myrtenol: Design, Spectral Characteristics, and Possibilities for Practical Application." Inorganics 11, no. 6 (June 3, 2023): 241. http://dx.doi.org/10.3390/inorganics11060241.

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The synthesis of new fluorescent probes, based on biocompatible luminophors and exhibiting various specificities, is intensively developed worldwide. Many luminophors contain a hydrophobic group that limits their application for cell staining under vital conditions. Herein, we report the synthesis of two BODIPY molecules—BF2-meso-(4-butan/pentanamido-N-(((1S,5R)-6,6-dimethylbicyclo [3.1.1]hept-2-en-2-yl)methyl)-N,N-dimethylpropan-1-aminium)-3,3′,5,5′-tetramethyl-2,2′-dipyrromethene bromides—designed as 10, 11 with a spacer of either four or three CH2 groups in length, respectively. These molecules present conjugates of BODIPY luminophors with (+)-myrtenol via a quaternary ammonium group. Both terpene-BODIPY conjugates demonstrated high fluorescence efficiency in various solvents such as OctOH, DMSO and water, and were characterized by their stability at pH 1.65–9.18. The fusion of the myrtenol, a monocyclic terpene, to the BODIPY fluorophore in the meso-substituent facilitated their penetration into the filamentous fungi Fusarium solani, while impairing the binding of the latter with S. aureus, K. pneumoniae and P. aeruginosa. The additional quaternary ammonium group between the myrtenol and fluorophore moieties restored the bacterial cell-staining while it did not affect the staining of fungi. Finally, the BODIPY conjugate 11 was able to stain both Gram-positive and Gram-negative bacteria by its interaction with their cell wall (or the membrane), as well as penetrating into filamentous fungi F. solani and staining their mitochondria.

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Rostamnia, Sadegh. "In situ generation and protonation of the isocyanide/acetylene adduct: a powerful catalyst-free strategy for multicomponent synthesis of ketenimines, aza-dienes, and heterocycles." RSC Advances 5, no. 117 (2015): 97044–65. http://dx.doi.org/10.1039/c5ra20455k.

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In addition to isocyanide-based Ugi, Passerini, van Leusen, and Orru multicomponent reactions, a new class of isocyanide/acetylene-based multicomponent reactions, using zwitterionic adducts, have emerged as powerful methods to synthesize biologically interesting molecules.

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Nguyen, Manh Tien, and Qing Shao. "Effects of zwitterionic molecules on ionic association in ethylene oxide-based electrolytes." Fluid Phase Equilibria 515 (July 2020): 112572. http://dx.doi.org/10.1016/j.fluid.2020.112572.

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Belov, Feodor, Alexander Villinger, and Jan von Langermann. "(R)-Baclofen [(R)-4-amino-3-(4-chlorophenyl)butanoic acid]." Acta Crystallographica Section E Crystallographic Communications 78, no. 1 (January 1, 2022): 33–35. http://dx.doi.org/10.1107/s2056989021012809.

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This article provides the first single-crystal XRD-based structure of enantiopure (R)-baclofen (form C), C10H12ClNO2, without any co-crystallized substances. In the enantiopure title compound, the molecules arrange themselves in an orthorhombic crystal structure (space group P212121). In the crystal, strong hydrogen bonds and C—H...Cl bonds interconnect the zwitterionic molecules.

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Climent, Estela, Mandy Hecht, and Knut Rurack. "Loading and Release of Charged and Neutral Fluorescent Dyes into and from Mesoporous Materials: A Key Role for Sensing Applications." Micromachines 12, no. 3 (February 28, 2021): 249. http://dx.doi.org/10.3390/mi12030249.

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The aim of this study is to determine the efficiency of loading and release of several zwitterionic, neutral, anionic and cationic dyes into/from mesoporous nanoparticles to find the optimum loading and release conditions for their application in detection protocols. The loading is carried out for MCM-41 type silica supports suspended in phosphate-buffered saline (PBS) buffer (pH 7.4) or in acetonitrile, involving the dyes (rhodamine B chloride, rhodamine 101 chloride, rhodamine 101 perchlorate, rhodamine 101 inner salt, meso-(4-hydroxyphenyl)-boron–dipyrromethene (BODIPY), sulforhodamine B sodium salt and fluorescein 27). As a general trend, rhodamine-based dyes are loaded with higher efficiency, when compared with BODIPY and fluorescein dyes. Between the rhodamine-based dyes, their charge and the solvent in which the loading process is carried out play important roles for the amount of cargo that can be loaded into the materials. The delivery experiments carried out in PBS buffer at pH 7.4 reveal for all the materials that anionic dyes are more efficiently released compared to their neutral or cationic counterparts. The overall best performance is achieved with the negatively charged sulforhodamine B dye in acetonitrile. This material also shows a high delivery degree in PBS buffer.

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Raskolupova, Valeria I., Tatyana V. Popova, Olga D. Zakharova, Anastasia E. Nikotina, Tatyana V. Abramova, and Vladimir N. Silnikov. "Human Serum Albumin Labelling with a New BODIPY Dye Having a Large Stokes Shift." Molecules 26, no. 9 (May 3, 2021): 2679. http://dx.doi.org/10.3390/molecules26092679.

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BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. These are widely used as chemosensors, laser materials, and molecular probes. At the same time, BODIPY dyes have small or moderate Stokes shifts like most other fluorophores. Large Stokes shifts are preferred for fluorophores because of higher sensitivity of such probes and sensors. The new boron containing BODIPY dye was designed and synthesized. We succeeded to perform an annulation of pyrrole ring with coumarin heterocyclic system and achieved a remarkable difference in absorption and emission maximum of obtained fluorophore up to 100 nm. This BODIPY dye was equipped with linker arm and was functionalized with a maleimide residue specifically reactive towards thiol groups of proteins. BODIPY residue equipped with a suitable targeting protein core can be used as a suitable imaging probe and agent for Boron Neutron Capture Therapy (BNCT). As the most abundant protein with a variety of physiological functions, human serum albumin (HSA) has been used extensively for the delivery and improvement of therapeutic molecules. Thiolactone chemistry provides a powerful tool to prepare albumin-based multimodal constructions. The released sulfhydryl groups of the homocysteine functional handle in thiolactone modified HSA were labeled with BODIPY dye to prepare a labeled albumin-BODIPY dye conjugate confirmed by MALDI-TOF-MS, UV-vis, and fluorescent emission spectra. Cytotoxicity of the resulting conjugate was investigated. This study is the basis for a novel BODIPY dye-albumin theranostic for BNCT. The results provide further impetus to develop derivatives of HSA for delivery of boron to cancer cells.

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Dzyuba, Sergei V. "BODIPY Dyes as Probes and Sensors to Study Amyloid-β-Related Processes." Biosensors 10, no. 12 (November 27, 2020): 192. http://dx.doi.org/10.3390/bios10120192.

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Amyloid formation plays a major role in a number of neurodegenerative diseases, including Alzheimer’s disease. Amyloid-β peptides (Aβ) are one of the primary markers associated with this pathology. Aβ aggregates exhibit a diverse range of morphologies with distinct pathological activities. Recognition of the Aβ aggregates by using small molecule-based probes and sensors should not only enhance understanding of the underlying mechanisms of amyloid formation, but also facilitate the development of therapeutic strategies to interfere with amyloid neurotoxicity. BODIPY (boron dipyrrin) dyes are among the most versatile small molecule fluorophores. BODIPY scaffolds could be functionalized to tune their photophysical properties to the desired ranges as well as to adapt these dyes to various types of conditions and environments. Thus, BODIPY dyes could be viewed as unique platforms for the design of probes and sensors that are capable of detecting and tracking structural changes of various Aβ aggregates. This review summarizes currently available examples of BODIPY dyes that have been used to investigate conformational changes of Aβ peptides, self-assembly processes of Aβ, as well as Aβ interactions with various molecules.

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Cortizo-Lacalle, Diego, Calvyn T. Howells, Upendra K. Pandey, Joseph Cameron, Neil J. Findlay, Anto Regis Inigo, Tell Tuttle, Peter J. Skabara, and Ifor D. W. Samuel. "Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells." Beilstein Journal of Organic Chemistry 10 (November 18, 2014): 2683–95. http://dx.doi.org/10.3762/bjoc.10.283.

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Two novel triads based on a diketopyrrolopyrrole (DPP) central core and two 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) units attached by thiophene rings have been synthesised having high molar extinction coefficients. These triads were characterised and used as donor materials in small molecule, solution processable organic solar cells. Both triads were blended with PC71BM as an acceptor in different ratios by wt % and their photovoltaic properties were studied. For both the triads a modest photovoltaic performance was observed, having an efficiency of 0.65%. Moreover, in order to understand the ground and excited state properties and vertical absorption profile of DPP and BODIPY units within the triads, theoretical DFT and TDDFT calculations were performed.

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Ozdemir, Mehmet, Donghee Choi, Guhyun Kwon, Yunus Zorlu, Bunyemin Cosut, Hyekyoung Kim, Antonio Facchetti, Choongik Kim, and Hakan Usta. "Solution-Processable BODIPY-Based Small Molecules for Semiconducting Microfibers in Organic Thin-Film Transistors." ACS Applied Materials & Interfaces 8, no. 22 (May 23, 2016): 14077–87. http://dx.doi.org/10.1021/acsami.6b02788.

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Wang, Jiale, Zhao Jiang, Cheng Huang, Shimao Zhao, Senqiang Zhu, Rui Liu, and Hongjun Zhu. "Self-Assembled BODIPY Nanoparticles for Near-Infrared Fluorescence Bioimaging." Molecules 28, no. 7 (March 28, 2023): 2997. http://dx.doi.org/10.3390/molecules28072997.

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In vivo optical imaging is an important application value in disease diagnosis. However, near-infrared nanoprobes with excellent luminescent properties are still scarce. Herein, two boron–dipyrromethene (BODIPY) molecules (BDP-A and BDP-B) were designed and synthesized. The BODIPY emission was tuned to the near-infrared (NIR) region by regulating the electron-donating ability of the substituents on its core structure. In addition, the introduction of polyethylene glycol (PEG) chains on BODIPY enabled the formation of self-assembled nanoparticles (NPs) to form optical nanoprobes. The self-assembled BODIPY NPs present several advantages, including NIR emission, large Stokes shifts, and high fluorescence quantum efficiency, which can increase water dispersibility and signal-to-noise ratio to decrease the interference by the biological background fluorescence. The in vitro studies revealed that these NPs can enter tumor cells and illuminate the cytoplasm through fluorescence imaging. Then, BDP-B NPs were selected for use in vivo imaging due to their unique NIR emission. BDP-B was enriched in the tumor and effectively illuminated it via an enhanced penetrability and retention effect (EPR) after being injected into the tail vein of mice. The organic nanoparticles were metabolized through the liver and kidney. Thus, the BODIPY-based nanomicelles with NIR fluorescence emission provide an effective research basis for the development of optical nanoprobes in vivo.

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Raskolupova, Valeria I., Tatyana V. Popova, Olga D. Zakharova, Tatyana V. Abramova, and Vladimir N. Silnikov. "New BODIPY Dye with a Large Stokes Shift for Biopolymer Labelling." Chemistry Proceedings 3, no. 1 (November 14, 2020): 72. http://dx.doi.org/10.3390/ecsoc-24-08304.

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As the most abundant protein with a variety of physiological functions, human serum albumin (HSA) has been used extensively for the delivery and improvement of therapeutic molecules. Thiolactone chemistry provides a powerful tool to prepare albumin-based multimodal imaging probes and agents for boron neutron capture therapy (BNCT). For this purpose, boron containing 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dye was designed and synthesized. BODIPY dyes are photostable neutral derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene. These are widely used as chemosensors, laser materials and molecular probes. At the same time, BODIPY dyes, like most other fluorophores, have small or moderate Stokes shifts. Large Stokes shifts are preferred for fluorophores because of higher sensitivity of such probes and sensors. We succeeded in performing an annulation of pyrrole ring with coumarin heterocyclic system and achieved a remarkable difference in absorption and emission maximum of obtained fluorophore up to 100 nm. Moreover, this BODIPY dye was equipped with a linker arm and was functionalized with a maleimide residue specifically reactive towards thiol groups of proteins. The released sulfhydryl groups of the homocysteine functional handle in thiolactone modified HSA was labeled with BODIPY dye to prepare a labeled albumin-BODIPY dye conjugate confirmed by MALDI-TOF-MS, UV-vis and fluorescent emission spectra. The cytotoxicity of HSA conjugate was evaluated by MTT assay in cell lines MCF-7 and T98G. This is the basis for a novel BODIPY dye -albumin theranostic for BNCT. These results provide further impetus to develop derivatives of HSA for delivery of boron to cancer cells.

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Yarullin, Daniil N., Maksim N. Zavalishin, George A. Gamov, Michail M. Lukanov, Alexander A. Ksenofontov, Natalia A. Bumagina, and Elena V. Antina. "Prediction of Sensor Ability Based on Chemical Formula: Possible Approaches and Pitfalls." Inorganics 11, no. 4 (April 6, 2023): 158. http://dx.doi.org/10.3390/inorganics11040158.

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This review presents an analysis of different algorithms for predicting the sensory ability of organic compounds towards metal ions based on their chemical formula. A database of chemosensors containing information on various classes of suitable compounds, including dipyrromethenes, BODIPY, Schiff bases, hydrazones, fluorescein, rhodamine, phenanthroline, coumarin, naphthalimide derivatives, and others (a total of 965 molecules) has been compiled. Additionally, a freely available software has been developed for predicting the sensing ability of chemical compounds, which can be accessed through a Telegram bot. This tool aims to assist researchers in their search for new chemosensors.

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Goncharenko, Aleksandr A., Ilya A. Tarasyuk, Yuriy S. Marfin, Kirill V. Grzhegorzhevskii, Albert R. Muslimov, Andrey B. Bondarenko, Maxim D. Lebedev, et al. "DDAO Controlled Synthesis of Organo-Modified Silica Nanoparticles with Encapsulated Fluorescent Boron Dipyrrins and Study of Their Uptake by Cancerous Cells." Molecules 25, no. 17 (August 21, 2020): 3802. http://dx.doi.org/10.3390/molecules25173802.

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The design of cargo carriers with high biocompatibility, unique morphological characteristics, and capability of strong bonding of fluorescent dye is highly important for the development of a platform for smart imaging and diagnostics. In this paper, BODIPY-doped silica nanoparticles were prepared through a “one-pot” soft-template method using a sol-gel process. Several sol-gel precursors have been used in sol-gel synthesis in the presence of soft-template to obtain the silica-based materials with the most appropriate morphological features for the immobilization of BODIPY molecules. Obtained silica particles have been shown to be non-cytotoxic and can be effectively internalized into the cervical cancer cell line (HeLa). The described method of synthesis allows us to obtain silica-based carriers with an immobilized fluorescent dye that provide the possibility for real-time imaging and detection of these carriers.

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Tarafdar, Gourav, Justin C. Johnson, Bryon W. Larson, and Praveen C. Ramamurthy. "BODIPY based A-D-A molecules: Effect of CF3 group substitution at meso phenyl group." Dyes and Pigments 177 (June 2020): 108289. http://dx.doi.org/10.1016/j.dyepig.2020.108289.

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Schlachter, Adrien, Alexandre Fleury, Kevin Tanner, Armand Soldera, Benoit Habermeyer, Roger Guilard, and Pierre D. Harvey. "The TDDFT Excitation Energies of the BODIPYs; The DFT and TDDFT Challenge Continues." Molecules 26, no. 6 (March 22, 2021): 1780. http://dx.doi.org/10.3390/molecules26061780.

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The derivatives of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) are pivotal ingredients for a large number of functional, stimuli-responsive materials and therapeutic molecules based on their photophysical properties, and there is a urgent need to understand and predict their optical traits prior to investing a large amount of resources in preparing them. Density functional theory (DFT) and time-dependent DFT (TDDFT) computations were performed to calculate the excitation energies of the lowest-energy singlet excited state of a large series of common BODIPY derivatives employing various functional aiming at the best possible combination providing the least deviations from the experimental values. Using the common “fudge” correction, a series of combinations was investigated, and a methodology is proposed offering equal or better performances than what is reported in the literature.

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Zhang, Li, Lu-Yi Zou, Jing-Fu Guo, Dan Wang, and Ai-Min Ren. "A theoretical study of a series of novel two-photon nitric oxide (NO) fluorescent probes based on BODIPY." New Journal of Chemistry 39, no. 11 (2015): 8342–55. http://dx.doi.org/10.1039/c5nj01023c.

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Liu, Fengfan, Huahui Su, Mengqian Li, Wanxuan Xie, Yunfeng Yan, and Qi Shuai. "Zwitterionic Modification of Polyethyleneimine for Efficient In Vitro siRNA Delivery." International Journal of Molecular Sciences 23, no. 9 (April 30, 2022): 5014. http://dx.doi.org/10.3390/ijms23095014.

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Polyethylenimine (PEI) has been widely used in gene delivery. However, its high cytotoxicity and undesired non-specific protein adsorption hinder the overall delivery efficacy and the practical applications of PEI-based gene delivery systems. In this study, we prepared hydrophobically modified PEIs (H-PEIs) via the reaction of octanal with 40% of primary amines in PEI25k and PEI10k, respectively. Two common zwitterionic molecules, 1,3-propanesultone and β-propiolactone, were then used for the modification of the resulting H-PEIs to construct polycationic gene carriers with zwitterionic properties (H-zPEIs). The siRNA delivery efficiency and cytotoxicity of these materials were evaluated in Hela-Luc and A549-Luc cell lines. Compared with their respective parental H-PEIs, different degrees of zwitterionic modification showed different effects in reducing cytotoxicity and delivery efficiency. All zwitterion-modified PEIs showed excellent siRNA binding capacity, reduced nonspecific protein adsorption, and enhanced stability upon nuclease degradation. It is concluded that zwitterionic molecular modification is an effective method to construct efficient vectors by preventing undesired interactions between polycationic carriers and biomacromolecules. It may offer insights into the modification of other cationic carriers of nucleic acid drugs.

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Wei, Peilin, Yu Duan, Chen Wang, Panpan Sun, and Na Sun. "Co-Assembled Supramolecular Organohydrogels of Amphiphilic Zwitterion and Polyoxometalate with Controlled Microstructures." Molecules 29, no. 10 (May 12, 2024): 2286. http://dx.doi.org/10.3390/molecules29102286.

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The organization of modifiable and functional building components into various superstructures is of great interest due to their broad applications. Supramolecular self-assembly, based on rationally designed building blocks and appropriately utilized driving forces, is a promising and widely used strategy for constructing superstructures with well-defined nanostructures and diverse morphologies across multiple length scales. In this study, two homogeneous organohydrogels with distinct appearances were constructed by simply mixing polyoxometalate (phosphomolybdic acid, HPMo) and a double-tailed zwitterionic quaternary ammonium amphiphile in a binary solvent of water and dimethyl sulfoxide (DMSO). The delicate balance between electrostatic attraction and repulsion of anionic HPMo clusters and zwitterionic structures drove them to co-assemble into homogeneous organohydrogels with diverse microstructures. Notably, the morphologies of the organohydrogels, including unilamellar vesicles, onion-like vesicles, and spherical aggregates, can be controlled by adjusting the ionic interactions between the zwitterionic amphiphiles and phosphomolybdic acid clusters. Furthermore, we observed an organohydrogel fabricated with densely stacked onion-like structures (multilamellar vesicles) consisting of more than a dozen layers at certain proportions. Additionally, the relationships between the self-assembled architectures and the intermolecular interactions among the polyoxometalate, zwitterionic amphiphile, and solvent molecules were elucidated. This study offers valuable insights into the mechanisms of polyoxometalate-zwitterionic amphiphile co-assembly, which are essential for the development of materials with specific structures and emerging functionalities.

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Almodôvar, Vítor A. S., and Augusto C. Tomé. "Porphyrin–diketopyrrolopyrrole conjugates and related structures: Synthesis, properties and applications." Journal of Porphyrins and Phthalocyanines 24, no. 01n03 (January 2020): 43–66. http://dx.doi.org/10.1142/s1088424619300271.

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A large diversity of porphyrin–diketopyrrolopyrrole conjugates and related structures formed by diketopyrrolopyrrole units and pyrrole-based moieties such as phthalocyanine, porphycene, calix[4]pyrrole or BODIPY have been reported since 2010. The new compounds, whether small molecules or polymeric materials, exhibit very interesting photophysical properties and have been tested in a range of technical or biological applications. This review summarizes the advances in the synthesis of such compounds. Their photophysical properties and potential applications are also briefly discussed.

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Jafar Mazumder, Mohammad A. "New, Amino Acid Based Zwitterionic Polymers as Promising Corrosion Inhibitors of Mild Steel in 1 M HCl." Coatings 9, no. 10 (October 17, 2019): 675. http://dx.doi.org/10.3390/coatings9100675.

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The zwitterionic monomers, N,N’-diallylamino propanephosphonate and amino acid residual N,N’-diallyl-l-methionine hydrochloride were synthesized, with excellent yields. These monomers were utilized in the preparation of zwitterionic homo and co-cyclopolymers 5–7 in aqueous solution using 2,2′-azobis (2-methylpropionamidine) dihydrochloride as an initiator. The polymers were characterized by FT-IR, NMR, and TGA. The performance of these synthesized polymers on mild steel in acidic solution was investigated by gravimetric method, Tafel extrapolation, linear polarization resistance, and electrochemical impedance spectroscopy. At 313 K, the maximum inhibition efficiencies of corrosion inhibitors 5–7 at 4.50 × 10−4 mol L−1 were found to be 85.2%, 83.3%, and 99.5%, respectively. The inhibition efficiencies obtained from gravimetric weight loss, potentiodynamic polarization, and electrochemical impedance spectroscopy measurements were in good agreement. Different adsorption isotherms were also explored to find the best fit, and found to obey Langmuir adsorption isotherm. The thermodynamic parameters, such as activation energy (Ea), standard enthalpy of activation (ΔH*), standard entropy of activation (ΔS*), adsorption–desorption equilibrium constant (Kads), and standard free energy of adsorption (ΔGoads), were determined. Electrochemical data indicated that the zwitterionic copolymer 7 acts as a mixed type inhibitor under the influence of anodic control. The surface morphology of mild steel corrosion was evaluated without and with corrosion inhibitors by AFM, SEM-EDX, and XPS, which confirmed the adsorption of inhibitor molecules on the metal surface.

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Mills, Jordan, Gaelle Level, Chirangano Mangwandi, and Marijana Blesic. "Aqueous biphasic systems formed in (zwitterionic salt+inorganic salt) mixtures." Pure and Applied Chemistry 91, no. 8 (August 27, 2019): 1351–60. http://dx.doi.org/10.1515/pac-2018-1222.

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Abstract The manuscript reports on a new class of aqueous biphasic systems (ABSs) formed in mixtures of inorganic salts (ISs) and zwitterionic salts (ZWSs). Aqueous ternary phase diagrams characterized by a binodal curve were determined for systems consisting of four ISs, K3PO4, K2HPO4, K2HPO4/KH2PO4, and K2CO3, and three structurally similar ZWSs differing in hydrophobicity. Comparison of phase behaviour of ABSs composed of ZWSs, ionic liquids (ILs) and zwitterions was provided. Potential of ZWSs based systems for extraction of aromatic molecules and amino acids, such as glycine, L-tryptophan, DL-phenylalanine, eugenol, and phenol was examined. Feasibility and limitations of isolation of products after partition and recovery of ZWS were discussed.

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Acikgoz, Sabriye, Hasan Yungevis, Amitav Sanyal, and M. Naci Inci. "Humidity sensing mechanism based on the distance dependent interactions between BODIPY dye molecules and gold thin films." Sensors and Actuators A: Physical 227 (May 2015): 21–30. http://dx.doi.org/10.1016/j.sna.2015.04.003.

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Jurgutis, Dziugas, Greta Jarockyte, Vilius Poderys, Jelena Dodonova-Vaitkuniene, Sigitas Tumkevicius, Aurimas Vysniauskas, Ricardas Rotomskis, and Vitalijus Karabanovas. "Exploring BODIPY-Based Sensor for Imaging of Intracellular Microviscosity in Human Breast Cancer Cells." International Journal of Molecular Sciences 23, no. 10 (May 19, 2022): 5687. http://dx.doi.org/10.3390/ijms23105687.

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BODIPY-based molecular rotors are highly attractive imaging tools for imaging intracellular microviscosity in living cells. In our study, we investigated the ability to detect the microviscosity of biological objects by using BDP-NO2 and BDP-H molecular rotors. We describe in detail the optical properties of BDP-NO2 and BDP-H molecular rotors in aqueous media with and without proteins, together with their accumulation dynamics and localization in live and fixed human breast cancer cells. Furthermore, we investigate the applicability of these molecules to monitor microviscosity in the organelles of human breast cancer cells by fluorescence lifetime imaging microscopy (FLIM). We demonstrate that the BDP-NO2 molecular rotor aggregates in aqueous media and is incompatible with live cell imaging. The opposite effect is observed with BDP-H which preserves its stability in aqueous media, diffuses through the plasma membrane and accumulates in lipid droplets (LDs) and the cytosol of both live and fixed MCF-7 and MDA-MB-231 cancer cells. Finally, by utilizing BDP-H we demonstrate that LD microviscosity is significantly elevated in more malignant MDA-MB-231 human breast cancer cells, as compared to MCF-7 breast cancer cells. Our findings demonstrate that BDP-H is a water-compatible probe that can be successfully applied to measure microviscosity in the LDs of living cells.

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Kazemi, Shahrzad, Youngwoo Jang, Anuradha Liyanage, Paul Karr, and Francis D'Souza. "(Invited) A Carbon Nanotube Binding Bis(pyrenylstyryl)Bodipy-C60 Nano Tweezer: Formation and Photoinduced Charge Separation in Supramolecular C60-Bodipy-SWCNT Triads." ECS Meeting Abstracts MA2022-01, no. 11 (July 7, 2022): 825. http://dx.doi.org/10.1149/ma2022-0111825mtgabs.

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Electron donor-acceptor hybrids comprised of single-wall carbon nanotubes (SWCNT) are promising functional structures having direct applications in energy conversion schemes and molecular optoelectronics. For building such hybrids and exfoliation of SWCNTs, the p-stacking ability of large aromatic compounds such as pyrene is one of the commonly employed approaches. Often, the desired donor or acceptor entities are functionalized to carry one or more pyrene entities and allowed to interact with CNTs. As a suitable electron donor, BODIPYs stand out owing to their ease of structural modifications and rich spectral and redox properties. Consequently, several donor-acceptor conjugates comprised of BF2-chelated dipyrromethene, BODIPY, and the well-known electron acceptor, C60 have been developed. In the present study, we have newly synthesized a nano tweezer comprised of covalently linked BODIPY-C60 carrying two pyrenylstyryl arms, 1. Compound 1 is further allowed to interact with SWCNT(6,5) and SWCNT(7,6) to form the supramolecular C60-BODIPY-SWCNT triads. Upon spectral, electrochemical, and computational characterization, pump-probe spectroscopic studies covering a wide femto-to-millisecond time scale have been performed to establish the occurrence of photoinduced charge separation. The presence of CNT prolonged the lifetime of the charge-separated states revealing the success of the present molecular design strategy for energy harvesting applications. D’Souza, F.; Sandanayaka, A. S. D.; Ito, O. ‘SWNT-Based Supramolecular Nanoarchitectures with Photosensitizing Donor and Acceptor Molecules’ Phys. Chem. Letts. 2010, 1. 2586-2593. B. KC, G. N. Lim, and F. D’Souza, ‘Accelerated Charge Separation in Graphene Decorated Multi-Modular Tripyrene-Subphthalocyanine-Fullerene Donor-Acceptor Hybrids,’ Angew. Chem. Int. Ed. 2015, 54, 5088-5092. Barrejon, L. M. Arellano, F. D’Souza, F. Langa, ‘Bidirectional charge transfer in carbon-based hybrid nanomaterials’ Nanoscale, 2019, 11, 14978-14992. Figure 1

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Contreras-García, Elena, Carmen Lozano, Cristina García-Iriepa, Marco Marazzi, Arthur H. Winter, Carmen Torres, and Diego Sampedro. "Controlling Antimicrobial Activity of Quinolones Using Visible/NIR Light-Activated BODIPY Photocages." Pharmaceutics 14, no. 5 (May 17, 2022): 1070. http://dx.doi.org/10.3390/pharmaceutics14051070.

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Controlling the activity of a pharmaceutical agent using light offers improved selectivity, reduction of adverse effects, and decreased environmental build-up. These benefits are especially attractive for antibiotics. Herein, we report a series of photoreleasable quinolones, which can be activated using visible/NIR light (520–800 nm). We have used BODIPY photocages with strong absorption in the visible to protect two different quinolone-based compounds and deactivate their antimicrobial properties. This activity could be recovered upon green or red light irradiation. A comprehensive computational study provides new insight into the reaction mechanism, revealing the relevance of considering explicit solvent molecules. The triplet excited state is populated and the photodissociation is assisted by the solvent. The light-controlled activity of these compounds has been assessed on a quinolone-susceptible E. coli strain. Up to a 32-fold change in the antimicrobial activity was measured.

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Gangemi, Chiara Maria Antonietta, Tania Maria Grazia Salerno, Anna Barattucci, Fabio Cucinotta, Paola Bonaccorsi, Giovanna Calabrese, Paola Poma, Maria Giovanna Rizzo, Sebastiano Campagna, and Fausto Puntoriero. "A Curcumin-BODIPY Dyad and Its Silica Hybrid as NIR Bioimaging Probes." International Journal of Molecular Sciences 23, no. 17 (August 23, 2022): 9542. http://dx.doi.org/10.3390/ijms23179542.

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In this paper we describe the synthesis of a novel bichromophoric system in which an efficient photoinduced intercomponent energy transfer process is active. The dyad consists of one subunit of curcumin and one of BODIPY and is able to emit in the far-red region, offering a large Stokes shift, capable of limiting light scattering processes for applications in microscopy. The system has been encapsulated in MCM-41 nanoparticles with dimensions between 50 and 80 nm. Both the molecular dyad and individual subunits were tested with different cell lines to study their effective applicability in bioimaging. MCM-41 nanoparticles showed no reduction in cell viability, indicating their biocompatibility and bio-inertness and making them capable of delivering organic molecules even in aqueous-based formulations, avoiding the toxicity of organic solvents. Encapsulation in the porous silica structure directed the location of the bichromophoric system within cytoplasm, while the dyad alone stains the nucleus of the hFOB cell line.

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Hao, W., V. S. Molchanov, Yu M. Chesnokov, P. R. Podlesnyi, and O. E. Philippova. "Effect of Electrostatic Interactions in Wormlike Micelles of Surfactants Based on Betaine and Charged Tertiary Amine with the Same Hydrophobic Groups." Colloid Journal 86, no. 2 (April 2024): 306–14. http://dx.doi.org/10.1134/s1061933x23601373.

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Abstract The viscoelastic properties and structure of solutions of mixed wormlike micelles based on a zwitterionic surfactant, oleylamidopropyldimethylcarboxybetaine (OAPB), and positively charged oleylamidopropyldimethylamine (OAPA) have been studied at different ratios between the components. At a small fraction of the cationic surfactant, OAPA, the solution exhibits viscoelastic properties characteristic of semidiluted solutions of entangled wormlike micelles, the presence of which has been confirmed by cryogenic electron microscopy data. It has been found that, as the molar fraction of the charged surfactant increases to 0.1, the viscosity and relaxation time of the solutions decrease by a factor of three, and the values of the storage modulus remain unchanged at short stress action times. The studied surfactants have a similar structure; therefore, when replacing zwitterionic OAPB molecules by positively charged OAPA molecules, the main factor of variations in the properties and structure is the enhancement of the electrostatic repulsion on the micelle surface. It has been shown that this factor leads to a decrease in the average length of micelles and an increase in their number, which have a weak effect on the rheological properties of the system as long as the length of the micelles is larger than the length of the subchains in the network. With an increase in the molar fraction of OAPA from 0.1 to 0.5, the viscosity and relaxation time drop drastically by several orders of magnitude and the viscoelastic response of the solution is lost; i.e., the network is destroyed. This transition from a semidilute solution to a dilute one is explained by a decrease in the length of the wormlike micelles and the formation of spherical ones. Cryogenic electron microscopy images have confirmed the formation of a mixture of long and short wormlike micelles with spherical micelles at an OAPA molar fraction of 0.5.

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Aleksakhina, E. L., Yu S. Marfin, D. A. Merkushev, I. K. Tomilova, and E. V. Rumyantsev. "Studying the blood clotting investigation in prescence of boron-dipyrrin fluorescent dyes." Kazan medical journal 96, no. 5 (October 15, 2015): 792–98. http://dx.doi.org/10.17750/kmj2015-792.

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Aim. To study the blood clotting in prescence of boron-dipyrrin fluorescent dyes. Methods. Photophysical properties of several boron-dippiryn based fluorescent dyes were examined in presence of blood plasma biomolecules and in model system containing bovine serum albumin using electron absorption spectroscopy and fluorescence spectroscopy. Results. The interaction between the investigated dyes and protein plasma components changes spectral characteristics of the dyes and leads to bathochromic and hypochromic shifts of absorption spectra accompanied by changing of fluorescence intensity. The mechanism of fluorescence changing was defined within the Stern-Folmer theory. It was shown that the static factor prevails due to dye-biopolymers molecular complex formation at plasma protein concentration up to 1 g/l, while the higher levels are characterized mainly by nonspecific interactions of fluorophores. The increase of fluorescent characteristics of phenyl-substituted BODIPY in the presence of proteins caused by resonance energy transfer and physicochemical features changes of the fluorophore molecular environment was shown. Conclusion. The gained results demonstrate the possibility of using the BODIPY dye for determination of blood clotting activity. Specific interactions of dye molecules with studied biological objects allows to analyze the contents and dynamic processes in biological objects at blood serum clotting.

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Jadhav, Thaksen, Rajneesh Misra, S. Biswas, and Ganesh D. Sharma. "Bulk heterojunction organic solar cells based on carbazole–BODIPY conjugate small molecules as donors with high open circuit voltage." Physical Chemistry Chemical Physics 17, no. 40 (2015): 26580–88. http://dx.doi.org/10.1039/c5cp04807a.

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Rasheed, Ashraf Saad, and Ali Saad Ali. "A Study of Retention Behavior and Method Development of Salbutamol Sulfate in Hydrophilic Interaction Chromatography." International Journal of Drug Delivery Technology 10, no. 03 (September 25, 2020): 344–48. http://dx.doi.org/10.25258/ijddt.10.3.6.

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Abstract:

For chromatographical separation and estimation of salbutamol sulfate, zwitterionic stationary phases with large capacity were obtained by zwitter-molecules attached to a polystyrene-divinylbenzene (PS/DVB) particle. Salbutamol sulfate retention activity was studied with eluent at various pH mobile phase, mobile phase concentrations, and acetonitrile (ACN) percentage. The methods of separation are based on separating the salbutamol sulfate into hydrophobic and cations interactions. Linearity of 0.01 to 0.9 μg.mL-1 for two columns was developed with direct calibration curves, %RSD percent (0.48 ± 0.12 and 0.49 ± 0.22), LoD (0.058 and 0.04 μg.mL-1), and LoQ (0.203 and 0.14 μg.mL-1) were created, respectively.

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Journal articles on the topic 'BODIPY based zwitterionic molecules'

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