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Yunjian Xu, Teng Feng, Tianshe Yang, Huanjie Wei, Huiran Yang, Guo Li, Menglong Zhao, Shujuan Liu, Wei Huang, Qiang Zhao
Photothermal therapy (PTT) as a kind of noninvasive tumor treatment has attracted increasing research interest. However, the efficiency of existing PTT agents in the near-infrared (NIR) region is the major problem that has hindered further development of PTT. Herein, we present an effective strategy to construct the efficient photothermal agent by utilizing an intramolecular photoinduced electron transfer (PeT) mechanism, which is able to dramatically improve photothermal conversion efficiency in NIR region...
April 20, 2018: ACS Applied Materials & Interfaces
Anna-Christina Schulz-Fincke, Michael Blaut, Annett Braune, Michael Gütschow
Human leukocyte elastase plays a crucial role in a variety of inflammatory disorders and represents an important subject of biomedical studies. The chemotype of peptidic phosphonates was employed for the design of a new activity-based probe for human leukocyte elastase. Its structure combines the phosphonate warhead with an adequate peptide portion and a BODIPY fluorophore with a clickable ethinylphenyl moiety at meso position. The probe 6 was assembled by copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition...
April 12, 2018: ACS Medicinal Chemistry Letters
Thumuganti Gayathri, A Vijayalakshmi, Sreejith Mangalath, Joshy Joseph, N Madhusudhana Rao, Surya Prakash Singh
We report a series of four efficient photosensitizers (PSs) based on a Bodipy core for photodynamic therapy (PDT). In the absence of hydrophilic functional groups, these PSs have been encapsulated in liposomes and examined for photocytotoxicity against human ovarian carcinoma cell line (SK-OV-3). The IC50 values obtained are as low as 0.350 μM, which compete with the classical photosensitizer chlorine E6 (IC50 = 0.39 μM) under similar experimental conditions.
April 12, 2018: ACS Medicinal Chemistry Letters
Sayani Das, Anindita Sarkar, Ananya Rakshit, Ankona Datta
We report the serendipitous discovery of an optical mercury sensor while trying to develop a water-soluble manganese probe. The sensor is based on a pentaaza macrocycle conjugated to a hemicyanine dye. The pentaaza macrocycle earlier designed in our group was used to develop photoinduced electron transfer (PET)-based "turn-on" fluorescent sensors for manganese. (1) In an attempt to increase the water-solubility of the manganese sensors we changed the dye from BODIPY to hemicyanine. The resultant molecule qHCM afforded a distinct reversible change in the absorption features and a concomitant visible color change upon binding to Hg2+ ions, leading to a highly water-soluble mercury sensor with a 10 ppb detection limit...
April 18, 2018: Inorganic Chemistry
Raghu Chitta, Disha Soni, Naresh Duvva, Deepak Badgurjar, Tapta Kanchan Roy, Surendra Nimesh, Geeta Arya, Lingamallu Giribabu
A highly water soluble phenothiazine (PTZ)-borondipyrromethene (BODIPY) based electron donor-acceptor dyad, WS-Probe, containing BODIPY as the signaling antennae and PTZ as the OCl- reactive group was designed and used as a fluorescent chemosensor for the detection of OCl-. Upon addition of incremental amounts of NaOCl, the quenched fluorescence of WS-Probe was enhanced drastically, indicating the inhibition of reductive photo-induced electron transfer (PET) from PTZ to 1BODIPY* and the detection limit was calculated to be 26...
April 16, 2018: Chemistry, An Asian Journal
Mahdi Chaari, Nerea Gaztelumendi, Justo Cabrera-González, Paula Peixoto-Moledo, Clara Viñas, Elba Xochitiotzi-Flores, Norberto Farfan, Abdelhamid Ben Salah, Carme Nogues, Rosario Nuñez
A series of novel fluorescent BODIPY-anionic boron cluster conjugates bearing [B12H12]2- (5, 6), [3,3'-Co(1,2-C2B9H11)2]- (7, 8), and [3,3'-Fe(1,2-C2B9H11)2]- (9) anions have been readily synthesized from meso-(4-hydroxyphenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY 4), and their structure and photoluminescence properties have been assessed. Linking anionic boron clusters to the BODIPY (4) does not alter significantly the luminescent properties of the final fluorophores, showing all of them similar emission fluorescent quantum yields (3-6%)...
April 16, 2018: Bioconjugate Chemistry
E Varela, J Rey, E Plaza, P Muñoz de Propios, J M Ortiz-Rodríguez, M Álvarez, L Anel-López, L Anel, P De Paz, M C Gil, J M Morrell, C Ortega-Ferrusola
Contaminating bacteria present in stallion ejaculates may compromise sperm quality during storage. Different procedures have been used to reduce the load of microorganisms in semen and avoid bacterial growth during storage. The aims of this study were: 1) to evaluate different techniques to eliminate bacteria in semen 2) to study the relationship between total microflora load (TML) and ROS production; and 3) to determine if TML affects the functionality of cool-stored sperm. Ejaculates from 11 stallions were split and processed in 3 ways: A...
March 26, 2018: Theriogenology
Jozef Kováčik, Sławomir Dresler, Viera Peterková, Petr Babula
Short-term (24 h) responses of Cladonia arbuscula subsp. mitis and Cladonia furcata to copper (CuII) or chromium (CrIII) excess (10 or 100 μM) were compared. C. arbuscula accumulated more Cu and Cr at higher metal doses but both species revealed depletion of K and/or Ca amount. Not only Cu but also Cr typically elevated reactive oxygen species (ROS) formation (fluorescence microscopy detection of total ROS and hydrogen peroxide) and depleted nitric oxide (NO) signal, with Cu showing more negative impact on lipid peroxidation (BODIPY 581/591 C11 staining reagent)...
March 19, 2018: Chemosphere
Ildikó Bacsa, Csilla Konc, Anna Boglárka Orosz, Gábor Kecskeméti, Réka Rigó, Csilla Özvegy-Laczka, Erzsébet Mernyák
Novel BODIPY-estrone conjugates were synthesized via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). Estrone-alkynes or an estrone-azide as starting compounds were synthesized via Michael addition or Sonogashira reaction as key steps. Fluorescent dyes based on BODIPY-core were provided by azide or alkyne functional groups. Fluorescent labeling of estrone was efficiently achieved at the C-2 or C-15 position. The newly-elaborated coupling procedures might have a broad applicability in the synthesis of fluorescent-labeled estrone conjugates suitable for biological assays...
April 3, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Aurimas Vysniauskas, Ismael Lopez Duarte, Alex J Thompson, James A Bull, Marina Kuimova
Surface functionalisation with viscosity sensitive dyes termed 'molecular rotors' can potentially open up new opportunities in sensing, for example for non-invasive biological viscosity imaging, in studying the effect of shear stress on lipid membranes and in cells, and in imaging contacts between surfaces upon applied pressure. We have functionalised microscope slides with BODIPY-based molecular rotor capable of viscosity sensing via its fluorescence lifetime. We have optimised functionalisation conditions and prepared the slides with the BODIPY rotor attached directly to the surface of glass slides and through linkers of ∼40 nm and ∼300 nm in length...
April 3, 2018: Methods and Applications in Fluorescence
Philipp Wilhelm, Jakob Schedlbauer, Florian Hinderer, Daniel Hennen, Sigurd Höger, Jan Vogelsang, John M Lupton
The breaking of molecular symmetry through photoexcitation is a ubiquitous but rather elusive process, which, for example, controls the microscopic efficiency of light harvesting in molecular aggregates. A molecular excitation within a π-conjugated segment will self-localize due to strong coupling to molecular vibrations, locally changing bond alternation in a process which is fundamentally nondeterministic. Probing such symmetry breaking usually relies on polarization-resolved fluorescence, which is most powerful on the level of single molecules...
April 2, 2018: Proceedings of the National Academy of Sciences of the United States of America
Akira Abe, Miki Hiraoka, James A Shayman, Hiroshi Ohguro
Lysosomal phospholipase A2 (LPLA2) is a key enzyme involved in the homeostasis of cellular phospholipids. Recently, LPLA2 was reported to preferentially degrade some truncated oxidized phospholipids at the sn-1 position. A commercially available, truncated oxidized phospholipid conjugated with a fluorescent dye, 1-palmitoyl-2-glutaroyl-sn-glycero-3-phosphoethanolamine-N-[4-(dipyrrometheneboron difluoride) butanoyl] (PGPE-BODIPY), was used to develop a specific assay for this enzyme. When recombinant mouse LPLA2 was incubated with liposomes consisting of 1,2-O-octadecyl-sn-glycero-3-phosphocholine/PGPE-BODIPY under acidic conditions, PGPE-BODIPY was converted to palmitic acid and a polar BODIPY-product...
March 29, 2018: Analytical Biochemistry
Carina Nicu, Jennifer Pople, Laura Bonsell, Ranjit Bhogal, David M Ansell, Ralf Paus
Dermal white adipose tissue (DWAT) is a main component of human skin, composed of individual lipid-laden mesenchymal cells known as dermal adipocytes (DAs). Besides their well-known role in lipid storage and release, DAs also promote skin immunity, wound healing and hair follicle cycling and are important players in cutaneous neuro-endocrinology. The ever-growing insights into DWAT functions, albeit mostly in mice, have invited speculation that it may be involved in multiple skin diseases ranging from fibrosis to alopecia and psoriasis, thus designating human DWAT a clinically relevant, but as yet insufficiently investigated skin compartment...
March 30, 2018: Experimental Dermatology
Irina Smirnova, Vladimir Kasho, Xiaoxu Jiang, Hong-Ming Chen, Stephen G Withers, H Ronald Kaback
Binding kinetics of α-galactopyranoside homologs with fluorescent aglycones of different sizes and shapes were determined with the lactose permease (LacY) of Escherichia coli by FRET from Trp151 in the binding site of LacY to the fluorophores. Fast binding was observed with LacY stabilized in an outward-open conformation ( k on = 4-20 μM-1 ·s-1 ), indicating unobstructed access to the binding site even for ligands that are much larger than lactose. Dissociation rate constants ( k off ) increase with the size of the aglycone so that K d values also increase but remain in the micromolar range for each homolog...
March 30, 2018: Proceedings of the National Academy of Sciences of the United States of America
Lingling Li, Kun Li, Meng-Yang Li, Lei Shi, Yan-Hong Liu, Hong Zhang, Sheng-Lin Pan, Nan Wang, Qian Zhou, Xiaoqi Yu
The viscosity of lysosome is reported to be a key indicator of lysosomal functionality. However, the existing mechanical methods of viscosity measurement can hardly be applied at the cellular or sub-cellular level. Herein, a BODIPY-based two-photon fluorescent probe was presented for monitoring lysosomal viscosity with high spatial and temporal resolution. By installing two morpholine moieties to the fluorophore as target and rotational groups, the TICT effect between the two morpholine rings and the main fluorophore scaffold endowed the probe with excellent viscosity sensitivity...
March 30, 2018: Analytical Chemistry
Pei Sun, Hongping Deng, Linzhu Zhou, Yan Wu, Xin Jin, Gangsheng Tong, Xuemei Yu
A novel type of multivalent and highly specific fluorescent hyperbranched glycopolymers h-P(GalEA-co-VBPT-co-BYMA) (hPGVB) is designed and prepared successfully via a facile "bottom-up" strategy. The acetylated hPGVB is prepared by one-pot reversible addition-fragmentation chain transfer (RAFT) copolymerization of acrylate-type galactose monomers AcGalEA and methacrylate-type fluorescent monomers BYMA in presence of an inimer-type RAFT chain transfer agent. After deacetylation, the resulting amphiphilic hPGVB can self-assemble into stable nanoparticles in aqueous media, showing strong green fluorescence with relative high quantum yields and good photostability...
March 30, 2018: Macromolecular Bioscience
Anila Hoskere A, Sreejesh Sreedharan, Firoj Ali, Carl G Smythe, Jim A Thomas, Amitava Das
A new physiologically benign and cell membrane permeable BODIPY based molecular probe, MB-Sn, specifically senses intracellular hydrogen polysulfides (H2Sn, n > 1) localized in the endoplasmic reticulum. This reagent is suitable for mapping the intracellular distribution of H2Sn by wide-field as well as super-resolution Structured Illumination Microscopy (SIM).
March 28, 2018: Chemical Communications: Chem Comm
Robert Cantu, Sairaman Seetharaman, Eric M Babin, Paul A Karr, Francis D'Souza
Hexaoxatriphenylene, a scaffold linker often utilized in building covalent organic frameworks, is shown to be electroactive and a useful entity to build light energy harvesting donor-acceptor systems. To demonstrate this, new donor-acceptor conjugates have been synthesized by employ-ing BODIPY as a sensitizer. Excited state electron transfer leading to high energy charge sepa-rated states, useful to drive energy demanding photocatalytic reactions, from the electron rich hexa oxa triphenylene to 1BODIPY*, in the synthesized tri BODIPY-triphenylene 'paddle-wheel' conjugates, has been successfully demonstrated using femtosecond transient absorption spectroscopy...
March 27, 2018: Journal of Physical Chemistry. A
Weijiang He, Yang Bai, Xiangchao Shi, Yuncong Chen, Chengcheng Zhu, Yang Jiao, Zhong Han, Zijian Guo
With the different polarity response, coumarin and BODIPY were hybridized to construct polarity fluorescent sensors, CBDP and iso-CBDP, to overcome the disadvantages of solvatochromic sensors in ratiometric polarity sensing. Only CBDP displayed that the emission ratio (Icou/IBDP, coumarin to BODIPY emissions) increased with an exponential dependence on medium relative permittivity in a wide polarity range. This sensing ability of CBDP was not interfered by medium pH, viscosity, and most intracellular species especially reactive oxygen, nitrogen, and sulfur species...
March 25, 2018: Chemistry: a European Journal
Di Gao, Shawkat M Aly, Paul-Ludovic Karsenti, Pierre D Harvey
π-Stacking is the most common structural feature that dictates the optical and electronic properties of chromophores in the solid state. Herein, a unidirectional singlet-singlet energy-transfer dyad has been designed to test the effect of π-stacking of zinc(II) porphyrin, [Zn2 ], as a slipped dimer acceptor using a BODIPY unit, [bod], as the donor, bridged by the linker C6 H4 C≡CC6 H4 . The rate of singlet energy transfer, kET (S1 ), at 298 K ( kET (S1 ) = 4.5 × 1010 s-1 ) extracted through the change in fluorescence lifetime, τF , of [bod] in the presence (27...
March 23, 2018: Inorganic Chemistry
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