- A diketopyrrolopyrrole-based fluorescent probe for investigating mitochondrial zinc ions
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We demonstrate a strategy to asymmetrically introduce a Zn2+ chelator (MeO-DPEN) and a mitochondrial-targeting group (TPP) at the N-positions of both lactam moieties of diketopyrrolopyrrole (DPP) fluorophore. And two probes DPP-Mito and DPP-C2
- Du, Chenchen,Fu, Shibo,Ren, Xiaolei,Wang, Xiaohua,Wang, Zhong,Zhou, Juan,Wang, Hongyu
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Read Online
- Synthesis and characterization of novel positively charged organocobaloximes as catalysts for the fixation of CO2 to cyclic carbonates
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A series of cobaloxime complexes (1-6) and corresponding to positively charged phosphonium linked cobaloximes (called cobaloximes-PCPL) (1a-6a) have been prepared in high yields and characterized by means of NMR (1H, 13C, and 31
- Kilic, Ahmet,Durgun, Mustafa,Aytar, Emine,Yavuz, Rahime
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Read Online
- A mitochondria-targeted thiazoleorange-based photothermal agent for enhanced photothermal therapy for tumors
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Organic small molecules with near-infrared (NIR) absorption hold great promise as the phototheranostic agents for clinical translation by virtue of their inherent merits such as well-defined chemical structure, high purity and good reproducibility. Probes
- Bian, Wangqing,Pan, Zhenxing,Wang, Yakun,Long, Wei,Chen, Zefeng,Chen, Niping,Zeng, Yaoxun,Yuan, Jiongpeng,Liu, Xujie,Lu, Yu-Jing,He, Yan,Zhang, Kun
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Read Online
- A long-linker conjugate of fluorescein and triphenylphosphonium as mitochondria-targeted uncoupler and fluorescent neuro- and nephroprotector
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Background Limited uncoupling of oxidative phosphorylation is known to be beneficial in various laboratory models of diseases. Linking a triphenyl-phosphonium cation to fluorescein through a decyl (C10) spacer yields a fluorescent uncoupler, co
- Antonenko, Yuri N.,Denisov, Stepan S.,Silachev, Denis N.,Khailova, Ljudmila S.,Jankauskas, Stanislovas S.,Rokitskaya, Tatyana I.,Danilina, Tatyana I.,Kotova, Elena A.,Korshunova, Galina A.,Plotnikov, Egor Y.,Zorov, Dmitry B.
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Read Online
- Fluorescent Probe HKSOX-1 for imaging and detection of endogenous superoxide in live cells and in vivo
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Superoxide anion radical (O2-) is undoubtedly the most important primary reactive oxygen species (ROS) found in cells, whose formation and fate are intertwined with diverse physiological and pathological processes. Here we report a highly sensitive and selective O2- detecting strategy involving O2- cleavage of an aryl trifluoromethanesulfonate group to yield a free phenol. We have synthesized three new O2- fluorescent probes (HKSOX-1, HKSOX-1r for cellular retention, and HKSOX-1m for mitochondria-targeting) which exhibit excellent selectivity and sensitivity toward O2- over a broad range of pH, strong oxidants, and abundant reductants found in cells. In confocal imaging, flow cytometry, and 96-well microplate assay, HKSOX-1r has been robustly applied to detect O2- in multiple cellular models, such as inflammation and mitochondrial stress. Additionally, our probes can be efficiently applied to visualize O2- in intact live zebrafish embryos. These probes open up exciting opportunities for unmasking the roles of O2- in health and disease.
- Hu, Jun Jacob,Wong, Nai-Kei,Ye, Sen,Chen, Xingmiao,Lu, Ming-Yang,Zhao, Angela Qian,Guo, Yuhan,Ma, Alvin Chun-Hang,Leung, Anskar Yu-Hung,Shen, Jiangang,Yang, Dan
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Read Online
- Synthesis, crystal and structural characterization, Hirshfeld surface analysis and DFT calculations of three symmetrical and asymmetrical phosphonium salts
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Three stable phosphonium salts of 1,4-butanediylebis(triphenylphosphonium) dibromide I, butane-4?bromo-1-(triphenylphosphonium) bromide II and 1,3-propanediylbis(triphenylphosphonium) tetrahydroborate III were synthesized and structurally characterized. Single crystal X-ray diffraction analysis, spectroscopic methods and thermal analysis methods were used for the characterization of titled compounds. Crystallographic data showed that compound I crystallized in the triclinic crystal system with Pī space group and compound II crystallized in the monoclinic crystal system with P21/c space group. The crystal packing structures of I and II were stabilized by various intermolecular interactions, especially of C–H···π contacts. The molecular Hirshfeld surface analysis and 2D fingerprint revealed that the C···H contacts have 24.3% and 18.4% contributions in the crystal packings of compounds I and II, respectively. In addition, the H···Br (28.5%) contact has a considerable contribution to the crystal architecture of compound II. Theoretical studies were performed by DFT method to investigate the structural properties of the titled compounds. The isotopic ratio of boron in tetrahydroborate anion of compound III calculated by 1H NMR spectroscopy. The isotopic ratio for 10B/11B was 19.099 / 80.900%. Reduction of some carbonyl compounds to corresponding alcohols was performed by compound III and the optimum conditions were determined.
- Delaram, Behnaz,Gholizadeh, Mostafa,Makari, Faezeh,Nokhbeh, Seyed Reza,Salimi, Alireza
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- Two Are Better Than One: A Design Principle for Ultralong-Persistent Luminescence of Pure Organics
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Because of their innate ability to store and then release energy, long-persistent luminescence (LPL) materials have garnered strong research interest in a wide range of multidisciplinary fields, such as biomedical sciences, theranostics, and photonic devices. Although many inorganic LPL systems with afterglow durations of up to hours and days have been reported, organic systems have had difficulties reaching similar timescales. In this work, a design principle based on the successes of inorganic systems to produce an organic LPL (OLPL) system through the use of a strong organic electron trap is proposed. The resulting system generates detectable afterglow for up to 7 h, significantly longer than any other reported OLPL system. The design strategy demonstrates an easy methodology to develop organic long-persistent phosphors, opening the door to new OLPL materials.
- Alam, Parvej,Leung, Nelson L. C.,Liu, Junkai,Cheung, Tsz Shing,Zhang, Xuepeng,He, Zikai,Kwok, Ryan T. K.,Lam, Jacky W. Y.,Sung, Herman H. Y.,Williams, Ian D.,Chan, Christopher C. S.,Wong, Kam Sing,Peng, Qian,Tang, Ben Zhong
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- Organic super-long room-temperature phosphorescent material, triple anti-counterfeiting organic ink and application
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The invention discloses an organic super-long room-temperature phosphorescent material which is an organic phosphonium salt prepared by taking triphenylphosphine as a raw material, the compound can still continuously emit light for a period of time after
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Paragraph 0028-0032
(2020/09/16)
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- A SET OF MITOCHONDRIA-TARGETED COMPOUNDS
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Here are described SkQ compounds containing cations of various types: alkyl(triphenyl)phosphonium cation, quaternary ammonium cations, including pH -dependent and permanent cations of rhodamines, berberine and palmatine alkaloids.
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Page/Page column 11
(2019/01/17)
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- BODIPY-based high-sensitivity fluorescent probe and synthesis method and application thereof
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The invention relates to a BODIPY-based high-sensitivity fluorescent probe and a synthesis method and application thereof. A structural general formula of the probe is shown as (I), wherein Trigger is stimulant triggering groups, R1 and R2 are groups for regulating and controlling fluorescent transmission wavelength of the probe and introducing organelle targeting, and R1 and R2 are defined in the description. By the probe, detection of different substrates can be realized without changing mother nucleus structure of the probe by only changing different Trigger groups. In addition, according to different needs on wavelength and targeting, the mother nucleus structure of the probe can be quickly modified. By changing R1 and R2, maximum fluorescent emission wavelength of the probe can be changed, and the probe can target mitochondrion to realize detection of active substances in the mitochondrion. The probe has good biocompatibility, thereby being applicable to detecting biological systems. Application value of the fluorescent probe in the aspect of detecting bioactive molecules and protease over-expressed in inflammatory or tumor tissue has potential social benefit and economic benefit.
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Paragraph 0039; 0041; 0045
(2018/03/24)
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- Enhanced etherification of calix[4]arenes by microwave irradiation
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Microwave irradiation has been found to be a highly efficient method for etherification of p-tert-butylcalix[4]arene with alkyl bromides or ditosylate. The corresponding products were obtained as a pure form in modest yield within short reaction time when
- Xu, Zhen,Lü, Zao Sheng,Chen, Lei
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- Kinetics and mechanistic investigation of epoxy-anhydride compositions cured with quaternary phosphonium salts as accelerators
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Mechanism and curing kinetics of bisphenol A epoxy resin-iso-methyltetrahydrophthalic anhydride compositions using quaternary phosphonium salts as accelerators were investigated by differential scanning calorimetry (DSC) and electrospray mass-spectrometry (ESI-MS). The DSC method was applied to investigate curing kinetics and apparent activation energy values for the overall curing process. The DSC results showed that some of the phosphonium salts lead to a lower activation energy, that means they are more effective accelerators for the curing of epoxy-anhydride systems. The mechanism of curing was studied by ESI-MS using the model reaction of epichlorohydrin (E) with phthalic anhydride (PA) in the presence of phosphonium salts or 2-methylimidazole. Products containing the alkyl moiety of the phosphonium salt in form of alkyl esters could be identified. This suggests that the phosphonium salts activate the anhydride by electrophilic attack.
- Amirova, Lyaysan R.,Burilov, Alexander R.,Amirova, Liliya M.,Bauer, Ingmar,Habicher, Wolf D.
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p. 1088 - 1097
(2016/03/12)
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- Synthesis of 2,3-Disubstituted Quinolines via Ketenimine or Carbodiimide Intermediates
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Cyclopenta[b]quinolines and cyclohexa[b]quinolines were prepared via the reactions of α-diazo ketones with N-(2-cyclopropylidenemethylphenyl)phosphanimines and N-(2-cyclobutylidenemethylphenyl) phosphanimine, respectively. The reaction proceeds in a cascade involving ketenimine formation, 6 π-electron ring closure, and 1,3-alkyl shift. A similar approach was developed for the synthesis of dihydropyrrolo-[2,3-b]quinolines from N-(2-cyclopropylidenemethylphenyl)phosphanimines and isocyanates.
- Zhao, Hongyang,Xing, Yanpeng,Lu, Ping,Wang, Yanguang
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supporting information
p. 15144 - 15150
(2016/10/11)
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- BISTRIFILATE-BASED FLUOROGENIC PROBES FOR DETECTION OF SUPEROXIDE ANION RADICAL
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The invention provides fluorogenic compounds and probes that can be used as reagents for measuring, detecting and/or screening superoxide. The fluorogenic compounds of the invention can produce fluorescence colors, such as green, yellow, red, or far-red. The invention further provides fluorogenic compounds for selectively staining superoxide in the mitochondria of living cells. The invention also provides methods that can be used to measure, directly or indirectly, the presence and/or amount of superoxide in chemical samples and biological samples such as cells and tissues in living organisms, and a high-throughput screening methods for detecting or screening superoxide or compounds that can increase or decrease the level of superoxide in chemical and biological samples.
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Page/Page column 28
(2015/11/02)
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- Polymer grafted with asymmetrical dication ionic liquid as efficient and reusable catalysts for the synthesis of cyclic carbonates from CO2 and expoxides
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Polymer grafted with asymmetrical dication ionic liquid (IL) based on imidazolium and phosphonium ([P-Im-C4H8Ph 3P]Br2) was fabricated, and for the first time evaluated as catalyst for the synthesis of cyclic ca
- Dai, Wei-Li,Bi, Jin,Luo, Sheng-Lian,Luo, Xu-Biao,Tu, Xin-Man,Au, Chak-Tong
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- Catalytic fixation of CO2 to cyclic carbonates over biopolymer chitosan-grafted quarternary phosphonium ionic liquid as a recylable catalyst
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We prepared chitosan-grafted quarternary phosphonium ionic liquid (1-butyl-triphenylphosphonium bromide) by a simple method and used it as catalyst for the synthesis of cyclic carbonates through CO2 cycloaddition to epoxides in the absence of c
- Jing-Xian, Chen,Bi, Jin,Wei-Li, Dai,Sen-Lin, Deng,Liu-Ren, Cao,Zong-Jie, Cao,Sheng-Lian, Luo,Xu-Biao, Luo,Xin-Man, Tu,Chak-Tong, Au
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- IONIZABLE CATIONIC LIPIDS
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Disclosed herein are novel compounds, pharmaceutical compositions comprising such compounds and related methods of their use. The compounds described herein are useful, e.g., as liposomal delivery vehicles to facilitate the delivery of encapsulated polynu
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Paragraph 0164
(2013/10/21)
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- A straightforward synthesis of K-7174, a GATA-specific inhibitor
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K-7174, a GATA-specific inhibitor, is a putative anti-inflammatory agent that attenuates effects of inflammatory cytokines in certain cell types. An expeditious four-step synthesis of K-7174 is described in this paper. The route employs Wittig olefination
- Majik, Mahesh S.,Yu, Jin Ha,Jeong, Lak Shin
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p. 2903 - 2906
(2012/10/29)
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- Fixed-charge labels for simplified reaction analysis: 5-hydroxy-1,2,3- triazoles as byproducts of a copper(I)-catalyzed click reaction
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High-resolution multistage mass spectrometric studies of isotope-labelled derivatives of a fixed-charge labelled sugar triazole assisted the identification of 5-hydroxy-1,2,3-triazoles as byproducts of the copper(I)-catalyzed cycloaddition of azides and t
- Chen, Xingqiang,Khairallah, George N.,O'Hair, Richard A.J.,Williams, Spencer J.
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supporting information; experimental part
p. 2750 - 2753
(2011/06/19)
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- One-pot synthesis of fused benzo[c]carbazoles by photochemical intramolecular annulation of 3-acyl-2-haloindoles with tethered styrenes
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An efficient procedure for the synthesis of fused benzo[c]carbazoles has been achieved in moderate to high yields by the one-pot photochemical annulation of 3-acyl-2-haloindoles with tethered styrenes by photoinduced electron-transfer coupling, electrocyclic reactions, and deacylative aromatization in the presence of pyridine. Fused furo[2,3-c]carbazoles were also synthesized under the same conditions. 5,6-Dihydrobenzo[c]pyrrolo[1,2,3-lm] carbazoles were oxidized by DDQ to afford aromatic benzo[c]pyrrolo[1,2,3-lm] carbazole products in moderate to high yields.
- Lu, Shen-Ci,Wei, Shi-Chao,Wang, Wei-Xia,Zhang, Wei,Tu, Zhi-Feng
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supporting information; experimental part
p. 5905 - 5910
(2011/11/06)
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- First total synthesis of the irciniasulfonic acids
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A flexible and concise first total synthesis of the irciniasulfonic acids is reported.
- Dobbs, Adrian P.,Venturelli, Alberto,Butler, Laura A.,Parker, Robert J.
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p. 652 - 654
(2007/10/03)
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- Stereospecific synthesis of Z olefins bearing an ω-azido group.
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Ylides derived from ω-azidoalkyltriphenylphosphonium salts were generated at low temperature.They are stable at -80 deg C for several hours and react smoothly and stereospecifically with typical aldehydes to form Z-ω-azido olefins which are the precursors of ω-unsaturated primary and secondary amines.
- Chhen, A.,Vaultier, M.,Carrie, R.
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p. 4953 - 4956
(2007/10/02)
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- A NEW ROUTE TO HETEROCYCLIC α-DEHYDRO α-AMINO ESTERS
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Heterocyclic α-dehydro α-amino esters are obtained by the reaction of ethyl N-carbomethoxy oxamate with ω-halogened phosphorus ylids.
- Bazureau, J. P.,Le Roux, J.,Le Corre, M.
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p. 1921 - 1922
(2007/10/02)
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- Preparative-Scale Syntheses of Bicyclobutylidene, Methylenecyclobutane and Cyclobutanone
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One-pot syntheses of bicyclobutylidene (3) and methylenecyclobutane (4) are described.Both 3 and 4 are valuable precursors of cyclobutanone (5).
- Fitjer, Lutz,Quabeck, Ulrike
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p. 299 - 300
(2007/10/02)
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- Notes Unsymmetrical Bis(phosphorus) Compounds: Synthesis of Unsymmetrical Ditertiary Phosphines, Phosphine Oxides, and Diquaternary Phosphonium Salts
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A convenient preparative route to the unsymmetrical bidentate phosphines R2P(CH2)nPPh2 (R=Me or Et; n=3 or 4) is described.This involves the synthesis of unsymmetrical diphosphonium salts, Br2, and diphosphine oxides, R2P(O)(CH2)nPPh2, as intermediates.The symmetrical ligand Et2P(CH2)3PEt2 was also prepared by the same route.New co-ordination complexes of manganese(II) with these ligands have been isolated.
- Benn, Roger F.,Briggs, Josie C.,McAuliffe, Charles A.
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p. 293 - 296
(2007/10/02)
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- Synthesis, NMR Spectra, and Crystal Structure of Triphenylphosphonium Cyclobutylide, (C6H5)3P=C3
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Crystalline samples of the title compound 2 were obtained from the reaction of (4-bromobutyl)triphenylphosphonium bromide (1) with sodium amide in liquid ammonia.The NMR data of this salt-free compound indicate significant deviation from a planar carbanion geometry usually typical of unstrained phosphonium ylides.An X-ray diffraction analysis confirms this for the crystalline state.The bond to the approximately tetrahedral onium centre is inclined to the neighbouring plane of the puckered cyclobutane ring (16.7 deg) by 19.3 deg.Yet, the ylidic P-C bond of 166.8(3) pm shows significant multiple bond character.
- Schmidbaur, Hubert,Schier, Annette,Neugebauer, Dietmar
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p. 2173 - 2179
(2007/10/02)
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- ACYLOXYALKYLIDENEPHOSPHORANES-II; ETUDE DES Ω-ACYLOXY N-BUTYLIDENETRIPHENYLPHOSPHORANES. NOUVELLE VOIE D'ACCES AUX DIHYDRO-3,4 2H-PYRANNES
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ω-Acyloxy n-butylidenetriphenylphosphoranes give α-acyl n-butylidenetriphenylphosphoranes by intermolecular condensation in t-BuOH, and 3,4-dihydro-(2H)-pyrans by intramolecular condensation in toluene.The α-acyl n-butylidene phosphoranes, which are the t
- Hercouet, A.,Corre Le, M.
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p. 2861 - 2866
(2007/10/02)
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