- A novel colorimetric chemosensor for Cu2+ with high selectivity and sensitivity based on rhodamine B
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9-formyl-8-hydroxy-2,3,6,7-tetrahydro-1H, 5H-benzo[ij]-quinolizine rhodamine B hydrazone (FHQRH), a novel colorimetric chemosensor for Cu2+, was synthesized by a three-step synthetic route. It was found that FHQRH showed a high selectivity for Cu2+ ions and excellent anti-interference capability toward other metal ions. The FHQRH solution exhibited a visual color change after the addition of Cu2+, owing to the open spirocyclic structure via coordination with Cu2+. The complexation coefficient of FHQRH toward Cu2+ was measured to be 1:1. Furthermore, this Cu2+ chemosensor has a remarkable low detection limit of 0.45 μM, which is 2 % of the toxic level (20 μM) in drinking water as defined by the US Environment Protection Agency (EPA).
- Li, Changjiang,Xiang, Kaiqiang,Liu, Yunchang,Zheng, Yuchuan,Tian, Baozhu,Zhang, Jinlong
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Read Online
- Synthesis of a NIR fluorescent dye and its application for rapid detection of HSO3? in living cells
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SO2 and its derivatives (HSO3?, SO32?) play a significant important role in many industries and organisms. Based on coumarin and benzopyranose, a promising NIR ratiometric fluorescent probe BAOA (11-oxo-2,2′,3,3′,6,7,7′,8′-octahydro -1H,1′H,5H,6′H,11H- [10,12′-bipyrano [2,3-f] pyrido [3,2,1-ij] quinolin]-13′-ium perchlorate) was designed and developed to detect HSO3? rapidly and sensitively. The sensing mechanism was Michael addition reaction, in which, strongly nucleophilic HSO3? attacked carbon-carbon double bonds and BAOA-HSO3 was formed. A superior linear calibration curve between the fluorescence ratio I490/I722 and concentrations of HSO3? was obtained in the range of 1.25–8.75 μmol/L and the LOD was figured out as 63.0 nmol/L. Cell experiments showed that BAOA could not only locate mitochondria, lysosomes, ER and Golgi but also detect exogenous HSO3? in living cells.
- Bu, Dandan,Li, Zhanxian,Ren, Haohui,Yu, Mingming,Zhang, Hongyan,Zhang, Qiang
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- Three lysocolorimetric/lysofluorescent probes with mitochondria/lysosome dual targeting positioning
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The invention discloses a preparation method of three lysocolorimetric/lysofluorescent probes with mitochondria/lysosome dual targeting positioning and application thereof in biological imaging, which belong to the technical field of chemical analysis and detection. The structure and the detection mechanism of the lysocolorimetric/lysofluorescent probes are as follows: the probes prepared have stronger solvent-induced discoloration characteristics, and the fluorescent quantum yield is relatively high. Cell experiments show that the prepared probe has a good mitochondria/lysosome positioning effect.
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Paragraph 0044; 0047
(2021/05/01)
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- A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation
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Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.
- Zhang, Yanhui,Teng, Hao,Gao, Ying,Afzal, Muhammad Wasim,Tian, Jingye,Chen, Xi,Tang, Haoyang,James, Tony D.,Guo, Yuan
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supporting information
p. 2917 - 2920
(2020/03/13)
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- A novel fluorescent probe with dual-sites for simultaneously monitoring metabolisms of cysteine in living cells and zebrafishes
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Understanding cellular metabolism holds immense potential for developing new drugs that regulate metabolic pathways. Two gas signal molecules, SO2 and H2S, are the main metabolites from cysteine (Cys) via oxidation and desulfurization pathways, respectively. However, a few fluorescent probes for real-time monitor of the metabolic pathways of cysteine have been reported. To understand metabolic alterations of cysteine, we have rationally designed and prepared a dual-signal fluorescent probe HN, which could differentiate SO2 and H2S through two different fluorescence channels simultaneously, along with similar reaction kinetics and both “off-on” fluorescence responses. Probe HN exhibits the potential to monitor the metabolism pathways of cysteine, and the distinguishment of cancer cells from normal cells could be realized. This methodology will promote further understanding of the physiological and pathological roles of cysteine.
- Gan, Yabing,Li, Haitao,Liu, Meiling,Yao, Shouzhuo,Yin, Guoxing,Yin, Peng,Yu, Ting,Zhang, Youyu,Zhou, Li
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- Near-infrared fluorescent probe for simultaneously detecting DNA and RNA under double channels as well as preparation method and application of the near-infrared fluorescent probe
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The invention discloses a fluorescent probe for simultaneously detecting DNA and RNA in cells under double channels as well as a preparation method and application of the fluorescent probe. The structure of the fluorescent probe is shown as a formula (I) or (II), wherein the Ar is an aromatic ring or an aromatic heterocyclic ring; the R1 and R2 are respectively and independently hydrogen, N-piperazine, N-methyl piperazine, -NH(CH2)nR3 and -NR3R4; the n is any integer from 1 to 5, and R3 and R4 are respectively and independently hydrogen, C1-C5 alkyl or C1-C5 haloalkyl; the A- is halide ions orp-toluenesulfonic acid ions. The fluorescent probe disclosed by the invention can be used for simultaneously detecting DNA and RNA in vitro and in cells under double channels; meanwhile, the fluorescent probe has the characteristics of rapid synthesis, near-infrared emission wavelength, good light stability, high detection sensitivity and the like, and is convenient to popularize and apply.
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Paragraph 0056; 0058; 0061
(2020/05/30)
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- Endoplasmic reticulum targeted fluorescent probe for the detection of hydrogen sulfide based on a twist-blockage strategy
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Hydrogen sulfide (H2S) is very important for humans and is involved in many physiological processes. Here, we designed and reported a new naked-eye colorimetric fluorescent probe Z1 for detecting H2S in absolute HEPES solution. The fluorescence intensity, after the reaction of the probe and H2S, is about 32 times that of the probe alone. When the concentration of H2S is 0-100 μM, the detection limit (DL) is rather low at about 0.15 μM (3σ/slope). The response mechanism is based on the leaving of the 2,4-dinitrobenzene moiety, followed by intramolecular cyclization to give a fluorescent iminocoumarin-benzothiazole group. Moreover, Z1 was applied to endogenous and exogenous H2S imaging in living cells. The high overlap coefficient proved that probe Z1 has good ER-tracker localization in living cells.
- Zhang, Yongru,Zhang, Beibei,Li, Zipeng,Wang, Lianbang,Ren, Xueling,Ye, Yong
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supporting information
p. 8778 - 8783
(2019/10/16)
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- A novel colorimetric and ratiometric fluorescent probe for selective detection of bisulfite in real samples and living cells
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An abnormal level of bisulfite can induce toxicological effects associated with lung cancer, cardiovascular and neurological disorders. Therefore, it is of significance to develop an effective fluorescent probe to detect bisulfite in living cells. Herein, a novel fluorescent probe QPCT, based on a 1,4-addition mechanism, was constructed for the colorimetric and ratiometric detection of bisulfite. QPCT displayed high selectivity and anti-interference ability to bisulfite over other anions and biothiols. The probe renders a sensitive ratiometric response to bisulfite with a remarkable fluorescence blue shift from 590 to 537 nm and the fluorescence ratio was linear with bisulfite concentration over the range of 0–120 μM. More importantly, QPCT has been successfully applied to detect bisulfite in sugars and living A549 cells, which indicated that QPCT had a great capability for monitoring bisulfite in complex systems.
- Li, Jin,Gao, Ying,Guo, Haoran,Li, Xiaokang,Tang, Haoyang,Li, Jian,Guo, Yuan
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p. 285 - 290
(2019/01/03)
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- (7-Dialkylamino-3-coumarinyl)pyrazolines – new effective push-pull photogenerators of acidity
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(7-Dialkylamino-3-coumarinyl)pyrazolines and their julolidine analog have been synthesized and proved as new effective photogenerators of acidity. Having D-π-linker ?A conjugated system of push-pull type these compounds possess intensive absorption in visible region of electronic spectra, high photosensitivity and undergo photodehydrogenation with proton elimination in the presence of CCl4 or C2Cl6 with a high speed.
- Traven,Cheptsov,Vershinina,Solovjeva,Chibisova,Dolotov,Ivanov
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- Reaction-based fluorescent turn-on probe for selective detection of thiophenols in aqueous solution and living cells
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A novel turn-on florescent probe based on a nucleophilic substitution reaction was developed for the detection of thiophenols in aqueous solution and in living cells. In this probe, 10-hydroxyl derivative of coumarin 6H was selected as fluorophore, 2, 4-dinitrophenlate moiety acted simultaneously as recognition unit and fluorophore quencher. This probe features a remarkable large Stokes shift (128?nm) and shows a highly selective detection process for thiophenols with significant fluorescence turn-on response. Notably, biothiols, aliphatic thiols, amino acids and reducing anions do not interfere with the sensing of thiophenols. The probe shows good linearity ranges with low detection limit of 36?nM for thiophenols. More importantly, it was successfully applied for practical detection of thiophenols in real water samples with a good recovery and imaging of thiophenols in living cells, demonstrating its practical application in environmental samples and biological systems.
- Wang, Xiao-Bo,Hao, Xue,Zhang, Datong,Jiang, Yan
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p. 167 - 174
(2017/03/24)
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- Preparation method of large emission wavelength fluorescent dye
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The invention discloses a preparation method of a large emission wavelength fluorescent dye, comprising the following steps: first, modifying a naphthalimide by three-step reaction to obtain naphthalimide with activated methyl; second, carrying out four-step reaction to obtain aldehyde modified coumarin; third, reacting the naphthalimide with the activated methyl with the aldehyde modified coumarin to obtain a target product, the large emission wavelength fluorescent dye. Compared with the existing fluorescent dyes, the fluorescent dye synthesized in the invention has a near-infrared emission spectrum and Stokes shift up to 150 nm and is applicable to the fields such as laser, electroluminescence and fluorescent probes.
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Paragraph 0013
(2016/10/10)
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- Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies
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Three novel iminocoumarin derivatives with high quantum yield are synthesized from 3-benzimidazole substituted coumarin and different aromatic aldehydes. The photophysical behavior of the synthesized compounds was studied using UV-visible and fluorescence spectroscopy in polar and non-polar solvents. The compounds show absorption maxima at around 450 nm and emission maxima at around 500 nm. The quantum yields of compounds in dichloromethane and chloroform are more than 0.90. The absorption, emission and quantum yield of compounds are dependent on the polarity of solvents. Along with an intense absorption, these compounds show shoulder absorption peak in the studied solvents. The solvent polarity plots revealed the charge transfer process in the synthesized molecules from donor to acceptor. Density Functional Theory and Time Dependent Density Functional Theory computations have been used to have more understanding of the structural, molecular, electronic and photophysical parameters of the dyes. The dyes were characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis.
- Chemate, Santosh B.,Sekar, Nagaiyan
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p. 1615 - 1628
(2015/11/24)
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- A fluorescent probe for H2S in vivo with fast response and high sensitivity
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In this work, we design and synthesize a new near-infrared (NIR) ratiometric fluorescent probe FD-H2S for the highly sensitive (DL 68.2 nM) detection of H2S with fast response (15 s), large emission shift (220 nm) and excellent enhancement (168-fold in ratiometric value). The probe could be applied for monitoring and imaging of exogenous or endogenous H2S in live MCF-7 cells and in live mice with the fastest response.
- Li,Yao,Fan,Jiang,Wang,Xia,Peng
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supporting information
p. 16225 - 16228
(2015/11/16)
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- A highly selective water-soluble optical probe for endogenous peroxynitrite
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A colorimetric and fluorescent probe C-Py-1 for ONOO- was prepared and it could exhibit high sensitivity and excellent selectivity toward ONOO- among reactive oxygen species (ROS) and reactive nitrogen species (RNS) with a rapid response time in 100% water solution. Meanwhile, C-Py-1 was successfully applied in the imaging of endogenous ONOO- in RAW264.7 cells.
- Hou, Ji-Ting,Yang, Jin,Li, Kun,Liao, Ye-Xin,Yu, Kang-Kang,Xie, Yong-Mei,Yu, Xiao-Qi
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supporting information
p. 9947 - 9950
(2014/08/18)
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- Extensive reduction in back electron transfer in twisted intramolecular charge-transfer (TICT) coumarin-dye-sensitized TiO2 nanoparticles/film: A femtosecond transient absorption study
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We report the synthesis, characterization, and optical and electrochemical properties of two structurally similar coumarin dyes (C1 and C2). These dyes have been deployed as sensitizers in TiO2 nanoparticles and thin films, and the effect of molecular structure on interfacial electron-transfer dynamics has been studied. Steady-state optical absorption, emission, and time-resolved emission studies on both C1 and C2, varying the polarity of the solvent and the solution pH, suggest that both photoexcited dyes exist in a locally excited (LE) state in solvents of low polarity. In highly polar solvents, however, C1 exists in an intramolecular charge-transfer (ICT) state, whereas C2 exists in both ICT and twisted intramolecular charge-transfer (TICT) states, their populations depending on the degree of polarity of the solvent and the pH of the solution. We have employed femtosecond transient absorption spectroscopy to monitor the charge-transfer dynamics in C1- and C2-sensitized TiO2 nanoparticles and thin films. Electron injection has been confirmed by direct detection of electrons in the conduction band of TiO 2 nanoparticles and of radical cations of the dyes in the visible and near-IR regions of the transient absorption spectra. Electron injection in both the C1/TiO2 and C2/TiO2 systems has been found to be pulse-width limited (2 system than in the C1/TiO2 system. The involvement of TICT states in C2 is solely responsible for the higher electron injection yield as well as the slower BET process compared to those in the C1/TiO2 system. Further pH-dependent experiments on C1- and C2-sensitized TiO2 thin films have corroborated the participation of the TICT state in the slower BET process in the C2/TiO2 system.
- Debnath, Tushar,Maity, Partha,Lobo, Hyacintha,Singh, Balvant,Shankarling, Ganapati S.,Ghosh, Hirendra N.
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supporting information
p. 3510 - 3519
(2014/04/03)
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- Lighting up fluoride ions in cellular mitochondria using a highly selective and sensitive fluorescent probe
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We report a highly selective and sensitive fluorescent probe (FP) for detecting fluoride ions, for the first time, lighting up the fluoride ions in mitochondria with a strong green fluorescence. FP could be easily prepared as fluoride paper test strips to detect fluoride ions in aqueous solutions with a detection limit as low as 19 ppb.
- Zhang, Shiling,Fan, Jiangli,Zhang, Shuangzhe,Wang, Jingyun,Wang, Xianwu,Du, Jianjun,Peng, Xiaojun
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supporting information
p. 14021 - 14024
(2015/02/19)
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- Rational design and efficient synthesis of a fluorescent-labeled jasmonate
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A fluorescent-labeled jasmonate was rationally designed based on examination of the model of interaction between the jasmonate and its receptor. An efficient synthetic route has been developed for this molecule. The biological activity of this fluorescent probe was retained which was similar to that of the methyl jasmonate as examined by root growth inhibition bioassay. This fluorescent probe will greatly facilitate biological studies of jasmonates through fluorescent imaging.
- Liu, Songbai,Wang, Wu-Hong,Dang, Ya-Li,Fu, Yuanqing,Sang, Ruocheng
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supporting information; experimental part
p. 4235 - 4239
(2012/09/07)
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- Ruthenium(II)-polyimine-coumarin light-harvesting molecular arrays: Design rationale and application for triplet-triplet-annihilation-based upconversion
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RuII-bis-pyridine complexes typically absorb below 450 nm in the UV spectrum and their molar extinction coefficients are only moderate (Iμ-1cm-1). Thus, Ru II-polyimine complexes that show intense visible-light absorptions are of great interest. However, no effective light-harvesting ruthenium(II)/organic chromophore arrays have been reported. Herein, we report the first visible-light-harvesting RuII-coumarin arrays, which absorb at 475 nm (Iμ up to 63300M-1cm-1, 4-fold higher than typical RuII-polyimine complexes). The donor excited state in these arrays is efficiently converted into an acceptor excited state (i.e., efficient energy-transfer) without losses in the phosphorescence quantum yield of the acceptor. Based on steady-state and time-resolved spectroscopy and DFT calculations, we proposed a general rule for the design of Ru II-polypyridine-chromophore light-harvesting arrays, which states that the 1IL energy level of the ligand must be close to the respective energy level of the metal-to-ligand charge-transfer (MLCT) states. Lower energy levels of 1IL/3IL than the corresponding 1MLCT/3MLCT states frustrate the cascade energy-transfer process and, as a result, the harvested light energy cannot be efficiently transferred to the acceptor. We have also demonstrated that the light-harvesting effect can be used to improve the upconversion quantum yield to 15.2% (with 9,10-diphenylanthracene as a triplet-acceptor/annihilator), compared to the parent complex without the coumarin subunit, which showed an upconversion quantum yield of only 0.95%. Copyright
- Wu, Wanhua,Ji, Shaomin,Wu, Wenting,Shao, Jingyin,Guo, Huimin,James, Tony D.,Zhao, Jianzhang
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supporting information; scheme or table
p. 4953 - 4964
(2012/06/04)
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- Development of an ICT-based ratiometric fluorescent hypochlorite probe suitable for living cell imaging
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We have judiciously constructed a novel ICT-based ratiometric OCl - probe capable of ratiometric imaging in the live cells based on the new OCl--promoted de-diaminomaleonitrile reaction. The Royal Society of Chemistry 2011.
- Yuan, Lin,Lin, Weiying,Song, Jizeng,Yang, Yueting
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supporting information; experimental part
p. 12691 - 12693
(2012/01/12)
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- Two-photon uncaging with fluorescence reporting: Evaluation of the o-hydroxycinnamic platform
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This paper evaluates the ohydroxycinnamic platform for designing efficient caging groups with fluorescence reporting upon one- and two-photon excitation. The model cinnamates are easily prepared in one step by coupling commercial or readily available synthons. They exhibit a large one-photon absorption that can be tuned in the near-UV range. Uncaging after one-photon excitation was investigated by 1H NMR, UV-vis absorption, and steady-state fluorescence emission. In the whole investigated series, the caged substrate is quantitatively released upon photolysis. At the same time, uncaging releases a strongly fluorescent coproduct that can be used as a reporter for quantitative substrate delivery. The quantum yield of double bond photoisomerization leading to uncaging after one-photon absorption mostly lies in the 10% range. Taking advantage of the favorable photophysical properties of the uncaging coproduct, we use a series of techniques based on fluorescence emission to measure the action uncaging cross sections with two-photon excitation of the present cinnamates. Exhibiting values in the 1-10 GM range at 750 nm, they satisfactorily compare with the most efficient caging groups reported to date. Noticeably, the uncaging behavior with two-photon excitation is retained in vivo as suggested by the results observed in living zebrafish embryos. Reliable structure property relationships were extracted from analysis of the present collected data. In particular, the careful kinetic analysis allows us to discuss the relevance of the ohydroxycinnamic platform for diverse caging applications with one- and two-photon excitation.
- Gagey, Nathalie,Neveu, Pierre,Benbrahim, Chouaha,Goetz, Bernard,Aujard, Isabelle,Baudin, Jean-Bernard,Jullien, Ludovic
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p. 9986 - 9998
(2008/02/12)
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- A fluorogenic dye activated by the Staudinger ligation
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Specific labeling of biomolecules with biochemical and biophysical probes is a central element of proteomics research. Here we describe a coumarin-phosphine dye that undergoes activation of coumarin fluorescence upon Staudinger ligation with azides. Since azides can be metabolically incorporated into cellular proteins and oligosaccharides, this dye may be a useful tool for profiling proteins and their posttranslational modifications. Copyright
- Lemieux, George A.,De Graffenried, Christopher L.,Bertozzi, Carolyn R.
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p. 4708 - 4709
(2007/10/03)
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- Isoquinoline compound melanocortin receptor ligands and methods of using same
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The invention relates to melanocortin receptor ligands and methods of using the ligands to alter or regulate the activity of a melanocortin receptor. The invention further relates to tetrahydroisoquinoline aromatic amines that function as melanocortin receptor ligands and as agents for controlling cytokine-regulated physiologic processes and pathologies, and combinatorial libraries thereof.
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- Chemiluminescence of Organic Peroxides: Intramolecular Electron-Exchange Luminescence from a Secondary Perester
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The reaction of an aminocoumarincarboxylic acid chloride (Coumarin 343) with 1-phenethyl hydroperoxide results in light emission that is easily detected with the unaided eye.This reaction proceeds through a secondary perester intermediate.Intramolecular electron exchange, modeled after the analogous process in the bioluminescence of the firefly, is proposed as the mechanism for light generation.Attempts to carry out this reaction under conditions where the coumarin acid is recycled were not successful.
- Gompel, Joseph Van,Schuster, Gary B.
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p. 1465 - 1468
(2007/10/02)
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- KETOCOUMARINS. A NEW CLASS OF TRIPLET SENSITIZERS
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Several derivatives of 3-ketocoumarins were prepared and are shown to have many of the photophysical criteria required for efficient triplet sensitizers.These compounds include 3-aroylcoumarins (1) and 3,3'-carbonyl-biscoumarins (2).The aryl groups in 1 are either phenyl and substituted phenyl derivatives or heterocyclic groups such as thienyl and benzofuryl.The substituents on the coumarin moiety in 1 and 2, if any, are alkoxy or dialkylamino.These compounds, with absorption maxima between 330 and 450 nm, have extinction coefficients in the range of 1E4 to almost 1E5, which is an important criterion for efficient sensitization of thin films of polymers as those used in photoresists and litography.The singlet-triplet intersystem crossing (isc) efficiencies of several derivatives approach unity.In others, however, a radiationless decay process competes with the isc.The decay process is particularly dominant in the assymetrically substituted derivatives of 2, but seems to be considerably supressed in polymeric matrices.The triplet energies of these compounds range from ca. 48 to 60 kcal/mol.Some of these ketocoumarins show phosphorescence spectra that suggest the presence of "frozen-in" rotamers.
- Specht, Donald P.,Martic, Peter A.,Farid, Samir,++
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p. 1203 - 1211
(2007/10/02)
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