- Switching of C-C and C-N Coupling/Cleavage for Hypersensitive Detection of Cu2+by a Catalytically Mediated 2-Aminoimidazolyl-Tailored Six-Membered Rhodamine Probe
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A robust six-membered rhodamine spirocyclic probe 1 containing a versatile 2-aminoimidazolyl moiety was elaborately designed and synthesized via an attractive C-C and C-N coupling strategy to improve the performance in the detection of ultralow transition
- Yang, Lin-Lin,Tang, A-Ling,Wang, Pei-Yi,Yang, Song
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- Highly sensitive and fast responsive fluorescence turn-on chemodosimeter for Cu2+ and its application in live cell imaging
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A rhodamine B derivative 4 containing a highly electron-rich S atom has been synthesized as a fluorescence turn-on chemodosimeter for Cu2+. Following Cu2+-promoted ring-opening, redox and hydrolysis reactions, comparable amplifications of absorption and fluorescence signals were observed upon addition of Cu2+; this suggests that chemodosimeter 4 effectively avoided the fluorescence quenching caused by the paramagnetic nature of Cu2+. Importantly, 4 can selectively recognize Cu2+ in aqueous media in the presence of other trace metal ions in organisms (such as Fe3+, Fe2+, Cu+, Zn2+, Cr 1+, Mn2+, Co2+, and Ni2+), abundant cellular cations (such as Na+, K+, Mg2+, and Ca2+), and the prevalent toxic metal ions in the environment (such as Pb2+ and Cd2+) with high sensitivity (detection limit ≤10ppb) and a rapid response time (≤1 min). Moreover, by virtue of the chemodosimeter as fluorescent probe for Cu2+, confocal and two-photon microscopy experiments revealed a significant increase of intracellular Cu 2+ concentration and the subcellular distribution of Cu2+, which was internalized into the living HeLa cells upon incubation in growth medium supplemented with 50 μM CuCl2 for 20 h.
- Yu, Mengxiao,Shi, Mei,Chen, Zhigang,Li, Fuyou,Li, Xinxin,Gao, Yanhong,Xu, Jia,Yang, Hong,Zhou, Zhiguo,Yi, Tao,Huang, Chunhui
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- A rhodamine based fluorescent chemodosimeter for the selective and sensitive detection of copper (II) ions in aqueous media and living cells
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A rhodamine-based fluorescent probe, integrated with phosphonate group, demonstrated highly selective and sensitive recognition towards copper (II) ions over other metal species. Operating via ring opening reaction, the probe molecule (RhP) offered extensive properties such as “turn-on” fluorescence response, naked-eye detection, low detection limit (15 nM) and fast response time (a biological application is also successfully reported.
- Karaku?, Erman
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- A Highly Sensitive Fluorescent Sensor for Palladium and Direct Imaging of Its Ecotoxicity in Living Model Organisms
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Rhodamine is an ideal platform for fluorescence probes owing to its spiro-lactam framework and excellent photochemical properties. Herein, a novel rhodamine-based palladium fluorescent chemosensor, Rd-Eb, showing a fast response time (3 min), high sensitivity for palladium species over other ions, and a low detection limit (1.91×10-7 m), was synthesized. It can act as an obvious colorimetric as well as a fluorescent "off/on" sensor for Pd2+. In addition, it is also an excellent sensor for in vivo imaging of Pd2+ in zebra fish and Daphnia magna, illuminating the impact of palladium on organisms at different growth stages with respect to biological toxicology.
- Liu, Fei,Du, Juan,Xu, Meiying,Sun, Guoping
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- One-pot synthesis of new acid photogenerators for Rhodamine laser dyes fluorescence activation
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New aryl(hetaryl)pyrazolines fitted for fluorescence activation of Rhodamine laser dyes have been obtained via one-pot tandem Michael addition of two arylhydrazine molecules with 2-(4′-R-cinnamyliden)-2Н-furo[3,2-?]coumarin-3-ones. These aryl(hetaryl)pyra
- Traven, Valerii F.,Pozharskaya, Natalya A.,Solovjova, Natalya P.,Novikov, Roman A.,Medvedev, Michael G.,Chernyshev, Vladimir V.,Dolotov, Sergei M.,Ivanov, Ivan V.
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- Solvatochromism and thermochromism of rhodamine solutions
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Electronic absorption spectra of rhodamine B have been examined in 16 protic and 14 aprotic solvents.Rhodamine B exists in solution as a highly colored zwitterion, a colorless lactone and an intensely colored cation.Protic solvents stabilize the zwitterion: the position of the lactone-zwitterion equilibrium depends upon solvent-dye hydrogen bonding and solvent dielectric/polarizability properties.From its temperature dependencene, thermodynamic parameters (ΔG0, ΔH0, ΔS0) for this equilibrium were determined in water, n-propanol and n-octanol.The zwitterion is not stable in aprotic solvents, in which the cation or lactone is favored according to the acidity or basicity of the medium.Absorption spectra of rhodamine 6G, an esterfied dye which does not exhibit the above equilibria, are only modestly altered by most variations of solvent and temperature.
- Hinckley, Daniel A.,Seybold, Paul G.,Borris, David P.
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- A Fluorogenic ONOO--Triggered Carbon Monoxide Donor for Mitigating Brain Ischemic Damage
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Ischemia-reperfusion (I/R) injuries are from the secondary radicals of ONOO-. Direct radical scavenging is difficult because of their high reactivity. ONOO- is longer-lived than the radicals in the biological milieu. Scavenging ONOO- suppresses radical generation preventively. CO is neuroprotective during ischemia. With the scaffold of carbon-caged xanthene, we designed an OONO-triggered CO donor (PCOD585). Notably, PCOD585 exhibited a concomitant fluorescence turn-on upon ONOO-detection, facilitating microscopic monitoring. PCOD585 was cytoprotective in oxygen-glucose deprivation (OGD)-insulted PC-12 cells. It was permeable to the blood-brain barrier and further exhibited neuroprotective effects to MCAO rats by reducing infarction volume, cell apoptosis, and brain edema.
- Chen, Xiaohua,Guo, Xinjian,Li, Jin,Lu, Xicun,Luo, Xiao,Qi, Suhua,Qian, Xuhong,Sun, Haitao,Sun, Zhenrong,Wang, Bin,Xing, Linfeng,Yang, Youjun
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- Rhodamine hydrazide derivative and method for detecting copper and hypochlorite using the same
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The present invention relates to a rhodamine hydrazide derivative and a method of detecting copper and hypochlorite by using the same, wherein the rhodamine hydrazide derivative is developed as a fluorescent turn-on probe for detecting Cu^2+ and ClO^- ions. In the presence of Cu^2+ and ClO^- ions, the probe exhibits a fluorescence turn-on signal showing color change from colorlessness to pink color at 587 nm. Therefore, the Rhodamine hydrazide derivative of the present invention is capable of easily detecting Cu^2+ and ClO^- ions at the same time, thereby being widely used in chemical, biological and environmental engineering processes.COPYRIGHT KIPO 2019
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Paragraph 0016; 0065-0068; 0070-0073
(2019/08/27)
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- Rhodamine derivative, method for preparing the same and method for detecting Cu(Ⅱ) ion using the same
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The present invention relates to a rhodamine derivative, a method for preparing the same, and a method for detecting Cu(ii) ion using the same. According to the present invention, the rhodamine derivative can detect Cu^2+ ions by the hydrolysis of acyl-hy
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(2018/03/13)
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- Synthesis, chemical reactivity, and photophysical properties of 2′,7′ phenylated rhodamine dyes
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While exploring water soluble rhodamine based fluorescent polymeric systems for biological imaging applications we came across new rhodamine derivatives that possess interesting optical properties. We report the synthesis of three different 2′,7′-diphenylated rhodamine derivatives (1-3) with distinct photophysical properties. The three rhodamine derivatives differ by the number of methyl groups present on the nitrogens and their absorption maxima are red-shifted on increased methylation. We observed an unusual inertness of these compounds toward traditional DCC-DMAP esterification conditions, which we attribute to the ease of lactonization in the presence of even minute amounts of the nucleophile/base DMAP (pKa = 9.2). Synthesis of acrylate esters was successfully accomplished using MSNT (1-(Mesitylene-2-sulfonyl)-3-nitro-1,2, 4-triazole) coupling conditions using a much milder nucleophile/base, for example, N-methyl imidazole (pKa = 6.95).
- Natarajan, Arunkumar,Boden, Eugene P.,Burns, Andrew,McCloskey, Patrick J.,Rishel, Michael J.
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p. 4222 - 4226
(2014/07/22)
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- Bioimaging of peroxynitrite in MCF-7 Cells by a new fluorescent probe rhodamine b phenyl hydrazide
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Peroxynitrite is a potent oxidizing and nitrating agent which has detrimental effects on cells by altering the structure and function of biomolecules present within. A fluorescent probe rhodamine B phenyl hydrazide (RBPH) has been proposed for peroxynitrite (ONOO-) imaging in MCF-7 cells based on its oxidation property, which converts RBPH to pink colored and highly fluorescent rhodamine B. The fluorescence emission intensity of the rhodamine B produced in the above process is linearly related to the concentration of peroxynitrite. The method obeys Beer's law in the concentration range 2-20 nM and the detection limit has been found to be 1.4 nM. The possible reaction mechanism of peroxynitrite with RBPH to produce rhodamine B has been discussed with spectroscopic evidence. The Probe is selective to the peroxynitrite in the pH range 6-8 which is near physiological pH. Fluorescence microscopic studies suggest that the probe is cell permeable and hence peroxynitrite was imaged in MCF-7 cells.
- Ambikapathi, Gopi,Kempahanumakkagari, Suresh Kumar,Ramappa Lamani, Babu,Kuramkote Shivanna, Devaraju,Bodagur Maregowda, Harish,Gupta, Anushree,Malingappa, Pandurangappa
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p. 705 - 712
(2013/07/26)
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- Highly selective fluorescence turn-on chemodosimeter based on rhodamine for nanomolar detection of copper ions
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A highly selective fluorescent chemodosimeter based on rhodamine is synthesized which undergoes Cu2+ driven hydrolysis in aqueous media to produce fluorescence turn-on changes with a detection limit up to the nanomolar range.
- Kumar, Manoj,Kumar, Naresh,Bhalla, Vandana,Sharma, Parduman Raj,Kaur, Tandeep
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body text
p. 406 - 409
(2012/02/15)
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- A fast-responsive fluorescent probe for detection of gold ions in water and synthetic products
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We have constructed a fast-responsive fluorescent gold ion probe based on the unexpected gold ion-mediated hydrolysis of acylsemicarbazides to carboxylic acids. The probe has been applied for sensing gold ions in the living cells and detecting residual go
- Yuan, Lin,Lin, Weiying,Yang, Yueting,Song, Jizeng
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supporting information; experimental part
p. 4703 - 4705
(2011/06/22)
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- Activity-based proteome profiling of potential cellular targets of orlistat - An FDA-approved drug with anti-tumor activities
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Orlistat, or tetrahydrolipstatin (THL), is an FDA-approved antiobesity drug with potential antitumor activities. Cellular off-targets and potential side effects of Orlistat in cancer therapies, however, have not been extensively explored thus far. In this study, we report the total of synthesis of THL-like protein-reactive probes, in which extremely conservative modifications (i.e., an alkyne handle) were introduced in the parental THL structure to maintain the native biological properties of Orlistat, while providing the necessary functionality for target identification via the bio-orthogonal click chemistry. With these natural productlike, cell-permeable probes, we were able to demonstrate, for the first time, this chemical proteomic approach is suitable for the identification of previously unknown cellular targets of Orlistat. In addition to the expected fatty acid synthase (FAS), we identified a total of eight new targets, some of which were further validated by experiments including Western blotting, recombinant protein expression, and site-directed mutagenesis. Our findings have important implications in the consideration of Orlistat as a potential anticancer drug at its early stages of development for cancer therapy. Our strategy should be broadly useful for off-target identification against quite a number of existing drugs and/or candidates, which are also covalent modifiers of their biological targets.
- Yang, Peng-Yu,Liu, Kai,Ngai, Mun Hong,Lear, Martin J.,Wenk, Markus R.,Yao, Shao Q.
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supporting information; scheme or table
p. 656 - 666
(2010/03/25)
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- A new fluorescent chemodosimeter for Hg2+: Selectivity, sensitivity, and resistance to Cys and GSH
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[Chemical equation presented] On the basis of the mechanism of Hg 2+-promoted hydrolysis, a new fluorescent chemodosimeter (Rho-Hg1) is reported for single-selective and parts per billion level-sensitive detection of Hg2+ in natural
- Du, Jianjun,Fan, Jiangli,Peng, Xiaojun,Sun, Pingping,Wang, Jingyun,Li, Honglin,Sun, Shiguo
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scheme or table
p. 476 - 479
(2010/05/18)
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