- Rhodamine-based 'turn-on' fluorescent probe for Cu(II) and its fluorescence imaging in living cells
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A novel rhodamine spirolactam derivative 3′,6′- Bis(diethylamino)-2-(2-hydroxyethylamino) spiro[isoindoline-1,9′-xanthen]- 3-one (RO1) was synthesized, and characterized by high-resolution mass spectrometry (HRMS), X-ray crystallography, Infrared spectroscopy (IR), and 1H NMR and 13C NMR spectroscopy. RO1 exhibited highly sensitive and exclusively selective fluorescence response toward Cu2+ over other metal ions with a detection limit of 0.56 ppb in mixed aqueous solution. The fluorescence was pH-independent in the wide range pH 3.1-11.6. The turn-on fluorescence enhancement of the probe is based on Cu2+ induced ring-opening mechanism of the rhodamine spirolactam. Moreover, by means of fluorescence microscopy experiments, it was demonstrated that RO1 could monitor trace Cu2+ changes by live cell imaging.
- Tian, Mao-Zhong,Hu, Ming-Ming,Fan, Jiang-Li,Peng, Xiao-Jun,Wang, Jing-Yun,Sun, Shi-Guo,Zhang, Rong
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- Perimedine-linked rhodamine dye in visual sensing of Al3+, Fe3+ and Fe2+ ions in aqueous organic medium under different experimental conditions
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Perimedine labelled rhodamine dye 1 has been designed and synthesised. Metal ion binding studies of 1 have been performed in CH3CN/H2O (3:1, v/v, 10 mM Tris-HCl buffer, pH = 6.90). Compound 1 senses multiple metal ions such as Al3+, Fe3+ and Fe2+ by exhibiting turn on fluorescence and colour change (colourless to pink) under different experimental conditions. Concentration variation distinguishes Al3+ from Fe3+ ion. At low concentration (c = 1 x 10?4 M), only Al3+ ion can exhibit turn on fluorescence with sharp colour change. Sensing of Fe2+ ion through turn on fluorescence and colour change has been possible via in situ oxidation by following Fenton’s reaction.
- Mondal, Subhendu,Ghosh, Kumaresh
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- Development of a rhodamine-benzimidazol hybrid derivative as a novel FRET based chemosensor selective for trace level water
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A newly designed rhodamine-benzimidazol hybrid molecule has been developed as a FRET-based chemosensor for the selective detection of trace level water in both polar protic and aprotic organic solvents. This journal is the Partner Organisations 2014.
- Pal, Siddhartha,Mukherjee, Manjira,Sen, Buddhadeb,Lohar, Somenath,Chattopadhyay, Pabitra
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- Rapid and selective visualization of mitochondrial hypochlorite by a red region water-soluble fluorescence probe
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Hypochlorite (?OCl) has long been recognized as an effective microbicidal agent in immune system. Herein, we report the design, preparation and spectral characteristics of a ?OCl fluorescent probe (FI-Mito). The probe exhibited remarkable fluorescence turn-on signal in the red region upon ?OCl titration with the detection limit as low as 0.9 nM. FI-Mito displayed specific response for ?OCl in completely aqueous solution. Meanwhile, the introduction of quaternized pyridine realized mitochondria-targeting ability. FI-Mito was further applied to monitor the generation of endogenous ?OCl in the mitochondria of macrophage cells and mice. Therefore, it was established that FI-Mito may serve as a useful molecular tool for ?OCl detection in vivo.
- Cao, Xiao-Qun,Huang, Xiao-Qing,Shen, Shi-Li,Wang, Tian-Ran,Zhang, Xiao-Fan
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- Purification of rhodamine B by alcohol-modified air bubble flotation
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A simple and rapid method for the purification of a basic dye, Rhodamine B (RB) was developed. It was conducted by adding crude RB to an aqueous solution containing 0.2% (v/v) ethanol followed by air bubble flotation in a cylindrical glass vessel having a sintered glass filter at the bottom. By feeding air bubbles, RB was enriched into foam on the water surfaces within 3min, while source materials (phthalic acid and N,Ndiethyl-3-aminophenol), intermediate compound {2-(4-diethyl-amino-2-hydroxybenzoyl)}, and other organic impurities remained in the bulk aqueous solution. The foam containing enriched RB was taken up with suction and placed into another flotation vessel for repeated separation. An HPLC-grade RB was successfully obtained by 3-fold air bubble flotation.
- Kodama, Koki,Oiwa, Mako,Saitoh, Tohru
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p. 1210 - 1214
(2021/05/17)
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- A turn-on fluorescent and colorimetric chemodosimeter for selective detection of Au3+ ions in solution and in live cells: Via Au3+-induced hydrolysis of a rhodamine-derived Schiff base
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A chromogenic and off-on fluorogenic chemodosimeter (L) based on a naphthalene-rhodamine B derivative was designed, synthesized and characterized for the selective and sensitive detection of Au3+ ions in mixed acetonitrile aqueous medium in the presence of other competitive analytes. Probe L displayed a 696-fold turn-on fluorescence signal enhancement toward Au3+ ions with the detection limit of Au3+ of about 1.51 μM. In the presence of Au3+ ions, probe L also exhibited a visible color change from colorless to pink that could be easily identified by the naked eye. This colorimetric and fluorometric changes were mainly due to the Au3+ ion-triggered imine bond (CN) hydrolysis sensing mechanism. Moreover, theoretical calculations were performed to explain the experimental results. In addition to these features, the off-on probe was successfully used to monitor intracellular Au3+ ions in living MC3T3 cells through fluorescence imaging.
- Datta, Pallab,Ghosh, Aritri,Mandal, Debasish,Manna, Saikat Kumar,Mondal, Sanchita,Mukhopadhyay, Subrata,Pathak, Sudipta
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p. 7954 - 7961
(2020/06/17)
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- Based on rhodamine B derivatives of the fluorescent probe and its preparation method and application
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The invention provides a fluorescence probe based on a rhodamine B derivative as well as a preparation method and application thereof. The chemical structure formula of the rhodamine B derivative is shown as the specification. The rhodamine B derivative can be selectively combined with bivalent copper ions, and is changed into red color from no color; the fluorescence probe has a fluorescence enhanced effect and can realize naked-eye distinguishing detection, particularly the application of the fluorescence probe to the convenient detection of the copper ions in cells.
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Paragraph 0032-0034
(2017/08/25)
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- XANTHENE-BASED PURPLE DYE COMPOUND, COLORING RESIN COMPOSITION FOR COLOR FILTER CONTAINING SAME AND COLOR FILTER USING SAME
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The present disclosure relates to a purple dye compound for a color filter and a coloring resin composition for a color filter containing the same. The novel xanthene-based purple dye compound or the polymer dye compound obtained using the same as a monomer has superior solvent resistance and superior miscibility with a pigment in an organic solvent. Further, it exhibits superior heat resistance, chemical resistance, light resistance and brightness due to the homopolymer structure. Accordingly, a coloring resin composition containing the same can be used widely as a dye for synthetic resins and synthetic fibers, as a coloring agent for polymer materials, for a color filter used in LCDs, PDPs, etc., and so forth.
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Paragraph 0064
(2015/11/30)
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- Rhodamine derived colorimetric and fluorescence mercury(ii) chemodosimeter for human breast cancer cell (MCF7) imaging
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Condensation of rhodaminehydrazone with naphthalene-1-carboxaldehyde generates a colourless probe, RDHDNAP that can selectively detect Hg2+ through generation of a pink color along with significant fluorescence enhancement. The binding constant and lowest detection limit for Hg2+ are 2.0 × 105 M-1 and 3 × 10-7 M respectively. Hg2+ imaging in human breast cancer cells (MCF7) under a fluorescence microscope is achieved. This journal is
- Kumari, Babli,Lohar, Sisir,Adhikari, Sangita,Sengupta, Archya,Chattopadhyay, Ansuman,Brand?o, Paula,Félix, Vítor,Das, Debasis
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p. 21797 - 21802
(2015/03/30)
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- A rhodamine-quinoline based chemodosimeter capable of recognising endogenous OCl- in human blood cells
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A rhodamine-quinoline based chemodosimeter (RHQ) has been designed, synthesized and characterized in this paper. The structure of the sensor is confirmed through single crystal X-ray study. It detects hypochlorite (OCl -) selectively among other analytes studied. It showed colorimetric and orange-red fluorescence "turn-on" upon addition of OCl -. The OCl--promoted ring opening of the rhodamine spirolactam ring in RHQ evokes a large absorbance as well as fluorescence enhancement in water-acetonitrile (1/1, v/v) medium with no significant response to other competitive analytes. Furthermore, we demonstrate here that RHQ can endogenously detect OCl- in human blood cells (peripheral blood mononuclear cells). It also exhibits excellent performance in the "dip stick" method. The optimized structure of the probe is calculated by density functional theory calculations. Moreover, the limit of detection of the probe is in the 10-8 M range.
- Goswami, Shyamaprosad,Das, Sangita,Aich, Krishnendu,Nandi, Prasanta Kumar,Ghoshal, Kakali,Quah, Ching Kheng,Bhattacharyya, Maitree,Fun, Hoong-Kun,Abdel-Aziz, Hatem A.
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p. 24881 - 24886
(2014/07/07)
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- Rhodamine-pyrene conjugated chemosensors for ratiometric detection of Hg2+ ions: Different sensing behavior between a spirolactone and a spirothiolactone
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Two novel rhodamine-pyrene conjugated chemosensors were successfully designed and synthesized, which exhibited high affinity to Hg2+ ions. As ratiometric chemosensors, each displayed highly selective and sensitive colorimetric and fluorogenic dual-responses toward Hg2+. The comparison of two chemosensors indicated that the spirothiolactone containing sensor was superior to the spirolactone analog in sensing behavior when detecting Hg2+, presumably due to the thiophilic nature of mercury and the different sensing mechanisms in operation. Upon interaction with Hg 2+, the spirothiolactone showed a 1:1 stoichiometry for the Hg 2+ complex, accompanied with a weakened fluorescence resonance energy transfer (FRET) behavior. However, the spirolactone was hydrolyzed and consequently induced the monomer-excimer switch of the resulted pyrene in the presence of Hg2+ ions.
- Chu, Kai-Hui,Zhou, Yi,Fang, Yuan,Wang, Li-Hong,Li, Ju-Ying,Yao, Cheng
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p. 339 - 346
(2013/07/19)
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- Substractive single label comparative hybridization
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Provided are methods of determining differences between nucleic acids in a test sample and a reference sample. In certain embodiments the methods are used for detecting and mapping chromosomal or genetic abnormalities associated with various diseases or with predisposition to various diseases, or to detecting the phenomena of large scale copy number variants. In particular, provided are advanced methods of performing array-based comparative hybridization that allow reproducibility between samples and enhanced sensitivity by using the same detectable label for both test sample and reference sample nucleic acids. Invention methods are useful for the detection or diagnosis of particular disease conditions such as cancer, and detecting predisposition to cancer based on detection of chromosomal or genetic abnormalities and gene expression level. Invention methods are also useful for the detection or diagnosis of hereditary genetic disorders or predisposition thereto, especially in prenatal samples. Moreover, invention methods are also useful for the detection or diagnosis of de novo genetic aberrations associated with post-natal developmental abnormalities.
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- Fluorogenic and chromogenic rhodamine spirolactam based probe for nitric oxide by spiro ring opening reaction
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(Chemical Equation Presented) A new fluorogenic and chromogenic probe rhodamine B spirolactam (1) was developed that in aqueous solutions exhibited a highly selective and sensitive turn-on type spectral response toward NO detection following a NO-induced spiro-ring opening reaction in 1.
- Zheng, Hong,Shang, Gui-Qin,Yang, Shi-Yao,Gao, Xia,Xu, Jin-Gou
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supporting information; body text
p. 2357 - 2360
(2009/05/27)
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- Oligonucleotides comprising a molecular switch
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This invention relates to oligonucleotides comprising a molecular switch which may exist in an “open” or “closed” position. The molecular switch portion of the probe is particularly sensitive to the identity of sequences complementary to the molecular switch. Oligonucleotides containing a molecular switch are applicable to all kinds of hybridization processes. Due to the sensitivity of the switch domain of the oligonucleotide, probes containing a molecular switch are particularly useful in the identification of single point mismatches. More specifically, a portion, but not all, of the oligonucleotide becomes unbound from a mismatched target. The invention further relates to methods of using said oligonucleotides for research reagents, and clinical diagnostics. An exemplary oligonucleotide comprises a first hybridizable domain, a second bridging block domain, and a third binding domain.
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- Activatable probes and methods for in vivo gene detection
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Probes for detecting a target polynucleotide are provided. One aspect provides a molecular beacon probe set wherein the donor molecular beacon comprises a quantum dot and an acceptor molecular beacon comprises at least one reporter. The probes optionally comprise a protein transduction domain, targeting signal, or a combination thereof. Methods for detecting target polynucleotides using the disclosed probes are also provided.
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- Dual resonance energy transfer nucleic acid probes
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Dual nucleic acid probes with resonance energy transfer moieties are provided. In particular, fluorescent or luminescent resonance energy transfer moieties are provided on hairpin stem-loop molecular beacon probes that hybridize sufficiently near each other on a subject nucleic acid, e.g. mRNA, to generate an observable interaction. The invention also provides lanthanide chelate luminescent resonance energy transfer moieties on linear and stem-loop probes that hybridize sufficiently near each other on a subject nucleic acid to generate an observable interaction. The invention thereby provides detectable signals for rapid, specific and sensitive hybridization determination in vivo. The probes are used in methods of detection of nucleic acid target hybridization for the identification and quantification of tissue and cell-specific gene expression levels, including response to external stimuli, such as drug candidates, and genetic variations associated with disease, such as cancer.
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- Nucleic acid amplification oligonucleotides with molecular energy transfer labels and methods based thereon
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The present invention provides labeled nucleic acid amplification oligonucleotides, which can be linear or hairpin primers or blocking oligonucleotides. The oligonucleotides of the invention are labeled with donor and/or acceptor moieties of molecular energy transfer pairs. The moieties can be fluorophores, such that fluorescent energy emitted by the donor is absorbed by the acceptor. The acceptor may be a fluorophore that fluoresces at a wavelength different from the donor moiety, or it may be a quencher. The oligonucleotides of the invention are configured so that a donor moiety and an acceptor moiety are incorporated into the amplification product. The invention also provides methods and kits for directly detecting amplification products employing the nucleic acid amplification primers. When labeled linear primers are used, treatment with exonuclease or by using specific temperature eliminates the need for separation of unincorporated primers. This "closed-tube" format greatly reduces the possibility of carryover contamination with amplification products, provides for high throughput of samples, and may be totally automated.
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- Photoactivatable compositions and to methods for the diagnosis and treating medical conditions
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A broad class of photosensitive compounds having enhanced in vivo target tissue selectivity and versatility in photodynamic therapy. Many furocoumarin compounds, such as psoralens, exhibit cytostatic activity when photoactivated but exhibit little in vivo specificity for selectively accumulating in any particular target tissue such as atheromatous plaques. Reactive Oxygen Producing Photosensitizers ("ROPPs") are photoactivatable compounds having an affinity for hyperproliferating cells (such as atheromatous plaque cells), which when photoactivated, produce cytotoxic reaction products. The photoactivity of a ROPP, such as a porphyrin, may be reduced by metalating the porphyrin while the selective affinity of the metalized ROPP for hyperproliferating tissue remains substantially unchanged. By linking a furocoumarin compound to a ROPP to form a F-ROPP, the cytostatic properties of the furocoumarin portion of the F-ROPP can be exploited while the selective affinity of the ROPP portion of the compound for hyperproliferating cells such as atheromatous plaque provides enhanced tissue selectivity without cytotoxicity. In vivo, certain F-ROPPs may be forced to selectively accumulate in a target tissue by illuminating only the target tissue with light having a wavelength operable for photoactivating the F portion of the F-ROPP thereby causing the F-ROPP to either form a monoadduct with or crosslink the cellular DNA in the target tissue. Light of a second wavelength can then be delivered to the target tissue to photoactivate the ROPP portion causing further interference with cellular activity.
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- Process for the preparation of rhodamines
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A process for preparing rhodamines represented by the following general formula (I) or (II): wherein R1, R2, and R3 are independently hydrogen or a lower alkyl, group, but R1 and R2 are not both hydrogen which comprises subjecting phthalic anhydride and N-substituted-m-aminophenols represented by the following general formula (III): wherein R1, R2, and R3 have the above-described meanings, to condensation reaction in one or more organic solvents selected from the group consisting of halogentated and/or alkylated aromatic hydrocarbons or aliphatic hydrocarbons.
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