- A new visible light triggered Arrhenius photobase and its photo-induced reactions
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Arrhenius photobases are of potential use for excited state hydroxide ion dissociation (ESHID), photo-induced pOH jump experiments, and base-catalyzed reactions. However, previously studied Arrhenius photobases have to be excited by UV light and undergo ESHID reactions only in protic solvents. These characteristics have become a disadvantage to their application in many fields of research. In this work, we have designed and synthesized a new Arrhenius photobase (NO2-Acr-OH), the ESHID reaction of which is readily triggered by visible light excitation. In contrast to previously studied Arrhenius photobases, NO2-Acr-OH undergoes ESHID reactions in protic solvents as well as in polar aprotic solvents. Solvent-dependent photo-induced reactions of NO2-Acr-OH are comprehensively studied by time-resolved fluorescence spectroscopy. Molecular designs for visible light triggered acridinol-based Arrhenius photobases with a large ΔpKb value are proposed.
- Joung, Joonyoung F.,Lee, Jeeun,Hwang, Joungin,Choi, Kihang,Park, Sungnam
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- Acridone Derivate Simultaneously Featuring Multiple Functions and Its Applications
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Compared with plenty of single-functional molecules, multifunctional molecules are scarce and have high demand in further research. In this work, a multifunctional molecule called 10-methyl-2-amino-acridone (MAA) is presented. Interestingly, MAA simultaneously features electrochemistry, two-photon fluorescence, visible-light-induced oxidase mimic, and photoelectrochemistry (PEC) activity, and the related properties are studied in detailed. Multiple functions integrated into one molecule allow MAA to become a versatile signal probe. Therefore, the MAA acted as an electrochemical indicator to detect exosomal total protein with high sensitivity at first. In addition, MAA is used for one- or two-photon fluorescence imaging in vitro and in vivo, including cells, three-dimensional (3D) tumor spheroids, zebrafish, and exosomes. The results suggest that MAA not only possesses favorable photostability, but it is also suitable for imaging in deep tissue. Furthermore, the visible-light-induced oxidase mimic and photoelectrochemical activities of MAA are selectively inhibited by Cu2+, and the relevant mechanism is carefully analyzed. On the basis of this phenomenon, we develop a dual-modal detection strategy for detection of Cu2+ in river water. Compared with a single signal readout model, this strategy is able to avoid false positive and negative detection through two series of data mutually validating each other. Therefore, our study shows that the "multiple-in-one" MAA provides a blueprint for the investigation and application of a multifunctional organic molecule.
- Xia, Yaokun,He, Wenhui,Li, Juan,Zeng, Lupeng,Chen, Tingting,Liao, Yijuan,Sun, Weiming,Lan, Jianming,Zhuo, Shuangmu,Zhang, Jing,Yang, Huanghao,Chen, Jinghua
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- SULFONATED 2(7)-AMINOACRIDONE AND 1-AMINOPYRENE DYES AND THEIR USE AS FLUORESCENT TAGS, IN PARTICULAR FOR CARBOHYDRATE ANALYSIS
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Sulfonated 2(7)-aminoacridone and 1-aminopyrene dyes and their use as fluorescent tags, in particular for carbohydrate analysis The invention relates to fluorescent dyes with multiple negatively charged groups in their ionized form which are aminoacridone
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- Fluorescent nitric oxide donor for the detection and killing of: Pseudomonas aeruginosa
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The epidemic of multidrug-resistant bacteria calls for the improvement of both detection methods for bacterial infections and methods of treatment. Nitric oxide is a known potent antibacterial agent, but due to its gaseous and highly reactive nature, it is difficult to incorporate into a stable antibacterial compound. In this paper, we synthesize a nitric oxide donor attached to a fluorescent compound, creating a material that can both detect and kill the deadly multi-drug resistant bacteria strain Pseudomonas aeruginosa. Detection occurs through a bacterial enzyme-activated color change, showing a clear and obvious change from blue to yellow under UV light. The synthesized compound spontaneously releases 853 μmol of nitric oxide/g from a 10 mM initial concentration. Antibacterial efficacy studies after exposing Pseudomonas aeruginosa to a 10 mM dose of the synthesized compound show a 55-75% reduction in bacteria after 24 hours. This work is the first instance of a small molecule dual-function material that can both detect and kill bacteria.
- Hibbard, Hailey A. J.,Reynolds, Melissa M.
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supporting information
p. 2009 - 2018
(2019/03/26)
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- Two-photon fluorescent probe 10-methyl-2-amino-acridone as well as preparation method and application thereof
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The invention discloses two-photon fluorescent probe 10-methyl-2-amino-acridone as well as a preparation method and application thereof. The 10-methyl-2-amino-acridone is used as a fluorescent probe and is used for living imaging of cells and zebra fishes. The structural formula of the 10-methyl-2-amino-acridone is shown in the description. The compound has good water solubility; emission wavelength of the compound is a green light wave band; with good two-photon activity, bioautofluorescence and self-absorption can be well reduced, and the compound is successfully applied to imaging of the cells and the zebra fishes; meanwhile, the compound has good electrochemical activity, and is expected to be applied to the field of electrochemical sensing as a novel electro-active indicator.
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Paragraph 0014
(2017/11/30)
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- Synthesis of o -(dimethylamino)aryl ketones, acridones, acridinium salts, and 1 H -indazoles by the reaction of hydrazones and arynes
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A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.
- Dubrovskiy, Anton V.,Larock, Richard C.
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p. 11232 - 11256
(2013/02/23)
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- Nitration of the Acetanilide-type Compounds
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Some aromatic compounds containing the imino group (NH) were nitrated in acetic acid or anhydride, and the ortho/para ratios were measured.N-Methyl derivatives of the aforementioned compounds are much less reactive when nitrated under comparable conditions and give significantly lower o/p ratios.These results along with the literature data support the hypothesis that the acetanilide-type compounds are nitrated via N-nitro intermediates.
- Daszkiewicz, Zdzislaw,Kyziol, Janusz B.
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- The Preparation of Some 2-Nitroacridines and Related Compounds
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The reaction of 2-fluoro-5-nitrobenzaldehyde with a wide variety of arylamines gives, in general, mixtures of the corresponding 2-arylamino-5-nitrobenzaldehydes and their related anils.Both aldehydes and anils readily underwent acid-catalysed cyclization to give the corresponding 2-nitroacridines.The effect of substituent on the rate of cyclization of these aldehydes and of some related anilino-benzaldehydes and -acetophenones has been studied in trifluoroacetic acid solution by means of 1H n.m.r. spectroscopy.A solution of 2-(N-methylanilino)-5-nitrobenzaldehydein trifluoroacetic acid appears to contain a substituted acridinium ion; treatment of this solution with alkali gave 10-methyl-2-nitroacridone. 1H n.m.r. data for a wide variety of substituted 2-nitroacridines are discussed.
- Rosevear, Judi,Wilshire, John F. K.
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p. 839 - 853
(2007/10/02)
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