10441-41-5Relevant articles and documents
Development of Targetable Two-Photon Fluorescent Probes to Image Hypochlorous Acid in Mitochondria and Lysosome in Live Cell and Inflamed Mouse Model
Yuan, Lin,Wang, Lu,Agrawalla, Bikram Keshari,Park, Sung-Jin,Zhu, Hai,Sivaraman, Balasubramaniam,Peng, Juanjuan,Xu, Qing-Hua,Chang, Young-Tae
, p. 5930 - 5938 (2015)
Hypochlorous acid (HOCl), as a highly potent oxidant, is well-known as a key "killer" for pathogens in the innate immune system. Recently, mounting evidence indicates that intracellular HOCl plays additional important roles in regulating inflammation and cellular apoptosis. However, the organelle(s) involved in the distribution of HOCl remain unknown, causing difficulty to fully exploit its biological functions in cellular signaling pathways and various diseases. One of the main reasons lies in the lack of effective chemical tools to directly detect HOCl at subcellular levels due to low concentration, strong oxidization, and short lifetime of HOCl. Herein, the first two-photon fluorescent HOCl probe (TP-HOCl 1) and its mitochondria- (MITO-TP) and lysosome- (LYSO-TP) targetable derivatives for imaging mitochondrial and lysosomal HOCl were reported. These probes exhibit fast response (within seconds), good selectivity, and high sensitivity (20 nM) toward HOCl. In live cell experiments, both probes MITO-TP and LYSO-TP were successfully applied to detect intracellular HOCl in corresponding organelles. In particular, the two-photon imaging of MITO-TP and LYSO-TP in murine model shows that higher amount of HOCl can be detected in both lysosome and mitochondria of macrophage cells during inflammation condition. Thus, these probes could not only help clarify the distribution of subcellular HOCl, but also serve as excellent tools to exploit and elucidate functions of HOCl at subcellular levels. (Chemical Equation Presented).
Construction of an alkaline phosphatase-specific two-photon probe and its imaging application in living cells and tissues
Zhang, Huatang,Xiao, Peng,Wong, Yin Ting,Shen, Wei,Chhabra, Mohit,Peltier, Raoul,Jiang, Yin,He, Yonghe,He, Jun,Tan, Yi,Xie, Yusheng,Ho, Derek,Lam, Yun-Wah,Sun, Jinpeng,Sun, Hongyan
, p. 220 - 229 (2017)
Alkaline phosphatase (ALP) is a family of enzymes involved in the regulation of important biological processes such as cell differentiation and bone mineralization. Monitoring the activity of ALP in serum can help diagnose a variety of diseases including bone and liver diseases. There has been growing interest in developing new chemical tools for monitoring ALP activity in living systems. Such tools will help further delineate the roles of ALP in biological and pathological processes. Previously reported fluorescent probes has a number of disadvantages that limit their application, such as poor selectivity and short-wavelength excitation. In this work, we report a new two-photon fluorescent probe (TP-Phos) to selectively detect ALP activity. The probe is composed of a two-photon fluorophore, a phosphate recognition moiety, and a self-cleavable adaptor. It offers a number of advantages over previously reported probes, such as fast reaction kinetics, high sensitivity and low cytotoxicity. Experimental results also showed that TP-Phos displayed improved selectivity over DIFMUP, a commonly utilized ALP probe. The selectivity is attributed to the utilization of an ortho-functionalised phenyl phosphate group, which increases the steric hindrance of the probe and the active site of phosphatases. Moreover, the two-photon nature of the probe confers enhanced imaging properties such as increased penetration depth and lower tissue autofluorescence. TP-Phos was successfully used to image the endogenous ALP activity of hippocampus, kidney and liver tissues from rat.
Dual-emissive difluoroboron naphthyl-phenyl β-diketonate polylactide materials: Effects of heavy atom placement and polymer molecular weight
Samonina-Kosicka, Jelena,Derosa, Christopher A.,Morris, William A.,Fan, Ziyi,Fraser, Cassandra L.
, p. 3736 - 3746 (2014)
Luminescent materials are important for imaging and sensing. Aromatic difluoroboron β-diketonate complexes (BF2bdks) are classic fluorescent molecules that have been explored as photochemical reagents, two-photon dyes, and oxygen sensors. A series of BF2bdks with naphthyl and phenyl groups was synthesized, and photophysical properties were investigated in both methylene chloride and poly(lactic acid) (PLA). Polymer molecular weight and dye attachment site along with bromide heavy atom placement were varied to tune optical properties of dye-PLA materials. Systems without heavy atoms have long phosphorescence lifetimes, which is useful for lifetime-based oxygen sensing. Bromine substitution on the naphthyl ring resulted in intense, clearly distinguishable fluorescence and phosphorescence peaks important for ratiometric oxygen sensing and imaging.
A novel reaction-based fluorescent probe for sensitive and selective detection of Cu2+
Ren, Aishan,Zhu, Dongjian,Xie, Wei,He, Xingcun,Duan, Zhenhua,Luo, Yanghe,Zhong, Xing,Song, Mubo,Yan, Xiaowei
, p. 136 - 141 (2018)
A novel reaction-based fluorescent probe (2) for Cu2+ was designed and synthesized. 2 exhibited remarkable fluorescence enhancement (65-fold) after the addition of Cu2+. Base on the absorption spectra, fluorescence spectra, ESI-MS and 1H NMR spectra analysis, the fluorescence response was attributed to Cu2+-promoted hydrolysis of the picolinate moiety to yield a highly fluorescent product, 6-acetyl-2-hydroxynaphthalene (1). Moreover, 2 not only displayed a rapid response time (within 6 min), high sensitivity (detection limit of 8.5 nM), and high selectivity for Cu2+ over other metal ions, but also could detect Cu2+ by absorption spectra, fluorescence spectra, even an obvious fluorescence color change at room temperature.
Synthesis and crystal structure of 2-acetylnaphthalen-6-yl 4-methylbenzosulfonate
Jia-Rong, Li,Guang, Zhang
, p. 789 - 793 (2005)
The title compound has been synthesized by the reaction of 1-(6-hydroxy-2-naphthyl)-1-ethanone (2) with p-toluenesulfonyl chloride. Its structure was determined by single crystal X-ray diffraction. 2-Acetylnaphthalen-6-yl 4-methylbenzosulfonate (3) crystallizes in the orthorhombic space group Pbca with a = 12.727(3) A, b = 14.560 (3) A, c = 17.688 (4) A, V = 3277.8 (11) A3, and Z = 8. The results demonstrate that the dihedral angle between the benzene ring and the naphthalene ring is 116.5°, and the length (1.417 A) of single C - O bond of 3 is longer than that of single C - O bond in the relative compounds.
A FRET-based two-photon probe for: In vivo tracking of pH during a traumatic brain injury process
Zhai, Baoping,Zhai, Shuyang,Hao, Ruilin,Xu, Jianjun,Liu, Zhihong
, p. 17018 - 17022 (2019)
The traumatic brain injury (TBI) process, a significant cause of neurodegenerative diseases, is generally thought to be accompanied by a decrease in pH of the intracellular environment. In this work, a fluorescence resonance energy transfer (FRET)-based ratiometric two-photon fluorescent pH probe, FRET-pH, has been designed and fully characterized to monitor the pH change so as to understand the extent of the TBI process. FRET-pH, which has nearly 100% energy transfer efficiency and ～100-fold ratio signal changes, is constructed from a naphthalene derivative ADN as a two-photon fluorophore and SRhB as a recognition domain for pH. FRET-pH displays both one- A nd two-photon ratiometric responses towards pH in aqueous solution. The appropriate pKa value (5.89) supports its use in subsequent biological applications. Finally, two-photon microscopic imaging of pH in living HeLa cells, BV-2 cells and rat brain tissue has been achieved.
Light-Harvesting Systems Based on Organic Nanocrystals To Mimic Chlorosomes
Chen, Peng-Zhong,Weng, Yu-Xiang,Niu, Li-Ya,Chen, Yu-Zhe,Wu, Li-Zhu,Tung, Chen-Ho,Yang, Qing-Zheng
, p. 2759 - 2763 (2016)
We report the first highly efficient artificial light-harvesting systems based on nanocrystals of difluoroboron chromophores to mimic the chlorosomes, one of the most efficient light-harvesting systems found in green photosynthetic bacteria. Uniform nanocrystals with controlled donor/acceptor ratios were prepared by simple coassembly of the donors and acceptors in water. The light-harvesting system funneled the excitation energy collected by a thousand donor chromophores to a single acceptor. The well-defined spatial organization of individual chromophores in the nanocrystals enabled an energy transfer efficiency of 95%, even at a donor/acceptor ratio as high as 1000:1, and a significant fluorescence of the acceptor was observed up to donor/acceptor ratios of 200 000:1.
Loss of thioredoxin reductase function in a mouse stroke model disclosed by a two-photon fluorescent probe
Zhao, Jintao,Qu, Yuan,Gao, Hao,Zhong, Miao,Li, Xinming,Zhang, Fang,Chen, Yaxiong,Gan, Lu,Hu, Guodong,Zhang, Hong,Zhang, Shengxiang,Fang, Jianguo
, p. 14075 - 14078 (2020)
Thioredoxin reductase (TrxR) enzymes are critical in regulating redox homeostasis in cells. We report the first two-photon fluorescent probe of mammalian TrxR (TP-TRFS). TP-TRFS retains high specificity in recognizing TrxR. More importantly, the two-photon absorbing character of TP-TRFS enables it to be used in vivo. With the aid of TP-TRFS, a remarkable decline of the TrxR function was observed in the brain of a mouse model of stroke for the first time, providing a mechanistic link of TrxR dysfunction with stroke. This journal is
Low-energy collision-induced fragmentation of negative ions derived from ortho-, meta-, and para-hydroxyphenyl carbaldehydes, ketones, and related compounds
Attygalle, Athula B.,Ruzicka, Josef,Varughese, Deepu,Bialecki, Jason B.,Jafri, Sayed
, p. 1207 - 1217 (2007)
Collision-induced dissociation (CID) mass spectra of anions derived from several hydroxyphenyl carbaldehydes and ketones were recorded and mechanistically rationalized. For example, the spectrum of m/z 121 ion of deprotonated ortho-hydroxybenzaldehyde shows an intense peak at m/z 93 for a loss of carbon monoxide attributable to an ortho-effect mediated by a charge-directed heterolytic fragmentation mechanism. In contrast, the m/z 121 ion derived from meta and para isomers undergoes a charge-remote homolytic cleavage to eliminate an ?H and form a distonic anion radical, which eventually loses CO to produce a peak at m/z 92. In fact, for the para isomer, this two-step homolytic mechanism is the most dominant fragmentation pathway. The spectrum of the meta isomer on the other hand, shows two predominant peaks at m/z 92 and 93 representing both homolytic and heterolytic fragmentations, respectively. 18O-isotope-labeling studies confirmed that the oxygen in the CO molecule that is eliminated from the anion of meta-hydroxybenzaldehyde originates from either the aldehydic or the phenolic group. In contrast, anions of ortho-hydroxybenzaldehyde and 2-hydroxy-1-naphthaldehyde, both of which show two consecutive CO eliminations, specifically lose the carbonyl oxygen first, followed by that of the phenolic group. Anions from 2-hydroxyphenyl alkyl ketones lose a ketene by a hydrogen transfer predominantly from the α position. Interestingly, a very significant charge-remote 1,4-elimination of a H2 molecule was observed from the anion derived from 2,4-dihydroxybenzaldehyde. For this mechanism to operate, a labile hydrogen atom should be available on the hydroxyl group adjacent to the carbaldehyde functionality. Copyright
Photo-Fries Rearrangements of 2-Naphthyl Acylates as Probes of the Size and Shape of Guest Sites Afforded by Unstretched and Stretched Low-Density Polyethylene Films. A Case of Remarkable Selectivity
Cui, Changxing,Weiss, Richard G.
, p. 9820 - 9821 (1993)
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A TP-FRET-based two-photon fluorescent probe for ratiometric visualization of endogenous sulfur dioxide derivatives in mitochondria of living cells and tissues
Yang, Xiaoguang,Zhou, Yibo,Zhang, Xiufang,Yang, Sheng,Chen, Yun,Guo, Jingru,Li, Xiaoxuan,Qing, Zhihe,Yang, Ronghua
, p. 10289 - 10292 (2016)
A ratiometric two-photon fluorescent probe for SO2 derivatives was first proposed based on acedan-merocyanine dyads via a TP-FRET strategy. It was successfully applied to visualization of the fluctuations of enzymatically generated SO2 derivatives in the mitochondria of HepG2 cells and rat liver tissues using two-photon fluorescence microscopy imaging.
The Synthesis of a Two-Photon Fluorescence Labelling Probe and its Immunochromatographic Strip for Rapid Diagnosis of COVID-19
Huang, Chibao,Kang, Shuai,Yu, Fuxun,Wei, Zairong
, p. 522 - 528 (2021/03/03)
A two-photon fluorescence labelling probe (LP) was synthesised, and LP-Ag was obtained by LP labelling the N-protein antigen (Ag) of COVID-19. LP-Ag was made into an immunochromatographic strip. When a blood sample was added to the sample hole of the test card, it would move forward along the nitrocellulose (NC) film. If the sample contained IgM, the IgM bound to LP-Ag and formed an M line with the coated mouse anti-human IgM antibody, giving a positive response to the presence of IgM of COVID-19. The sensitivity, specificity, and accuracy of the immunochromatographic strip based on the LP was compared with those of the nucleic acid detection method and the colloidal gold method, proving it to be much simpler than the nucleic acid detection method, which can greatly shorten the detection period, and to be much more stable than the colloidal gold method, which can overcome uncertainty. LP-Ag can be used to image lung tissue with COVID-19 by two-photon fluorescence microscopy (TFM).
Double-photon fluorescence labeling probe, synthetic method thereof and application of new coronavirus diagnosis (by machine translation)
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Paragraph 0012; 0059; 0063-0065, (2020/08/17)
The probe is provided with 3 - (N - methyl - N N-(6 - acetyl -2 - naphthyl) amino) propionic acid - N N-hydroxysuccinimide ester, and can be used for rapidly detecting ?datdatdate? N protein antigen 2019 - nCoV. (by machine translation)
