10441-41-5Relevant academic research and scientific papers
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).
Synthesis and optical properties of 4-(2-{[6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl] (methyl)amino} ethoxy)-4-oxobutanoic acid fluorescent probe for β-amyloid
Fa, HuanBao,Zhou, JingTing,Zhang, Dong,Yin, Wei,Zhang, HaiFeng,Huo, DanQun,Hou, ChangJun,Luo, XiaoGang,Mao, YaLi,Zhang, Jin
, p. 3243 - 3260 (2015)
Abstract A novel 4-(2-{[6-(1,1-dicyanoprop-1-en-2-yl)naphthalen-2-yl](methyl)amino} ethoxy)-4-oxobutanoic acid (5) fluorescent probe for β-amyloids was synthesized by catalytic acylation using 4-dimethylaminopyridine between succinic anhydride and (1-{6-[(2-hydroxyethyl)(methyl) amino]-2-naphthyl}ethylidene)malononitrile (4). The structures of all compounds were identified by proton nuclear magnetic resonance spectroscopy, infrared spectroscopy, mass spectrometry, and ultraviolet-visible (UV-Vis) spectroscopy. The UV-Vis and fluorescence spectra of 1-{6-[(2-hydroxyethyl)(methyl) amino]-2-naphthyl}ethan-1-one (3), 4, and 5 in solvents with different polarities were investigated, and the effects of solvent polarity on the optical properties of the three compounds were studied. The objective product 5 showed high binding affinities toward Aβ(1-40) aggregates in vitro (K d = 29.4 nmol/L) by fluorophotometry. This study provides a powerful fluorescent probe for the molecular diagnosis of Alzheimer's disease.
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.
Environment-sensitive two-photon probe for intracellular free magnesium ions in live tissue
Kim, Hwan Myung,Jung, Cheol,Kim, Bo Ra,Jung, Soon-Young,Hong, Jin Hee,Ko, Young-Gyu,Lee, Kyoung J.,Cho, Bong Rae
, p. 3460 - 3463 (2007)
(Figure Presented) "Green" emission: A novel two-photon fluorescent probe that can detect intracellular free Mg2+ ions at a depth of a few hundred micrometers in live tissue was developed. The emission from the Mg2+-probe complex (green) shows little interference from association of the probe with other intracellular metal ions or with the cell membrane (blue).
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.
Investigation of the photo-fries rearrangements of two 2-naphthyl alkanoates by experiment and theory. Comparison with the acid-catalyzed reactions
Cui, Changxing,Wang, Xiaochun,Weiss, Richard G.
, p. 1962 - 1974 (1996)
A detailed investigation of the photochemistry of 2-naphthyl acetate (1a) and 2-naphthyl myristate (1b) has been conducted under a variety of conditions. Factors related to the reactions such as temperature and solvent type have been explored. The results, most easily interpreted by photo-Fries type processes, are contrasted with those from the Lewis-acid catalyzed (dark) Fries reactions of 1a. They are also compared to the predictions of semiempirical and ab initio calculations using 2-naphthyl propanoate (1c) and species derived from it as models. Unsuccessful triplet sensitization experiments with benzophenone and calculations point to the excited singlet states of 1 as the immediate precursor to the acyl/2-naphthoxy radical pairs that recombine to form keto intermediates 2, reform 1, or diffuse apart and eventually yield 2-naphthol (4); enolization of 2 results in the isolated rearrangement products, n-acyl-2-naphthols (n-3). Static and dynamic fluorescence studies provide some insights into the nature of the lysis process. Irradiation of a mixture of appropriately labeled derivatives of 1 led to none of the expected "cross-over" products, indicating that the intermediates 2 arise from recombination of radical pairs from the same parent molecule. Irradiation of 1b in ethanol and 1-octanol provides no evidence for the intermediacy of dodecylketene and supports out-of-cage mechanisms as the exclusive source of 4. There are indications of subtle solvent effects and a conformational dependence on the distribution of photoproducts.
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.
Studies on acedan-based mononuclear zinc complexes toward selective fluorescent probes for pyrophosphate
Rao, Alla Sreenivasa,Singha, Subhankar,Choi, Wonyoung,Ahn, Kyo Han
, p. 8410 - 8417 (2012)
We have demonstrated that mononuclear Zn(ii)-dipicolylamine (DPA) complexes with an auxiliary ligand can fluorescently discriminate pyrophosphate over ATP with as high selectivity as the known fast responding dinuclear bis(ZnDPA) complexes.
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 colorimetric and fluorescent probe for fluoride ions based on 6-acetyl-2-naphthol
Hou, Peng,Chen, Song,Song, Xiangzhi
, p. 423 - 426 (2014)
A colorimetric and turn-on fluorescent probe for fluoride ions, tert-butyldimethylsilane 6-acetyl-2-naphtholate, was readily synthesized from 6-acetyl-2-naphthol and tert-butyldimethylchlorosilane (TBSCl). The probe exhibits high sensitivity and good selectivity for fluoride ions in acetonitrile. The inherent mechanism involves the cleavage of the Si-O bond in the probe, which induced yellow color formation and prominent fluorescence enhancement. Copyright
