- A nitroreductase and glutathione responsive nanoplatform for integration of gene delivery and near-infrared fluorescence imaging
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A novel platform rationally integrating indocyanine green analogues and an arginine-rich dendritic peptide with both nitroreductase (NTR) and glutathione (GSH) reduction responsive linkers was developed. This multifunctional platform can enable selective
- Barz, Matthias,Bi, Qunjie,Chen, Xiaobing,Hu, Ao,Jin, Rongrong,Ke, Bowen,Liang, Hong,Nie, Yu,Song, Xu
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Read Online
- Rationally Optimized Fluorescent Probe for Imaging Mitochondrial SO2 in HeLa Cells and Zebrafish
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Organisms have built up immunological systems, where mitochondrial SO2 plays conflicting roles in regulating cell apoptosis. However, no exploration on the influence and regulating principle of mitochondrial SO2 to the specific apoptosis type can be found, which brings about a challenge to fluorescent probes. Herein, we optimize the fluorophore and develop a new fluorescent probe FHMI ((E)-4-(3-formyl-4-hydroxystyryl)-1-methylpyridin-1-iumiodide) by equipping an ICT (intramolecular charge transfer) fluorophore HMII ((E)-4-(4-hydroxystyryl)-1-methylpyridin-1-ium iodide) with an aldehyde group that serves as both fluorescence quencher and reporting group. After the optimization, although the nonconjugated electron donor is formed when sensing SO2, the preset ICT fluorophore HMII is permitted to release the fluorescence at the enlarged wavelength. Compared with the traditional design, the probe FHMI exhibits obvious enhanced fluorescence with large red shift. FHMI is successfully applied to the mechanistic exploration of the dichotomous effects of mitochondrial SO2 to cells apoptosis, showing that mitochondrial SO2 regulates the early apoptosis of HeLa cells via the reduction of mitochondrial membrane potential. FHMI is applied to explore the dichotomous bioinfluence of mitochondrial SO2 to HeLa cells under oxidative stress, visualizing the regulative role of mitochondrial SO2 in the apoptotic process. For the first time, the mitochondrial SO2 is visually found to be closely associated with the early apoptosis of HeLa cells. Moreover, FHMI proves to be readily applicable to monitoring endogenous SO2 in zebrafish. This probe can act as an effective optical tool for exploring SO2 in biospecimen.
- Chen, Guang,Zhou, Wei,Zhao, Chenyang,Liu, Yuxia,Chen, Tao,Li, Yulin,Tang, Bo
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Read Online
- Synthesis, characterization, and UV–visible study of some new photochromic formyl-containing 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives
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The spiropyran derivatives can exist in two forms, the closed-ring spiropyran form and the open-ring merocyanine (MC) form. The SP form could be converted into the MC form upon UV irradiation. In this work, some 1′,3′,3′-trimethylspiro[chromene-2,2′-indoline] derivatives containing the nitro and formyl groups are synthesized via the reaction of 1,3,3-trimethyl-2-methylene-5-nitroindoline with the corresponding salicylaldehyde derivatives. These compounds have different photochromic behaviors. The synthesized photochromic molecules are characterized by the FT-IR, 1H-NMR, and 13C-NMR spectroscopic techniques. In order to investigate the photochromic properties of these compounds, the UV–visible spectroscopic analyses of their methanolic solutions before and after exposure to a UV lamp (in the spectral range of 360–400?nm) are studied. Graphic abstract: [Figure not available: see fulltext.].
- Sepehr, Zeinalabedin,Nasr-Isfahani, Hossein,Mahdavian, Ali Reza,Amin, Amir Hossein
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p. 3061 - 3067
(2021/05/27)
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- Fluorescent probe for fluorine ion detection, application of fluorescent probe and method for detecting fluorine ions in to-be-detected sample
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The invention belongs to the technical field of analytical chemistry, and particularly relates to a fluorescent probe for fluorine ion detection, application of the fluorescent probe and a method for detecting fluorine ions in a to-be-detected sample. The invention provides a compound as shown in a formula I, or an optical isomer or salt thereof, and provides application of the compound as a fluorine ion detection fluorescent probe. According to the method for detecting the fluorine ions in the to-be-detected sample, the compound, or the optical isomer or the salt of the compound is used as a fluorine ion detection fluorescent probe for detection. The fluorescent probe has the advantages of good water solubility, high selectivity, high response speed, low detection limit, good stability, wide applicable pH range and good application prospect.
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Paragraph 0047; 0051; 0056-0057
(2021/08/06)
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- A selective and sensitive near-infrared fluorescent probe for real-time detection of Cu(i)
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The disruption of copper homeostasis (Cu+/Cu2+) may cause neurodegenerative disorders. Thus, the need for understanding the role of Cu+ in physiological and pathological processes prompted the development of improved methods of Cu+ analysis. Herein, a new near-infrared (NIR) fluorescent turn-on probe (NPCu) for the detection of Cu+ was developed based on a Cu+-mediated benzylic ether bond cleavage mechanism. The probe showed high selectivity and sensitivity toward Cu+, and was successfully applied for bioimaging of Cu+ in living cells. This journal is
- Liu, Yiqing,Kang, Ting,He, Qian,Hu, Yuefu,Zuo, Zeping,Cao, Zhihua,Ke, Bowen,Zhang, Weiyi,Qi, Qingrong
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p. 14824 - 14828
(2021/05/17)
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- Cyanine fluorescent probe as well as preparation method and application thereof
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The invention discloses a cyanine fluorescent probe as well as a preparation method and application thereof. The fluorescent probe has a structure as shown in a structural general formula I, a one Doner-two Accepter structure is formed on a methine chain
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Paragraph 0114-0118
(2021/09/04)
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- 'Triangle electron push-pull' mitochondria target type detection SO2 Fluorescent probe as well as preparation method and application thereof
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The invention relates to a triangular electron push-pull chondriosome targeted SO2 detection fluorescence probe as well as a preparation method and application thereof. Phenol is dissolved into toluene and glacial acetic acid; under the catalysis effect o
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Paragraph 0059-0081
(2020/10/12)
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- Near-infrared fluorescent probe for measuring palladium ions based on cyanine structure and preparation method and application thereof
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The invention provides a near-infrared fluorescent probe for measuring palladium ions based on a cyanine structure and a preparation method and application thereof, and the structural formula of the fluorescent probe is as defined in the specification. Th
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Paragraph 0018; 0019
(2019/01/24)
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- NIRF turn-on nanoparticles based on the tumor microenvironment for monitoring intracellular protein delivery
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A dual responsive NIRF turn-on protein delivery system incorporating an NIRF turn-on probe and protein into one single nanoparticle has been constructed. It can be taken up efficiently by A549 cells, where protein release and NIRF recovery happen simultaneously in response to low pH and excessive H2O2. This work provides a novel system for monitoring intracellular protein delivery.
- Xu, Huaibao,Wang, Yi,Pei, Zhichao,Ji, Wei,Pei, Yuxin
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supporting information
p. 14930 - 14933
(2019/12/24)
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- Fluorescent probe for detecting fluoride ions
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The invention discloses a fluorescent probe for detecting fluoride ions in an organism, and belongs to the technical field of analytical chemistry. The fluorescent probe uses a cyanine dye QCy7 as a parent body, a silicon-oxygen bond as a switch and hydroxybenzyl as a linker, and the chemical structure general formula of the fluorescent probe is as shown in a formula (I). The fluorescent probe hassimple synthesis and is convenient to use, can specifically react with the fluoride ions, breaks the silicon-oxygen bond, and releases fluorescence of fluorogen QCy7 through electron transfer. The fluorescent probe is not interfered with other ions in the process of detecting the fluoride ions, has good selectivity to the fluoride ions, and can accurately detect the fluoride ions in the organism.
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Paragraph 0014; 0027; 0029
(2019/11/12)
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- Design, synthesis and biological evaluation of 2-(4-alkoxy-3-cyano)phenyl-6-oxo-1,6-dihydropyrimidine-5-carboxylic acid derivatives as novel xanthine oxidase inhibitors
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In our previous study, we reported a series of 1-hydroxy-2-phenyl-1H-imidazole-5-carboxylic acid derivatives that presented excellent in vitro xanthine oxidase (XO) inhibitory potency. To further investigate the structure-activity relationships of these compounds, the imidazole ring was transformed to a pyrimidine ring to design 2-(4-alkoxy-3-cyano)phenyl-6-oxo-1,6-dihydropyrimidine-5-carboxylic acids (8a-8j), 2-(4-alkoxy-3-cyano)phenyl-4-methyl-6-oxo-1,6-dihydropyrimidine-5-carboxylic acids (9c, 9e, 9j, 9l) and 2-(4-alkoxy-3-cyano)phenyl-6-imino-1,6-dihydropyrimidine-5-carboxylic acids (10c, 10e, 10j, 10l). These compounds exhibited remarkable in vitro XO inhibitory potency with IC50 values ranging from 0.0181 μM to 0.5677 μM. Specifically, compounds 10c and 10e, with IC50 values of 0.0240 μM and 0.0181 μM, respectively, emerged as the most potent XO inhibitors, and their potencies were comparable to that of febuxostat. Structure-activity relationship analysis revealed that the methyl group at 4-position of pyrimidine ring could damage the potency, and the XO inhibitory potency was maintained when carbonyl group was changed to an imino group. Lineweaver-Burk plot analysis revealed that the representative compound 10c acted as a mixed-type inhibitor. A potassium oxonate induced hyperuricemia model in rats was chosen to further confirm the hypouricemic effect of compound 10c, and the results showed that compound 10c (5 mg/kg) was able to significantly lower the serum uric acid level. Furthermore, in acute oral toxicity study, no sign of toxicity was observed when the mice were administered with a single 2000 mg/kg oral dose of compound 10c. These results suggested that compound 10c was a potent and promising uric acid-lowing agent for the treatment of hyperuricemia.
- Mao, Qing,Dai,Xu, Gaoyang,Su, Yu,Zhang, Bing,Liu, Dan,Wang, Shaojie
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- Preparation method and use of 2-phenyl-1,6-dihydropyrimidine-5-carboxylic acid derivative
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The invention belongs to the technical field of medicines, and relates to a preparation method and a use of a 2-phenyl-1,6-dihydropyrimidine-5-carboxylic acid derivative. The invention provides the 2-phenyl-1,6-dihydropyrimidine-5-carboxylic acid derivative represented by general formula I, or a pharmaceutically acceptable salt, an isomer, a polymorph and a medicinal solvate thereof, and further provides an intermediate for preparing the 2-phenyl-1,6-dihydropyrimidine-5-carboxylic acid derivative or the pharmaceutically acceptable salt thereof. The structure of the intermediate is representedby general formula II, III or IV; and in the formulas, R, R and R are as defined in claims and the description.
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Paragraph 0059; 0072-0073
(2019/09/14)
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- Near-infrared dye, its targeting imaging agent, nano-carrier and anti-cancer drug and application (by machine translation)
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This invention relates to a near-infrared fluorescent dye, its construction of targeted imaging agent, nano-carrier and anti-cancer drug and application. The invention said near infrared fluorescent dyes with the hydrophilic glycodendrimer through environmental sensitive key connected to form having self-assembling ability of the amphiphilic dendrimers. Hydrophilic dendrimers to lysine and arginine as the skeleton structure, has good tumor target and puts on the membrane. Amphipathic molecule also having a nitro reductase response, can be self-assembled into nano liposome or micelle or vesicle, for gene and/or pharmaceutical carrier, the carrier in the tumor micro-environment de-assembly, and/or drug release gene, in order to realize the purpose of treatment. The amphiphilic molecule also can be in the near-infrared illumination to generate active oxygen, can be used for photodynamic therapy. Said molecule self-assembly after assembling the front and rear reconciliation are fluorescent quenching state, only in the tumor cell nitro reductase under the action of the strong fluorescent will only be, and penetration force is stronger, more precise. (by machine translation)
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Paragraph 0123; 0136-0138
(2019/01/16)
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- A functional applied material on recognition of metal ion zinc based on the double azine compound
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A colorimetric and fluorescent probe L has been designed and synthesized, which bearing the double azine moiety and showing a detection limit of 2.725?×?10?7?M towards Zn2+. Based on the basic recognition mechanism of ESIPT and CHEF effect, the L has high selectivity and sensitivity to only Zn2+ (not Fe3+, Hg2+, Ag+, Ca2+, Co2+, Ni2+, Cd2+, Pb2+, Cr3+, and Mg2+) within the physiological pH range (pH?=?7.0–8.4) and showed a fluorescence switch. Moreover, this detection progress occured in the DMSO/H2O?~?HEPES buffer (80/20, v/v; pH 7.23) solution which can conveniently used on test strip.
- Wei, Taibao,Liang, Guoyan,Chen, Xiaopeng,Qi, Jin,Lin, Qi,Zhang, Youming,Yao, Hong
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supporting information
p. 2938 - 2942
(2017/04/26)
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- A new fluorescence chemosensor based on benzothiazole derivative for Zn2+ and its logic gate behavior
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A novel benzothiazole derivative J as a fluorescent chemosensor for Zn2+ has been designed and synthesized. The chemosensor J exhibits high selectivity and sensitivity to Zn2+ as fluorescence “turn-on” behavior, which the other cations do not make sense. The detection limit calculated by fluorescence titration method was 1.64 × 10?8 M. Furthermore, the generated J-Zn2+ ensemble could recover the enhanced fluorescence upon the addition of EDTA generating an “on-off-on” recycle. In addition, the test strip based on J was fabricated, which could act as a convenient and efficient Zn2+ test kit.
- Hu, Jing-Han,Qi, Jing,Sun, You,Pei, Peng-Xiang
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p. 565 - 569
(2017/05/01)
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- A visual reversible ratio fluorescence probe and its preparation method and application
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The invention discloses a visible and reversible fluorescent probe which comprises a cyanine fluorescent group and a benzothiazole group, and the general formula of the probe is shown in the description. The preparation method of the reversible fluorescent probe comprises the following steps: (1) dropwise adding phosphorus oxychloride into salicylaldehyde and paraformaldehyde for reaction, so as to obtain a product 1; (2) enabling the product 1 and hexamethylene-tetramine to react, so as to obtain a product 2; (3) enabling the product 2 and 2-aminobenzenethiol to react at the room temperature, so as to obtain a product 3; (4) enabling the product 3 and a compound 4 to react, so as to obtain the visible and reversible fluorescent probe. According to the ratiometric fluorescent probe provided by the invention, obvious color variation can be found out under natural light or an ultra-violet lamp, and the qualitative detection of sulfur dioxide gas can be implemented under natural light or a hand-held ultra-violet lamp, so that the operation is simple, high convenience and quickness are achieved, and the effect is remarkable; the fluorescent probe can effectively prevent interference from other impurities in samples, and is excellent in selectivity; in addition, the cumbersome pre-processing process of samples is avoided, so that the detection efficiency is high.
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Paragraph 0018; 0048; 0059; 0069; 0080
(2017/10/20)
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- A simple pincer-type chemosensor for reversible fluorescence turn-on detection of zinc ion at physiological pH range
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A new, highly selective and sensitive pincer-type chemosensor (Y) for zinc ion with turn-on fluorescence behavior in physiological pH range solution was developed. Y is based on bi-hydrazone derivatives, which contain pyridine as the fluorescent group and a hydrazone bond as recognition site. The selectivity mechanism of Y for zinc is based on the combined effects of the inhibition of excited-state intramolecular proton transfer (ESIPT) and -HC=N- isomerization, as well as chelation-enhanced fluorescence. The entire process takes less than 15 seconds. The minimum detection limit of Y for zinc reaches 1.39 × 10-8 M. Moreover, Y can conveniently detect zinc in test strip form, and it can be recycled.
- Lin, Qi,Cai, Yi,Li, Qiao,Chang, Jing,Yao, Hong,Zhang, You-Ming,Wei, Tai-Bao
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p. 4162 - 4167
(2015/05/20)
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- Synthesis of salicylaldehydes from phenols via copper-mediated duff reaction
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A copper-mediated Duff reaction for ortho-selective formylation of phenols has been developed. In the presence of copper species, significant improvements of yield and ortho-selectivity of the Duff formylation were achieved, which provides an easy access to salicylaldehydes from phenols.
- Fu, Xue-Wen,Pu, Wen-Chen,Zhang, Guo-Lin,Wang, Chun
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p. 8147 - 8158
(2015/02/19)
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- Rational design of a NIR-emitting Pd(ii) sensor via oxidative cyclization to form a benzoxazole ring
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By using the substituent effect to tune the palladium(ii)-involved reactivity, a new probe is found to respond quantitatively to Pd(ii). Unexpectedly, the probe gave an emission band in the desirable near-infrared (NIR) region (780 nm), thus providing the
- Chen, Weihua,Wright, Brian D.,Pang, Yi
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supporting information; experimental part
p. 3824 - 3826
(2012/05/20)
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- A study on the heterobinuclear site of Co(salen)/TiO2-SiO 2 catalysts in the oxidative carbonylation of aniline
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Titania-silica immobilized Co(salen) complexes containing the heterobinuclear site were prepared by the sol-gel method for the catalytic synthesis of methyl N-phenylcarbamate (MPC) by the oxidative carbonylation of aniline. It was found that the Ti: Si mole ratio had an important effect on the catalytic performance of Co(salen) complexes. When the Ti: Si ratio was 0.1, titania-silica supported Co(salophen) showed the best catalytic activity. Under the reaction conditions, Co(salophen)/TS-0.1, 0.5 g, aniline 11 mmol, methanol 25 ml, KI 2.2 mmol, CO:O2 9:1, total pressure 6 MPa, 150 C, 3 h, the conversion of aniline and the selectivity of MPC were 60.7 and 88.1%, respectively. The XRD studies showed that titania was highly dispersed in the silica matrix. Co(salophen)/TS-0.1 was reused five times with no significant loss of the activity, and no Co leaching was observed in the reaction. Copyright
- Mei, Fu-Ming,Chen, Li-Juan,Li, Guang-Xing
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experimental part
p. 86 - 91
(2010/11/19)
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- Synthesis of chromanones: A novel palladium-catalyzed Wacker-type oxidative cyclization involving 1,5-hydride alkyl to palladium migration
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A series of 2-methylchromanone derivatives have been prepared by using a novel palladium-catalyzed Wacker-type oxidative cyclization, in which a 1,5-hydride alkyl to palladium migration and a direct chirality transfer were involved. The Royal Society of Chemistry.
- Zhang, Zuhui,Pan, Chongfeng,Wang, Zhiyong
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p. 4686 - 4688
(2008/10/09)
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- A soluble complex of Zn(II) with N2O4 core: A structural study
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A soluble complex of Zn(II) with 1-hydroxy-3-hydroxy-2-hydroxymethyl-2-(5′-formyl-salicylidimino) propane resulting in a distorted octahedral ZnN2O4 core has been synthesized and characterized by analytical and spectral methods and the structure has been established by single crystal XRD.
- Sah, Ajay K.,Ali, Amjad,Wegelius,Rissanen,Rao, Chebrolu P.
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p. 1888 - 1891
(2007/10/03)
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- An efficient and convenient synthesis of 5-formylsalicylaldehyde
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5-Formylsalicylaldehyde 1, which is a key intermediate of spiropyran dye and a recently developed insulin sensitivity enhancer (ISE) compounds, was prepared from 5-iodosalicylaldehyde by the palladium-catalyzed coupling reaction with ethyl acrylate follow
- Lee, Seung Hwan,Cho, Young Jin,Bae, Jong Woo,Yoon, Cheol Min
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p. 1003 - 1008
(2007/10/03)
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- Fischer's base as a protecting group: Protection and deprotection of 2- hydroxybenzaldehydes
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The hydroxyl and aldehyde groups of 2-hydroxybenzaldehydes were protected by the reaction with Fischer's base and deprotected by the ozonolysis in methanol at -78°C to give the corresponding 2- hydroxybenzaldehydes in good to high yields. (C) 2000 Elsevier Science Ltd.
- Cho, Young Jin,Lee, Seung Hwan,Bae, Jong Woo,Pyun, Hyung-Jung,Yoon, Cheol Min
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p. 3915 - 3917
(2007/10/03)
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- Process for the preparation of 3-carboxy-4-hydroxybenzaldehides and derivatives thereof
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The present invention concerns a process for the preparation of 3-carboxy-4-hydroxybenzaldehydes and derivatives thereof from phenolic compounds carrying formyl and/or hydroxymethyl groups in the 2 and 4 positions. The invention also concerns the preparation of 4-hydroxybenzaldehydes from 3-carboxy-4-hydroxybenzaldehydes. More particularly, the invention concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde, respectively known as "vanillin" and "ethylvanillin". The process for the preparation of 3-carboxy-4-hydroxybenzaldehyde is characterized in that the group in the 2 position in a phenolic compound carrying formyl and/or hydroxymethyl groups in the 2 and 4 positions is selectively oxidized to a carboxy group, and optionally a hydroxymethyl group in the 4 position is selectively oxidized to a formyl group. A successive decarboxylation step for a 3-carboxy-4-hydroxybenzaldehyde produces a 4-hydroxybenzaldehyde.
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- Synthetic approaches to benzofuran containing Insulin Sensitivity Enhancer compounds for treatment of type II diabetes
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The search for Insulin Sensitivity Enhancer (ISE) compounds, for potential use in the treatment of Type II diabetes, has led to the synthesis of compounds that contain a benzofuran spacer between an aryloyl substituent and a 2,4-thiazolidinedione pharmacophore. Sequential combination of haloacetyl aryl substrates with 5-formylsalicylaldehyde gave the desired 2-aryloyl-5-formylbenzofuran intermediates. A related class of compounds, those with a methylene tether between the aromatic moiety and the benzofuran spacer, were also prepared through this strategy.
- Huff, Bret E.,Leffelman, Cindy L.,LeTourneau, Michael E.,Sullivan, Kevin A.,Ward, Jeffrey A.,Stille, John R.
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p. 1363 - 1384
(2007/10/03)
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- 5-Formyl salicylaldehyde as a linker for the synthesis of benzofuran containing insulin sensitivity enhancer compounds
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5-Formyl salicylaldehyde was prepared by treatment of 4-hydroxybenzaldehyde with HMTA in TFA. Reaction of this dialdehyde with α-haloacetyl aryl compounds gave 2,5-disubstituted benzofurans, from which an Insulin Sensitivity Enhancer compound was prepared.
- Stille, John R.,Ward, Jeffrey A.,Leffelman, Cindy,Sullivan, Kevin A.
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p. 9267 - 9270
(2007/10/03)
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- THE REIMER-TIEMANN REACTION IN SLIGHTLY HYDRATED SOLID-LIQUID MEDIUM: A NEW METHOD FOR THE SYNTHESIS OF FORMYL AND DIFORMYL PHENOLS
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Formylation of phenol in weakly hydrated heterogeneous solid-liquid medium makes it possible to transform phenol into slicylaldehide and parahydroxybenzaldehyde with a ratio of 4.5/1 with excellent yield.Use of methanol as cosolvent modifies the orientation of this reaction, which leads for the first time to simultaneous synthesis of salicylaldehyde and parahydroxybenzaldehyde, of 2-hydroxy 1,3-benzenedicarboxaldehyde, and of 2-hydroxy 1,3-benzenedicarboxaldehyde.Experimental conditions make it possible to easily extract each of this molecules.
- Thoer, A.,Denis, G.,Delmas, M.,Gaset, A.
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p. 2095 - 2102
(2007/10/02)
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