- A naphthalimide fluorescent sensor for Zn2+ based on photo-induced electron transfer
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A new Zn2+ fluorescent sensor NIDPA (1) which takes 1,8-naphthalimide as a reporting group and di-2-picolylamine (DPA) as a recognizing group has been synthesized via simple steps. Based on photo-induced electron transfer (PET) mechanism, NIDPA has a nearly 5-fold fluorescent enhancement under simulated physiological conditions corresponding to the binding of Zn2+. Apparent dissociation constant for Zn2+ (Kd) is in the sub-nM range, and Ca2+, Mg2+, Fe3+, Ni2+, and Cr3+ have little influence on fluorescence enhancement.
- Fan, Jiangli,Wu, Yunkou,Peng, Xiaojun
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- A Ratiometric Fluorescent Probe for Selective Detection of Hypochlorite Anion
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A new fluorescent probe based on rhodamine and naphthalimide was synthesized for the discrimination of hypochlorite anion. Upon addition of NaClO, the emission intensities ratio (I576 nm/I528 nm) of the probe 1 increased quickly accompanied with the obvious change of color. The probe 1 also exhibited highly selectivity and fast response to hypochlorite anion. Furthermore, the newly proposed probe has been applied for natural water samples, and a satisfied result was obtained.
- Ou, Zhijian,Shi, Lei,Huang, Wenli,Gong, Shengzhao,Liang, Haomei,Hong, Haojia
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- Imaging and inhibiting: A dual function molecular flare for cancer cells
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Wnt pathway is dysregulated and activated in many human malignancies. More than 90% of colon cancers have variations in the Wnt pathway. Sulindac targeting protein Dvl of the Wnt/Dvl/β-catenin pathway which regulates cancer gene expression, has been reported to significantly reduce the incidence and the risk of death from the colorectal and other types of cancer. Herein, a dual functional compound (SLN) containing Sulindac and a linked fluorophore has been reported firstly, to combine the functions of lighting up colon cancer cells as a flare and inhibiting colon tumor as a drug. SLN can not only mark the Dvl protein in Wnt pathway to recognize tumors layer by layer, but also achieve the effective inhibition of colon cancer, providing a promising reagent for chemotherapy and a fluorescence indicator for surgery during removing the colon tumor in situ.
- Zhang, Shuangzhe,Li, Miao,Xia, Wenxi,Fan, Jiangli,Wang, Jingyun,Li, Yueqing,Li, Yachen,Wang, Haibo,Dong, Chengyong,Ma, Dandan,Guo, Jianli,Peng, Xiaojun
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- Ibuprofen-derived fluorescence inhibitor of COX-2 for breast cancer imaging, prevention and treatment
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The integration of precise detection, long-term prevention and effective treatment are beneficial to monitor cancer bioactivity and prevent malignant metastasis for breast cancer patients. Herein, a novel fluorescence probe (IBLN) is designed and synthesized which contains a fluorophore (naphthalimide), a linker and a non-steroidal anti-inflammatory drug (ibuprofen). The specific optical imaging, prevention and treatment effects of breast cancer are relied on the introduction of a powerful cyclooxygenase-2-specific inhibitor, ibuprofen, which makes IBLN possible to successfully differentiate breast cancer cells from normal cells. In addition, fluorescent cellular imaging agent naphthalimide also has anticancer effects via inducing lysosomal membrane permeabilization (LMP). The multi-functional ibuprofen-derived fluorescence inhibitor IBLN realizes the imaging, prevention and treatment for breast cancer, which the selectivity and anticancer effects would be strengthened compared to the single naphthalimide or ibuprofen. Therefore, we envisage that the multi-function strategy in IBLN would be attractive way to explore potential reagent for fluorescence-visible breast cancer therapy in situ.
- Xia, Wenxi,Zhang, Shuangzhe,Li, Yueqing,Fan, Jiangli,Liu, Bin,Wang, Lei,Peng, Xiaojun
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- Antiproliferative and apoptosis-inducing activities of novel naphthalimide-cyclam conjugates through dual topoisomerase (topo) I/II inhibition
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A novel series of naphthalimide-cyclam conjugates were designed and synthesized. Among them, compounds 4c, 4d, 8c and 8d which bearing long lipophilic alkyl chains, displayed comparable or more potent cytotoxic activities against human tumor cell lines than amonafide. Furthermore, the four compounds were proved to possess strong inhibition against both topoisomerase I and II. The representative compound 8c exhibited moderate DNA intercalation activity. Molecular modeling studies identified the possible interaction of compound 8c with the molecular target by forming topoisomerase/DNA/drug ternary complex. Finally, derivatives with long lipophilic alkyl chains could efficiently induce apoptosis.
- Tan, Shaoying,Sun, Deheng,Lyu, Jiankun,Sun, Xiao,Wu, Fangshu,Li, Qiang,Yang, Yiqi,Liu, Jianxu,Wang, Xin,Chen, Zhuo,Li, Honglin,Qian, Xuhong,Xu, Yufang
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- Novel metal complexes of naphthalimide-cyclam conjugates as potential multi-target receptor tyrosine kinase (RTK) inhibitors: Synthesis and biological evaluation
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A novel series of metal complexes of naphthalimide-cyclam conjugates were synthesized and their in vitro antitumor activities were evaluated. The newly-synthesized compounds showed huge diversity of antiproliferative potency due to variety of metal ions and length of alkyl chains, among which the Zn(II) and Cr(III) complexes exhibited comparable antiproliferative activities with amonafide via multiple tyrosine kinase inhibition. Further research revealed that the representative compound 8a displayed broad-spectrum antiproliferative activity against 15 cancer cell lines with average IC50 value 10.18 ± 3.25 μM, and effective antiangiogenic activity on human microvascular endothelial cells (HMEC-1). In brief, metal complexes of naphthalimide-cyclam conjugates were firstly designed and synthesized as multi-target tyrosine kinase inhibitors and proved of their antitumor capacities.
- Tan, Shaoying,Han, Kun,Li, Qiang,Tong, Linjiang,Yang, Yiqi,Chen, Zhuo,Xie, Hua,Ding, Jian,Qian, Xuhong,Xu, Yufang
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- Naphthalimides exhibit in vitro antiproliferative and antiangiogenic activities by inhibiting both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs)
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Novel naphthalimide derivatives were designed and synthesized to modulate both topoisomerase II (topo II) and receptor tyrosine kinases (RTKs). Most target compounds exhibited effective and selective antiproliferative activities against three cancer cell lines by inhibiting topo II. The IC50 values ranged from 1.5 to 19.1 μM. Moreover, compounds 8d and 12d moderately inhibited various angiogenesis-related RTKs, including FGFR1, VEGFR2 and PDGFRα. The representative compound 8d was then proved to possess antiangiogenic activity, which was evidenced by the inhibition of migration and tube formation activities of HMEC-1 cells. To our knowledge, it is the first time naphthalimides were identified as tyrosine kinases inhibitors (TKIs) besides their conventional cytotoxicity.
- Wang, Xin,Chen, Zhuo,Tong, Linjiang,Tan, Shaoying,Zhou, Wei,Peng, Ting,Han, Kun,Ding, Jian,Xie, Hua,Xu, Yufang
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- A new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide
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A new azacrown derived from 1,8-naphthalimide was prepared by a two steps reaction from 4-bromo-1,8-naphthalic anhydride. The spectroscopic properties of this flouroionophore are described both in the absence and in the presence of cations; the compound shows a strong affinity with Ca2+ and Ba2+.
- Cosnard, Frederic,Wintgens, Veronique
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- A novel fluorescent sensor for triplex DNA
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A novel triplex DNA fluorescent sensor which takes 4-aminonaphthalimide as a reporting group and a triplex-select intercalator as a recognizing group has been synthesized. The results show that the fluorescence of the sensor increases greatly upon addition of T?AT triplex, but the response to single strand DNA and duplex DNA is weak in PIPES 20 buffer (pH 7.0). A triplex DNA fluorescent sensor based on PET is described. The sensor takes 4-aminonaphthalimide as a reporting group and a triplex-select intercalator as a recognizing group. The results show that it is a selective sensor for T?AT triplex DNA in compared with duplex and ssDNA by fluorescence enhancement in PIPES 20 buffer.
- Lu, Erhu,Peng, Xiaojun,Song, Fengling,Fan, Jiangli
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- Smart PET based organic scaffold exhibiting bright “Turn–On” green fluorescence to detect Fe3+ ion: Live cell imaging and logic implication
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An efficient and simple photoinduced electron transfer (PET) based fluorescence turn–On probe 7 has been designed and synthesized by bridging naphthalimide and thiophene moieties through a piperazine unit. The photophysical behavior of probe and its affinity toward different metal ions have been investigated in partial aqueous medium, protein medium and live cells. The probe exhibited fluorescence “turn-On” response for Fe3+ ion with high sensitivity (limit of detection 0.373 μM) and selectively along with naked-eye sensitive visible green color in the medium. The significant change in photophysical behavior of the probe, upon a complexation between probe and Fe3+ is attributed to restriction in PET process. The probe 7 showed excellent biocompatibility and has been utilized in cellular imaging experiment to detect Fe3+ in MCF-7 live cells. Also, at molecular level probe 7 mimics the functions of a sequential logic circuit, corresponding to a memory device in which the two inputs (Fe3+ and AcO?) based sequential logic operations mimic the function of a memory element.
- Dwivedi, Sushil K.,Gupta, Ramesh C.,Ali, Rashid,Razi, Syed S.,Hira, Sumit K.,Manna, Partha P.,Misra, Arvind
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- Mechanistic Analysis of Solid-State Colorimetric Switching: Monoalkoxynaphthalene-Naphthalimide Donor-Acceptor Dyads
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There is growing interest in creating solids that are responsive to various stimuli. Herein we report the first molecular-level mechanistic picture of the thermochromic polymorphic transition in a series of MAN-NI dyad crystals that turn from orange to yellow upon heating with minimal changes to the microscopic morphology following the transition. Detailed structural analyses revealed that the dyads assemble to create an alternating bilayer type structure, with horizontal alternating alkyl and stacked aromatic layers in both the orange and yellow forms. The observed dynamic behavior in the solid state moves as a yellow wavefront through the orange crystal. The overall process is critically dependent on a complex interplay between the layered structure of the starting crystal, the thermodynamics of the two differently colored forms, and similar densities of the two polymorphs. Upon heating, the orange form alkyl chain layers become disordered, allowing for some lateral diffusion of dyads within their own layer. Moving to either adjacent stack in the same layer allows a dyad to exchange a head-to-head stacking geometry (orange) for a head-to-tail stacking geometry (yellow). This transition is unique in that it involves a nucleation and growth mechanism that converts to a faster cooperative wavefront mechanism during the transition. The fastest moving of the wavefronts have an approximately 38° angle with respect to the long axis of the crystal, corresponding to a nonconventional C-H···O hydrogen bond network of dyad molecules in adjacent stacks that enables a transition with cooperative character to proceed within layers of orange crystals. The orange-to-yellow transition is triggered at a temperature that is very close to the temperature at which the orange and yellow forms exchange as the more stable, while being lower than the melting temperature of the original orange, or final yellow, solids.
- Wight, Christopher D.,Xiao, Qifan,Wagner, Holden R.,Hernandez, Eduardo A.,Lynch, Vincent M.,Iverson, Brent L.
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- An unanticipated discovery towards novel naphthalimide corbelled aminothiazoximes as potential anti-MRSA agents and allosteric modulators for PBP2a
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Available therapeutic strategies are urgently needed to conquer multidrug resistance of MRSA. A visible effort was guided towards the advancement of novel antibacterial framework of naphthalimide corbelled aminothiazoximes, and desired to assert some insight on the conjunction of individual pharmacophore with distinct biological activities and unique action mechanism. Preliminary assessment displayed that dimethylenediamine derivative 13d presented a wonderful inhibition on MRSA (MIC = 0.5 μg/mL), and showed excellent membrane selectivity (HC50 > 200 μg/mL) from an electrostatic distinction of the electronegative bacterial membranes and the electroneutral mammalian membranes. Moreover, 13d could effectually relieve the development of MRSA resistance. Investigations into explaining the mechanism of anti-MRSA disclosed that 13d displayed strong lipase affinity, which facilitated its permeation into cell membrane, causing membrane depolarization, leakage of cytoplasmic contents and lactate dehydrogenase (LDH) inhibition. Meanwhile, 13d could exert interaction with DNA to hinder biological function of DNA, and disrupt the antioxidant defense system of MRSA through up-regulation of ROS subjected the strain to oxidative stress. In particular, the unanticipated mechanism for naphthalimide corbelled aminothiazoximes that 13d could suppress the expression of PBP2a by inducing allosteric modulation of PBP2a and triggering the open of the active site, was discovered for the first time. These findings of naphthalimide corbelled aminothiazoximes as a small-molecule class of anti-MRSA agents held promise in strategies for treatment of MRSA infections.
- Cai, Gui-Xin,Gopala, Lavanya,Zhang, Peng-Li,Zhang, Shao-Lin,Zhou, Cheng-He
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supporting information
(2021/12/20)
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- Piperazine-bridged naphthalimide aminothiazole oxime compound as well as preparation method and application thereof
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The invention relates to piperazine bridged naphthalimide aminothiazole oxime compounds as well as a preparation method and application thereof, and belongs to the technical field of chemical synthesis. The piperazine-bridged naphthalimide aminothiazole oxime compound is shown as a general formula I, has certain inhibitory activity on one or more of gram-positive bacteria, gram-negative bacteria and fungi, and can be used for preparing antibacterial and/or antifungal drugs, so that more efficient and safe candidate drugs are provided for clinical antimicrobial treatment, and the clinical treatment problems of increasingly serious drug resistance, stubborn pathogenic microorganisms, newly appearing harmful microorganisms and the like are favorably solved. The preparation raw materials are simple, cheap and easy to obtain, the synthetic route is short, and the method has important significance in anti-infection application.
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Paragraph 0036-0040
(2021/03/13)
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- Quantitative and systematic designing of fluorophores enables ultrasensitive distinguishing carbonyls
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Although the use of sophisticated fluorescent probes can improve the detection sensitivity, either the lack of quantitative design for fluorophores or the deficiency of selectivity towards individual species makes it extremely difficult to distinguish homologs accurately. Herein, this study reports a quantitative strategy for the systematic engineering of fluorophoresviadensity functional theory (DFT). A series of seven 1,8-naphthylamide hydrazine (NH-1-7) compounds was elaborately tailored on the basis of the PET mechanism, EPS charge population and the maximum HOMO overlap principle. The results showed that the obtainedNH-4exhibited 300-fold “off-on” signal towards carbonyls with extraordinary reactivity and high solubility. Importantly, the ultra-low limits of detection (LOD) towards multi-carbonyl homologs could reach 1.0 × 10?12M on the ultra-high pressure liquid chromatography (UHPLC) in an 8 min analysis window. This systematic and quantitative engineering of fluorophores lays a bridge between efficient development of novel fluorophores and trace level detection in various matrixes.
- Chen, Yu,Li, Yunyu,Mao, Wenle,Shi, Lei,Xia, Wei,Yan, Chenxu,Yang, Lixiang,Zhang, Lingfan,Zhang, Wenqing
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p. 12661 - 12668
(2021/07/25)
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- Selectivity of a bromoacridine-containing fluorophore for triplex DNA
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Fluorophore 1,8-naphthilamide was linked to 2-bromoacridine through an ethylenediamine spacer using a succinct synthetic route to give a bromoacridine-linked, bifunctional fluorophore conjugate for the detection of triplex DNA. Acridine is well known to intercalate into duplex DNA whereas introduction of a bulky bromine atom at position C2 redirects specificity for triplex over duplex DNA. In this work, photoelectron transfer assay was used to demonstrate that the synthesised 2-bromoacridine-linked fluorophore conjugate had good selectivity for the representative triplex DNA target sequence d(T*A.T)20 compared with double-stranded d(T.A)20, single-stranded dT20 or d(G/A)19 DNA sequences. Graphic abstract: [Figure not available: see fulltext.].
- Fraser, William,Sharma, Sanjeev Kumar
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p. 1013 - 1016
(2021/08/13)
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- A General Strategy to Enhance Donor-Acceptor Molecules Using Solvent-Excluding Substituents
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While organic donor-acceptor (D-A) molecules are widely employed in multiple areas, the application of more D-A molecules could be limited because of an inherent polarity sensitivity that inhibits photochemical processes. Presented here is a facile chemical modification to attenuate solvent-dependent mechanisms of excited-state quenching through addition of a β-carbonyl-based polar substituent. The results reveal a mechanism wherein the β-carbonyl substituent creates a structural buffer between the donor and the surrounding solvent. Through computational and experimental analyses, it is demonstrated that the β-carbonyl simultaneously attenuates two distinct solvent-dependent quenching mechanisms. Using the β-carbonyl substituent, improvements in the photophysical properties of commonly used D-A fluorophores and their enhanced performance in biological imaging are shown.
- Asbury, John B.,Hoelzel, Conner A.,Hu, Hang,Jung, Kwan Ho,Karim, Basel A.,Li, Xiaosong,Liu, Yu,Munson, Kyle T.,Wolstenholme, Charles H.,Yennawar, Hemant P.,Zhang, Han,Zhang, Xin
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supporting information
p. 4785 - 4792
(2020/02/11)
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- Naphthalimide/benzimide-based excited-state intramolecular proton transfer active luminogens: Aggregation-induced enhanced emission and potential for chemical modification
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Fluorescent organic particles are important in a number of areas, including medical imaging; hence, the development of organic materials that exhibit aggregation-induced emissions is an important objective. To that end, we report the synthesis of naphthalimide- and benzimide-based 2-(2-hydroxyphenyl)benzothiazole (HBT) derivatives (HNIBT and HPIBT, respectively) that exhibit aggregation-induced emission enhancement (AIEE), in contrast to most naphthalimide- or benzimide-based derivatives that are prone to aggregation-induced quenching. Experimental studies like single-crystal X-ray diffraction analysis and theoretical calculations demonstrate that the ability to undergo excited-state intramolecular proton transfer is pivotal for AIEE. Further studies revealed that a terminal alkynyl chain at the N-imide site of HPIBT has little impact on the emission behavior of the resultant compound (HPIBT-yl). HPIBT-Pe, an amphiphilic molecule obtained through the click reaction of HPIBT-yl and a tetraethylene-glycol-derived azide, self-assembled to form highly photostable particles that have long-term fluorescence imaging potential in cellular environments.
- Wang, Rong,Ding, Ju,Zhang, Yanrong
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p. 9152 - 9161
(2019/06/17)
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- Synthesis method of aggregated state fluorescent enhancement dye for fluoride ion probe
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The invention discloses a synthesis method of an aggregated state fluorescent enhancement dye based on a naphthalimide mother nucleus which can be used to design a fluoride ion probe, and belongs to the technical field of analytical chemistry. The high hydration energy of fluoride ion weakens the nucleophilicity, and the hydrophobic environment can enhance the nucleophilicity of fluoride ion, butmany fluorescent dyes show the aggregated state fluorescence quenching property in the hydrophobic environment. Through several steps, benzothiazole is introduced to the 2-position of 1-hydroxynaphthalimide, and the fluorescent dye with the aggregated state fluorescence enhancement characteristic is synthesized. The structure of the compound is characterized by NMR spectroscopy, the fluorescence spectra show that the excitation state proton transfer characteristic is the reason for the compound having the aggregated state fluorescence enhancement characteristic, the conclusion is supported bythe theoretical calculation, and thus the compound can be used to design the fluoride ion fluorescence probe with high sensitivity and selective specificity.
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Paragraph 0027; 0028
(2019/10/02)
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- New Synthetic Route for Cobalt(III) Dissymmetric Bisalkynyl Complexes Based on Cobalt(III)(cyclam)(C2NAPMes)
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The synthesis and characterization of dissymmetric CoIII-bis-alkynyl complexes supported by cyclam (1,4,8,11-tetraazacyclotetradecane) are reported. A series of trans-[Co(cyclam)(C2NAPR)Cl]Cl were prepared from the reaction between [Co(cyclam)Cl2]Cl and HC2NAPR in the presence of Et3N, where NAPR is N-R-1,8-naphthalimide with R as mesityl (Mes, 1a), methyl (Me, 1b), 1-ethylpropyl (Pen, 1c), 2-ethylhexyl (2-ethhex, 1d), or n-octyl (Oct, 1e). Treating compounds 1a and 1b with AgOTf in NCCH3 resulted in trans-[Co(cyclam)(C2NAPR)(NCCH3)](OTf)2 (2a and 2b, respectively), while reactions with 1c, 1d and 1e under the same conditions yielded only intractable mixtures. More soluble 2a reacted further with HC2Ar in the presence of Et3N to afford trans-[Co(cyclam)(C2NAPR)(C2Ar)](OTf) with Ar as C6H4-4-NMe2 (3a), NAPMes (3b) and Ph (3c). All new complexes were characterized using X-ray diffraction (1a, 1c and 3b), IR, 1H NMR, UV/Vis and fluorescent spectroscopy, and cyclic voltammetry.
- Banziger, Susannah D.,Zeller, Matthias,Ren, Tong
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p. 4766 - 4772
(2019/11/26)
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- ORGANIC LIGHT-EMITTING DISPLAY APPARATUS
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An organic light-emitting display apparatus includes a substrate, an organic light-emitting device disposed above the substrate, and an encapsulation unit disposed above the organic light-emitting device and sealing the organic light-emitting device, wherein the encapsulation unit includes a compound represented by Formula 1. [in-line-formulae][R1-(L1)a1]b1-(Ar1)c1-[(L2)a2-R2]b2.??Formula 1[/in-line-formulae]
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Paragraph 0239
(2019/02/25)
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- HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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Provided are a heterocyclic compound and an organic light-emitting device including the same, the heterocyclic compound being represented by Formula 1:
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Paragraph 0330; 0331; 0332
(2018/09/02)
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- Fluorescent probe molecule and its synthetic method and in the hypochlorite ion detection in the application of the (by machine translation)
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The invention discloses a fluorescence probe molecule and its synthetic method and in the hypochlorite ion detection in the application. The above fluorescent probe molecule, adding containing hypochlorite ions in the test sample, the test sample color changed significantly, and its ion selectivity of hypochlorous acid, and can be stably response hypochlorous acid. Can adopt different band by measuring the fluorescence of the strong ratio to calculate the ionic concentration of hypochlorous acid, the test process does not need to perform a complex physical and chemical testing method, the operation is simple, fast and efficient, the advantage of high sensitivity. (by machine translation)
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Paragraph 0052; 0053; 0054; 0055
(2018/03/25)
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- Dual Fluorophore Containing Efficient Photoinduced Electron Transfer Based Molecular Probe for Selective Detection of Cr3+ and PO43- Ions through Fluorescence " Turn-On-Off" Response in Partial Aqueous and Biological Medium: Live Cell Imaging and Logic Application
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The present work describes a new photoinduced electron transfer (PET) based molecular probe in which naphthalimide (NPI) and anthracene (AN) chromophores are linked through a molecular bridge of piperazine and triazole units by the Click reaction. A typical meaningful structural variation has made the present probe highly selective for Cr3+ ion (limit of detection (LOD), 5.567 × 10-8 M) that displayed enhanced, "turn-On" emission (due to the PET-Off photophysical mechanism) and naked-eye sensitive bright green color fluorescence in the environment of interfering and competitive ions, in Tris-HCl buffer. The minimum energy structure obtained through theoretical calculations (density functional theory (DFT) and time-dependent (TD)-DFT) revealed a "tub" shape structure for probe 10. Upon complexation, the conformation of piperazine fragment changes from chair to boat in which the triazole and piperazine units create a cavity to tether Cr3+. Moreover, the probe showed excellent biocompatibility and cell permeability to sense Cr3+ sensitively in live cells and, thus, holds great promise for application in biological and environmental sciences. Additionally, the sensitive "Off-On-Off" sensing behavior of probe 10 providing two chemical inputs (Cr3+ and PO43-) helps to construct an INHIBIT logic gate. Also the probe has been utilized as printing material to decode secret information through the Cr3+ ion containing "marker ink" under UV light.
- Dwivedi, Sushil K.,Gupta, Ramesh C.,Srivastava, Priyanka,Singh, Priya,Koch, Biplob,Maiti, Biswajit,Misra, Arvind
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p. 10974 - 10981
(2018/09/06)
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- Long alkyl side-chains impede exciton interaction in organic light harvesting crystals
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Side-chains at the imidic position of naphthalimide rendered a firm control(i) the degrees of π-π overlap and (ii) distances between the perylenimide units in a crystalline naphthalimide-perylenimide dyad as determined using single crystal XRD and Hirshfeld surface analyses. Steady-state and time-resolved electronic spectroscopy in addition to DFT calculations revealed a decline in intermolecular excitonic interaction due to interfering alkyl chains.
- Nagarajan, Kalaivanan,Gopan, Gopika,Cheriya, Rijo T.,Hariharan, Mahesh
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supporting information
p. 7409 - 7411
(2017/07/11)
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- Synthesis and photophysical properties of novel fluorescent materials containing 2,4,6-triphenylpyridine and 1,8-naphthalimide units using Suzuki reaction
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A series of novel 2,4,6-triphenylpyridine derivatives containing 1,8-naphthalimide groups have been prepared in good yields using Suzuki couplings reactions. The relationship of the photoluminescence property of the compounds was systematically investigated via a thermogravimetric analyzer, UV-vis, fluorescence and electrochemical analyzer.
- Liu, Hui-Yan,Chen, Liang-Feng,Wang, Hai-Ying,Wan, Yu,Wu, Hui
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p. 94833 - 94839
(2016/10/21)
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- Synthesis of novel fluorescent sensors based on naphthalimide fluorophores for the highly selective Hg2+-sensing
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With an aim to develop the new sensors for optical detection of Hg2+ ions, two novel fluorometric sensors were designed and successfully prepared using 2-(3-(2-aminoethylsulfanyl)propylsulfanyl)ethanamine and one or two N-methylnaphthalimide moieties (1 and 2). Sensor 1 was obtained via N-alkylation, N-imidation and a one-pot nucleophilic aromatic substitution, and N-formylation of the amine, while sensor 2 was prepared via N-alkylation, N-imidation, and nucleophilic aromatic substitution. The characterization, including 1H NMR, 13C NMR, and mass spectrometry, was then performed for 1 and 2. The Hg2+-binding behaviors of the sensors were investigated in terms of sensitivity and selectivity by fluorescence spectroscopy. Sensor 1 especially provided the reversible and highly Hg2+-selective ON-OFF fluorescence behavior by discriminating various interfering ions such as Pb2+, Co2+, Cd2+, Mn2+, Fe2+, K+, Na+, and in particular Cu2+ and Ag+ with a detection limit of 22 ppb toward Hg2+ ions.
- Tachapermpon, Yordkhuan,Piyanuch, Pornthip,Prapawattanapol, Narupon,Sukrat, Kanjarat,Suwatpipat, Kullatat,Wanichacheva, Nantanit
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- TWO-PHOTON FLUORESCENT PROBE USING NAPHTHALENE AS MATRIX AND PREPARATION METHOD AND USE THEREOF
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The present invention provides a novel category of naphthalene-based two-photon fluorescent probes having a general formula I, wherein: X is selected from the X1, X2, X3 and X4; The mentioned two-photon fluorescent probes have a low fluorescence background in the non-tumor cells and tissues, and have a strong and specific fluorescent signal in the tumor cells and tissues. These probes have a certain level of water-solubility, while having good membrane permeability. In addition, they have a bigger effective two-photon absorption cross section. The compounds of the present invention also have a lower biotoxicity, phototoxicity and photobleaching. There is sufficient difference between the spectral range thereof and that of a biological sample.
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Paragraph 0026; 0027
(2014/09/29)
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- Time-dependent solid-state polymorphism of a series of donor-acceptor dyads
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In order to exploit the use of favorable electrostatic interactions between aromatic units in directing the assembly of donor-acceptor (D-A) dyads, the present work examines the ability of conjugated aromatic D-A dyads with symmetric side chains to exhibit solid-state polymorphism as a function of time during the solid formation process. Four such dyads were synthesized, and their packing in the solid state from either slower (10-20 days) or faster (1-2 days) evaporation from solvent was investigated using single crystal X-ray analysis and powder X-ray diffraction. Two of the dyads exhibited tail-to-tail (A-A) packing upon slower evaporation from solvent and head-to-tail (D-A) packing upon faster evaporation from solvent. A combination of single-crystal analysis and XRD patterns were used to create models, wherein a packing model for the other two dyads is proposed. Our findings suggest that while side chain interactions in asymmetric aromatic dyads can play an important role in enforcing segregated D-A dyad assembly, slowly evaporating symmetrically substituted aromatic dyads allows for favorable electrostatic interactions between the aromatic moieties to facilitate the organization of the dyads in the solid state.
- Peebles, Cameron,Alvey, Paul M.,Lynch, Vincent,Iverson, Brent L.
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supporting information
p. 290 - 299
(2014/01/17)
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- A simple naphthalimide-based receptor for selective recognition of fluoride anion
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Synthesis of a simple fluorescent naphthalimide based receptor 4-aminobenzyl-N-methyl-1,8-naphthalimide 3 was carried out as a selective fluoride ion sensor. In acetonitrile, interaction of 3 with different anions such as, AcO-, F-, Cl-, Br-, I -, and SCN- revealed significant fluorescence quenching only with the F- anion. In the presence of the fluoride anion, the color of the solution changed from a fluorescent green to violet and this was visible to the naked eye. The probable mode of sensing mechanism by photo-induced electron transfer (PET) reaction is attributed to deprotonation of acidic NH proton in the presence of fluoride which was confirmed by change in optical properties intramolecular charge transfer (ICT) and 1H NMR spectral data analysis. The Job's plot analysis displayed a 1:1 stoichiometry for interaction between 3 and F-. The extent of fluorescence quenching was estimated by Stern-Volmer plot. ARKAT-USA, Inc.
- Misra, Arvind,Shahid, Mohammad,Dwivedi, Pratibha,Srivastava, Priyanka,Ali, Rashid,Razi, Syed S.
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p. 133 - 145
(2013/01/16)
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- An efficient naphthalimide based fluorescent dyad (ANPI) for F- and Hg2+ mimicking OR, XNOR and INHIBIT logic functions
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A fluorescent bischromophoric dyad combining anthracene and naphthalic anhydride units has been synthesized and characterized. The dyad shows a FRET mediated emission signal at ~535 nm when excited at λex. = 380/360 nm, with efficient energy transfer efficiency (ET = 93%) and quantum yield (Φ = 0.155). Upon interaction with F- and Hg 2+ ions selectively, a diminished (switched-Off) FRET signal is observed and the naked-eye sensitive color of the solution changed to dark red with enhanced emission corresponding to an anthracene moiety (switched-On). Job's plot analysis revealed a 1:1 stoichiometry between dyad and F -/AcO- and Hg2+ ions. The output fluorescence signals exhibited by dyad on chemical inputs of F-, AcO- and Hg2+ ions mimicked OR, XNOR and INHIBIT logic functions. A 1H NMR titration experiment suggested deprotonation of -NH proton and "Y-type or tweezer-like" H-bonding interaction in the presence of F- and AcO-, respectively, involving -NH, -CHN- and anthracene ring protons.
- Shahid, Mohammad,Srivastava, Priyanka,Misra, Arvind
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scheme or table
p. 1690 - 1700
(2011/10/04)
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- Stability of Hoogsteen-type triplexes - Electrostatic attraction between duplex backbone and Triplex-Forming Oligonucleotide (TFO) using an intercalating conjugate
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Syntheses are described for two novel twisted intercalating nucleic acid (TINA) monomers where the intercalator comprises a benzene ring linked to a naphthalimide moiety via an ethynediyl bridge. The intercalators Y and Z have a 2-(dimethylamino)ethyl and a methyl residue on the naphthalimide moiety, respectively. When used as triplex-forming oligonucleotides (TFOs), the novel naphthalimide TINAs show extraordinary high thermal stability in Hoogsteen-type triplexes and duplexes with high discrimination of mismatch strands. DNA Strands containing the intercalator Y show higher thermal triplex stability than DNA strands containing the intercalator Z. This observation can be explained by the ionic interaction of the protonated dimethylamino group under physiological conditions, targeting the negatively charged phosphate backbone of the duplex. This interaction leads to an extra binding mode between the TFO and the duplex, in agreement with molecular-modeling studies. We believe that this is the first example of an intercalator linking the TFO to the phosphate backbone of the duplex by an ionic interaction, which is a promising tool to achieve a higher triplex stability.
- Globisch, Daniel,Bomholt, Niels,Filichev, Vyacheslav V.,Pedersen, Erik B.
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scheme or table
p. 805 - 818
(2009/03/11)
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- Synthesis and optical properties of novel compounds containing carbazole and 1,8-naphthalimide groups
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A series of novel carbazole-naphthalimide compounds with moieties capable of carrier-balance and electroluminescence were synthesised and characterised, and theirs luminescent properties had been studied.
- Feng, Guo-Liang,Ji, Shun-Jun,Geng, Li-Jun,Bian, Bing,Liu, Yu
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scheme or table
p. 137 - 140
(2009/04/10)
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