- Synthesis and application of novel heterocyclic dyes based on 11-Amino-3-Bromo-13H-acenaphtho[1,2-e]pyridazino[3,2-b]-quinazoline-13-one
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Synthesized a new fused heterocyclic compound, 11-Amino-3-Bromo-13H-acenaphtho[1,2-e]pyridazino[3,2-b]-quinazoline-13-one and is used to synthesize a novel series of heterocyclic mono azo dyes by coupling with various naphthols. All the dyes were characterized by their percentage yield, melting point, UV-visible spectroscopy, elemental analysis, infrared spectroscopy and dyeing performance on nylon 66 and polyester fibres. The percentage dye bath exhaustion on different fibres has been found to be reasonably good and acceptable. The dyed fibres showed fair to fairly good fastness to light and very good to excellent fastness to washing, rubbing, perspiration and sublimation.
- Patel, Vijay H.,Patel, Manish P.,Patel, Ranjan G.
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- Synthesis of Triphenylethylene-Naphthalimide Conjugates as topoisomerase-IIα inhibitor and HSA binder
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A series of triphenylethylene-naphthalimide (TPE-naph) conjugates was synthesized by a molecular hybridization technique, and their anticancer activity was evaluated in vitro on 60 human cancer cell lines through their cytotoxicity. The ratios of E and Z isomers were determined on the basis of HPLC methodology and NMR spectroscopy. The structure-activity relationship for anticancer activity was deduced on the basis of the nature and bulkiness of the amine attached to the C-4 position of the naphthalene ring. Experimental and molecular modeling studies of the most active TPE-naph conjugate bearing a morpholinyl group showed that it was able to inhibit topoisomerase-II (TOPO-II) as a possible intracellular target. Moreover, the transportation behavior of TPE-naph conjugate towards human serum albumin (HSA) indicated efficient binding affinity. The steady-state and time-dependent fluorescent results suggested that this conjugate quenched HSA significantly through static as well as dynamic quenching. Thus, this report discloses the scope of triphenylethylene-naphthalimide (TPE-naph) conjugates as efficient anticancer agents.
- Rani, Sudesh,Luxami, Vijay,Paul, Kamaldeep
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- Synthesis of naphthalimide-phenanthro[9,10-d]imidazole derivatives: In vitro evaluation, binding interaction with DNA and topoisomerase inhibition
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The synthesis and characterization of a series of naphthalimide and phenanthro[9,10-d]imidazole conjugate is described. These compounds are evaluated in vitro for their cytotoxicity towards 60 human cancer cell lines. Derivative 16 shows excellent cytotoxic activity against these cancer cell lines with the range of growth inhibition from ?55.78 to 94.53. The most potent derivative (ethylpiperazine, 16) is further studied to evaluate the interaction with ct-DNA using absorption and emission spectroscopy as well as DNA viscosity measurement. The DNA binding studies indicate that compound 16 is significantly interacted with DNA through groove binding having binding constant value of 7.81 × 104 M?1 alongwith partial intercalation between the base pairs of DNA strands. Further, topoisomerase inhibition study suggests that compound 16 is induced apoptosis and inhibits human topoisomerase (Topo-IIα) as a possible intracellular target. Molecular docking study of compound 16 with ct-DNA shows good docking score.
- Luxami, Vijay,Paul, Kamaldeep,Singh, Iqubal
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- Blue emitting 1,8-naphthalimides with electron transport properties for organic light emitting diode applications
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In this article, the synthesis, characterization and use of two novel naphthalimides as electron-transporting emitter materials for organic light emitting diode (OLED) applications are reported. The molecules were obtained by substituting electron donating chloro-phenoxy group at the C-4 position. A detailed optical, thermal, electrochemical and related properties were systematically studied. Furthermore, theoretical calculations (DFT) were performed to get a better understanding of the electronic structures. The synthesized molecules were used as electron transporters and emitters in OLEDs with three different device configurations. The devices with the molecules showed blue emission with efficiencies of 1.89?cdA-1, 0.98?lmW?1, 0.71% at 100?cdm-2. The phosphorescent devices with naphthalimides as electron transport materials displayed better performance in comparison to the device without any electron transporting material and were analogous with the device using standard electron transporting material, Alq3. The results demonstrate that the naphthalimides could play a significant part in the progress of OLEDs.
- Ulla, Hidayath,Kiran, M. Raveendra,Garudachari,Ahipa,Tarafder, Kartick,Adhikari, Airody Vasudeva,Umesh,Satyanarayan
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- Electron-poor bowl-shaped polycyclic aromatic dicarboximides: Synthesis, crystal structures, and optical and redox properties
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Two new bowl-shaped polycyclic aromatic hydrocarbons, based on corannulene and naphthalene dicarboximide, are synthesized by an improved Suzuki-Miyaura cross-coupling and C-H arylation cascade reaction. Crystallographic analyses confirm structural assignments and provide insight into molecular interactions in the solid state. The new bowl-shaped molecules show reversible oxidation and reduction, intense visible range absorption, and high fluorescence quantum yields. These molecules can be considered bowl-shaped congeners of planar perylene dicarboximides.
- Shoyama, Kazutaka,Schmidt, David,Mahl, Magnus,Würthner, Frank
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- In vitro and in vivo imaging application of a 1,8-naphthalimide-derived Zn2+ fluorescent sensor with nuclear envelope penetrability
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A newly developed fluorescent sensor, Naph-BPEA, shows a specific turn-on response to Zn2+ and can be excited by visible light. The in situ nuclear Zn2+ imaging in HeLa and HepG2 cells reveals the nuclear envelope penetrability of the sensor. The specific sensor location in a zebrafish larva was also demonstrated.
- Zhang, Changli,Liu, Zhipeng,Li, Yunling,He, Weijiang,Gao, Xiang,Guo, Zijian
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- Functionalization of poly(amidoamine) dendrimer-based nano-architectures using a naphthalimide derivative and their fluorescent, dyeing and antimicrobial properties on wool fibers
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Novel naphthalimide-poly(amidoamine) dendrimer fluorescent dyes were synthesized, and their structures were identified and confirmed using different characterization methods such as Fourier transform infrared, 1H NMR, 13C NMR, differential scanning calorimetry, elemental analysis and UV-vis spectroscopy. The spectrophotometric studies demonstrated absorption maxima (λmax) and extinction coefficient (max) values in the ranges of 429-438 nm and 25,635-88,618 L/mol/cm, respectively. The dyeing, fastness and antimicrobial properties of dyed wool fibers were examined. Colorimetric measurements demonstrated a greenish-yellow hue with remarkable fluorescence intensity on dyed wool. Although the fastness properties of naphthalimide dye on wool fibers were poor/moderate, color fastness was appreciably improved through modification of the dye using dendrimers. The results revealed that the newly synthesized dyes are potent antimicrobial agents on wool fibers. Overall, it was deduced that poly(amidoamine) (PAMAM) dendrimers could be exploited as a promising tool in tailoring the different properties of naphthalimide dyes, being suitable for dyeing and antimicrobial finishing agents for wool fibers.
- Sadeghi-Kiakhani, Mousa,Safapour, Siyamak
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- Study on synthesis and fluorescence property of rhodamine–naphthalene conjugate
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In this study, a novel ligand (HL) consisting of 2-methyl quinoline-4-carboxylic acid, rhodamine and naphthalene moiety, was designed and synthesized, it could be developed a ratiometric fluorescent sensor for selective detection of Al3+ via fluorescence resonance energy transfer (FRET) from naphthalimide moiety to rhodamine moiety. The addition of Al3+ trigger the significant fluorescence enhancement of HL at 550 nm at the expense of the fluorescent emission of HL centered at 524 nm.
- Qin, Jing-can,Fu, Zhen-hai,Tian, Li-mei,Yang, Zheng-yin
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- Naphthalimide-based optical turn-on sensor for monosaccharide recognition using boronic acid receptor
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A highly selective and sensitive fluorescent sensor for the determination of fructose is developed. The fluorescent sensor was prepared by incorporating a new naphthalimide dye with a planar structure as a selectophore and graphene oxide (GO) nanoplatelets as a quencher for rapid optical detection of fructose. The designed probe, made with the high fusion loop-containing dye, along with the GO nanoplatelets, detected fructose over the other monosaccharides very well. The proposed sensor displays a linear response range of 7 × 10-5 to 3 × 10-2 M with a low limit of detection of 23 × 10-6 M in solution at pH 7.4. This sensor shows a good selectivity towards fructose with respect to other saccharides. The proposed sensor was then applied to the determination of fructose in human plasma with satisfactory results.
- Seraj, Sanaz,Rouhani, Shohre,Faridbod, Farnoush
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- Synthesis and fluorescence quenching mechanism of novel naphthalimide derivative by nanographene oxide
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Novel naphthalimide derivative with amine functional group was prepared, and its FTIR and 1H and 13C NMR spectral characteristics were reported. The fluorescence quenching of synthesized dye by nanographene oxide was studied using absorption and fluorescence measurements. From the stern-Volmer analysis, we observed that the quenching was mainly due to the dynamic mechanism. The CV plots indicate that the quenching also went through an electron transfer process. The binding constant (K) and the number of binding sites (n) were calculated based on the fluorescence quenching data. In addition, the free energy change (ΔG) for the electron transfer process was calculated.
- Rouhani, Shohre,Seraj, Sanaz
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- Preparation method 4 - bromo -5 - nitro -1, 8 - naphthalene anhydride (by machine translation)
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The invention belongs to the technical field of fine chemical engineering, and concretely relates to 4 - bromo -5 - nitro -1, 8 - naphthalene anhydride preparation method. 5 - Bromoacenaphthylene is added dropwise to obtain 5 - bromo 4 - nitroacenaphthylene;5 - bromo 4 - nitroacenaphthylene and a catalyst are added into glacial acetic acid to react to obtain -5 - bromo 4 - nitro -5 - and -1 8 - naphthalene anhydride. The method for preparing the target product has the advantages of cheap and easily available raw materials, low preparation cost, high product yield, mild preparation process conditions, good atomic economy and industrial mass production. (by machine translation)
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Paragraph 0021-0031
(2020/07/15)
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- On-line basis C3 Symmetric-n type organic semiconductor material as well as synthesis and application thereof (by machine translation)
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The invention discloses a base-based C system. 3 The symmetric-n type organic semiconductor material and its synthesis and application. of the organic semiconductor material of the present invention are represented by the following 1 structure as shown in the formula, C (, I) as one of the six-membered ring as the mother nucleus. 3 Symmetric outwardly extended perylene bisimide polycyclic aromatic hydrocarbons having an aspect ratio of at least one selected from the group :C consisting of, R. aromatic hydrocarbons and aromatic hydrocarbons. 2 - 60 Substituent- containing alkyl groups C of alkyl groups2 - 60 Alkyl (alkyl) alkyl group, C1 - 60 Substituted radicals of, alkoxy radicals C1 - 60 The present, invention for, the first time for the first, time of the, present invention for the first time of, the present invention to, synthesize a compound having a substituent and an, alkyl heterocyclic group having a substituent comprising a substituent and an. alkyl heterocyclic group having a Yamamoto - type coupling reaction substituent comprising a substituent. (by machine translation)
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Paragraph 0050-0052
(2020/02/10)
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- Anticancer activity and topoisomerase II inhibition of naphthalimides with Ω-hydroxylalkylamine side-chains of different lengths
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Background: The substituted 1,8-Naphthalimides (1H-benzo[de]isoquinoline-1,3(2H)- diones) are known as DNA intercalators stabilizing DNA-Topoisomerase II complexes. This interaction disrupts the cleavage-relegation equilibrium of Topo II, resulting in formation of broken strands of DNA. Objective: To investigate the influence of type of substituents and substitution positions in 1,8- naphthalimde skeleton on the inhibition of Topoisomerase II activity. Method: The starting 1,8-naphthalimide were prepared from acenaphthene by introduction of appropriate substituents followed by condensation with ω-hydroxylakylamines of different chain length. The substituents were introduced to 1,8-naphthalimide molecule by nucleophilic substitution of leaving groups like nitro or bromo present in 4 or 4,5- positions using the ω- hydroxylalkylamines. The bioactivity of obtained compounds was examined in model cell lines. Results: Antiproliferative activity of selected compounds against HCT 116 human colon cancer cells, human non-small cell lung cells A549 and non-tumorigenic BEAS-2B human bronchial epithelium cells was examined. Several of investigated compounds exhibit a significant activity (IC50 μM to 7 μM) against model cancer cell lines. It was demonstrated that upon treatment with concentration of 200 μM, all derivatives display Topo II inhibitory activity, which may be compared with activity of Amonafide. Conclusion: The replacement of the nitro groups in the chromophore slightly reduces its anticancer activities, whereas the presence of both nitro group and ω-hydroxylalkylamine chain resulted in seriously increased anticancer activity. Obtained compounds showed Topo II inhibitory activity, moreover, influence of the substitution pattern on the ability to inhibit Topo II activity and cancer cells proliferation was observed.
- Kasprzycki, Przemys?aw,Strama, Klaudia,Tomczyk, Mateusz D.,Walczak, Krzysztof Z.,Wawszków, Martyna,Wyrostek, Anna Byczek
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p. 550 - 560
(2019/07/12)
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- Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug
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A novel approach to the synthesis of pH-sensitive prodrugs has been proposed: thiourea drug modification. Resulting prodrugs can release the cytotoxic agent and the biologically active 2-thiohydantoin in the acidic environment of tumor cells. The concept of acid-catalyzed cyclization of thioureas to 2-thiohydantoins has been proven using a FRET model. Dual prodrugs of model azidothymidine, cytotoxic doxorubicin, and 2-thiohydantoin albutoin were obtained, which release the corresponding drugs in the acidic environment. The resulting doxorubicin prodrug was tested on prostate cancer cells and showed that the thiourea-modified prodrug is less cytotoxic (average IC50 ranging from 0.5584 to 0.9885 μM) than doxorubicin (IC50 ranging from 0.01258 to 0.02559 μM) in neutral pH 7.6 and has similar toxicity (average IC50 ranging from 0.4970 to 0.7994 μM) to doxorubicin (IC50 ranging from 0.2303 to 0.8110 μM) under mildly acidic conditions of cancer cells. Cellular and nuclear accumulation in PC3 tumor cells of Dox prodrug is much higher than accumulation of free doxorubicin.
- Krasnovskaya, Olga O.,Malinnikov, Vladislav M.,Dashkova, Natalia S.,Gerasimov, Vasily M.,Grishina, Irina V.,Kireev, Igor I.,Lavrushkina, Svetlana V.,Panchenko, Pavel A.,Zakharko, Marina A.,Ignatov, Pavel A.,Fedorova, Olga A.,Jonusauskas, Gediminas,Skvortsov, Dmitry A.,Kovalev, Sergey S.,Beloglazkina, Elena K.,Zyk, Nikolay V.,Majouga, Alexander G.
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p. 741 - 750
(2019/03/02)
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- Probing the Formation of a Seleninic Acid in Living Cells by the Fluorescence Switching of a Glutathione Peroxidase Mimetic
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Glutathione peroxidase (GPx) is a selenoenzyme that protects cells against oxidative damage. Although the formation of a seleninic acid (-SeO2H) by this enzyme during oxidative stress has been proposed, a selenic acid has not been identified in cells. Herein, we report that the formation of a seleninic acid can be monitored in living cells by using a redox-active ebselen analogue with a naphthalimide fluorophore. The probe reacts with H2O2 to generate the highly fluorescent seleninic acid. The electron withdrawing nature of the -SeO2H moiety and strong Se???O interactions, which prevent the photoinduced electron transfer, are responsible for the fluorescence.
- Ungati, Harinarayana,Govindaraj, Vijayakumar,Narayanan, Megha,Mugesh, Govindasamy
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supporting information
p. 8156 - 8160
(2019/05/17)
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- Fluorescent dye based on naphthalimide and preparation method, and application thereof
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The invention relates to a fluorescent dye based on naphthalimide, and a preparation method and an application thereof. Specifically, the invention provides a naphthalimide fluorophore which has a structure as shown in a general formula I which is described in the speicification, wherein groups in the formula I are described in the specification. The compound provided by the invention has good water solubility and high fluorescent quantum yield in an aqueous solution, and can be used for two-photon imaging and co-localization imaging to living cells.
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Paragraph 0113-0116
(2019/12/29)
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- A series of selective and sensitive fluorescent sensors based on a thiophen-2-yl-benzothiazole unit for Hg2+
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Different types of fluorescent probes for Hg2+ based on the 5-thiophen-2-yl-benzothiazole derivatives (TBT, 2-thiophen-2-yl-benzothiazole; CTBT, 9-(5-benzothiazol-2-yl-thiophen-2-yl)-9H-carbazole; DTBT, 2-(5-acenaphthen-5-yl-thiophen-2-yl)-benzothiazole; and NTBT, 6-(5-benzothiazol-2-yl-thiophen-2-yl)-2-hexyl-benzo[de]isoquinoline-1,3-dione) were realized by changing the subsituents. Multisignaling changes were observed through UV-vis absorption and fluorescence spectra upon addition of Hg2+. The addition of Hg2+ on TBT induced a remarkable OFF/ON-type fluorescence signaling behavior. With the introduction of electron-donating carbazole, the detection behavior of CTBT was just the reverse of what TBT displayed, while a ratiometric fluorescent probe based on DTBT for Hg2+ was prepared by introducing the weak electron-drawing group acenaphthene. Moreover, the dichloromethane solution of CTBT and DTBT showed a distinct color change from colorless to yellow with the addition of Hg2+, which indicated that these two probes would facilitate the naked-eye detection of Hg2+. However, both UV-vis absorption and fluorescence spectra of NTBT with strong electron-withdrawing substituents showed no obvious change upon addition of Hg2+. It would be concluded that the electronic properties of the molecule was one of the vital factors in designing chemosensor molecules.
- Mei, Qunbo,Tian, Ruqiang,Shi, Yujie,Hua, Qingfang,Chen, Chen,Tong, Bihai
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p. 2333 - 2342
(2016/03/19)
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- Putting corannulene in its place. Reactivity studies comparing corannulene with other aromatic hydrocarbons
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A series of aromatic hydrocarbons were investigated so as to compare the reactivity of corannulene with planar aromatic hydrocarbons. Corannulene was found to be more reactive than benzene, naphthalene and triphenylene to Friedel-Crafts acylation whilst electrophilic aromatic bromination was also used to confirm that triphenylene was less reactive than corannulene and that pyrene, perylene and acenaphthene were more so. The stabilisation of a neighbouring carbocation by the various aromatic systems was investigated through consideration of the rates of methanolysis of a series of benzylic alcohols. The reactivity series was found to parallel that observed for the electrophilic aromatic substitutions and both series are supported by computational studies. As such, a reactivity scale was devised that showed that corannulene was less reactive than would be expected for an aromatic planar species of similar pi electron count.
- George, Stephen R. D.,Frith, Thomas D. H.,Thomas, Donald S.,Harper, Jason B.
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supporting information
p. 9035 - 9041
(2015/09/01)
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- The effect of the regioisomeric naphthalimide acetylide ligands on the photophysical properties of N^N Pt(ii) bisacetylide complexes
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Two N^N Pt(ii) bis(acetylide) complexes Pt-1 and Pt-2 with regioisomeric amino NI acetylide ligands (L-1 and L-2, L-1 = 5-amino-4-ethylnaphthaleneimide; L-2 = 3-amino-4-ethylnaphthaleneimide) were prepared. The photophysical properties of the complexes were studied by steady state and time-resolved spectroscopy. The two complexes with regioisomeric ligands (Pt-1 and Pt-2) show different photophysical properties such as maximal absorption wavelength (485 nm vs. 465 nm), triplet excited state lifetimes (23.7 μs vs. 0.9 μs), and different solvent-polarity dependences of the emission properties. The absorption of the complexes is red-shifted as compared with the previously reported Pt(ii) complex containing the 4-ethylnaphthaleneimide ligand. The two complexes with regioisomeric NI ligands were used as triplet photosensitizers for triplet-triplet annihilation (TTA) upconversion; drastically different upconversion quantum yields (15.0% vs. 1.1%) were observed. Our results are useful for designing new visible light-harvesting Pt(ii) bisacetylide complexes as triplet photosensitizers which can be used in areas such as photocatalysis, photodynamic therapy and TTA upconversion.
- Liu, Lianlian,Zhang, Caishun,Zhao, Jianzhang
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p. 13434 - 13444
(2014/11/07)
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- A new polymerizable fluorescent PET chemosensor of fluoride (F-) based on naphthalimide-thiourea dye
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A novel N-allyl-4-amino-substituted 1,8-naphthalimide dye, containing thiourea functional group with intense yellow-green fluorescence was successfully synthesized. Copolymerization was done with styrene. The photophysical characteristics of dye and its copolymer in solution and solid film were investigated in the presence of halide ions. The results reveal that the fluorescence emissions of the monomer dye and also its polymer were 'switched off' in the presence of fluoride ions. The dye showed spectral shifts and intensity changes in the presence of more fluoride ions which lead to detect certain fluoride concentrations of 10-150 mM at visible wavelengths. By adding the fluoride ions, green-yellow to purple color changes occurs and the green fluorescence emission quenches, all of which easily observed by naked eyes. These phenomena are essential for producing a dual responsive chemosensor for fluoride ions. The polymeric sensor, in the film state exhibited a fast response to the fluoride ions.
- Alaei, Parvaneh,Rouhani, Shohre,Gharanjig, Kamaladin,Ghasemi, Jahanbakhsh
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scheme or table
p. 85 - 92
(2012/04/23)
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- Synthesis and characterization of sulfonated polyimides bearing sulfonated aromatic pendant group for DMFC applications
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A novel side-chain-type sulfonated aromatic diamine, 5-[1,1-bis(4-aminophenyl)-2,2,2- trifluoroethyl]-2-(4-sulfophenoxy)benzenesulfonic acid (BABSA) was synthesized and characterized. Two series of sulfonated polymides (SPI-N and SPI-B) were prepared from 1,4,5,8-naphthalene tetracarboxylic dianhydride (NTDA) or 4,4'-binaphthyl-1,1',8,8'-tetracarboxylic dianhydride (BNTDA), sulfonated diamine BABSA and various non-sulfonated aromatic diamines. The resulting sulfonated polyimide (SPI) membranes exhibited good dimensional stability with isotropic swelling of 7-22% and high thermal stability with desulfonation temperature of 283-330 °C. These membranes also displayed excellent oxidation stability and good water stability. The SPI membranes exhibited better permselectivity than Nafion 115 membrane due to their much lower methanol permeability. The ratios of proton conductivity to methanol permeability (F{cyrillic}) for the SPI membranes were almost two to three times of that for Nafion 115. The SPI-N membranes exhibited excellent conducting performance with the proton conductivity higher than Nafion 115 as the temperature over 40 °C, which attributed to their good hydrophobic/hydrophilic microphase separation structure.
- Sun, Fei,Wang, Taipeng,Yang, Shiyong,Fan, Lin
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p. 3887 - 3898
(2011/11/07)
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