- Naphthalimide-Based DNA-Coupled Hybrid Assembly for Sensing Dipicolinic Acid: A Biomarker for Bacillus anthracis Spores
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We have designed and synthesized a novel, water-soluble naphthalimide-histidine receptor (1) with excellent fluorescent properties. Functioning of the synthesized receptor was performed through developing their DNA-receptor hybrid assembly (DRHA), which has shown significant changes in the emission profile upon interactions with dipicolinic acid (DPA), a biomarker for Bacillus anthracis spores. DRHA showed fluorescence enhancement upon binding with DPA with the characteristic of internal charge transfer. It is notable that this assembly exhibited a significant limit of detection (12 nM) toward DPA. The mechanism of sensing was fully defined using ethidium bromide (EtBr) interaction studies as well as Fourier transform infrared spectroscopic analysis, which describes the binding mode of DRHA with DPA. This assembly selectively interacts with DPA over other anions, common cellular cations, and aromatic acids in aqueous media.
- Verma, Meenakshi,Kaur, Navneet,Singh, Narinder
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- An indolium ion functionalized naphtha imide chemodosimeter for detection of cyanide in aqueous medium
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A naphthalimide platform based indolium ion functionalized colorimetric as well as fluorometric chemodosimeter (L) has been synthesized and characterized. This can selectively sense cyanide (CN?) in aqueous medium with a low limit of detection (approximately 0.5 μM), which is around four times lower than the value of 1.9 μM set by WHO. The UV–vis and PL studies have been carried out in 40% aqueous-acetonitrile medium which shows a significant change in the visible region allowing naked eye colorimetric detection of CNˉ. The mass spectrometry and 1H NMR spectroscopy are used to characterize the corresponding cyanide adduct which has also been corroborated by time-dependent density functional theory (TD-DFT) during the establishment of the sensing mechanism.
- Maji, Siddhartha,Chowdhury, Bijit,Pal, Sanchari,Ghosh, Pradyut
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- Naphthalimide-gold-based nanocomposite for the ratiometric detection of okadaic acid in shellfish
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Okadaic acid (OA) is one of the known marine biotoxins produced by various dinoflagellates and exists in seafood such as shellfish. The consumption of contaminated shellfish with OA leads to diarrheic shellfish poisoning (DSP), which results in the inhibition of protein phosphatase enzymes in humans. This poisoning can cause immunotoxicity and tumor promotion due to the accumulation of okadaic acid in more than the allowed limit in bivalve molluscs. The reported methods for the detection of okadaic acid include mouse bioassays, immunoassays, chromatography coupled with spectroscopic techniques, electrochemical sensors and immunosensors. We have developed a naphthalimide-gold-based nanocomposite for the detection of okadaic acid. Individually, the organic nanoparticles (ONPs) of synthesized naphthalimide-based receptors and gold-coated ONPs are less sensitive for detection. However, fabrication of the composite of Au?ONPs and ONPs enhance the sensing properties and selectivity. The composite shows a ratiometric response in the UV-Vis absorption spectrum and quenching in the fluorescence profile with a detection limit of 20 nM for OA in aqueous medium. In cyclic voltammetry, a shift was observed in the cathodic peak (-0.532 V to -0.618 V) as well as in the anodic peak (-0.815 V to -0.847 V) with the addition of okadaic acid. To study the quick binding of the composite with OA, a time response experiment was performed. Also, the developed sensor retains its sensing ability in the pH range of 5-9 and in high salt conditions. Our developed composite can be used for the detection of OA in real applications.
- Chaudhary, Monika,Kaur, Navneet,Singh, Amanpreet,Singh, Narinder,Verma, Meenakshi
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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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p. 1821 - 1831
(2021/03/31)
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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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- 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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supporting information
(2019/12/24)
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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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- Naphthaline derivative fluorescent dye as well as preparation method and use thereof
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The invention discloses a naphthaline derivative fluorescent dye as well as a preparation method and use thereof. The naphthaline derivative fluorescent dye has a structure as shown in a general formula I. The fluorescent dye has relatively low fluorescent background in living cells, has a relatively strong fluorescent signal in a mitochondrion area in the living cells which generate click reaction with medicines, and the radical which generates click reaction in the living cells has a strong special mark. The compound has water solubility of a certain level, and has good cell membrane permeability. The compound further has relatively low biotoxicity, light toxicity and light bleaching property. The difference between a spectrum range of the naphthaline derivative fluorescent dye and a spectrum range of a biological sample is big enough. (The general formula I is as shown in specification).
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Paragraph 0089; 0090; 0091; 0092; 0093
(2019/02/17)
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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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- 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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p. 17933 - 17940
(2019/06/24)
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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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p. 8156 - 8160
(2019/05/17)
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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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- The Remarkable Effect of Halogen Substitution on the Membrane Transport of Fluorescent Molecules in Living Cells
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Small-molecule-based fluorescent probes have become important tools in biology for sensing and imaging applications. However, the biological applications of many of the fluorescent molecules are hampered by low cellular uptake and high toxicity. In this paper, we show for the first time that the introduction of halogen atoms enhances the cellular uptake of fluorescent molecules and the nature of halogen atoms plays a crucial role in the plasma membrane transport in mammalian cells. The remarkably higher uptake of iodinated compounds compared to that of their chloro or bromo analogues suggests that the strong halogen bonding ability of iodine atoms may play an important role in the membrane transport. This study provides a novel strategy for the transport of fluorescent molecules across the plasma membrane in living cells.
- Ungati, Harinarayana,Govindaraj, Vijayakumar,Mugesh, Govindasamy
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p. 8989 - 8993
(2018/07/25)
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- Synthesis and photophysical properties of blue-emitting fluorescence dyes derived from naphthalimide derivatives containing a diacetylene linkage group
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Four naphthalimide-based dyes with a diacetylene linkage at the 3- or 4-position were synthesized to improve the thermal stability of the fluorescence dye as well as the efficiency of fluorescent emission at blue region. The absorption and fluorescence properties of the synthesized dyes were also investigated. The geometries and molecular orbitals of the dyes prepared were simulated using by density functional theory and time-dependent density functional theory using Gaussian 09. Furthermore, the suitability of the dyes for application in light-conversion films was examined. N-Phenyl groups were found to have a greater effect on the fluorescence of naphthalimide-based dyes than analogue containing an N-alkyl group. In addition, investigation of the effect of diacetylene linkages at the 3- or 4-positions of naphthalimide-based dyes showed that the fluorescence was influenced by the electron-donating effect of the diacetylene linkage which could afford more conjugation of π orbitals of the dyes. Four blue fluorescence dyes derived from 1,8-naphthalimide containing a diacetylene linkage were synthesized and then coated in PE film. The photophysical properties were analyzed using density functional theory (DFT) calculations, and excitations from the highest occupied molecular orbitals (HOMOs) to the lowest unoccupied molecular orbitals (LUMOs) of the dyes were simulated at the B3LYP/6-31G level of theory via the Gaussian 09 suite of programs. Using these methods, the influences of the position of the ethynyl linkages, alkyl groups, and phenyl groups on the electronic and fluorescence properties of the dyes were also clarified.
- Kim, Kyung-Won,Kim, Geun-Hyeong,Kwon, Su-Hyeon,Yoon, Hyo-In,Son, Jung-Eek,Choi, Jae-Hong
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p. 353 - 361
(2018/06/06)
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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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- 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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p. 344 - 354
(2017/05/08)
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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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p. 1005 - 1012
(2016/05/09)
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- Synthesis, in vitro evaluation and DNA interaction studies of N-allyl naphthalimide analogues as anticancer agents
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A novel series of 2-allyl-6-substituted-benzo[de]isoquinoline-1,3-diones has been synthesized and evaluated against 60 human tumor cell lines for their in vitro antitumor activities. Compound 6b proved to be the most active member at a single dose concentration of 10 μM and broad spectrum of antitumor activity with GI50, TGI and LC50 values of 84.2 nM, 27.6 μM and 89.3 μM respectively at five dose concentration levels. The DNA binding properties of this compound has been investigated by a UV-Vis and fluorescence spectrophotometer as well as thermal denaturation experiments. Molecular docking studies of compound 6b have also supported the corresponding biological data.
- Verma, Meenakshi,Luxami, Vijay,Paul, Kamaldeep
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p. 41803 - 41813
(2015/05/27)
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- Synthesis, in vitro evaluation and molecular modelling of naphthalimide analogue as anticancer agents
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A series of amine substituted naphthalimide analogue were synthesized and evaluated for in vitro anti-tumour activities against 60 tumour cell lines at a single dose concentration of 10 μM. These new analogue showed potential anticancer activities against various cancer cell lines. Compound 5d exhibited significant growth inhibition and was evaluated as 60 cell panel at five dose concentration levels. Compound 5d proved to be fivefold more active than standard antitumour drug 5-fluorouracil (5-FU) with MG-MID GI50 and TGI values of 5.05 and 38.71 respectively. ct-DNA binding studies of most active compound 5d revealed strong interacting properties. Molecular docking studies in the active binding site provided complementary theoretical support for the experimental biological data acquired.
- Verma, Meenakshi,Luxami, Vijay,Paul, Kamaldeep
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p. 352 - 360
(2013/10/01)
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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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p. 11430 - 11432
(2013/12/04)
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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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- Solvatochromic reagents for multicomponent reactions and their utility in the development of cell-permeable macrocyclic peptide vectors
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Sensitive scaffolds: An isocyanide equipped with an environment-sensitive fluorophore was used to synthesize peptide macrocycles. The photophysical properties of the product macrocycles are sensitive to both peptide sequence and configuration. A mitochondria-penetrating peptide was constrained within a cyclic peptide framework and showed increased uptake and localization relative to a linear control (see scheme). Copyright
- Rotstein, Benjamin H.,Mourtada, Rida,Kelley, Shana O.,Yudin, Andrei K.
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supporting information; experimental part
p. 12257 - 12261
(2011/12/15)
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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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experimental part
p. 1690 - 1700
(2011/10/04)
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- Synthesis of a novel oxoxanthenoisoquinoline via a palladium-catalysed cross-coupling reaction; as a fluorophore
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Suzuki cross-coupling of a bromoaromatic anhydride with 2-methoxyboronic acid afforded a novel oxoxanthenoisoquinoline. Subsequent coupling with 2,3,4,6-tetra-O-acetyl-D-galactose-1,3-diyl phosphate gave a fluorophore. (C) 2000 Elsevier Science Ltd.
- Prickett, Mark P.,Singh, Gurdial,Vankayalapati, Hariprasad
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p. 2987 - 2990
(2007/10/03)
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- Transformations of polycyclic ketones. XV. Ammonolysis of 4-hydroxyphenalenone
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The ammonolysis of 4-hydroxyphenalenone leads to the formation of a mixture of isomeric 4- and 7-aminophenalenones, from which the corresponding bromophenalenones were synthesized.The structure of the obtained compounds was determined by oxidation to the known 2- and 4-bromonaphthalic anhydrides.
- Solodar', S. L.,Vinogradov, L. M.
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p. 1102 - 1104
(2007/10/02)
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