Articles de revues : « Naphthalimide »

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Fedko, Nadiia F., Valeriy F. Anikin et Vira V. Veduta. « The synthesis of N-substituted 4-fluoro-1,8-naphthalimides ». Journal of Organic and Pharmaceutical Chemistry 20, n^o 3 (21 novembre 2022) : 25–30. http://dx.doi.org/10.24959/ophcj.22.263203.

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Aim. To synthesize 4-fluoro-1,8-naphthalic acid imide and its derivatives substituted in the imide ring.Results and discussion. 4-Fluoro-1,8-naphthalimide was obtained using acenaphthene as the starting material. N-alkyl-4-fluoro-1,8-naphthalimides were synthesized via the phase transfer catalytic alkylation of 4-fluoro-1,8-naphthalimide with haloalkanes. Imidation of 4-fluoro-1,8-naphthalic anhydride with aminoacids resulted in the formation of N-carboxyalkyl-1,8-naphthalimides. These substances can be considered as potential fluorescent labels capable of binding to amino groups of various biological molecules as they contain carboxylic functionality in their structure.Experimental part. The structure of the compounds synthesized was confirmed by FT-IR, 1H NMR and 13C NMR spectroscopy, and mass-spectrometry.Conclusions. It has been shown that 4-fluoro-1,8-naphthalinedicarboxylic acid imide can be obtained following the synthetic route “acenaphthene – 5-fluoroacenaphthene – 4-fluoro-1,8-naphthalic anhydride – 4-fluoro-1,8-naphthalimide”. 4-Fluoro-1,8-naphthalimide can be alkylated by butyl iodide and octyl bromide using tetraalkylammonium salts as a phase transfer catalyst resulted in N-butyl-4-fluoro-1,8-naphthalimide and N-octyl-4-fluoro-1,8-naphthalimide. As a result, N-carboxyalkyl-4-fluoro-1,8-naphthalimides have been obtained for the first time by aminolysis of 4-fluoro-1,8-naphthalic anhydride with glycine, β-alanine and 6-aminocaproic acid.

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Yang, Jian Xin, et Xiang Hui Wang. « The Synthesis and Electroluminescence Properties of 4-Benzofuranyl-1,8-Naphthalimide Derivatives ». Advanced Materials Research 557-559 (juillet 2012) : 1031–36. http://dx.doi.org/10.4028/www.scientific.net/amr.557-559.1031.

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A series of fluorescence compounds, 4-benzofuranyl-1,8-naphthalimides, were prepared through cycloaddition reaction from 4-ethynyl-1,8-naphthalimides and o-iodophenols which catalyzed by a Pd(PPh3)2Cl2 / CuI system under mild conditions. The intermediate material, 4-ethynyl-1,8- naphthalimide, was synthesized from 4-bromo-1,8- naphthalimide and trimethylsilyl- acetylene. The absorption and fluorescence spectra of 4-benzofuranyl-1,8- naphthalimides were studied and the quantum yields were measured. The maximum UV/vis absorption spectra were in the range of 375-400 nm and the maximum emission spectra were in the range of 470-510 nm. The electro- luminescent properties were also mensurated through a doped electroluminescent device which contains 1% 1,8-naphthalimides and 99% CBP (4,4'-N,N'-dicarbazole-biphenyl), It’s shown the maximum brightness reached 3700 cd/ m2 at 22.5V.

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Calatrava-Pérez, Elena, Jason M. Delente, Sankarasekaran Shanmugaraju, Chris S. Hawes, Clive D. Williams, Thorfinnur Gunnlaugsson et Eoin M. Scanlan. « Correction : Glycosylated naphthalimides and naphthalimide Tröger's bases as fluorescent aggregation probes for Con A ». Organic & ; Biomolecular Chemistry 17, n^o 8 (2019) : 2287. http://dx.doi.org/10.1039/c9ob90017a.

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Correction for ‘Glycosylated naphthalimides and naphthalimide Tröger's bases as fluorescent aggregation probes for Con A’ by Elena Calatrava-Pérez et al., Org. Biomol. Chem., 2019, DOI: 10.1039/c8ob02980f.

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Santonocito, Rossella, Ivana Maria Caruso et Giuseppe Trusso Sfrazzetto. « N-isobutyl-1,8-bis(isobutylamino)-naphthalimide ». Molbank 2023, n^o 1 (27 janvier 2023) : M1568. http://dx.doi.org/10.3390/m1568.

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Naphthalimides make up a class of organic molecules characterised by excellent spectroscopic properties due to their extended conjugate system. Furthermore, various asymmetric or symmetric compounds can be obtained from naphthalimides by the different functionalization that can be performed on the nitrogen and/or on the aromatic rings. The introduction of a wide range of substituents in different positions allows chemical and spectroscopic properties to be regulated. In this contribution, we report the synthesis and characterization of a new 4,5-amino-1,8-naphthalimide bearing three isobutyl substituents.

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Kantarod, Kritchasorn, Phiphob Naweephattana, Vichai Reutrakul, Manat Pohmakotr, Darunee Soorukram, Chutima Kuhakarn, Panida Surawatanawong et Pawaret Leowanawat. « Synthesis of peri-Diarylated Naphthalimides via Double Decarboxylative Cross-Coupling Reaction ». Synthesis 51, n^o 15 (3 avril 2019) : 2915–22. http://dx.doi.org/10.1055/s-0037-1611762.

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A facile method for the synthesis of peri-diarylated naphthalimides was developed by using a palladium-catalyzed double decarboxylative cross-coupling reaction. The present work offers a convenient approach for tuning the optical properties of naphthalimide derivatives.

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Qi, Qi, Fan Qi, Yu Qiao Wang, Zheng Jian Qi et Yue Ming Sun. « Spectroscopic Properties Calculation of some 1, 8-Naphthalimide Derivatives ». Advanced Materials Research 760-762 (septembre 2013) : 724–27. http://dx.doi.org/10.4028/www.scientific.net/amr.760-762.724.

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The absorption and emission spectra of 1,8-naphthalimide derivatives have been calculated by time-dependent density functional theory. Their lowest singlet transition states can be described as the promotion of electrons from the HOMO to the LUMO. Substituents on naphthalimic ring seldom extend the conjugation of the central naphthalimic system.

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Khan, Ayad Kareem, Suaad Mohammed Hussain, Mohammed Rifat Ahmad, Fitua Manwar Aziz et Shimaa Mutasim Abdulah***. « Synthesis, Characterization and Antimicrobial Screening of Some Bioactive 1,8-Naphthalimide Derivatives. » Al Mustansiriyah Journal of Pharmaceutical Sciences 14, n^o 2 (1 décembre 2014) : 33–47. http://dx.doi.org/10.32947/ajps.v14i2.145.

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This research include developing new heterocyclic derivatives of 1,8-naphthalimides bearing oxazoline, thiazoline, oxadiazole, thiadiazole and aminotriazole moieties as the following steps: N-ester-1,8-naphthalimide (1) was obtained by direct imidation of 1,8- naphthalic anhydride with ethylglycinate in dimethylsulfoxide. Compound (1) was treated with hydrazine hydrate in absolute ethanol to give N-acetohydrazide-1,8-naphthalimide (2).N-Acetophenylsemicarbazide-1,8-naphthalimide (3) and N-Aceto phenylthiosemicarbazide- 1,8-naphthalimide (7) were synthesized via reaction of compound (2) with phenylisocyanate and phenylisothiocyanate in absolute ethanol respectively.Cyclization of compounds (3) and (7) with p-substituted phenacyl bromide gives the oxazoline derivatives (4-6) and thiazoline derivatives (9-11) respectively. N-Methyl-[(5- (phenyl amino)-1,3,4-thiadiazol-2-yl)]-1,8-naphthalimide (8) prepared via treatment of compound (7) with phosphoric acid. Reaction of the prepared hydrazide (2) with carbon disulfide in the presence of potassium hydroxide producing N-Methyl-[potassium dithiocarbazate]-1,8-naphthalimide (12). Acidifying of the obtained salt (12) with 4N hydrochloric acid give N-Methyl-[1,3,4-oxadiazol-2-yl-5-thiol]-1,8-naphthalimide (13). The obtained salt (12) also treated with hydrazine hydrate to afford the desirable N-Methyl-[1,2,4- triazol-3-yl-4-amino-5-thiol]-1,8-naphthalimide (14).All the prepared compounds in this research were characterized by recording their melting points, FTIR, 1HNMR, 13CNMR spectra, checked by TLC, physical properties and some specific chemical tests also. Some of the new prepared compounds were evaluated for the antimicrobial screening in vitro against two types of Gram positive bacteria including (Staphylococcus aureus, Bacillus subtilis) and two types of Gram negative bacteria including (Escherichia coli, Pseudomonas aeuroginosa).More, antifungal activities of some prepared compounds performed against the yeastlike pathogenic fungus (Candida albicans). The antimicrobial screening carried out in three concentrations of prepared compounds. Sulfamethoxazole/Clotrimazole was used as standard drugs. The results showed that most of the tested compounds have good biological activity against the mentioned organisms compared with standard drugs above

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Tomczyk, Mateusz D., Anna Byczek-Wyrostek, Klaudia Strama, Martyna Wawszków, Przemysław Kasprzycki et Krzysztof Z. Walczak. « Anticancer Activity and Topoisomerase II Inhibition of Naphthalimides with ω-Hydroxylalkylamine Side-Chains of Different Lengths ». Medicinal Chemistry 15, n^o 5 (2 juillet 2019) : 550–60. http://dx.doi.org/10.2174/1573406414666180912105851.

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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. Methods: 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.

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Gawron, Katarzyna, Dorota G. Piotrowska, Graciela Andrei, Dominique Schols, Robert Snoeck et Iwona E. Głowacka. « Synthesis, Antiviral and Cytostatic Activity of New Series of Naphthalimide Derivatives ». Acta Poloniae Pharmaceutica - Drug Research 80, n^o 5 (21 novembre 2023) : 775–93. http://dx.doi.org/10.32383/appdr/171434.

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A new series of N-(diethylphosphonoalkyl)-1,8-naphthalimides were synthesized via direct reaction of 1,8-naphthalic anhydride or its 3-nitro- and 4-bromo- derivatives with selected ɷ-aminoalkylphosphonates and evaluated against a broad-spectrum of viruses as well as for their cytostatic properties toward selected cell lines. N-(diethylphosphonomethyl)-3-nitro-1,8-naphthalimide 15a exhibited inhibitory activity toward coxsackie virus B4 in Vero cells (EC50 = 9.45 μM), whereas 3-nitro-1,8-naphthalimides 15b and 15d containing short 2-carbon linker showed moderate activity against herpes simplex virus-2 (G) and herpes simplex virus-1 TK– KOS ACVr. Furthermore, compounds 15a, 15b and 15d showed antiviral potency against human coronavirus. Several naphthalimides exhibited cytostatic activity toward tested cancerous cell lines as well as normal retina cells. Transformation of selected diethyl phosphonates 13, 14 and 15 into ammonium phosphonates 21, 22 and 23 improved the solubility, however, did not result in the enhancement of antiviral and cytostatic potency of the compounds.

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Jia, Xiaotong, Yu Yang, Yufang Xu et Xuhong Qian. « Naphthalimides for labeling and sensing applications ». Pure and Applied Chemistry 86, n^o 7 (22 juillet 2014) : 1237–46. http://dx.doi.org/10.1515/pac-2013-1025.

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AbstractNaphthalimide has now become a class of most popular fluorophores for probe design, along with coumarin, fluorescein, rhodamine, BODIPY and cyanine. This account aims at the first-year graduate students as the primary audience and showcases the versatile design principles applicable to the naphthalimide fluorophore when designing a probe or label, with focused examples from the Qian research laboratory. We also provide a general synthetic scheme to naphthalimides of various substitution patterns.

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Rychlewska, Urszula, Agnieszka Plutecka, Marcin Hoffmann, Paweł Skowronek, Krystyna Gawrońska et Jacek Gawroński. « Probing the shapes of chiral bis-(o-naphthalimidobenzoyl) systems using X-ray and circular dichroism methods ». Acta Crystallographica Section B Structural Science 65, n^o 1 (15 janvier 2009) : 86–95. http://dx.doi.org/10.1107/s0108768108041827.

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CD (circular dichroism) and X-ray investigations have been carried out in order to identify the prevalent conformations and define the forces that determine the molecular and supramolecular organization of the alkyl-bridged bichromophoric [NAB, ortho-(1,8-naphthalimido)benzoyl] units, each consisting of the benzoyl substituted in the ortho position with the 1,8-naphthalimide group. The results reveal that NAB bichromophores incorporated into the same molecule exist in a variety of conformation/helicity combinations. The molecular structures are largely stabilized by local 1,3-CH/CO dipole–dipole interactions, while the crystal packing besides dispersive H...H interactions is mostly governed by multiple C—H...O(=C) and C—H...π interactions. The relatively small contribution of π...π interactions comes from a pairwise off-face stacking between naphthalimide rings or from pairwise carbonyl...π interactions. All these types of intermolecular interactions have been summarized quantitatively by means of a Hirshfeld surface analysis.

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Rykowski, Sebastian, Dorota Gurda-Woźna, Marta Orlicka-Płocka, Agnieszka Fedoruk-Wyszomirska, Małgorzata Giel-Pietraszuk, Eliza Wyszko, Aleksandra Kowalczyk et al. « Design, Synthesis, and Evaluation of Novel 3-Carboranyl-1,8-Naphthalimide Derivatives as Potential Anticancer Agents ». International Journal of Molecular Sciences 22, n^o 5 (9 mars 2021) : 2772. http://dx.doi.org/10.3390/ijms22052772.

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We synthesized a series of novel 3-carboranyl-1,8-naphthalimide derivatives, mitonafide and pinafide analogs, using click chemistry, reductive amination and amidation reactions and investigated their in vitro effects on cytotoxicity, cell death, cell cycle, and the production of reactive oxygen species in a HepG2 cancer cell line. The analyses showed that modified naphthalic anhydrides and naphthalimides bearing ortho- or meta-carboranes exhibited diversified activity. Naphthalimides were more cytotoxic than naphthalic anhydrides, with the highest IC50 value determined for compound 9 (3.10 µM). These compounds were capable of inducing cell cycle arrest at G0/G1 or G2M phase and promoting apoptosis, autophagy or ferroptosis. The most promising conjugate 35 caused strong apoptosis and induced ROS production, which was proven by the increased level of 2′-deoxy-8-oxoguanosine in DNA. The tested conjugates were found to be weak topoisomerase II inhibitors and classical DNA intercalators. Compounds 33, 34, and 36 fluorescently stained lysosomes in HepG2 cells. Additionally, we performed a similarity-based assessment of the property profile of the conjugates using the principal component analysis. The creation of an inhibitory profile and descriptor-based plane allowed forming a structure–activity landscape. Finally, a ligand-based comparative molecular field analysis was carried out to specify the (un)favorable structural modifications (pharmacophoric pattern) that are potentially important for the quantitative structure–activity relationship modeling of the carborane–naphthalimide conjugates.

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Carretero, Gustavo Penteado Battesini, Greice Kelle Viegas Saraiva, Magali Aparecida Rodrigues, Sumika Kiyota, Marcelo Porto Bemquerer, Hernan Chaimovich et Iolanda Midea Cuccovia. « Naphthalimide-Containing BP100 Leads to Higher Model Membranes Interactions and Antimicrobial Activity ». Biomolecules 11, n^o 4 (8 avril 2021) : 542. http://dx.doi.org/10.3390/biom11040542.

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In a large variety of organisms, antimicrobial peptides (AMPs) are primary defenses against pathogens. BP100 (KKLFKKILKYL-NH2), a short, synthetic, cationic AMP, is active against bacteria and displays low toxicity towards eukaryotic cells. BP100 acquires a α-helical conformation upon interaction with membranes and increases membrane permeability. Despite the volume of information available, the action mechanism of BP100, the selectivity of its biological effects, and possible applications are far from consensual. Our group synthesized a fluorescent BP100 analogue containing naphthalimide linked to its N-terminal end, NAPHT-BP100 (Naphthalimide-AAKKLFKKILKYL-NH2). The fluorescence properties of naphthalimides, especially their spectral sensitivity to microenvironment changes, are well established, and their biological activities against transformed cells and bacteria are known. Naphthalimide derived compounds are known to interact with DNA disturbing related processes as replication and transcription, and used as anticancer agents due to this property. A wide variety of techniques were used to demonstrate that NAPHT-BP100 bound to and permeabilized zwitterionic POPC and negatively charged POPC:POPG liposomes and, upon interaction, acquired a α-helical structure. Membrane surface high peptide/lipid ratios triggered complete permeabilization of the liposomes in a detergent-like manner. Membrane disruption was driven by charge neutralization, lipid aggregation, and bilayer destabilization. NAPHT-BP100 also interacted with double-stranded DNA, indicating that this peptide could also affect other cellular processes besides causing membrane destabilization. NAPHT-BP100 showed increased antibacterial and hemolytic activities, compared to BP100, and may constitute an efficient antimicrobial agent for dermatological use. By conjugating BP100 and naphthalimide DNA binding properties, NAPHT-BP100 bound to a large extent to the bacterial membrane and could more efficiently destabilize it. We also speculate that peptide could enter the bacteria cell and interact with its DNA in the cytoplasm.

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Zhang, Guang Hua, Li Juan Liu et Wei Ling Sun. « Preparation and Properties of 1,8-Naphthalimide Derivatives Grafted onto Chitosan ». Advanced Materials Research 393-395 (novembre 2011) : 1359–62. http://dx.doi.org/10.4028/www.scientific.net/amr.393-395.1359.

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A kind of 1,8-naphthalimide derivative grafted onto Chitosan was synthesized with Chitosan, 4-bromo-N-(2-aminoethyl)-1,8-naphthalimide and 4-bromo-1,8- naphthalic anhydride via substitution and amidation. The structures of compounds was characterized by FT-IR．Thermal stability and fluorescence spectra of the target product were investigated. Compared with 4-bromo-N-(2-aminoethyl)-1,8-naphthalimide, the maximum fluorescent intensity of the 1,8-naphthalimide derivative grafted onto Chitosan was increased 1.25 folds.

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Calatrava-Pérez, Elena, Jason M. Delente, Sankarasekaran Shanmugaraju, Chris S. Hawes, Clive D. Williams, Thorfinnur Gunnlaugsson et Eoin M. Scanlan. « Glycosylated naphthalimides and naphthalimide Tröger's bases as fluorescent aggregation probes for Con A ». Organic & ; Biomolecular Chemistry 17, n^o 8 (2019) : 2116–25. http://dx.doi.org/10.1039/c8ob02980f.

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Hawes, Chris S., Amy D. Lynes, Kevin Byrne, Wolfgang Schmitt, Gavin Ryan, Matthias E. Möbius et Thorfinnur Gunnlaugsson. « A resilient and luminescent stimuli-responsive hydrogel from a heterotopic 1,8-naphthalimide-derived ligand ». Chemical Communications 53, n^o 44 (2017) : 5989–92. http://dx.doi.org/10.1039/c7cc03482b.

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Calatrava-Pérez, Elena, Sandra A. Bright, Stefan Achermann, Claire Moylan, Mathias O. Senge, Emma B. Veale, D. Clive Williams, Thorfinnur Gunnlaugsson et Eoin M. Scanlan. « Glycosidase activated release of fluorescent 1,8-naphthalimide probes for tumor cell imaging from glycosylated ‘pro-probes’ ». Chemical Communications 52, n^o 89 (2016) : 13086–89. http://dx.doi.org/10.1039/c6cc06451e.

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Wang, Shuxin, Jian Cao et Chenhong Lu. « A naphthalimide-based thermometer : heat-induced fluorescence “turn-on” sensing in a wide temperature range in ambient atmosphere ». New Journal of Chemistry 44, n^o 11 (2020) : 4547–53. http://dx.doi.org/10.1039/c9nj06101k.

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Zhang, Jing, Nicolas Zivic, Frédéric Dumur, Pu Xiao, Bernadette Graff, Jean Pierre Fouassier, Didier Gigmes et Jacques Lalevée. « N-[2-(Dimethylamino)ethyl]-1,8-naphthalimide derivatives as photoinitiators under LEDs ». Polymer Chemistry 9, n^o 8 (2018) : 994–1003. http://dx.doi.org/10.1039/c8py00055g.

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Four N-[2-(dimethylamino)ethyl]-1,8-naphthalimide derivatives (ANNs) with different substituents in the naphthalimide skeleton have been synthesized and can be used as versatile photoinitiators under various LEDs.

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Kusano, Shuhei, Sakuya Nakamura, Masanori Izumi et Shinya Hagihara. « Development of 1,8-naphthalimide dyes for rapid imaging of subcellular compartments in plants ». Chemical Communications 58, n^o 11 (2022) : 1685–88. http://dx.doi.org/10.1039/d1cc05798g.

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Fedko, N. F., V. F. Anikin, V. V. Veduta, V. V. Stankevich et A. V. Balatska. « SYNTHESIS AND PROPERTIES OF IMIDATION PRODUCTS OF MONOSUBSTITUTED AND DISUBSTITUTED NAPHTHALIC ANHYDRIDES WITH P-AMINOBENZOIC ACID ». Odesa National University Herald. Chemistry 26, n^o 4(80) (29 décembre 2021) : 15–25. http://dx.doi.org/10.18524/2304-0947.2021.4(80).248290.

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4-Monosubstituted and 4,5-disubstituted halogeno- and nitro- N-(4-carboxyphenylnaphthalimides) were synthesized by imidation of the corresponding 4-monosubstituted and 4,5-disubstituted naphthalic anhydrides with para-aminobenzoic acid using acetic acid as solvent with 75-85% yields. 4-Amino-N- (4-carboxyphenyl)naphthalimide and 4,5-diamino-N-(4-carboxyphenyl)naphthalimide were obtained by reduction of corresponding nitrosubstituted N-(4-carboxyphenyl)naphthalimides using sodium dithionite as reducing agent in mixed ethanol-water solvent. The completion of reaction was monitored by thin layer chromatography with disappearance of the spot of the corresponding starting naphthalic anhydride. Starting 4-monosubstituted and 4,5-disubstituted naphthalic anhydrides were obtained by oxidation of corresponding substituted acenaphthenes with sodium dichromate in acetic acid. The synthesized N-carboxyphenylnaphthalimides with chlorine and bromine in positions 4 or 4 and 5 are yellow crystal substances with blue fluorescence; 4-nitro- and 4,5-dinitro-N-carboxyphenylnaphthalimides are orange crystal substances without fluorescence; 4-amino-, 4-dimethylamino and 4,5-diamino-N-carboxyphenylnaphthalimides are orange crystal substances with orange fluorescence. The structure of all the synthesized products was confirmed by IR and NMR 1H spectroscopy. The results of computer screening of the synthesized compounds using the PASS Online Internet service confirm a wide range of biological activity of N-carboxyphenylnaphthalimides, which makes them promising substances for further biological testing.

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Tian, Ye, Miao Li et Ying Liu. « Detection Sensitivity Enhancement of Naphthalimide PET Fluorescent Probes by 4-Methoxy-Substitution ». Molecules 25, n^o 19 (29 septembre 2020) : 4465. http://dx.doi.org/10.3390/molecules25194465.

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Naphthalimide photoinduced electron transfer (PET) fluorescent probes are widely used in fluorescence imaging. Thereinto, detection sensitivity is the vital parameter of PET probes. However, the modulation of detection sensitivity is yet to be reported for naphthalimide PET probes. Herein, the detection sensitivity enhancement of naphthalimide PET fluorescent probes through 4-methoxy-substitution is proposed in this work. Taking Zn2+ detection an example, 4-methoxy-naphthalimide PET probe 2-(2-(bis(pyridin-2-ylmethyl)amino)ethyl)-6-methoxy-1H-benzo[de]isoquinoline-1,3(2H)-dione (BPNM) and control PET probe 2-(2-(bis(pyridin-2-ylmethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (BPN) are separately synthesized. The addition of 4-methoxy group with ability of strong electron donating to naphthalimide facilitates the construction of electronic push-pull system in the fluorophore resulting in the bathochromic shift of absorption and fluorescence emission spectra of BPNM and is further conducive to the enhancement of molar extinction coefficient ε and fluorescence quantum yield Φf of BPNM. Compared with BPN, BPNM shows lower Zn2+ detection limit in titration assays. Meanwhile, the fluorescence signal change (off-on) before and after Zn2+ addition of intracellular BPNM is more obvious and easier to control in confocal laser scanning imaging. Therefore, 4-methoxy-substitution improves the detection sensitivity of naphthalimide PET probe, which is favorable for the precise sensing of analyte, and further lays a good foundation for the synthesis of PET probe with high sensitivity.

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Chen, Rui, Caiying Yuan, Yogini Jaiswal, Lini Huo, Dianpeng Li, Leonard Williams, Jing Zhong et Yan Liang. « Synthesis and Biological Evaluation of Some 1,8-Naphthalimide-Acridinyl Hybrids ». Journal of Chemistry 2020 (5 août 2020) : 1–11. http://dx.doi.org/10.1155/2020/7989852.

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In the present study, the synthesis of three 1,8-naphthalimide-acridinyl hybrids (2a, 2b, and 5b) using N-amido-1,8-naphthalimides (1 and 4) and acridinyl isothiocyanates is reported. The newly synthesized hybrids were evaluated for their anticancer activity in six human cancer cell lines (HL-60, MT-4, HepG2, HeLa, SK-OV-3, and MCF-7). Their inhibition activity against DNA-topoisomerase I (Topo I) and Electrophorus electricus acetylcholinesterase (AChE) was also studied. The results indicate that 2b displayed good cytotoxicity for MT-4, HepG2, HeLa, and SK-OV-3 with the IC50 values of 14.66 ± 0.31, 27.32 ± 2.67, 17.51 ± 0.34, and 32.26 ± 1.74 μM, respectively. All compounds, especially 2b, exhibited obvious bands corresponding to DNA fragments at 0.5 mM concentration, further confirming the pharmacological mechanism related to the Topo I inhibitory activities. In addition, compound 2a exhibited higher inhibition activity against AChE than 2b and 5b, with IC50 values of 0.32 ± 0.04 mM, and the acridinyl ring may contribute to the activity of 2a.

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Gao, Yong-Guang, Uzair Alam, Quan Tang, You-Di Shi, Ying Zhang, Ruibing Wang et Zhong-Lin Lu. « Functional lipids based on [12]aneN3 and naphthalimide as efficient non-viral gene vectors ». Organic & ; Biomolecular Chemistry 14, n^o 26 (2016) : 6346–54. http://dx.doi.org/10.1039/c6ob00917d.

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Small organic non-viral gene vectors with the structural combinations of (aliphatic chain)–naphthalimide–[12]aneN₃ (11a, b) and naphthalimide–(aliphatic chain)–[12]aneN₃ (12a–c) were synthesized and fully characterized.

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Sheshashena Reddy, T., et A. Ram Reddy. « Synthesis and fluorescence study of Naphthalimide-Coumarin, Naphthalimide-Luminol conjugates ». Journal of Fluorescence 24, n^o 6 (3 septembre 2014) : 1571–80. http://dx.doi.org/10.1007/s10895-014-1440-x.

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Case, Derek R., Alyssa Spear, Adam F. Henwood, Max Nanao, Sara Dampf, Timothy M. Korter, Thorfinnur Gunnlaugsson, Jon Zubieta et Robert P. Doyle. « [Re(CO)3(5-PAN)Cl], a rhenium(i) naphthalimide complex for the visible light photocatalytic reduction of CO2 ». Dalton Transactions 50, n^o 10 (2021) : 3479–86. http://dx.doi.org/10.1039/d0dt04116e.

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A rhenium(i) naphthalimide complex [Re(CO)₃(5-PAN)Cl] (Re(5-PAN); 5-PAN = 1-(1,10-phenanthroline)-4-nitro-naphthalimide) was synthesized, characterized, and evaluated as a photocatalyst for CO₂ reduction.

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Hearn, Kyle N., Trent D. Ashton, Rameshwor Acharya, Zikai Feng, Nuri Gueven et Frederick M. Pfeffer. « Direct Amidation to Access 3-Amido-1,8-Naphthalimides Including Fluorescent Scriptaid Analogues as HDAC Inhibitors ». Cells 10, n^o 6 (15 juin 2021) : 1505. http://dx.doi.org/10.3390/cells10061505.

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Methodology to access fluorescent 3-amido-1,8-naphthalimides using direct Buchwald–Hartwig amidation is described. The protocol was successfully used to couple a number of substrates (including an alkylamide, an arylamide, a lactam and a carbamate) to 3-bromo-1,8-naphthalimide in good yield. To further exemplify the approach, a set of scriptaid analogues with amide substituents at the 3-position were prepared. The new compounds were more potent than scriptaid at a number of histone deacetylase (HDAC) isoforms including HDAC6. Activity was further confirmed in a whole cell tubulin deacetylation assay where the inhibitors were more active than the established HDAC6 selective inhibitor Tubastatin. The optical properties of these new, highly active, compounds make them amenable to cellular imaging studies and theranostic applications.

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Cho, Dae Won, Patrick S. Mariano et Ung Chan Yoon. « Direct and indirect single electron transfer (SET)-photochemical approaches for the preparation of novel phthalimide and naphthalimide-based lariat-type crown ethers ». Beilstein Journal of Organic Chemistry 10 (27 février 2014) : 514–27. http://dx.doi.org/10.3762/bjoc.10.47.

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In this review, we describe direct and indirect photochemical approaches that have been developed for the preparation of phthalimide- and naphthalimide-based, lariat-type crown ethers. The direct route utilizes a strategy in which nitrogen-linked side chains containing polyethoxy-tethered phthalimides and naphthalimides, possessing terminal α-trialkylsilyl groups, are synthesized utilizing concise routes and UV-irradiation to form macrocyclic ring systems. In contrast, the indirect route developed for the synthesis of lariat-type crown ethers employs sequences in which SET-promoted macrocyclization reactions of α-trialkylsilyl-terminated, polyethoxy-tethered phthalimides and naphthalimides are followed by a side chain introduction through substitution reactions at the amidol centers in the macrocyclic ethers. The combined observations made in these investigations demonstrate the unique features of SET-promoted photocyclization reactions that make them well-suited for the use in the synthesis of functionalized crown ethers. In addition, while some limitations exist for the general use of SET-photochemical reactions in large-scale organic synthesis, important characteristics of the photoinduced macrocyclization reactions make them applicable to unique situations in which high temporal and spatial control is required.

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Abogunrin, Anthony A., Stephen A. Healy, Orla Fenelon et Robert B. P. Elmes. « Head vs. Tail Squaramide–Naphthalimide Conjugates : Self-Assembly and Anion Binding Behaviour ». Chemistry 4, n^o 4 (18 octobre 2022) : 1288–99. http://dx.doi.org/10.3390/chemistry4040085.

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The syntheses of two squaramide–naphthalimide conjugates (SN1 and SN2) are reported; the structures of SN1 and SN2 differ by the attachment of a squaramide—either at the ‘head’ or the ‘tail’ of the naphthalimide fluorophore. Both compounds displayed weak fluorescence due to the inclusion of a nitro-aromatic squaramide which efficiently quenches the emission of the naphthalimide. Both compounds were also shown to undergo self-aggregation as studied by 1H NMR and scanning electron microscopy (SEM). Furthermore, SN1 and SN2 gave rise to stark colourimetric changes in response to basic anions such as AcO−, SO42− HPO42−, and F−. The observed colour changes are thought to be due to deprotonation of a squaramide NH. The same basic anions also result in a further quenching of the naphthalimide emission. No colour change or emission modulations were observed in the presence of Cl−; however, 1H NMR studies suggest that moderate H-bonding occurs between this anion and both SN1 and SN2.

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Zhang, Ye, Gui-Ming Han, Qiang Wu et Heng-Shan Wang. « 2-Benzyl-6-(benzylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione ». Acta Crystallographica Section E Structure Reports Online 63, n^o 11 (17 octobre 2007) : o4336. http://dx.doi.org/10.1107/s1600536807049975.

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The title compound, C26H20N2O2, is a 1,8-naphthalimide derivative. Molecules are arranged into stacks via π–π interactions between the naphthalimide systems, with interplanar distances of 3.379 (2) and 3.630 (2) Å. In addition, the crystal structure is stabilized by weak intermolecular C—H...O interactions.

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Crenshaw, Michael D., et C. C. Cheng. « A FACILE REDUCTION OF 1,8-NAPHTHALIMIDE TO 1,2,3,4-TETRAHYDRO-1,8-NAPHTHALIMIDE ». Organic Preparations and Procedures International 21, n^o 5 (octobre 1989) : 655–56. http://dx.doi.org/10.1080/00304948909356433.

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Bisceglie, Franco, Giorgio Pelosi, Nicolò Orsoni, Marianna Pioli, Mauro Carcelli, Paolo Pelagatti, Silvana Pinelli et Peter J. Sadler. « Light Triggers the Antiproliferative Activity of Naphthalimide-Conjugated (η6-arene)ruthenium(II) Complexes ». International Journal of Molecular Sciences 23, n^o 14 (10 juillet 2022) : 7624. http://dx.doi.org/10.3390/ijms23147624.

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We report the synthesis and characterization of three half-sandwich Ru(II) arene complexes [(η6-arene)Ru(N,N′)L][PF6]2 containing arene = p-cymene, N,N′ = bipyridine, and L = pyridine meta- with methylenenaphthalimide (C1), methylene(nitro)naphthalimide (C2), or methylene(piperidinyl)naphthalimide (C3). The naphthalimide acts as an antenna for photoactivation. After 3 h of irradiation with blue light, the monodentate pyridyl ligand had almost completely dissociated from complex C3, which contains an electron donor on the naphthalimide ring, whereas only 50% dissociation was observed for C1 and C2. This correlates with the lower wavelength and strong absorption of C3 in this region of the spectrum (λmax = 418 nm) compared with C1 and C2 (λmax = 324 and 323 nm, respectively). All the complexes were relatively non-toxic towards A549 human lung cancer cells in the dark, but only complex C3 exhibited good photocytoxicity towards these cancer cells upon irradiation with blue light (IC50 = 10.55 ± 0.30 μM). Complex C3 has the potential for use in photoactivated chemotherapy (PACT).

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Zhang, Peng-Li, Gopala Lavanya, Yang Yu, Bo Fang et Cheng-He Zhou. « Identification of a novel antifungal backbone of naphthalimide thiazoles with synergistic potential for chemical and dynamic treatment ». Future Medicinal Chemistry 13, n^o 23 (décembre 2021) : 2047–67. http://dx.doi.org/10.4155/fmc-2021-0162.

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Aim: The high incidence and prevalence of fungal infections call for new antifungal drugs. This work was to develop naphthalimide thiazoles as potential antifungal agents. Results & methodology: These compounds showed significant antifungal potency toward some tested fungi. Especially, naphthalimide thiazole 4h with excellent anti- Candida tropicalis efficacy possessed good hemolysis level, low toxicity and no obvious resistance. Deciphering the mechanism showed that 4h interacted with DNA and disrupted the antioxidant defense system of C. tropicalis. Compound 4h also triggered membrane depolarization, leakage of cytoplasmic contents and LDH inhibition. Simultaneously, 4h rendered metabolic inactivation and eradicated the formed biofilms of C. tropicalis. Conclusion: The multifaceted synergistic effect initiated by naphthalimide thiazoles is a reasonable treatment window for prospective development.

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Udhayakumari, Duraisamy. « Various Sensing Mechanisms for the Design of Naphthalimide based Chemosensors Emerging in Recent Years ». Recent Innovations in Chemical Engineering (Formerly Recent Patents on Chemical Engineering) 13, n^o 4 (2 juin 2020) : 262–89. http://dx.doi.org/10.2174/2405520413666200217125754.

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In the design of novel fluorescent chemosensors, investigation of new sensing mechanisms between recognition and signal reporting units is of increasing interest. In recent years, a smart chemosensor probe containing a 1,8-naphthalimide moiety could be developed as a fluorescent and colorimetric sensor for toxic anions, metal ions, biomolecules, nitroaromatics, and acids and be further applied to monitor the relevant biological applications. In this field, several problems and challenges still exist. This critical review is mainly focused on various sensing mechanisms that have emerged in the past few years, such as Photo-Induced Electron Transfer (PET), Intramolecular Charge Transfer (ICT), Fluorescence Resonance Energy Transfer (FRET), Excited-State Intramolecular Proton Transfer (ESIPT), hydrogen bonding and displacement approach. The review concludes with some current and future perspectives, including the use of the naphthalimides for sensing anions, metal ions, biomolecules, nitroaromatics and acids and their potential uses in various fields.

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Bodedla, Govardhana Babu, Lingling Li, Yuanyuan Che, Yijiao Jiang, Jun Huang, Jianzhang Zhao et Xunjin Zhu. « Enhancing photocatalytic hydrogen evolution by intramolecular energy transfer in naphthalimide conjugated porphyrins ». Chemical Communications 54, n^o 82 (2018) : 11614–17. http://dx.doi.org/10.1039/c8cc06919k.

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Three new isomeric naphthalimide conjugated porphyrins are developed for photocatalytic H₂ production. The para-substituted isomer, ZnT(p-NI)PP delivers the highest rate (ηH₂) of 973 μmol g⁻¹ h⁻¹ due to the efficient intramolecular energy transfer from the naphthalimide to the porphyrin core.

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Sun, Jie, Ai-lin Yuan, Hai-Bo Wang et Jie Sun. « N-(2-Hydroxyethyl)-1,8-naphthalimide ». Acta Crystallographica Section E Structure Reports Online 65, n^o 6 (7 mai 2009) : o1210. http://dx.doi.org/10.1107/s1600536809015621.

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In the molecule of the title compound, C14H11NO3, the naphthalimide ring system is nearly planar (r.m.s. deviation 0.0139 Å). In the crystal structure, intermolecular O—H...O hydrogen bonds link the molecules into centrosymmetric dimers formingR22(14) ring motifs. π–π contacts between the naphthalimide rings [centroid–centroid distances = 3.648 (3), 3.783 (3), 3.635 (3), 3.722 (3) and 3.755 (3) Å] may further stabilize the structure.

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Cao, Zhi, Premchendar Nandhikonda, Adriana Penuela, Stephanie Nance et Michael D. Heagy. « N-Aryl Arenedicarboximides as Tunable Panchromatic Dyes for Molecular Solar Cells ». International Journal of Photoenergy 2010 (2010) : 1–7. http://dx.doi.org/10.1155/2010/264643.

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Three organic dyes designed as molecular dyads were prepared that feature a common naphthalimide acceptor andN-aryl donors. One of these incorporated an additional cyanoacrylic acid linker and conjugated thiophene bridge inserted between donor and acceptor groups. Electrochemical and photochemical characterizations have been carried out on nanocrystalline TiO2dye-sensitized solar cells which were fabricated with these dyes as the sensitizing component. HOMO and LUMO energies were also calculated using TDDFT methods and validated by the cyclic voltammetry method. A key finding from this study indicates that computational methods can provide energy values in close agreement to experimental for theN-aryl-naphthalimide system. Relative to HOMO/LUMO energy levels ofN719, the dyes based on naphthalimide chromophore are promising candidates for metal-free DSSCs.

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Voloshchuk, Roman, Mariusz Tasior, Adina I. Ciuciu, Lucia Flamigni et Daniel T. Gryko. « Corrole–imide dyads — Synthesis and optical properties ». Journal of Porphyrins and Phthalocyanines 19, n^o 01-03 (janvier 2015) : 479–91. http://dx.doi.org/10.1142/s1088424615500339.

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Two rarely seen building blocks have been incorporated into light absorbing arrays: corroles and 2,3-naphthalimides. General synthetic strategy consisting in direct condensation of formyl substituted aromatic imides with dipyrranes led to diverse range of trans-A2B-corroles in acceptable yields. Spectroscopic properties of all five dyads studied suggest that regardless the imide's structure, components are weakly electronically coupled. Positioning 2,3-naphthalimide unit partially above the corrole core leads to slight alteration of their optical properties. Dyads bearing blue-absorbing imide components display different behavior depending on their structure. In corrole linked with naphthalenyl-naphthalene-1,8-carboximide a 100% effective energy transfer reaction from the imide component to the corrole component occurred. On the contrary, in small, strongly polarized amino-cyano-phthalimide neither efficient energy-nor electron-transfer could be detected and excitation leads to fluorescence from both components.

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D. Jawale Patil, Pramod, Rajita D. Ingle, Sopan M. Wagalgave, Rajesh S. Bhosale, Sidhanath V. Bhosale, Rajendra P. Pawar et Sheshanath V. Bhosale. « A Naphthalimide-Benzothiazole Conjugate as Colorimetric and Fluorescent Sensor for Selective Trinitrophenol Detection ». Chemosensors 7, n^o 3 (14 août 2019) : 38. http://dx.doi.org/10.3390/chemosensors7030038.

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Although chemical structural modification of naphthalimides is widely employed for the purpose of sensing explosives, the effects of such modification have been little explored. Herein, we report the design and synthesis of a new naphthalimide-benzothiazole conjugate (1) and its ability to sense various nitrophenols by means of its colorimetric and fluorescent characteristics. Under long-range UV light (365 nm), 1 displayed a color change of its solution from bluish to colorless only upon addition of 2,4,6-trinitrophenol (TNP). Photoluminescence spectroscopy showed quantitative fluorescence quenching by TNP of the emission peaks of 1 at 398 nm and 418 nm due to donor–acceptor electron transfer. The interaction of 1 with TNP was via a cooperative, non-covalent hydrogen-bonding interaction. Receptor 1 exhibited high sensitivity and selectivity towards TNP over various aromatic nitro analytes. The binding constant (K) and Stern–Volmer constant (Ksv) between 1 and TNP were found to be 5.332 × 10−5 M and 2.271 × 106 M−1, respectively. Furthermore, the limit of detection was calculated and found to be as low as 1.613 × 10−10 M.

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Ahanj, Negin, Mehdi Taghavi et Ayyub Mojaddami. « Evaluation of Cytotoxicity and Molecular Docking Studies of Phthalimide and Naphthalimide Derivatives as Potential Anticancer Agents ». Jundishapur Journal of Medical Sciences 20, n^o 4 (1 octobre 2021) : 366–75. http://dx.doi.org/10.32598/jsmj.20.4.2456.

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Background and Objectives Cancer is the second leading cause of death in the world after cardiovascular disease, so the aim of the present study was to investigate phthalimide and naphthalimide derivatives in order to develop anticancer compounds. Subjects and Methods In this study, the cytotoxic activity of six phthalimed and naphthalamide derivatives was evaluated using MTT method on three cancerous cell lines, including breast cancer (MCF-7), ovarian cancer (SKOV3) and lung cancer (A549) cell line. Molecular Docking studies were also performed to determine the binding energy and the compounds interaction with DNA as a possible target of these compounds. Results Based on MTT results, compound C1, a naphthalimide derivative, showed the highest cytotoxic activity. IC50 values of this compound against MCF-7, SKOV3 and A549 cancer cell lines were 1.7, 6.2 and 9.5 μM, respectively. Also, comparison of phthalimide and naphthalimide derivatives showed that compounds C1, C3, C5 with carboxyl group had better effects than other compounds, C2, C6, C4, which bearing 5-amidoisophthalic acid moiety. Conclusion In general, naphthalimide derivatives showed better cytotoxicity than phthalimide derivatives. Compound C1 has the highest cytotoxic activity on all three cancer cell lines and can be further studied in the development of new anti-cancer compounds.

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Ning, Bo, Jun-Wen Cao, Xiao-Teng Zhou, He Qin, Ling-Xiao Li et Cheng-You Kan. « Synthesis and characterization of a novel, reactive, yellow fluorescent organosilicon dye and its polysiloxanes ». Journal of Chemical Research 43, n^o 11-12 (30 août 2019) : 461–68. http://dx.doi.org/10.1177/1747519819872098.

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A novel, reactive, yellow fluorescent organosilicon dye, N-propyl-(diethoxy)methyl-silane-4-dimethylamino-naphthalimide, is designed and synthesized and is used to fabricate a covalently yellow fluorescent silicone oil by polycondensation of hydroxy-terminated polydimethylsiloxane. The chemical structure and optical properties of the N-propyl-(diethoxy)methyl-silane-4-dimethylamino-naphthalimide and covalently yellow fluorescent silicone oil are characterized by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, mass spectrometry, Fourier transform infrared, UV–Vis, and fluorescence spectra. The results indicate that the fluorescence quantum yields of N-propyl-(diethoxy)methyl-silane-4-dimethylamino-naphthalimide and covalently yellow fluorescent silicone oil are 2.61% and 3.5%, respectively. The λmax values of their dichloromethane solutions are 416 nm, and their λex and λem are 430 and 509 nm, respectively. Furthermore, covalently yellow fluorescent silicone rubbers are prepared using tetraethoxysilane as a cross-linker, and some of their properties are investigated. Thermogravimetric analysis and dynamic mechanical analysis show that heat resistance and tan δ of the covalently yellow fluorescent silicone rubber are improved in comparison with silicone rubbers without N-propyl-(diethoxy)methyl-silane-4-dimethylamino-naphthalimide moieties. Solvent extraction experiments indicate that the solvent resistance of the covalently yellow fluorescent silicone rubber is much better than that of noncovalently yellow fluorescent silicone rubber.

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Liu, Yuanyuan, Jingyi Zhang, Tian Feng et Yi Li. « Synthesis, structure–fluorescence relationships and density functional theory studies of novel naphthalimide–piperazine–pyridine-based polystyrene sensors for Hg(ii) detection ». RSC Advances 10, n^o 42 (2020) : 25281–89. http://dx.doi.org/10.1039/d0ra04557h.

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Sambol, Matija, Patricia Benčić, Antonija Erben, Marija Matković, Branka Mihaljević, Ivo Piantanida, Marijeta Kralj et Nikola Basarić. « Photochemical Reactivity of Naphthol-Naphthalimide Conjugates and Their Biological Activity ». Molecules 26, n^o 11 (2 juin 2021) : 3355. http://dx.doi.org/10.3390/molecules26113355.

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Quinone methide precursors 1a–e, with different alkyl linkers between the naphthol and the naphthalimide chromophore, were synthesized. Their photophysical properties and photochemical reactivity were investigated and connected with biological activity. Upon excitation of the naphthol, Förster resonance energy transfer (FRET) to the naphthalimide takes place and the quantum yields of fluorescence are low (ΦF ≈ 10−2). Due to FRET, photodehydration of naphthols to QMs takes place inefficiently (ΦR ≈ 10−5). However, the formation of QMs can also be initiated upon excitation of naphthalimide, the lower energy chromophore, in a process that involves photoinduced electron transfer (PET) from the naphthol to the naphthalimide. Fluorescence titrations revealed that 1a and 1e form complexes with ct-DNA with moderate association constants Ka ≈ 105–106 M−1, as well as with bovine serum albumin (BSA) Ka ≈ 105 M−1 (1:1 complex). The irradiation of the complex 1e@BSA resulted in the alkylation of the protein, probably via QM. The antiproliferative activity of 1a–e against two human cancer cell lines (H460 and MCF 7) was investigated with the cells kept in the dark or irradiated at 350 nm, whereupon cytotoxicity increased, particularly for 1e (>100 times). Although the enhancement of this activity upon UV irradiation has no imminent therapeutic application, the results presented have importance in the rational design of new generations of anticancer phototherapeutics that absorb visible light.

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Wang, Zhaohui, Jingwei Zhu, Kongchang Chen et He Tian. « Synthesis of Novel Ferrocene–Naphthalimide Dyads ». Journal of Chemical Research 23, n^o 7 (juillet 1999) : 438–39. http://dx.doi.org/10.1177/174751989902300717.

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Dong, Hong-Qiang, Tai-Bao Wei, Xiao-Qiang Ma, Qing-Yu Yang, Yun-Fei Zhang, Yu-Jiao Sun, Bing-Bing Shi, Hong Yao, You-Ming Zhang et Qi Lin. « 1,8-Naphthalimide-based fluorescent chemosensors : recent advances and perspectives ». Journal of Materials Chemistry C 8, n^o 39 (2020) : 13501–29. http://dx.doi.org/10.1039/d0tc03681a.

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Pablos, Jesús L., Esther Hernández, Fernando Catalina et Teresa Corrales. « Solid Fluorescence pH Sensors Based on 1,8-Naphthalimide Copolymers Synthesized by UV Curing ». Chemosensors 10, n^o 2 (11 février 2022) : 73. http://dx.doi.org/10.3390/chemosensors10020073.

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Novel water-swollen photo-crosslinked membranes were obtained by copolymerization of the N-vinylpyrrolidone, butyl acrylate and ethyl methacrylate monomers functionalized with naphthalimide groups, as pH sensitive fluorescence probes. For that purpose, two monomers with pending naphthalimide groups anchored to ethyl methacrylate through alkyl chains with different length, were previously synthesized. The membranes were characterized using different techniques. The pH dependence of absorbance and the corresponding quenching of fluorescence were investigated and related to the structure of naphthalimide substituents linked to the membrane. The new solid sensors exhibited sensitive fluorescence changes at pH < 3, and lower time response was determined for membranes where the sensing group was linked through longer alkyl chain to the polymer matrix. The membranes were solid, thermally stable and easily handled to be applied as sensor materials, and showed a reversible behavior, which is an important feature for further fabrication of an economical on-site tool for the acidity detection in aqueous environments.

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Srivastava, Ambika, Pooja Singh, Arti Srivastava et Rajesh Kumar. « Amphiphilic Fluorescent Well-Defined Living Polymer from Indole-3-Carboxaldehyde and 4-Bromo-1, 8-Naphthalic Anhydride : Synthesis and Characterization ». Journal of Polymers 2014 (10 mars 2014) : 1–9. http://dx.doi.org/10.1155/2014/325930.

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We reported a well-defined amphiphilic fluorescent polymer bearing indole repeating units with naphthalimide pendants obtained by ATRP followed by chemical modification. The obtained polymer poly (N-allyl indole-2-(4-hydroxybutyl)-1, 8-naphthalimide) (PAIHN) was characterized by 1H NMR, FTIR, and GPC. The polymer showed a specific fluorescence emission maximum at 538 nm excited at 435 nm in aqueous solution. The amphiphilic nature of the polymer was investigated in aqueous solution using two spectroscopic methods, namely, absorption and emission spectroscopy. The Critical Miceller Concentration values obtained by UV-visible and fluorescence are in good agreement with each other. The micelles were characterized by TEM at concentration of 0.014 mg/mL. The polymer PAIHN prepared after tweaking exhibits green fluorescence at 538 nm due to the significant effect of naphthalimide moieties, whereas before tweaking the polymer poly (1-allyl indole-3-carbaldehyde) (PAIC) exhibits blue fluorescence at 425 nm due to indole repeating units of the polymer.

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Liu, Zhi-Wei, Fan Liu, Chun-Tao Shao, Guo-Ping Yan et Jiang-Yu Wu. « Synthesis and Characterization of Sulfonamide-Containing Naphthalimides as Fluorescent Probes ». Molecules 29, n^o 12 (11 juin 2024) : 2774. http://dx.doi.org/10.3390/molecules29122774.

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A tumor-targeting fluorescent probe has attracted increasing interest in fluorescent imaging for the noninvasive detection of cancers in recent years. Sulfonamide-containing naphthalimide derivatives (SN-2NI, SD-NI) were synthesized by the incorporation of N-butyl-4-ethyldiamino-1,8-naphthalene imide (NI) into sulfonamide (SN) and sulfadiazine (SD) as the tumor-targeting groups, respectively. These derivatives were further characterized by mass spectrometry (MS), nuclear magnetic resonance spectroscopy (1H NMR), Fourier transform infrared spectroscopy (FT-IR), ultraviolet–visible spectroscopy (UV), and a fluorescence assay. In vitro properties, including cell cytotoxicity and the cell uptake of tumor cells, were also evaluated. Sulfonamide-containing naphthalimide derivatives possessed low cell cytotoxicity to B16F10 melanoma cells. Moreover, SN-2NI and SD-NI can be taken up highly by B16F10 cells and then achieve good green fluorescent images in B16F10 cells. Therefore, sulfonamide-containing naphthalimide derivatives can be considered to be the potential probes used to target fluorescent imaging in tumors.

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Grabchev, Ivo, et Jean-Marc Chovelon. « Photophysical and Photochemical Properties of Green Fluorescent Liquid Crystalline Systems ». Zeitschrift für Naturforschung A 58, n^o 1 (1 janvier 2003) : 45–50. http://dx.doi.org/10.1515/zna-2003-0107.

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The photophysical properties of polymer-dispersed liquid crystal systems, containing naphthalimide dye as fluorescent units are reported. Investigations have been carried out on some 1,8- naphtalimide derivatives both in isotropic and anisotropic media, and their photophysal properties have been described. The orientational order parameters of the dyes in nematic liquid crystal ZLI 1840 have been determined. The photostability of the dye/liquid crystal systems has been investigated and the effect that the substituents in the naphthalimide structure have upon the orientation of the dye was discussed.

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Liu, Yu, Hai-Ying Wang, Gang Chen, Xiao-Ping Xu et Shun-Jun Ji. « Synthesis and Properties of Novel 'Ethyne-linked' Compounds Containing Carbazole and 1, 8-naphthalimide Groups ». Australian Journal of Chemistry 62, n^o 8 (2009) : 934. http://dx.doi.org/10.1071/ch08411.

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A series of the novel ‘ethyne-linked’ compounds containing carbazole and 1,8-naphthalimide groups have been synthesized by Pd/Cu-catalyzed Sonogashira reaction. These compounds were fully characterized by means of Fourier-transform IR, 1H, 13C NMR, and high resolution mass spectroscopy. The thermal, optical, and electrochemical properties were also investigated. As we expected, the results indicated that these compounds could improve charge-transport ability and fluorescent quantum yield by introducing the electron-transporting emitting moieties naphthalimide and the alkyne group to carbazole moieties.

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