- Excimer emission induced by metal ion coordination in 1,8-naphthalimide-tethered iminopyridine ligands
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Ligands 2-5, containing the light-emitting subunit 1,8-naphthalimide, have been prepared and their photophysical properties studied by absorption and emission spectroscopy. Ligand 2 interacts in solution with several cations according to a 1 : 2 (metal : ligand) stoichiometry, the 1 : 3 species being not favoured probably because of steric hindrance, while ligands 3-5 form 1 : 3 adducts with all the investigated metal ions. The interaction of ligands 2-5 with metal ions induces considerable variations on the photophysical properties of the light-emitting subunit. The coordination of genuine transition metal ions (FeII, CoII, NiII, CuII) causes the emission intensity to decrease in all the investigated systems, while ZnII or CdII induce a fluorescence enhancement (system 2) or the formation of a new band in the emission spectra (systems 3-5) which can be ascribed to an intramolecular excimeric species. Excimeric emission is not observed in the complexes of 2, possibly because the ethylenic chain bridging the naphthalimide and the iminopyridine units is too short to allow the intramolecular interaction. The excimeric species disappears on increasing the metal ion (ZnII or CdII) concentration, as a result of the disassembling of the 1 : 3 complexes and the consecutive formation of 1 : 2 and 1 : 1 species, in which the intramolecular interaction is less probable or no longer possible. The appearance and disappearance of an excimer band in the emission spectrum can be described as a convenient way to monitor a metal-driven assembling/disassembling process.
- Licchelli, Maurizio,Orbelli Biroli, Alessio,Poggi, Antonio,Sacchi, Donatella,Sangermani, Corrado,Zema, Michele
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- Syntheses and evaluation of acridone-naphthalimide derivatives for regulating oncogene PDGFR-β expression
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Upregulation of platelet-derived growth factor receptor β (PDGFR-β) has been found to be associated with development of various types of cancers, which has become an attractive target for anti-tumor treatment. Previously, we have synthesized and studied an acridone derivative B19, which can selectively bind to and stabilize oncogene c-myc promoter i-motif, resulting in down-regulation of c-myc transcription and translation, however its effect on tumor cells apoptosis requires improvement. In the present study, we synthesized a variety of B19 derivatives containing a known anti-cancer fluorescent chromophore naphthalimide for the purpose of enhancing anti-cancer activity. After screening, we found that acridone-naphthalimide derivative WZZ02 could selectively stabilize PDGFR-β promoter G-quadruplex and destabilize its corresponding i-motif structure, without significant interaction to other oncogenes promoter G-quadruplex and i-motif. WZZ02 down-regulated PDGFR-β gene transcription and translation in a dose-dependent manner, possibly due to above interactions. WZZ02 could significantly inhibit cancer cell proliferation, and induce cell apoptosis and cycle arrest. WZZ02 exhibited tumor growth inhibition activity in MCF-7 xenograft tumor model, which could be due to its binding interactions with PDGFR-β promoter G-quadruplex and i-motif. Our results suggested that WZZ02 as a dual G-quadruplex/i-motif binder could be effective on both oncogene replication and transcription, which could become a promising lead compound for further development with improved potency and selectivity. The wide properties for the derivatives of 1,8-naphthalimide could facilitate further in-depth mechanistic studies of WZZ02 through various fluorescent physical and chemical methods, which could help to further understand the function of PDGFR-β gene promoter G-quadruplex and i-motif.
- Zhang, Meiling,Wei, Zuzhuang,Gong, Xue,Li, Xiaoya,Kang, Shuangshuang,Wang, Jing,Liu, Bobo,Huang, Zhi-Shu,Li, Ding
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- Selective sensing of citrate by a supramolecular 1,8-naphthalimide/calix[4] arene assembly via complexation-modulated pKa shifts in a ternary complex
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(Figure Presented) A water-soluble supramolecular sensing assembly, composed of an imidazolium-substituted calix[4]arene and a fluorescent aminodiacetate derivative of 1,8-naphthalimide, was studied. Addition of citrate led to a large fluorescence enhancement, while tartrate, acetate, as well as selected inorganic anions gave smaller effects. The sensing principle and selectivity for citrate rely on the formation of a ternary fluorophore-host- anion complex and complexation-induced pKa shifts of an amino group attached to the fluorophore. The complexation of citrate induces a protonation of the amino group, which switches off intramolecular photoinduced electron transfer as the fluorescence quenching pathway, leading to an enhancement of the optical output signal. The intricate sensor principle was corroborated by pH titrations, binding constants, and structural information as obtained by 1H NMR spectroscopy.
- Koner, Apurba L.,Schatz, Juergen,Nau, Werner M.,Pischel, Uwe
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- Design and synthesis of naphthalimide group-bearing thioglycosides as novel β-N-acetylhexosaminidases inhibitors
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GH20 human β-N-acetylhexosaminidases (hsHex) and GH84 human O-GlcNAcase (hOGA) are involved in numerous pathological processes and emerged as promising targets for drug discovery. Based on the catalytic mechanism and structure of the catalytic domains of these β-N-acetylhexosaminidases, a series of novel naphthalimide moiety-bearing thioglycosides with different flexible linkers were designed, and their inhibitory potency against hsHexB and hOGA was evaluated. The strongest potency was found for compound 15j (Ki = 0.91 μM against hsHexB; Ki > 100 μM against hOGA) and compound 15b (Ki = 3.76 μM against hOGA; Ki = 30.42 μM against hsHexB), which also exhibited significant selectivity between these two enzymes. Besides, inhibitors 15j and 15b exhibited an inverse binding patterns in docking studies. The determined structure–activity relationship as well as the established binding models provide the direction for further structure optimizations and the development of specific β-N-acetylhexosaminidase inhibitors.
- Shen, Shengqiang,Chen, Wei,Dong, Lili,Yang, Qing,Lu, Huizhe,Zhang, Jianjun
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- Design, synthesis, and identification of a novel napthalamide-isoselenocyanate compound NISC-6 as a dual Topoisomerase-IIα and Akt pathway inhibitor, and evaluation of its anti-melanoma activity
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Synthesis and anti-melanoma activity of novel naphthalimide isoselenocyanate (NISC) and naphthalimide selenourea (NSU) analogs are described. The novel agents were screened for growth inhibition of different human melanoma cell lines including those having BRAFV600E mutation (UACC903, 1205Lu, and A375M) and BRAFWT (CHL-1). In general, the NISC analogs (4a-d) were more effective in inhibiting the cell viability than the NSU analogs (7a-b). Overall, NISC-6 (4d), having a six-carbon alkyl chain, was identified as the most cytotoxic compound in both BRAFV600E mutated and BRAFWT cells. NISC-6 docked strongly into the binding sites of Akt1 and human topoisomerase IIα (Topo-IIα), and the docking results were supported by experimental findings showing NISC-6 to inhibit of both Akt pathway and Topo-IIα activity in a dose dependent manner. Furthermore, NISC-6 effectively induced apoptosis in human melanoma cells, inhibited tumor growth by ~69% in a melanoma mouse xenograft model, and showed excellent compliance with the Lipinski’ rule of five, suggesting both its efficacy and drug-like behavior under physiological conditions.
- Karelia, Deepkamal N.,Sk, Ugir Hossain,Singh, Parvesh,Gowda, A.S. Prakasha,Pandey, Manoj K.,Ramisetti, Srinivasa R.,Amin, Shantu,Sharma, Arun K.
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- Development of novel naphthalimide derivatives and their evaluation as potential melanoma therapeutics
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Synthesis and anti-melanoma activity of various naphthalimide analogs, rationally modified by introducing isothiocyanate (ITC) and thiourea (TU) functionalities, found in well-known anti-cancer agents, is described. The structure-activity relationship comparison of the novel agents in inhibiting cancer cell growth was evaluated in various melanoma cell lines. Both ITC and TU analogs effectively inhibited cell viability and induced apoptosis in various human melanoma cells. Nitro substitution and increase in alkyl chain length, in general, enhanced the apoptotic activity of ITC derivatives. All the new compounds were well tolerated when injected intraperitoneal (i.p.) in mice at effective doses at which both the ITC and TU derivatives inhibited melanoma tumor growth in mice following i.p. xenograft. The nitro substituted naphthalimide-ITC derivative 3d was found to be the most effective in inducing apoptosis, and in inhibiting melanoma cell and tumor growth.
- Sk, Ugir Hossain,Prakasha Gowda,Crampsie, Melissa A.,Yun, Jong K.,Spratt, Thomas E.,Amin, Shantu,Sharma, Arun K.
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- Novel near-infrared pH-sensitive cyanine-based fluorescent probes for intracellular pH monitoring
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Real-time monitoring of intracellular pH fluctuation is of great significance for diagnosis of diseases and study of related physiological and pathological processes. A novel near-infrared (NIR) pH-activated parent probe 4 was developed, and further functionalized to afford probes 6 and 7. With the decrease of pH from 11 to 2, they all exhibited a new absorption peak and strong fluorescence emission in NIR region, accompanied by rapid solution color change from pink to pale green. Moreover, the probes’ fluorescence responses toward pH fluctuations were reversible and stable, and the pseudo-linear relationship between the fluorescence intensity and pH value can be used to detect pH value in 2.76–6.45 range quantitatively. Finally, probe 6 and 7 were successfully applied to monitor the fluctuation of intracellular pH by a fluorescence turn-on mode, and the imaging results confirmed their low cytotoxicity and satisfactory cell-membrane permeability, as well as their application prospect in disease diagnosis (such as tumor specific imaging) or assist in study of pH-related biological processes in wide acidic environment.
- Jin, Di,Wang, Bowei,Hou, Yuqing,Du, Yuchao,Li, Xue,Chen, Ligong
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- Selective inhibition of β-N-acetylhexosaminidases by thioglycosyl–naphthalimide hybrid molecules
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To develop selective inhibitors for β-N-acetylhexosaminidases which are involved in a myriad of physiological processes, a series of novel thioglycosyl–naphthalimide hybrid inhibitors were designed, synthesized and evaluated for inhibition activity agains
- Chen, Wei,Shen, Shengqiang,Dong, Lili,Zhang, Jianjun,Yang, Qing
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- Modular design for fluorophore homodimer probes using diethylentriamine as a common spacer
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Cationic fluorophore homodimer probes 1 and 2 bearing 7-aminocoumarin and naphthalimide dyes, respectively, connected via diethylenetriamine (DETA) spacer, have been developed to demonstrate the validity of our modular probe design on the basis of the triamine-based spacer.
- Kusano, Shuhei,Matsumoto, Keisuke,Hayashida, Osamu
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- Proton-induced fluorescence switching in novel naphthalimide-dansylamide dyads
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Three novel bichromophoric dyads containing dansylamide and 1,8-naphthalimide linked by oligomethylene spacers of varying length were prepared. The fluorescent moiety can be reversibly selected by protonation/deprotonation of the dansyl residue via control of singlet-singlet energy transfer and photoinduced electron transfer, leading to a molecular optical switch with two spectrally distinguished on states.
- Abad, Sergio,Kluciar, Marek,Miranda, Miguel A.,Pischel, Uwe
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- Ferrocene appended naphthalimide derivatives: Synthesis, DNA binding, and in vitro cytotoxic activity
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Three novel ferrocene appended naphthalimide derivatives (2a, 2b and 6) were synthesized and characterized by IR, 1H NMR and mass spectroscopies. In electrochemical experiments, all of the ferrocene appended naphthalimide derivatives exhibited reversible one-electron oxidation in CV curves. And the DNA binding ability of the compounds was studied by ethidium bromide displacement experiments and UV–visible spectrophotometry. The ferrocene appended naphthalimide derivative 6 also exhibited the highest DNA binding ability in all the tested compounds. According to the viscosity results, all of the synthesized compounds displayed the partial intercalation binding mode to DNA duplex. Bis-naphthalimide compound 5 was used as reference compound to evaluate the synergistic effect of the ferrocene group in ferrocene appended naphthalimide derivative 6. The cytotoxicity of the synthesized compounds against 4 different human cancer cell lines (EC109, BGC823, SGC 7901 and HepG2) was studied by MTT assay. The ferrocene appended bis-naphthalimide derivative 6 showed the best cytotoxicity against tested human cancer cells in all the synthesized naphthalimide derivatives and control drug amonafide. The uptake of naphthalimide derivative 6 was proved by laser confocal images. In addition, the DNA damage induced by naphthalimide derivative 6 was studied by comet assay.
- Jia, Deng-Guo,Zheng, Jia-An,Fan, Yan-Ru,Yu, Jian-Qiang,Wu, Xiu-Li,Wang, Bo-Jin,Yang, Xin-Bin,Huang, Yu
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- Design of fluorescence turn-on sensors with novel response mechanism based on C[dbnd]N isomerization
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A series of new type naphthalimide-based fluorescent molecules linking aniline-like groups via a coupling chain with –C[dbnd]N– structure were developed as novel fluorescence chemosensors with high sensitivity and selectivity toward H+ in solut
- Chen, Xingliang,Jin, Shu,Liu, Hailing,Zhong, Kailiang
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- 1, 8-naphthalimide amide compound and application thereof
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The invention discloses a 1, 8-naphthalimide amide compound and a synthesizing and application method thereof. The structural formula of the 1, 8-naphthalimide amide compound is shown as the formula I, wherein R is selected from A, B, C or D. The 1, 8-nap
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Paragraph 0022-0025; 0033
(2018/08/28)
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- Novel naphthalimide–aminobenzamide dyads as OFF/ON fluorescent supramolecular receptors in metal ion binding
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A series of novel naphthalimide–aminobenzamide (NAPIM-2ABZ) dyads 3 connected by different length polymethylene chains were synthesized and studied as fluorescent supramolecular receptors in metal ion binding. The photophysical properties were evaluated a
- Landey-álvarez, Marco A.,Ochoa-Terán, Adrián,Pina-Luis, Georgina,Martínez-Quiroz, Marisela,Aguilar-Martínez, Milagros,Elías-García, José,Miranda-Soto, Valentín,Ramírez, José-Zeferino,Machi-Lara, Lorena,Labastida-Galván, Victoria,Ordo?ez, Mario
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p. 892 - 906
(2016/10/24)
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- Consumer Product Compositions
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Consumer product compositions comprise a water soluble organic photoactivator, an electron acceptor which accepts an electron from the photoactivator when the photoactivator is in a photo-excited state and/or reduced state, and a benefit active precursor
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Page/Page column
(2015/08/04)
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- Photoactivators
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Photoactivators comprise a photoactive moiety and a hydrophilic moiety. The photoactivators preferably comprise less than about 35%, by weight of the photoactivator, of the photoactive moiety. The photoactivators can be activated to a photo-excited state
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Page/Page column
(2015/08/04)
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- Synthesis and electrochemical properties of novel, donor-acceptor pyrrole derivatives with 1,8-naphthalimide units and their polymers
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A new class of bipolar monomers with pyrrole or thiophene-pyrrole-thiophene as electron donor and 1,8-naphthalimide as electron acceptor unit is reported. Donor-acceptor conjugated polymers were generated electrochemically. The synthesis of monomers, opti
- Ledwon, Przemyslaw,Brzeczek, Alina,Pluczyk, Sandra,Jarosz, Tomasz,Kuznik, Wojciech,Walczak, Krzysztof,Lapkowski, Mieczyslaw
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p. 420 - 429
(2014/05/06)
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- Exploring unsymmetrical dyads as efficient inhibitors against the insect β-N-acetyl-d-hexosaminidase OfHex2
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The GH20 β-N-acetyl-d-hexosaminidase OfHex2 from the insect Ostrinia furnacalis (Guene?e) is a target potential for eco-friendly pesticide development. Although carbohydrate-based inhibitors against β-N-acetyl-d- hexosaminidases are widely studied, highly
- Chen, Qi,Guo, Peng,Xu, Lin,Liu, Tian,Qian, Xuhong,Yang, Qing
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p. 152 - 162
(2014/01/23)
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- Development of unsymmetrical dyads as potent noncarbohydrate-based inhibitors against human β-N-acetyl-D-hexosaminidase
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Human β-N-acetyl-D-hexosaminidase has gained much attention due to its roles in several pathological processes and been considered as potential targets for disease therapy. A novel and efficient skeleton, which was an unsymmetrical dyad containing naphthalimide and methoxyphenyl moieties with an alkylamine spacer linkage as a noncarbohydrate-based inhibitor, was synthesized, and the activities were valuated against human β-N-acetyl-D- hexosaminidase. The most potent inhibitor exhibits high inhibitory activity with Ki values of 0.63 μM. The straightforward synthetic manners of these unsymmetrical dyads and understanding of the binding model could be advantageous for further structure optimization and development of new therapeutic agents for Hex-related diseases.
- Guo, Peng,Chen, Qi,Liu, Tian,Xu, Lin,Yang, Qing,Qian, Xuhong
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supporting information
p. 527 - 531
(2013/07/26)
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- Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent∞
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Naphthalimmide (NI) and 1,4,5,8-naphthalentetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity. NDI derivatives 1-9 were more cytotoxic than the corresponding NI derivatives 10-18. The molecular mec
- Tumiatti, Vincenzo,Milelli, Andrea,Minarini, Anna,Micco, Marialuisa,Campani, Anna Gasperi,Roncuzzi, Laura,Baiocchi, Daniela,Marinello, Jessica,Capranico, Giovanni,Zini, Maddalena,Stefanelli, Claudio,Melchiorre, Carlo
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experimental part
p. 7873 - 7877
(2010/06/13)
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- Synthesis and evaluation of ethylnitrosoureas of substituted naphthalimides as anticancer compounds
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Four new ethylnitrosourea derivatives of substituted naphthalimides 3a-d have been synthesized from the respective N-(2-ethylamino)naphthalimides. Their chemical alkylating activity compared with the clinical drug CCNU and an experimental compound Mitonafide indicated that they possess lower alkylating activity than CCNU and comparable activity with the latter. Their anti-tumor efficacies were assessed in vivo in two murine ascites tumors namely Sarcoma-180 (S-180) and Ehrlich ascites carcinoma (EAC) by measuring the increase in median survival times (MST) of drug treated (T) over untreated control (C) mice. CCNU and Mitonafide were used as positive controls for comparison. The representative compound 3a has displayed marginal anti-tumoral activity in these tumors. Three compounds were further screened in vitro in 4 different human tumor cell lines but no significant activity was observed in those lines. These compounds moderately inhibit the synthesis of DNA and RNA in S-180 tumor cells.
- Pain, Anindita,Samanta, Suva,Dutta, Sushanta,Saxena, Ajit K.,Shanmugavel, Mutiah,Sharma, Madhunika,Qazi, Gulam N.,Sanyal, Utpal
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- Synthesis of novel C2 and C2-C8 linked pyrrolo[2,1-c][1,4]benzodiazepine-naphthalimide hybrids as DNA-binding agents
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Synthesis of C2 and C2-C8 linked pyrrolobenzodiazepine-naphthalimide hybrids have been prepared that exhibit significant DNA-binding affinity and cytotoxicity.
- Kamal, Ahmed,Srinivas,Ramulu,Ramesh,Kumar, P. Praveen
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p. 3577 - 3581
(2007/10/03)
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- Synthesis and antitumour activity of new dendritic polyamines-(imide-DNA-intercalator) conjugates: Potent Lck inhibitors
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A series of dendritic polyamines-(imide-DNA-intercalators) conjugates with different connectivity in their basic chain were synthesised and evaluated as antitumour compounds. Although their antiproliferative activity against HT-29 was not significant, con
- Bra?a, Miguel F.,Domínguez, Gema,Sáez, Beatriz,Romerdahl, Cynthia,Robinson, Simmon,Barlozzari, Teresa
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p. 541 - 551
(2007/10/03)
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- Synthesis of novel multi-chromophoric soluble perylene derivatives and their photosensitizing properties with wide spectral response for SnO2 nanoporous electrode
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Two series of new multi-chromophoric perylene-3,4:9,10-tetracarboxylic dianhydride dyes for solar cell sensitizers have been synthesized. One series consists of oxadiazole or naphthaldicarboximide that are linked with perylene units as N,N'-substituted chromophores. The other series has four substituents in the bay-region of the perylene core in addition to N,N'-substituents. These novel routes to highly efficient sensitizers for Gratzel-type solar cells avoid the complication of doping. A wide spectral photoresponse (from 310 to 700 nm) was observed with maximum IPCE (incident photon-to-current efficiency) of 24%. In addition, the sensitization is dependent on the energy match of the energy bands of the semiconductor and the redox potential of the segments in such assembled dyes.
- Tian,Liu,Zhu,Gao,Wu,Cai
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p. 2708 - 2715
(2007/10/03)
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