162265-51-2Relevant articles and documents
Excimer emission induced by metal ion coordination in 1,8-naphthalimide-tethered iminopyridine ligands
Licchelli, Maurizio,Orbelli Biroli, Alessio,Poggi, Antonio,Sacchi, Donatella,Sangermani, Corrado,Zema, Michele
, p. 4537 - 4545 (2003)
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.
Syntheses and evaluation of acridone-naphthalimide derivatives for regulating oncogene PDGFR-β expression
Zhang, Meiling,Wei, Zuzhuang,Gong, Xue,Li, Xiaoya,Kang, Shuangshuang,Wang, Jing,Liu, Bobo,Huang, Zhi-Shu,Li, Ding
, (2021)
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.
Selective sensing of citrate by a supramolecular 1,8-naphthalimide/calix[4] arene assembly via complexation-modulated pKa shifts in a ternary complex
Koner, Apurba L.,Schatz, Juergen,Nau, Werner M.,Pischel, Uwe
, p. 3889 - 3895 (2007)
(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.
Design and synthesis of naphthalimide group-bearing thioglycosides as novel β-N-acetylhexosaminidases inhibitors
Shen, Shengqiang,Chen, Wei,Dong, Lili,Yang, Qing,Lu, Huizhe,Zhang, Jianjun
, p. 445 - 452 (2018)
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.
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
Karelia, Deepkamal N.,Sk, Ugir Hossain,Singh, Parvesh,Gowda, A.S. Prakasha,Pandey, Manoj K.,Ramisetti, Srinivasa R.,Amin, Shantu,Sharma, Arun K.
, p. 282 - 295 (2017)
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.
Development of novel naphthalimide derivatives and their evaluation as potential melanoma therapeutics
Sk, Ugir Hossain,Prakasha Gowda,Crampsie, Melissa A.,Yun, Jong K.,Spratt, Thomas E.,Amin, Shantu,Sharma, Arun K.
, p. 3331 - 3338 (2011)
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.
Novel near-infrared pH-sensitive cyanine-based fluorescent probes for intracellular pH monitoring
Jin, Di,Wang, Bowei,Hou, Yuqing,Du, Yuchao,Li, Xue,Chen, Ligong
, (2019)
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.
Selective inhibition of β-N-acetylhexosaminidases by thioglycosyl–naphthalimide hybrid molecules
Chen, Wei,Shen, Shengqiang,Dong, Lili,Zhang, Jianjun,Yang, Qing
, p. 394 - 400 (2018)
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
Modular design for fluorophore homodimer probes using diethylentriamine as a common spacer
Kusano, Shuhei,Matsumoto, Keisuke,Hayashida, Osamu
, p. 3599 - 3603 (2019)
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.
Proton-induced fluorescence switching in novel naphthalimide-dansylamide dyads
Abad, Sergio,Kluciar, Marek,Miranda, Miguel A.,Pischel, Uwe
, p. 10565 - 10568 (2005)
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.
