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.
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, 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.
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.
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.
Ferrocene appended naphthalimide derivatives: Synthesis, DNA binding, and in vitro cytotoxic activity
Jia, Deng-Guo,Zheng, Jia-An,Fan, Yan-Ru,Yu, Jian-Qiang,Wu, Xiu-Li,Wang, Bo-Jin,Yang, Xin-Bin,Huang, Yu
, p. 16 - 23 (2019)
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.
