- Synthesis and characterization of novel monoazo N-ester-1,8-naphthalimide disperse dyestuffs
-
Five novel monoazo disperse dyestuffs based on N-ester-1,8-naphthalimide were synthesized. Acenaphthene was nitrated, then oxidized to 4-nitro-1,8-naphthalic anhydride. 4-Nitro-1,8-naphthalic anhydride was reacted with methyl and ethyl glycinate in alcoholic media, followed with reduction. 4-Amino-N-methyl and ethyl glycinate-1,8-naphthalimide were obtained. These products were diazotized and coupled with appropriate aromatic amines to give bluish-red or violet dyestuffs. All intermediates and dyestuffs were purified and characterized by 1H-NMR, FTIR, DSC, UV-VIS and Elemental Analysis. Dispersion of dyestuffs was prepared in water and applied to polyester fabrics. The dyed fabrics showed that four of the synthesized dyestuffs were suitable for coloring polyester fibers, producing deep bluish red with very good build up properties.
- Gharanjig, Kamaladin,Arami, Mokhtar,Rouhani, Shohre,Bahrami, Hajir,Movassagh, Barahman,Mahmoodi, Niyaz Mohammad
-
-
Read Online
- Study of a 1,8-naphtylimide derivative as uridine diphosphate selective probe: Synthesis, optical properties and in?vivo imaging application
-
A 1, 8-naphtylimide-based probe 1 was developed for fluorescence sensing of uridine diphosphate (UDP). Probe 1 selectively recognized UDP in solvant system (DMSO-H2O) over other structurally similar nucleotides. Among all the tested targets, only the addition of UDP resulted in fluorescence enhancement of about 13-fold. Probe 1, the first receptor moiety without metal center, could recognize UDP only by multi H-bonds formed between the organic ligand and the base group in nucleotide. Moreover, probe 1 exhibited excellent cell permeability. The fluorescence imaging of UDP by probe 1 in Hela cells and Caenorhabditis elegans (C.?elegans) demonstrated its potential as a fluorescent sensor for in?vivo imaging of UDP.
- Lv, Xue Wei,Wang, Guang Ke,Zou, Xiao Ju,Xie, Xiao Guang,Zhou, Ying
-
-
Read Online
- A substituent constant analysis of the interaction of substituted naphthalene monoimides with DNA
-
In a continuing analysis of substituent effects in intercalator-DNA interactions, an unsubstituted naphthalene monoimide, 1, with a 3-(dimethylamino)propyl group on the imide nitrogen has been prepared along with 3- and 4-nitro- (2 and 3) and 3- and 4-amino- (4 and 5) substituted derivatives. These derivatives allow an evaluation of the importance of the Hammett substituent constant and of the substituent position on the binding of naphthelene monoimides to DNA. Viscosity and spectrophotomeric analyses indicate that all five compounds bind to DNA by intercalation. The 4-nitro compound gives a smaller viscosity increase and binds only approximately one-third as strongly as the 3-nitro derivatives. It is postulated that this difference is due to significant angle that the 4-nitro group makes with the intercalated monoimide ring system. The 3-NO2 group can assume a coplanar configuration with the monoimide ring system, allowing more favorable interactions with DNA base pairs, larger viscosity increases, and stronger binding to DNA. The binding constants of the 3-substutited monoimides are in the order 2 > 4 > 1 and, thus, do not follow a substituent constant pattern. The T(m) values from thermal melting of DNA, on the other hand, are in the oder 2 > 1 > 4, suggesting that the enthalpy contributions are significantly different for the binding of the three compounds to DNA. van't Hoff plots support this finding and indicate that both enthalpy and entropy contribute significantly to the binding free energy of 1 and 2 while the binding of 4 is primarily an enthalpic process. Plots of T(m) and 65°C log K values as a function of substituent constant for 1, 2, and 4 are linear. CPK model building studies suggest that 4 can form a hydrogen bond with the 5' diester oxygen of the sugar-phosphate backbone of DNA in an intercalation complex. This would lead to more favorable energetics of binding but a loss of mobility and/or available binding configurations with a resulting enthalpy-entropy compensation in the binding free energy of 4. This series of compounds dramatically illustrates the steric and hydrogen bonding complexity that can arise in attempts to design drugs to favorably interact with a DNA intercalation site as a potential bioreceptor.
- Stevenson,Yen,Yang,Boykin,Wilson
-
-
Read Online
- ICT-Isomerization-Induced Turn-On Fluorescence Probe with a Large Emission Shift for Mercury Ion: Application in Combinational Molecular Logic
-
A unique turn-on fluorescent device based on a ferrocene-aminonaphtholate derivative specific for Hg2+ cation was developed. Upon binding with Hg2+ ion, the probe shows a dramatic fluorescence enhancement (the fluorescence quantum yield increases 58-fold) along with a large red shift of 68 nm in the emission spectrum. The fluorescence enhancement with a red shift may be ascribed to the combinational effect of C=N isomerization and an extended intramolecular charge transfer (ICT) mechanism. The response was instantaneous with a detection limit of 2.7 × 10-9 M. Upon Hg2+ recognition, the ferrocene/ferrocenium redox peak was anodically shifted by ΔE1/2 = 72 mV along with a "naked eye" color change from faint yellow to pale orange for this metal cation. Further, upon protonation of the imine nitrogen, the present probe displays a high fluorescence output due to suppression of the C=N isomerization process. Upon deprotonation using strong base, the fluorescence steadily decreases, which indicates that H+ and OH- can be used to regulate the off-on-off fluorescence switching of the present probe. Density functional theory studies revealed that the addition of acid leads to protonation of the imine N (according to natural bond orbital analysis), and the resulting iminium proton forms a strong H-bond (2.307 ?) with one of the triazole N atoms to form a five-membered ring, which makes the molecule rigid; hence, enhancement of the ICT process takes place, thereby leading to a fluorescence enhancement with a red shift. The unprecedented combination of H+, OH-, and Hg2+ ions has been used to generate a molecular system exhibiting the INHIBIT-OR combinational logic operation.
- Bhatta, Sushil Ranjan,Mondal, Bijan,Vijaykumar, Gonela,Thakur, Arunabha
-
-
Read Online
- A naphthalimide-polyamine conjugate preferentially accumulates in hepatic carcinoma metastases as a lysosome-targeted antimetastatic agent
-
Disseminated tumors lead to approximately 90% of cancer-associated deaths especially for hepatocellular carcinoma (HCC), indicating the imperative need of antimetastatic drugs and the ineffectiveness of current therapies. Recently polyamine derivatives have been identified as a promising prospect in dealing with metastatic tumors. Herein, a novel class of naphthalimide-polyamine conjugates 8a-8d, 13a-13c, 17 and 21 were synthesized and the mechanism was further determined. The polyamine conjugate 13b displayed remarkably elevated anti-tumor and anti-metastatic effects (76.01% and 75.02%) than the positive control amonafide (46.91% and 55.77%) at 5 mg/kg in vivo. The underlying molecular mechanism indicated that in addition to induce DNA damage by up-regulating p53 and γH2AX, 13b also targeted lysosome to modulate polyamine metabolism and function in a totally different way from that of amonafide. Furthermore, the HMGB1/p62/LC3II/LC3I and p53/SSAT/β-catenin pathways were mainly involved in the inhibition of 13b-induced HCC metastasis by targeting polyamine transporters (PTs) overexpressed in HCC. At last, 13b down-regulated the concentrations of Put, Spd and Spm by modulating polyamine metabolism key enzymes SSAT and PAO, which favored the suppression of fast growing tumor cells. Taken together, our study implies a promising strategy for naphthalimide conjugates to treat terminal cancer of HCC by targeting autophagy and tumor microenvironment with reduced toxicities and notable activities.
- Ma, Jing,Li, Linrong,Yue, Kexin,Zhang, Zhansheng,Su, Shihao,Chen, Yutong,Yu, Lu,Zhang, Pengfei,Ma, Ruijuan,Li, Yingguang,Ma, Yinxia,Jia, Huinan,Wang, Chaojie,Wang, Jiajia,Xie, Songqiang
-
-
- Design, photochemistry and antibacterial evaluation of novel light-harvesting antenna
-
Novel light-harvesting compound 6, based on 1,8-naphthalimide donors and perylenediimide acceptor were synthesized. The light-harvesting compound 6 showed intensive absorption band in range between 390 and 560 nm, that is 50 nm wider in comparison with the absorption of the model perylene dye. The novel antenna 6 has a higher ability to collect photons from environment in comparison with the single perylene diimide dyes. The chosen fluorophore units are suitable donor–acceptor pair for light-harvesting materials which was in agreement with their good antibacterial activity.
- Bojinov, Vladimir B.,Georgiev, Nikolai I.,Sakr, Alaa R.
-
supporting information
p. 1 - 9
(2020/07/14)
-
- Synthesis and dyeing performance of some amphiphilic naphthalimide azo disperse dyes on polyester fabrics
-
A series of monoazo disperse dyes were synthesized by coupling diazotized 4-amino-N-dodecyl-1,8-naphthalimide with N,N-dialkyl anilines and naphthol derivatives. The synthesized intermediates and the dyes were characterized using FTIR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental analysis (CHN). Visible absorption spectra of the dyes were examined in solvents of different polarities. The electronic absorption spectra cover a wavelength (λmax) range of 515-535 nm in DMF at uniformly absorption intensity between 1.59-3.00×104L mol-1cm-1. The dyes gave deep and bright intense hues of light violet, maroon, pink and neon red on polyester fabrics. The dyes generally showed good washing and perspiration rating but poor to moderate light fastness properties on woven polyester fabric and could be recommended for commercial outlets.
- Ameuru, Umar Salami,Yakubu, Mohammed Kabir,Bello, Kasali Ademola,Nkeonye, Peter Obinna,Halimehjani, Azim Ziyaei
-
p. 1253 - 1264
(2020/11/26)
-
- A Pt(IV)-based mononitro-naphthalimide conjugate with minimized side-effects targeting DNA damage response via a dual-DNA-damage approach to overcome cisplatin resistance
-
Platinum(Pt)(II) drugs and new Pt(IV) agents behave the dysregulation of apoptosis as the result of DNA damage repair and thus, are less effective in the treatment of resistant tumors. Herein, mononitro-naphthalimide Pt(IV) complex 10b with minimized side-effects was reported targeting DNA damage response via a dual-DNA-damage approach to overcome cisplatin resistance. 10b displayed remarkably evaluated antitumor (70.10percent) activities in vivo compared to that of cisplatin (52.88percent). The highest fold increase (FI) (5.08) for A549cisR cells and the lowest (0.72) for A549 indicated 10b preferentially accumulated in resistant cell lines. The possible molecular mechanism indicates that 10b targets resistant cells in a totally different way from the existing Pt drugs. The cell accumulation and the Pt levels in genomic DNA from 10b is almost 5 folds higher than that of cisplatin and oxaliplatin, indicating the naphthalimide moiety in 10b exhibits preferentially DNA damage. Using 5′-dGMP as a DNA model, the DNA-binding properties of 10b (1 mM) with 5′-dGMP (3 mM) in the presence of ascorbic acid (5 mM) deduced that 10b was generated by the combination of cisplatin with 5′-dGMP after reduction by ascorbic acid. Moreover, 10b promoted the expression of p53 gene and protein more effectively than cisplatin, leading to the increased anticancer activity. The up-regulated γH2A.X and down-regulated RAD51 indicates that 10b not only induced severe DNA damage but also inhibited the DNA damage repair, thus resulting in its higher cytotoxicity in comparison to that of cisplatin. Their preferential accumulation in cancer cells (SMMC-7721) compared to the matched normal cells (HL-7702 cells) demonstrated that they were potentially safe for clinical therapeutic use. In addition, the higher therapeutic indices of 10b for 4T1 cells in vivo indicated that naphthalimide-Pt(IV) conjugates behaved a vital function in the treatment of breast cancer. For the first time, our study implies a significant strategy for Pt drugs to treat resistance cancer targeting DNA damage repair via dual DNA damage mechanism in a totally new field.
- Li, Linrong,Li, Yingguang,Liu, Hanfang,Ma, Jing,Niu, Jie,Xie, Songqiang,Yue, Kexin
-
-
- Preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative
-
The invention provides a preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative. The preparation method is characterized by comprising thefollowing steps: S1, dissolving 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon and subgroup metal nitrate in an organic solvent, performing a nitration reaction under 10-60 DEG Cfor 4-10 h, and then monitoring by TLC (Thin layer chromatography) till a raw material point disappears to finish the reaction; S2, cooling a product obtained in S1 to room temperature, performing suction filtration, washing filter cake with 5-10 mL of H2O and anhydrous C2H5OH separately, and performing vacuum drying to obtain the 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative. According to the preparation method of the 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative, the product yield is 93%-96%; theproduct purity is 98%-99.5%; compared with the prior art, the preparation method has the characteristics of high product yield, high purity, low cost and simple process, and is easy to industrialize.
- -
-
Paragraph 0040-0051
(2019/08/06)
-
- Preparation method of 1,8-disubstituted naphthalene mononitration derivative
-
The invention provides a preparation method of 1,8-disubstituted naphthalene mononitration derivative. The preparation method is characterized by comprising the following steps: S1, taking 1,8-disubstituted naphthalene as a raw material, taking main group metal nitrate as a nitration reagent, dissolving the 1,8-disubstituted naphthalene and the main group metal nitrate in an organic solvent, performing a nitration reaction under 10-60 DEG C for 4-10 h, and then monitoring by TLC (Thin layer chromatography) till a raw material point disappears to finish the reaction; S2, cooling a product obtained in step S1 to room temperature, performing suction filtration, washing filter cake with 5-10 mL of H2O and anhydrous C2H5OH separately, and performing vacuum drying to obtain the 1,8-disubstitutednaphthalene mononitration derivative. According to the preparation method of the 1,8-disubstituted naphthalene mononitration derivative, the product yield can reach 90%-95%; the product purity reaches 98.5%-99.6%; compared with the prior art, the preparation method has the characteristics of high product yield, high purity, low cost and simple process, and is easy to industrialize.
- -
-
Paragraph 0041-0052
(2019/08/06)
-
- Anticancer activity and topoisomerase II inhibition of naphthalimides with Ω-hydroxylalkylamine side-chains of different lengths
-
Background: The substituted 1,8-Naphthalimides (1H-benzo[de]isoquinoline-1,3(2H)- diones) are known as DNA intercalators stabilizing DNA-Topoisomerase II complexes. This interaction disrupts the cleavage-relegation equilibrium of Topo II, resulting in formation of broken strands of DNA. Objective: To investigate the influence of type of substituents and substitution positions in 1,8- naphthalimde skeleton on the inhibition of Topoisomerase II activity. Method: The starting 1,8-naphthalimide were prepared from acenaphthene by introduction of appropriate substituents followed by condensation with ω-hydroxylakylamines of different chain length. The substituents were introduced to 1,8-naphthalimide molecule by nucleophilic substitution of leaving groups like nitro or bromo present in 4 or 4,5- positions using the ω- hydroxylalkylamines. The bioactivity of obtained compounds was examined in model cell lines. Results: Antiproliferative activity of selected compounds against HCT 116 human colon cancer cells, human non-small cell lung cells A549 and non-tumorigenic BEAS-2B human bronchial epithelium cells was examined. Several of investigated compounds exhibit a significant activity (IC50 μM to 7 μM) against model cancer cell lines. It was demonstrated that upon treatment with concentration of 200 μM, all derivatives display Topo II inhibitory activity, which may be compared with activity of Amonafide. Conclusion: The replacement of the nitro groups in the chromophore slightly reduces its anticancer activities, whereas the presence of both nitro group and ω-hydroxylalkylamine chain resulted in seriously increased anticancer activity. Obtained compounds showed Topo II inhibitory activity, moreover, influence of the substitution pattern on the ability to inhibit Topo II activity and cancer cells proliferation was observed.
- Kasprzycki, Przemys?aw,Strama, Klaudia,Tomczyk, Mateusz D.,Walczak, Krzysztof Z.,Wawszków, Martyna,Wyrostek, Anna Byczek
-
p. 550 - 560
(2019/07/12)
-
- Synthesis of disperse dyes derived from 4-amino-N-decyl-1, 8-naphthalimide and their dyeing properties on polyester fabrics
-
Novel series of amphiphilic monoazo dyes were synthesized using 4-amino-N-decyl-1, 8-naphthalimide by coupling with different substituted anilines and naphthalenes in appropriate reaction condition. The intermediates and the dyes were purified by recrystallization methods. The structures of the newly synthesized intermediates and the dyes were confirmed from elemental analysis (CHN), FT-IR, 1H and 13C NMR, MS and UV spectroscopic techniques. Spectrophotometric investigations of the synthesized dyes in different solvents were carried out in order to obtain their absorption maxima, molar extinction coefficients and solvatochromic effects. These dyes were applied on polyester fabrics as disperse dyes using high temperature exhaust dyeing method. The relevant dyeing characteristics, such as buildup on fabrics, wash, perspiration and light fastness were evaluated. Fabrics dyed with these dyes furnished generally deep and bright intense hues ranging from light yellow to orange to light red. The colour fastness of the dyed fabrics to washing and perspiration was assessed to be very good, however, the light fastness was found to be poor, moderate to very good.
- Ameuru, Umar Salami,Yakubu, Mohammed Kabir,Bello, Kasali Ademola,Nkeonye, Peter Obinna,Halimehjani, Azim Ziyaei
-
p. 190 - 197
(2018/05/22)
-
- Endoplasmic reticulum-targeted two-photon turn-on fluorescent probe for nitroreductase in tumor cells and tissues
-
Hypoxia conditions could increase the activity of intracellular nitroreductase (NTR) and lead to many malignant diseases. Therefore, monitoring the activity of NTR is of great significance to study the related diseases. Organelles play crucial roles in the metabolism of living cells. In these organelles, the endoplasmic reticulum (ER) possesses single membrane structure, and it is the largest organelle in the cell. ER performs the synthesis, processing and modification of proteins and lipid, stabilizing the intracellular Ca2+ concentration and other physiological functions in living cells. Therefore, it is of great significance to develop ER-target probes in living system. Toward this goal, a new endoplasmic reticulum-targeted two-photon fluorescence turn-on NTR probe Na-NTR-ER is designed and synthesized. Probe Na-NTR-ER has been proved to display high sensitivity (36 ng/mL) and selectivity to NTR. Particularly, probe Na-NTR-ER has been successfully applied for the monitoring of NTR in ER with a high the Pearson's colocalization coefficient as 0.90 in HeLa cells and cancerous mouse tissues up to the depth of 100 μm with significant fluorescence signals.
- Xu, An,Tang, Yonghe,Lin, Weiying
-
supporting information
p. 770 - 776
(2018/07/13)
-
- Pyrimidine naphthalimide derivatives, and preparation method and application thereof
-
The invention discloses a kind of pyrimidine naphthalimide derivatives, and a preparation method and application thereof. The derivatives have structures shown as formulas I to III shown as the accompanying drawing. In the formulas I, II and III, a is 0 or 1 or 2; m is 2 or 3 or 4; n is 2 or 3 or 4; x is an integer being 0 to 6; R1 is shown as the accompanying drawing; R2 is shown as the accompanying drawing; R3 is shown as the accompanying drawing. The invention provides a preparation method for building pyrimidine naphthalimide through introducing o-amino cyanogens by using acenaphthene as raw materials. According to the existing data, after the modification by polyamine with targeted carrying capability, the antitumor activity of naphthalimide is obviously improved; a strong inhibition effect is achieved on tumor transfer. According to the discovery, a series of pyrimidine naphthalimide derivatives are designed and synthesized. According to the display by primary test results, the kind of pyrimidine naphthalimide derivatives show good antitumor effect in vitro on various tumor cell strains. The important significance is realized on developing novel anti-tumor medicine.
- -
-
Paragraph 0036
(2017/04/03)
-
- Synthesis and Photophysical Studies on Naphthalimide Derived Fluorophores as Markers in Drug Delivery
-
Derivatives of 4-amino-1,8-naphthalimide containing a free alkyl chain bearing carboxyl group as linker and different substituents at 4-amino function have been synthesized, characterized and studied for their photophysical properties. Steady state fluorescence studies showed quantum yield varied from 0.45 to 0.65 with Stokes shift in the range of 5824–8558?cm?1. Spectroscopic and physicochemical parameters, like electronic absorption, emission, and extinction coefficient were investigated in order to explore the analytical potential of compounds. Solvatochromic studies demonstrated that all compounds were sensitive towards the polarity of different solvents showing the highest degree of fluorescence in acetonitrile. In addition, the compounds in the presence of ions, viz. Na+, K+ and Mg2+ at concentration of 0.1–2 equivalents, showed a decreasing trend in fluorescence with increasing ionic concentration. TCSPC set – up was used to measure the fluorescence lifetime of compounds, which was found to be bi-exponential with longer and shorter component at their respective amplitudes. The average lifetime of compounds was observed to be 5.76–9.96?ns indicating the possibility of their greater utilization in research and diagnosis.
- Singh, Nidhi,Srivastava, Ritika,Singh, Anuradha,Singh, Ramendra K.
-
p. 1431 - 1438
(2016/07/30)
-
- Assembly of New Merocyanine Chromophores with a 1,8-Naphthalimide Core by a New Method for the Synthesis of the Methine Function
-
A new method for the synthesis of the monomethine group using nitro as a leaving group in an SN-Ar reaction is described. A series of novel merocyanine dyes has been synthesised and their photophysical properties have been elucidated. The longest wavelength absorption occurs in the range 519-619nm and the molar absorptivities vary with the substituents and are in the range 1000-47700Lmol-1cm-1. The dyes show high chemical and photostability. One example from the series has the ability to distinguish methanol from ethanol. The introduction of a quinoid fragment into the structure leads to a pronounced intramolecular charge transfer and hence a noticeable positive solvatochromism. The structures and electronic properties of the compounds have been studied by density functional theory (DFT) and time-dependent DFT.
- Vasilev, Aleksey A.,Baluschev, Stanislav,Cheshmedzhieva, Diana,Ilieva, Sonia,Casta?o, Obis D.,Vaquero, Juan J.,Angelova, Silvia E.,Landfester, Katharina
-
p. 1399 - 1408
(2015/09/15)
-
- Highly selective off-on fluorescent probe for imaging thioredoxin reductase in living cells
-
The first fluorescent probe for mammalian thioredoxin reductase (TrxR), TRFS-green, was designed, synthesized, and fully evaluated. The probe features a 1,2-dithiolane scaffold with a quenched naphthalimide fluorophore. TRFS-green displays a green fluorescence off-on change induced by the TrxR-mediated disulfide cleavage and subsequent intramolecular cyclization to liberate the masked naphthalimide fluorophore. It was demonstrated in vitro that TRFS-green manifests high selectivity toward TrxR over other related enzymes and various small molecule thiols as well as biological reducing molecules. HPLC analyses indicated that TRFS-green was exclusively converted to naphthalimide catalyzed by TrxR. The ability in triggering on the fluorescence signal by cellular protein extracts correlates well with the endogenous TrxR activity in different cells. Furthermore, inhibition of TrxR by 2,4-dinitrochlorobenzene or depletion of TrxR by immunoprecipitation remarkably decreases the reduction of TRFS-green by cellular protein extracts. Finally, TRFS-green was successfully applied in imaging TrxR activity in living cells. The fluorescence signal of TRFS-green in living cells was inhibited by pretreating the cells with TrxR inhibitor in a dose-dependent manner, potentiating the development of living cell-based screening assay for identifying TrxR inhibitors. We expect the novel fluorescent probe TRFS-green would facilitate the discovery of TrxR-targeting small molecules for potential therapeutic agents and provide significant advances in understanding the physiological/pathophysiological functions of TrxR in vivo.
- Zhang, Liangwei,Duan, Dongzhu,Liu, Yaping,Ge, Chunpo,Cui, Xuemei,Sun, Jinyu,Fang, Jianguo
-
p. 226 - 233
(2014/01/23)
-
- Dithiaarsanes induce oxidative stress-mediated apoptosis in HL-60 cells by selectively targeting thioredoxin reductase
-
The selenoprotein thioredoxin reductase (TrxR) plays a pivotal role in regulating cellular redox homeostasis and has attracted increasing attention as a promising anticancer drug target. We report here that 2-(4-aminophenyl)-1,3,2- dithiarsinane (PAO-PDT, 4), a potent and highly selective small molecule inhibitor of TrxR, stoichiometrically binds to the C-terminal selenocysteine/cysteine pair in the enzyme in vitro and induces oxidative stress-mediated apoptosis in HL-60 cells. The molecular action of 4 in cells involves inhibition of TrxR, elevation of reactive oxygen species, depletion of cellular thiols, and activation of caspase-3. Knockdown of TrxR sensitizes the cells to 4 treatment, whereas overexpression of the functional enzyme alleviates the cytotoxicity, providing physiological relevance for targeting TrxR by 4 in cells. The simplicity of the structure and the presence of an easily manipulated amine group will facilitate the further development of 4 as a potential cancer chemotherapeutic agent.
- Liu, Yaping,Duan, Dongzhu,Yao, Juan,Zhang, Baoxin,Peng, Shoujiao,Ma, Huilong,Song, Yanlin,Fang, Jianguo
-
supporting information
p. 5203 - 5211
(2014/07/08)
-
- 1,8-Naphthalimide-based colorimetric and fluorescent sensor for recognition of GMP, TMP, and UMP and its application in in vivo imaging
-
In this study, a series of 1,8-naphthalimide-based analogs were developed for fluorescence imaging of nucleotides in Caenorhabditis elegans. In DMSO, compound 1 proved to be an effective and selective colorimetric and fluorescent sensor for recognition of GMP, TMP, and UMP over other structurally similar nucleotides. Among all the tested nucleotides, only the addition of GMP, TMP, and UMP resulted in a fluorescence color change from blue to brown with a fluorescence enhancement of more than 600-fold, with the colorless solution turning brown. NMR spectroscopic titration, theoretical calculations, and spectral tests performed using various solvent compositions confirmed that compound 1 formed multiple hydrogen bonds with the related base groups in the nucleotide. Compound 1 demonstrated its utility as a fluorescent chemosensor for detecting GMP, TMP, and UMP in in vivo imaging of GMP, TMP, and UMP in C. elegans.
- Zhang, Li Mei,Guo, Lin E.,Li, Xue Mei,Shi, Yong Gang,Wu, Gao Fen,Xie, Xiao Guang,Zhou, Ying,Zhao, Qi Hua,Zhang, Jun Feng
-
p. 6131 - 6136
(2015/02/02)
-
- Synthesis and study of antiproliferative, antitopoisomerase II, DNA-intercalating and DNA-damaging activities of arylnaphthalimides
-
A series of arylnaphthalimides were designed and synthesized to overcome the dose-limiting cytotoxicity of N-acetylated metabolites arising from amonafide, the prototypical antitumour naphthalimide whose biomedical properties have been related to its ability to intercalate the DNA and poison the enzyme Topoisomerase II. Thus, these arylnaphthalimides were first evaluated for their antiproliferative activity against two tumour cell lines and for their antitopoisomerase II in vitro activities, together with their ability to intercalate the DNA in vitro and also through docking modelization. Then, the well-known DNA damage response in Saccharomyces cerevisiae was employed to critically evaluate whether these novel compounds can damage the DNA in vivo. By performing all these assays we conclude that the 5-arylsubstituted naphthalimides not only keep but also improve amonafide's biological activities.
- Quintana-Espinoza, Patricia,Garcia-Luis, Jonay,Amesty, Angel,Martin-Rodriguez, Patricia,Lorenzo-Castrillejo, Isabel,Ravelo, Angel G.,Fernandez-Perez, Leandro,Machin, Felix,Estevez-Braun, Ana
-
supporting information
p. 6484 - 6495
(2013/10/22)
-
- Synthesis and spectral properties of 4-amino-and 4-acetylamino-N- arylnaphthalimides containing electron-donating groups in the N-aryl substituent
-
A method for the synthesis of N-aryl-substituted 4-amino-and 4-acetylaminonaphthalimide derivatives with mono-and dialkoxy groups or a 15-crown-5 moiety in the N-aryl substituent is described. The introduction of electron-donating alkoxy groups into the benzene ring of the N-aryl fragment results in fluorescence quenching of the naphthalimide chromophore, which is most pronounced in the spectra of N-acetyl derivatives. The photophysical properties of the synthesized 4-amino-and 4-acetylaminonaphthalimides depend on the solvent polarity and its specific solvating ability due to H-bonding. The crown-containing compounds are promising fluorescent chemosensors for metal cations. ; 2009 Springer Science+Business Media, Inc.
- Panchenko,Fedorova,Perevalov,Jonusauskas,Fedorov
-
scheme or table
p. 1233 - 1240
(2010/10/04)
-
- Synthesis and characterization of some monoazo disperse dyestuffs based on naphthalimide derivatives for dyeing of polyester fabrics
-
A series of monoazo dis perse dye stuffs de rived from naphthalimide were prepared. 4-Amino-N-methyl (alternatively N-ethyl, N-propyl,N-butyl) derivatives of naphthalimide were utilised as the diazo components and β-naphthol, N,N-diethyl-m-toluidine, and p-aminoacetophenone constituted the coupling components. To this end, acenaphthene was nitrated and then various unit processes such as oxidation, amination, reduction, diazotization, and coupling were carried out. The syn the sized monoazo dis perse dye stuffs were applied toalocally manufactured polyester fabric and their optical properties were in vestigated. Characterisation of the various intermediates as well as the dye stuffs were carried out by DSC, FTIR, H-NMR and UV-vis analytical techniques.
- Khosravi,Moradian,Gharanjig,Afshar Taromi
-
p. 495 - 502
(2007/10/03)
-
- Selective nitration of aromatic compounds with bismuth subnitrate and thionyl chloride
-
Bismuth subnitrate/thionyl chloride have been found to be an efficient combination of reagents for nitration of a wide range of aromatic compounds in dichloromethane. Phenols, in particular, were easily mononitrated and dinitrated with the reagents by controlling the stoichiometry.
- Muathen, Hussni A.
-
p. 593 - 598
(2007/10/03)
-
- Syntheses, characterisation and fluorescence study of some novel naphthalimide derivatives
-
Three fluorescent derivatives viz. 4-tosylamido-1,8-naphthalic anhydride, 4-dansylamido-1,8-naphthalimido-N-pentanol and 4-dabsylamido-1,8-naphthalimido-N-pentanol have been prepared and characterised. The comparative fluorescence studies and quantum yield estimation has been carried out in different solvents such as methanol, dioxane, water, water-methanol gradient, normal aqueous solutions of sodium carbonate, hydrochloric acid and buffers like ammonium acetate, 1 X TRIS-EDTA and the effect of inorganic salts like sodium chloride, potassium chloride, magnesium sulphate has also been studied. Thus, optimal conditions for maximum fluorescence yield has been worked out. The fluorescent derivatives reported herein have the potential to be used for covalent as well as non-covalent labelling of various biomolecules, specially to synthetic oligonucleotides. The labelled oligonucleotides have been proved to be of immense value as probes in clinical diagnostics.
- Singh, Yashveer,Misra, Arvind,Misra, Krishna
-
p. 1238 - 1245
(2007/10/03)
-
- Condensed heterocycles: Part XXVI - Synthesis of cycloalkaazaphenanthrenes and cycloalkaaza-acephenanthrenes
-
Various 2-formylcycloalkanones on reaction with α-naphthylamine furnish the corresponding 2-(α-naphthylaminomethylene)cycloalkanones (1 and 3) which on PPA cyclisation afford the desired cycloalkaazaphenanthrenes (2 and 4). 5-Aminoacenaphthene on a similar treatment with 2-formylcycloalkanones give the corresponding 2-(5-acenaphthylaminomethylene)cycloalkanones (5, 7 and 9) which undergo smooth cyclisation to provide the desired cycloalkaaza-acephenanthrenes (6, 8 and 10).The structures of the products have been elucidated by elemental analyses, IR and 1H NMR spectral data.
- Sharma, K. S.,Singh, S. P.,Kumari, Sharda
-
p. 1191 - 1192
(2007/10/02)
-
