The halogen as a kind of alkylating reagent is used to introduce new group to realize the fluorescence sensors efficient of metal ion detection. The substituent at C-4 position was double bromine, which defined that t...The halogen as a kind of alkylating reagent is used to introduce new group to realize the fluorescence sensors efficient of metal ion detection. The substituent at C-4 position was double bromine, which defined that the halogen as an alkylating reagent should be further researched and detected for Hg2＋. Therefore, the N-n-butyl-4-[di（bromoethyl）]amino-1,8-naphthalimide has been synthesized to detect some metal ions. The title compound has been prepared via substitute reaction and was characterized by IR, 1H NMR, 13 C NMR, and MS. It crystallizes in triclinic, space group P1 with a = 9.0071（18）, b = 9.804（2）, c = 13.073（3）A, α = 73.17（3）, β = 71.73（3）, γ = 62.95（3）°, Z = 2, V = 961.5（3） A3, Dc = 1.666 g/cm3, F（000） = 484, μ（Mo Kα） = 4.232 mm-1, R = 0.0429 and w R = 0.1004. The presence of intermolecular hydrogen bonds as well as π-π stacking interaction led to the stability of the compound. The fluorescence intensity was obviously lower than that of other ions when Hg2＋ was added with the concentration of 1 × 10^-5 mol·L-1.展开更多
The molecular geometries, frontier molecular orbital properties, and absorption and emission properties of three 4-phenoxy-1,8-naphthalimide derivatives, namely 4-phenoxy-N-（2-hydroxyethyl）-1,8-naphthalimide（1）,4-...The molecular geometries, frontier molecular orbital properties, and absorption and emission properties of three 4-phenoxy-1,8-naphthalimide derivatives, namely 4-phenoxy-N-（2-hydroxyethyl）-1,8-naphthalimide（1）,4-（2-tert-butylphenoxy）-N-（2-hydroxyethyl）-1,8-naphthalimide（2）, and 4-[2,4-di（tert-butyl）]phenoxy-N-（2-hydroxyethyl）-1,8-naphthalimide（3）, are investigated by density functional theory（DFT） and time-dependent density functional theory（TD-DFT） calculations in conjunction with polarizable continuum models（PCMs）. Four functionals and ten basis sets are employed for 1 to calculate the electron transition energies, which were compared with the experimental observations. Our results reveal that the B3LYP/6-311＋G（d,p） method is the best choice to reproduce the experimental spectra. Moreover, the effects of substituents on the molecular geometries, electronic structures, absorption and emission spectra are also studied at the B3LYP/6-311＋G（d,p） level. We find that the gap between the highest occupied molecular orbital（HOMO） and the lowest unoccupied molecular orbital（LUMO） decreases with increasing the number of tert-butyl substituents onto the phenoxy groups, suggesting red-shift of the absorption and emission bands. This is related to the increase of conjugation from 1 to 2 and 3. Our calculations are in good agreement with the experimental results.展开更多
Two 1,8-naphthalimide derivatives of 7H-benzimidazo[2,1,-a]benz[de] isoquino- lin-7-one（1） and 4-bromo-7H-benzimidazo[2,1,-a]benz[de]isoquinolin-7-one（2） have been synthesized and characterized by elemental analys...Two 1,8-naphthalimide derivatives of 7H-benzimidazo[2,1,-a]benz[de] isoquino- lin-7-one（1） and 4-bromo-7H-benzimidazo[2,1,-a]benz[de]isoquinolin-7-one（2） have been synthesized and characterized by elemental analysis, IR, 1H NMR, UV-Vis and fluorescence spectra. For the two compounds, density functional theory（DFT） calculations of the structures and natural population atomic charge analysis have been performed at the B3LYP/6-311G＊＊ level of theory. Based on Onsager reaction filed model and by using TD-DFT method at the B3LYP/6-311G＊＊ level, electron spectra of 1 and 2 with solvent effect in CHCl3 solvent have been predicted, which are in agreement with the experimental ones. Comparative studies on 1 and 2 indicate that introducing an electron-withdrawing group of Br into the 4-position of naphthalene ring in 2 does not significantly make the molecular geometry of 2 different from that of 1, but evidently changes the atomic charge redistribution, moves the positive-negative charges center and then changes the dipole moment in 2. Additionally, for compound 2, the existence of Br atom has also influenced the peak intensity and peak locations in both electron and fluorescence spectra.展开更多
Membrane permeability and intracellular diffusion of fluorescent probes determine staining selectivity of intracellular substructures.However,the relationship between the molecular structure of fluorescent probes and ...Membrane permeability and intracellular diffusion of fluorescent probes determine staining selectivity of intracellular substructures.However,the relationship between the molecular structure of fluorescent probes and their membrane permeability and intracellular distribution is poorly understood.In this paper,we reported a series of 1,8-naphthalimide dyes and carried out cell imaging experiments,and found that the presence of amino hydrogen in these dyes played a crucial role in their cell membrane permeability and intracellular distribution.The secondary amino group containing compounds 1-4 show excellent membrane permeability and strong fluorescence in living cells.While the tertiary amine containing dyes 5 and 6 can hardly permeate the cell membrane though they show extremely similar structure with compounds 2-4.Compound 1 can selectively image lipid droplets by selecting the wavelength of excitation light.With the specificity for lysosomes,2 and 4 have been used in long-term time-lapses imaging of lysosomal dynamics and tracking the process of lysosome-lysosome interaction,fusion and movement.The effect of hydrogen-containing amino substituent on the cell membrane permeability of fluorescent molecules is promising for the development of better biocompatible probes.展开更多
The ligand of N-（2-hydroxybenzylideneamino）-1,8-naphthalimide （HL） and its metal complexes of CuL2 （1） and CoL2 （2） have been synthesized. Elemental analysis, IR and X-ray single-crystal diffraction characteri...The ligand of N-（2-hydroxybenzylideneamino）-1,8-naphthalimide （HL） and its metal complexes of CuL2 （1） and CoL2 （2） have been synthesized. Elemental analysis, IR and X-ray single-crystal diffraction characterizations for 1 and 2 have been carried out. In the complexes of 1 and 2, the central metallic ions of Cu^2＋ and Co^2＋ coordinate with two deprotonated ligands of L-, respectively and adopt distorted square planar geometries. The thermal analysis result shows that the two complexes undergo two similar decomposition processes because of their similar geometric configurations. For the two complexes, fluorescence spectra measurements indicate that complex CoL2 emits stronger blue fluorescence than HL and the complex CuL2 does not emit fluorescence at all.展开更多
4-Amino-1,8-naphthalimide(ANI) represents a valuable fluorophore from which a large number of probes have been derived in order to meet the requirements from the fields of biological sensing and imaging. In this revie...4-Amino-1,8-naphthalimide(ANI) represents a valuable fluorophore from which a large number of probes have been derived in order to meet the requirements from the fields of biological sensing and imaging. In this review, the major progresses of ANI-based fluorescent probes in the past decade have been highlighted and categorized into three trends. The future development of ANI probes is also expected. This review provides a great deal of references and illuminating comments which will be helpful for the researchers designing and using fluorescent probes.展开更多
A series of new fluorescent chemosensors 5a--5e, composed of two aminonaphthalimide fluorophores and 2,6-bis（（N-aminoalkyl）aminocarboxy）pyridines, were prepared, characterized, and their fluorescent properties to-...A series of new fluorescent chemosensors 5a--5e, composed of two aminonaphthalimide fluorophores and 2,6-bis（（N-aminoalkyl）aminocarboxy）pyridines, were prepared, characterized, and their fluorescent properties to- wards heavy and transition metal （HTM） ions were investigated. Chemosensors 5e--Se exhibited high selectivity and sensitivity for Cu2＋ ion over other HTM ions with fluorescent quenching （green to colourless）. It clearly demonstrated that the length of the linkers （diamines） between the aminonaphthalimides and 2,6-dicarboxypyridine of 5a--Se was very important for their sensitivity and selectivity for Cu2~ ion over other HTM ions.展开更多
Ulcerative colitis(UC)is characterized by chronic relapsing intestinal inflammation.Currently,there is no effective treatment for the disease.According to our preliminary data,1,8-cineole,which is the main active comp...Ulcerative colitis(UC)is characterized by chronic relapsing intestinal inflammation.Currently,there is no effective treatment for the disease.According to our preliminary data,1,8-cineole,which is the main active compound of Amomum compactum Sol.ex Maton volatile oil and an effective drug for the treatment of pneumonia,showed remarkable anti-inflammatory effects on colitis pathogenesis.However,its mechanism of action and direct targets remain unclear.This study investigated the direct targets and mechanism through which 1,8-cineole exerts its anti-inflammatory effects using a dextran sulfate sodium salt-induced colitis mouse model.The effects of 1,8-cineole on macrophage polarization were investigated using activated bone marrow-derived macrophages and RAW264.7 cells.In addition,1,8-cineole targets were revealed by drug affinity responsive target stability,thermal shift assay,cellular thermal shift assay,and heat shock protein 90(HSP90)adenosine triphosphatases(ATPase)activity assays.The results showed that 1,8-cineole exhibited powerful anti-inflammatory properties in vitro and in vivo by inhibiting the macrophage M1 polarization and protecting intestinal barrier function.Mechanistically,1,8-cineole directly interacted with HSP90 and decreased its ATPase activity,also inhibited nucleotide-binding and oligomerization domain-,leucine rich repeat-,and pyrin domain-containing 3(NLRP3)binding to HSP90 and suppressor of G-two allele of SKP1(SGT1)and suppressed NLRP3 inflammasome activation in macrophages.These results demonstrated that 1,8-cineole is a potential drug candidate for UC treatment.展开更多
基金supported by the National Natural Science Foundation of China(No.31572042)the Research Science Foundation in Technology Innovation of Harbin(No.2015RAYXJ010)
文摘The halogen as a kind of alkylating reagent is used to introduce new group to realize the fluorescence sensors efficient of metal ion detection. The substituent at C-4 position was double bromine, which defined that the halogen as an alkylating reagent should be further researched and detected for Hg2＋. Therefore, the N-n-butyl-4-[di（bromoethyl）]amino-1,8-naphthalimide has been synthesized to detect some metal ions. The title compound has been prepared via substitute reaction and was characterized by IR, 1H NMR, 13 C NMR, and MS. It crystallizes in triclinic, space group P1 with a = 9.0071（18）, b = 9.804（2）, c = 13.073（3）A, α = 73.17（3）, β = 71.73（3）, γ = 62.95（3）°, Z = 2, V = 961.5（3） A3, Dc = 1.666 g/cm3, F（000） = 484, μ（Mo Kα） = 4.232 mm-1, R = 0.0429 and w R = 0.1004. The presence of intermolecular hydrogen bonds as well as π-π stacking interaction led to the stability of the compound. The fluorescence intensity was obviously lower than that of other ions when Hg2＋ was added with the concentration of 1 × 10^-5 mol·L-1.
基金supported by the Scientific Research Fund of Hubei Provincial Education Department(No.Q20122909)the Open Fund of Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province(No.PKLHB1314)the First-class Discipline of Forestry in Hubei Minzu University
文摘The molecular geometries, frontier molecular orbital properties, and absorption and emission properties of three 4-phenoxy-1,8-naphthalimide derivatives, namely 4-phenoxy-N-（2-hydroxyethyl）-1,8-naphthalimide（1）,4-（2-tert-butylphenoxy）-N-（2-hydroxyethyl）-1,8-naphthalimide（2）, and 4-[2,4-di（tert-butyl）]phenoxy-N-（2-hydroxyethyl）-1,8-naphthalimide（3）, are investigated by density functional theory（DFT） and time-dependent density functional theory（TD-DFT） calculations in conjunction with polarizable continuum models（PCMs）. Four functionals and ten basis sets are employed for 1 to calculate the electron transition energies, which were compared with the experimental observations. Our results reveal that the B3LYP/6-311＋G（d,p） method is the best choice to reproduce the experimental spectra. Moreover, the effects of substituents on the molecular geometries, electronic structures, absorption and emission spectra are also studied at the B3LYP/6-311＋G（d,p） level. We find that the gap between the highest occupied molecular orbital（HOMO） and the lowest unoccupied molecular orbital（LUMO） decreases with increasing the number of tert-butyl substituents onto the phenoxy groups, suggesting red-shift of the absorption and emission bands. This is related to the increase of conjugation from 1 to 2 and 3. Our calculations are in good agreement with the experimental results.
基金Supported by Doctor Foundation of Shandong Province(No.BS2010CL021)Natural Science Foundation of Shandong Province(ZR2009AL020)Jiangsu Key Laboratory for Chemistry of Low-dimensional Materials P.R.China(JSKC12106 and JSKC12107)
文摘Two 1,8-naphthalimide derivatives of 7H-benzimidazo[2,1,-a]benz[de] isoquino- lin-7-one（1） and 4-bromo-7H-benzimidazo[2,1,-a]benz[de]isoquinolin-7-one（2） have been synthesized and characterized by elemental analysis, IR, 1H NMR, UV-Vis and fluorescence spectra. For the two compounds, density functional theory（DFT） calculations of the structures and natural population atomic charge analysis have been performed at the B3LYP/6-311G＊＊ level of theory. Based on Onsager reaction filed model and by using TD-DFT method at the B3LYP/6-311G＊＊ level, electron spectra of 1 and 2 with solvent effect in CHCl3 solvent have been predicted, which are in agreement with the experimental ones. Comparative studies on 1 and 2 indicate that introducing an electron-withdrawing group of Br into the 4-position of naphthalene ring in 2 does not significantly make the molecular geometry of 2 different from that of 1, but evidently changes the atomic charge redistribution, moves the positive-negative charges center and then changes the dipole moment in 2. Additionally, for compound 2, the existence of Br atom has also influenced the peak intensity and peak locations in both electron and fluorescence spectra.
基金supported by the National Natural Science Foundation of China(Nos.22278394,22078314 and 21908216)Dalian Institute of Chemical Physics(Nos.DICPI202227 and DICPI202142).
文摘Membrane permeability and intracellular diffusion of fluorescent probes determine staining selectivity of intracellular substructures.However,the relationship between the molecular structure of fluorescent probes and their membrane permeability and intracellular distribution is poorly understood.In this paper,we reported a series of 1,8-naphthalimide dyes and carried out cell imaging experiments,and found that the presence of amino hydrogen in these dyes played a crucial role in their cell membrane permeability and intracellular distribution.The secondary amino group containing compounds 1-4 show excellent membrane permeability and strong fluorescence in living cells.While the tertiary amine containing dyes 5 and 6 can hardly permeate the cell membrane though they show extremely similar structure with compounds 2-4.Compound 1 can selectively image lipid droplets by selecting the wavelength of excitation light.With the specificity for lysosomes,2 and 4 have been used in long-term time-lapses imaging of lysosomal dynamics and tracking the process of lysosome-lysosome interaction,fusion and movement.The effect of hydrogen-containing amino substituent on the cell membrane permeability of fluorescent molecules is promising for the development of better biocompatible probes.
基金supported by the Fund of Jiangsu Key Laboratory for Chemistry of Low-dimensional Materials (JSKC08047)Fund of Huanyin Teachers College (08HSJSK003)
文摘The ligand of N-（2-hydroxybenzylideneamino）-1,8-naphthalimide （HL） and its metal complexes of CuL2 （1） and CoL2 （2） have been synthesized. Elemental analysis, IR and X-ray single-crystal diffraction characterizations for 1 and 2 have been carried out. In the complexes of 1 and 2, the central metallic ions of Cu^2＋ and Co^2＋ coordinate with two deprotonated ligands of L-, respectively and adopt distorted square planar geometries. The thermal analysis result shows that the two complexes undergo two similar decomposition processes because of their similar geometric configurations. For the two complexes, fluorescence spectra measurements indicate that complex CoL2 emits stronger blue fluorescence than HL and the complex CuL2 does not emit fluorescence at all.
基金supported by the National Natural Science Foundation of China (Nos. 21421005, 21576040 and 21776037)
文摘4-Amino-1,8-naphthalimide(ANI) represents a valuable fluorophore from which a large number of probes have been derived in order to meet the requirements from the fields of biological sensing and imaging. In this review, the major progresses of ANI-based fluorescent probes in the past decade have been highlighted and categorized into three trends. The future development of ANI probes is also expected. This review provides a great deal of references and illuminating comments which will be helpful for the researchers designing and using fluorescent probes.
文摘A series of new fluorescent chemosensors 5a--5e, composed of two aminonaphthalimide fluorophores and 2,6-bis（（N-aminoalkyl）aminocarboxy）pyridines, were prepared, characterized, and their fluorescent properties to- wards heavy and transition metal （HTM） ions were investigated. Chemosensors 5e--Se exhibited high selectivity and sensitivity for Cu2＋ ion over other HTM ions with fluorescent quenching （green to colourless）. It clearly demonstrated that the length of the linkers （diamines） between the aminonaphthalimides and 2,6-dicarboxypyridine of 5a--Se was very important for their sensitivity and selectivity for Cu2~ ion over other HTM ions.
基金supported by the National Natural Science Foundation of China(Grant Nos.:81830114,82004232,82174253,and 82104707)Guangdong Basic and Applied Basic Research Foundation,China(Grant Nos.:2021A1515011215 and 2022A1515110827)+6 种基金Guangzhou Basic and Applied Basic Research Foundation,China(Grant No.:2023A1515011149)China Postdoctoral Science Foundation(Grant Nos.:2020M683206 and 2021M701443)the Key Area Research and Development Program of Guangdong Province,China(Grant No.:2020B1111100010)Guangzhou Key Laboratory of Formula-Pattern of Traditional Chinese Medicine,China(Grant No.:202102010014)the Cross-disciplinary Special Project of Jinan University,China(Grant No.:21621115)the State Key Laboratory of Dampness Syndrome of Chinese Medicine,China(Grant No.:SZ2021KF13)the Outstanding Innovative Talents Cultivation Funded Programs for Doctoral Students of Jinan University,China(Grant No.:2021CXB024).
文摘Ulcerative colitis(UC)is characterized by chronic relapsing intestinal inflammation.Currently,there is no effective treatment for the disease.According to our preliminary data,1,8-cineole,which is the main active compound of Amomum compactum Sol.ex Maton volatile oil and an effective drug for the treatment of pneumonia,showed remarkable anti-inflammatory effects on colitis pathogenesis.However,its mechanism of action and direct targets remain unclear.This study investigated the direct targets and mechanism through which 1,8-cineole exerts its anti-inflammatory effects using a dextran sulfate sodium salt-induced colitis mouse model.The effects of 1,8-cineole on macrophage polarization were investigated using activated bone marrow-derived macrophages and RAW264.7 cells.In addition,1,8-cineole targets were revealed by drug affinity responsive target stability,thermal shift assay,cellular thermal shift assay,and heat shock protein 90(HSP90)adenosine triphosphatases(ATPase)activity assays.The results showed that 1,8-cineole exhibited powerful anti-inflammatory properties in vitro and in vivo by inhibiting the macrophage M1 polarization and protecting intestinal barrier function.Mechanistically,1,8-cineole directly interacted with HSP90 and decreased its ATPase activity,also inhibited nucleotide-binding and oligomerization domain-,leucine rich repeat-,and pyrin domain-containing 3(NLRP3)binding to HSP90 and suppressor of G-two allele of SKP1(SGT1)and suppressed NLRP3 inflammasome activation in macrophages.These results demonstrated that 1,8-cineole is a potential drug candidate for UC treatment.
