4-(氮杂-15-冠-5)-1,8-萘酰亚胺荧光探针的合成及性能研究

N-丁基-4-溴-1,8-萘酰亚胺与二乙醇胺反应, 合成了N-丁基-4-二(2-羟乙基)氨-1,8-萘酰亚胺, 进一步与对甲基苯磺酸二缩三乙二醇双酯反应合成了N-丁基-4-(氮杂-15-冠-5)-1,8-萘酰亚胺. 用NMR, IR, MS等表征了产物结构. 该化合物在二氯甲烷溶液中识别Li^＋和Na^＋, 识别后吸收光谱和荧光光谱蓝移.     

1,8-萘酰亚胺为发色团的Zn2+荧光探针的合成及性能研究

合成了以1,8-萘酰亚胺为发色团,以联吡啶为离子受体的Zn²⁺荧光探针,并进行了表征及离子识别性能的研究。研究表明该化合物对Zn²⁺具有良好的识别性能,同时相对于Ca²⁺, Cd²⁺, Co²⁺, Cu²⁺, Hg²⁺, Fe³⁺, Mn²⁺, Ni²⁺, Pb²⁺等金属离子具有良好的选择性。     

基于1,8-萘酰亚胺的多分析物荧光探针的构建和应用

生命受细胞内复杂的代谢过程控制。科学界正在进行的努力之一是研究和理解这些动态生化反应以及生物分子在维持生命中的作用。荧光探针具有操作简单、成本低、灵敏度高、可在活体中多通道和实时可视化等优点,已被广泛用于分析物在生理和病理过程中的可视化研究。然而,多数荧光探针只可响应单分析物,不适于复杂生物体系中多分析物的分析检测。近5年来,以1,8-萘酰亚胺为荧光报告基团的多分析物荧光探针在生物或环境领域得到了快速的发展。依据探针荧光发光机制,本文将其分为单发光机制(PET、ICT和FRET)、双发光机制(PET-ICT、PET-FRET和ICT-FRET等双机制协同作用)等方式,综述了国内外基于1,8-萘酰亚胺的多分析物荧光探针在设计策略、识别过程、光学性质和细胞成像等方面的新进展,并对此类荧光探针的发展趋势和挑战进行了展望。     

基于1,8-萘酰亚胺的Ag+荧光探针的合成及应用

通过N-丁基-4,5-二氨基-1,8-萘酰亚胺与2-噻吩甲醛缩合,构建了一种基于分子内电荷转移(ICT)的荧光探针NAPH-1(6-氨基-2-丁基-7-((噻吩-2-基亚甲基)氨基)-1H-苯并[de]异喹啉-1,3(2H-二酮)),其结构经¹H NMR、¹³C NMR、HRMS和元素分析确证。探究了该探针对Ag⁺选择性、荧光滴定、淬灭常数、检测限等性能。研究结果表明,NAPH-1对Ag⁺呈现出荧光淬灭效应,猝灭常数为2.96×10⁵L·mol^-1。值得关注的是,NAPH-1表现出对Ag⁺较好的选择性和响应性,检测限为0.32μmol·L^-1。水样中测定结果表明,NAPH-1可以作为一种潜在的Ag⁺检测工具。     

基于1,8-萘酰亚胺的半胱氨酸荧光探针的合成及在生物成像方面的应用

设计合成了一种用于检测半胱氨酸的新型荧光探针乙二醛(N-羟乙基-1,8-二甲酰亚胺-4-萘基)单腙(NAD),该荧光探针对半胱氨酸表现出较高的灵敏度和选择性.当半胱氨酸加入NAD溶液中,会形成分子内氢键,抑制C■N的异构化,导致荧光增强.此外,探针NAD可应用于细胞内半胱氨酸的检测,表明该类型探针在生物检测应用方面具有较大的潜力.     

基于萘酰亚胺的次氯酸荧光探针的合成及细胞成像性能研究

以萘酰亚胺结构为荧光发色团,设计开发了一种含C=C双键的、具有分子内电荷转移(ICT)效应的新型水溶性优化的次氯酸荧光探针3-(2-氰基丙烯酸乙酯基)-4-羟基-N-正丙基-1,8-萘酰亚胺(NAEC).添加次氯酸后,探针分子NAEC中的C=C双键被氧化,生成醛基,探针NAEC原有的ICT效应被破坏,产生荧光信号.经核...     

一种1,8-萘酰亚胺衍生物检测半胱氨酸荧光探针 的合成及其在活细胞和秀丽隐杆线虫中成像中的运用

基于1,8-萘酰亚胺衍生物,构建了一种检测半胱氨酸(Cys)的新型荧光探针TPFC-Acryloyl。光谱研究表明该探针能有效识别Cys且能够在1min内实现快速响应。探针对Cys的检测表现出高选择性,检测限为2.13μmol/L。经荧光光谱和质谱实验确证其检测机理为：Cys与TPFC-Acryloyl分子中的丙烯酸酯发生共轭加成-环化反应,进而羟基裸露的同时释放出黄色荧光。细胞毒性测试表明探针TPFC-Acryloyl的细胞毒性低。此外,该探针还被成功应用于活细胞和秀丽隐杆线虫中Cys的荧光成像。     

以苯并咪唑萘酰亚胺为荧光团高选择快速检测H2S的荧光探针

以1,8-萘二甲酸酐为起始原料合成一种萘酰亚胺衍生物3-叠氮基-7H-苯并[de]苯并[4,5]咪唑[2,1-a]异喹啉(DBNG),利用傅里叶变换红外光谱(FT-IR)和核磁共振波谱(NMR)等测试手段确定其结构,并将其作为小分子荧光探针用于检测H2S,系统研究了其荧光特性,结合理论计算,探究其可能的检测机制.结果表...     

一种罗丹明-氨乙基邻苯二甲酰胺衍生物的设计合成及其对Cr~(3+)离子的荧光-比色检测

本文合成、表征了一种结构简单的罗丹明-氨乙基邻苯二甲酰胺衍生物(RP1)。研究发现,在多种金属阳离子存在的条件下,RP1在丙酮/水溶液中对Cr3+具有高度选择性识别性能,在荧光增强的同时对Cr3+有明显的目视比色响应,颜色由无色变为粉红色,而其它共存的金属阳离子无干扰。定量分析结果显示RP1对Cr3+的结合计量比为1∶1,结合常数为3.43×104L/mol。识别机理研究表明,Cr3+通过可逆的配位诱导螺环开环机制与RP1进行相互作用,而非通过催化水解机制进行。     

A novel fluorescent sensor for metal cations and protons based of bis-1,8-naphthalimide

A newly synthesized bis-1,8-naphthalimide aimed to increase its fluorescence intensity in the presence of protons or metal cations has been investigated. Its spectral photophysical characteristics in acetonitrile and chloroform solutions are described. The influence of metal cations (Zn(2+), Ni(2+), Ce(3+), Co(2+), Cu(2+) and Ag(+)) and protons on the fluorescence intensity has been investigate with regard to obtain fluorescence sensors for this ions in the environment.     

A fluorescent PET chemosensor for Zn2+ cations based on 4-methoxy-1,8-naphthalimide derivative containing salicylideneamino receptor group

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A novel dansyl-based fluorescent probe for Fe3+

Research on Chemical Intermediates - A novel structurally simple dansyl-based fluorescent probe, 5-(dimethylamino)-N,N-bis(2-hydroxyethyl)naphthalene-1-sulfonamide, was synthesized from dansyl...     

A novel fluorescent molecule based on 1,8-naphthalimide: synthesis,spectral properties,and application in cell imaging

A novel naphthalimide molecule, 4-(2-methoxyethoxy)-N-butyl-1,8-naphthalimide (MEBN), has been synthesized and characterized. The UV–visible absorption and fluorescence emission spectral properties in n-hexane, toluene, CHCl₃, and CH₃OH were studied. Its optical properties depend on solvent polarity. The application of MEBN in cell imaging was investigated.     

A novel fluorescent sensor for Cr3+ based on rhodamine-cored poly (amidoamine) dendrimer

A novel poly (amidoamine) (PAMAM) dendrimer, comprising rhodamine B unit in the core and 1-phenyl-3-methyl-5-pyrazolone unit at the periphery, has been synthesized and characterized. The dendrimer shows dramatic increase in its fluorescence intensity in the presence of proton and metal cations, especially in the presence of Cr(3+). The complex formed by dendrimer and Cr(3+) in ethanol solution has also been studied, considering the potential application for Cr(3+) fluorescent sensor. The influence of the unique chemical structure and resulted photoinduced electron transfer, as well as spirolactam ring-opening on the photophysical properties of the product has been investigated.     

Microflow synthesis of fluorescent markers based on 1,8-naphthalimide for polylactide nanoparticles and bioimaging

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Bifunctional fluorescent probes for hydrogen peroxide and diols based on a 1,8-naphthalimide fluorophore

This report discloses a series of naphthalimide-based bifunctional fluorescent probes for hydrogen peroxide and diols.As a result,these molecules not only demonstrated high turn-on fluorescent response and good selectivity towards hydrogen peroxide over other relevant reactive oxygen species,but also displayed different responses to diols.Therefore,these fluorescent probes could be served as sensitive,selective and practical chemosensors for both hydrogen peroxide and diols under physiologicallike conditions.     

A novel 1,8-naphthalimide probe: synthesis and interactions with nucleic acid and its precursor

Three novel, water-soluble N-substituted 1,8-naphthalimides as the spectroscopic probes of nucleic acid, N-(2-hydroxyethyl)-1,8-naphthalimide (NI1), 1,8-naphthalimide-N-acetic acid (NI2) and 1,8-naphthalimide-N-caproic acid (NI3), were synthesized and photophysically characterized. The steady-state fluorescence quenching of the NI probes with nucleic acids (NA) and their precursors (nucleobases and nucleosides) were studied by Stern–Volmer correlation. The rate constants for bimolecular quenching were obtained in Tris buffer solution. The transient absorption spectroscopy by nanosecond laser flash photolysis were explored to identify the transient species and to determine the kinetics. The dynamic interaction mechanism was attributed to electron transfer (ET) and energy transfer via ³NI.     

Synthesis and spectral properties of fluorescent dyes based on 4-styryl-1,8-naphthalimide

The paper reports on synthesis and spectroscopic study of novel N-butyl-4-styryl-1,8-naphthalimide dyes bearing methoxy (1), dimethoxy (2), and dimethylamino (3) groups in the styryl fragment. It is shown that all synthesized compounds demonstrate positive solvatochromism, high values of Stokes shift in polar solvents, and fluorescence in the long wavelength part of visible range. These facts indicate a potential application of these compounds as fluorescent dyes in the biochemistry. The changes in the dipole moments of the molecules caused by excitation were estimated using Lippert—Mataga equation. The obtained results could be assigned to the formation of the excited states with intramolecular charge transfer. The formation of the twisted states with charge transfer was suggested in the case of compound 3, while the fluorescence quantum yield was significantly reduced in polar protic solvents.

     

Ratiometric detection of Cr3+ and Hg2+ by a naphthalimide-rhodamine based fluorescent probe

Newly synthesized rhodamine derivatives, L(1) and L(2), are found to bind specifically to Hg(2+) or Cr(3+) in presence of large excess of other competing ions with associated changes in their optical and fluorescence spectral behavior. These spectral changes are significant enough in the visible region of the spectrum and thus, allow the visual detection. For L(1), the detection limit is even lower than the permissible [Cr(3+)] or [Hg(2+)] in drinking water as per standard U.S. EPA norms; while the receptor, L2 could be used as a ratiometric sensor for detection of Cr(3+) and Hg(2+) based on the resonance energy transfer (RET) process involving the donor naphthalimide and the acceptor Cr(3+)/Hg(2+)-bound xanthene fragment. Studies reveal that these two reagents could be used for recognition and sensing of Hg(2+)/Cr(3+). Further, confocal laser microscopic studies confirmed that the reagent L(2) could also be used as an imaging probe for detection of uptake of these ions in A431 cells.