19125-99-6Relevant articles and documents
Aggregation-induced emission or aggregation-caused quenching? Impact of covalent bridge between tetraphenylethene and naphthalimide
Ma, Xiaoxie,Chi, Weijie,Han, Xie,Wang, Chao,Liu, Shenghua,Liu, Xiaogang,Yin, Jun
, p. 1790 - 1794 (2021/03/08)
Understanding the physical mechanisms governing aggregation-induced-emission (AIE) and aggregation-caused-quenching plays a vital role in developing functional AIE materials. In this work, tetraphenylethene (TPE, a classical AIEgen) and naphthalimide (NI, a popular fluorophore with ACQ characteristics) were connected through non-conjugated linkages and conjugated linkages. We showed that the nonconjugated-linkage of TPE to NI fragments leads to substantial PET in molecular aggregates and ACQ. In contrast, the conjugated connection between TPE and NI moieties results in the AIE phenomenon by suppressing twisted intramolecular charge transfer. This work provides an important guideline for the rational design of AIE materials.
Peroxynitrite (ONOO-) generation from the HA-TPP@NORM nanoparticles based on synergistic interactions between nitric oxide and photodynamic therapies for elevating anticancer efficiency
Jiang, Dawei,Yue, Tao,Wang, Guichen,Wang, Chaochao,Cao, Hongliang,Gao, Yun,Chen, Chao
, p. 162 - 170 (2019/12/26)
Due to biological safety and negligible toxicity, nitric oxide (NO) therapy has gained increasing interest in the field of cancer therapy during the past few years. However, individual NO cancer therapy normally exhibited limited therapeutic efficiency. In order to acquire satisfactory therapeutic outcomes, the NO therapy is usually combined with other therapeutic treatments, mostly chemotherapy. Herein, we constructed HA-TPP@NORM nanoparticles based on the co-assembly of an NO donor (NORM) and tetraphenylporphyrin (TPP)-modified hyaluronic acid, which can efficiently generate a highly biocidal molecule of peroxynitrite (ONOO-) via the synergistic interactions of the nitric oxide (NO) therapy and photodynamic therapy (PDT) to enhance the cancer therapeutic efficiency. In addition, MTT results exhibited that without light irradiation, the HA-TPP@NORM nanoparticles have favourable biocompatibility with the cell viability above 95% at the maximum TPP concentration (20 μg mL-1). Under simultaneous irradiation with 365 nm and 650 nm light, ONOO- can be efficiently produced in cancer cells via the direct coupling reaction of the generated NO and superoxide anion radical (O2-), which significantly enhanced the anticancer effect, when compared with individual NO therapy or PDT therapy. Therefore, the HA-TPP@NORM nanoparticles may provide a new insight into the design of efficiently NO-related cancer therapeutic systems.
Efficient Intersystem Crossing in the Tr?ger's Base Derived From 4-Amino-1,8-naphthalimide and Application as a Potent Photodynamic Therapy Reagent
Barbon, Antonio,Chen, Kepeng,Hou, Yuqi,Li, Shujing,Wang, Zhijia,Wu, Huijian,Yaglioglu, Halime Gul,Yildiz, Elif Akhuseyin,Zhang, Xue,Zhao, Jianzhang,Zhao, Yingjie
, (2020/03/05)
Intersystem crossing (ISC) was observed for naphthalimide (NI)-derived Tr?ger's base, and the ISC was confirmed to occur by a spin-orbital charge-transfer (SOCT) mechanism. Conventional electron donor/acceptor dyads showing SOCT-ISC have semirigid linkers. In contrast, the linker between the two chromophores in Tr?ger's base is rigid and torsion is completely inhibited, which is beneficial for efficient SOCT-ISC. Femtosecond transient absorption (TA) spectra demonstrated charge-separation and charge-recombination-induced ISC processes. Nanosecond TA spectroscopy confirmed the ISC, and the triplet state is long-lived (46 μs, room temperature). The ISC quantum yield is dependent on solvent polarity (8–41 %). The triplet state was studied by pulsed-laser-excited time-resolved EPR spectroscopy, and both the NI-localized triplet state and triplet charge-transfer state were observed, which is in good agreement with the spin-density analysis. The Tr?ger's base was confirmed to be a potent photodynamic therapy reagent with HeLa cells (EC50=5.0 nm).
Expanding the Breadth of 4-Amino-1,8-naphthalimide Photophysical Properties through Substitution of the Naphthalimide Core
Leslie, Kathryn G.,Jacquemin, Denis,New, Elizabeth J.,Jolliffe, Katrina A.
supporting information, p. 5569 - 5573 (2018/03/21)
Fluorescent sensors that illuminate specific molecules and chemical events allow the selective and sensitive study of the cellular environment. At the centre of this technology lies the fluorescent reporter molecule, and it is therefore crucial to provide a breadth of fluorophores with varying photophysical and biological behaviour. 4-Amino-1,8-naphthalimides are commonly employed in fluorescent sensors, but the narrow range of structural derivatives limits versatility of application. Here we report the synthesis and investigation of a set of twelve 4-amino-1,8-naphthalimides bearing an additional substituent on the aromatic core. Photophysical characterisation and time-dependent density functional theory studies provided insights into the structure–photophysical property relationships of these derivatives, which show an expanded range of emission wavelengths and other photophysical properties. These compounds could all be visualised within cells by confocal microscopy, showing cytoplasmic or lipid droplet localisation. Our studies have demonstrated that simple structural modification of 4-amino-1,8-naphthalimides provides derivatives with considerable breadth of behaviour that lend valuable versatility to the design of fluorescent sensors.
Nitric oxide donors, preparation and applications of nitric oxide donors
-
, (2018/03/24)
The invention relates to nitric oxide donors, preparation and applications of the nitric oxide donors. In particular, the invention provides compounds which have structures represented by a formula I, wherein R2 is H, a C3-C8 naphthenic group or C1-C6 alkyl which is substituted by 1-2 materials optionally selected from C1-C4 alkoxy, -S(O)2-OH, and a substituent group of hydroxyl, and N is connected with a benzene ring of a fluorophore molecule. The invention also provides preparation methods for the compounds represented by the formula I, compositions containing the compounds represented in the formula I, and the applications of the compounds which are used as the nitric oxide donors.
Photophysics, Electrochemistry, Morphology, and Bioimaging Applications of New 1,8-Naphthalimide Derivatives Containing Different Chromophores
Saini, Ankita,Thomas, K. R. Justin,Sachdev, Abhay,Gopinath, Packirisamy
, p. 2612 - 2622 (2017/10/07)
A series of 1,8-naphthalimide-based fluorophores containing different chromophores with varying conjugation and electron richness at the imidic nitrogen atom are synthesized and characterized. These amine-functionalized naphthalimides are bipolar in nature and exhibit interesting optical and morphological variations attributable to the nature of the N substituents. Despite the fact that the dyes are structurally different owing to variation of the substituent on the imidic nitrogen atom, their electronic characteristics are similar and originate from the 4-aminonaphthalimide segment. Nevertheless, they exhibit variations in morphology in the microscopic domain, and this is attributable to structural differences. Further, these fluorescent dyes display biocompatibility and are used in the bioimaging of cells.
Photocalibrated NO Release from N-Nitrosated Napthalimides upon One-Photon or Two-Photon Irradiation
Zhang, Ziqian,Wu, Jiayao,Shang, Zhihao,Wang, Chao,Cheng, Jiagao,Qian, Xuhong,Xiao, Yi,Xu, Zhiping,Yang, Youjun
, p. 7274 - 7280 (2016/07/27)
NO donors are routinely used as the exogenous source in in vitro studies. However, the kinetics or the dose of NO release from the existing donors is not readily monitored. This complicates the elucidation of the involvement of NO in a biological response. We report herein a series of NO donors (NOD545a-g), whose NO release is triggered by UV light at 365 nm or a two-photon laser at 740 nm, and importantly, their NO release is accompanied by a drastic fluorescence turn-on, which has been harnessed to follow the kinetics and dose of NO release in a real-time fashion with spectroscopic methods or microscopic methods in in vitro studies. These merits have rendered NOD545a-g useful molecular tools in NO biology.
A ratiometric fluorescent probe for the detection of hydroxyl radicals in living cells
Meng, Luyan,Wu, Yongquan,Yi, Tao
supporting information, p. 4843 - 4845 (2014/05/06)
A naphthalimide-naphthyridine derivative has been synthesized for the detection of hydroxyl radicals. It can distinguish hydroxyl radicals from other reactive oxygen species with high selectivity and short response time. Moreover, it has no cellular toxicity, and can be effectively used for intracellular detection of hydroxyl radicals. The Royal Society of Chemistry 2014.
Energy transfer in aminonaphthalimide-boron-dipyrromethene (BODIPY) dyads upon one-and two-photon excitation: Applications for cellular imaging
Collado, Daniel,Remon, Patricia,Vida, Yolanda,Najera, Francisco,Sen, Pratik,Pischel, Uwe,Perez-Inestrosa, Ezequiel
supporting information, p. 797 - 804 (2014/03/21)
Aminonaphthalimide-BODIPY energy transfer cassettes were found to show very fast (kEET≈1010-1011 s-1) and efficient BODIPY fluorescence sensitization. This was observed upon one-and two-photon excitation, which extends the application range of the investigated bichromophoric dyads in terms of accessible excitation wavelengths. In comparison with the direct excitation of the BODIPY chromophore, the two-photon absorption cross-section δ of the dyads is significantly incremented by the presence of the aminonaphthalimide donor [δ≈10 GM for the BODIPY versus 19-26 GM in the dyad at λexc=840 nm; 1 GM (Goeppert-Mayer unit)=10-50 cm4 s molecule-1 photon-1]. The electronic decoupling of the donor and acceptor, which is a precondition for the energy transfer cassette concept, was demonstrated by time-dependent density functional theory calculations. The applicability of the new probes in the one-and two-photon excitation mode was demonstrated in a proof-of-principle approach in the fluorescence imaging of HeLa cells. To the best of our knowledge, this is the first demonstration of the merging of multiphoton excitation with the energy transfer cassette concept for a BODIPY-containing dyad. Take two: Aminonaphthalimide-BODIPY energy transfer cassettes were designed in order to take advantage for bioimaging from one-and two-photon excitation coupled with energy transfer. The bichromophoric dyads showed ultrafast and highly efficient energy transfer and were used for confocal fluorescence microscopy imaging of HeLa cells as bio-relevant models. Copyright
A facile route to functionalized naphthalimide dyes via copper-catalyzed C-N, C-O, and C-S cross-coupling reactions in aqueous medium
Bardajee, Ghasem Rezanejade
, p. 4937 - 4941 (2013/08/28)
A mild, facile, and efficient synthesis of fluorescent naphthalimide dyes via CuI-catalyzed CN, CO, and CS Ullman-type condensation reactions using amines, alcohols, and thiols is described. The reactions were carried out in the presence of KF/Al2O3 as a mild basic support in water as a green solvent. This protocol tolerates a wide range of functional groups and provides functionalized naphthalimide dyes in good to excellent yields.
