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Upstream product

• 4053-08-1 p-chloro-1,8-naphthalicanhydride 
• 109-73-9 N-butylamine 
• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 109-65-9 1-bromo-butane 
• 55490-98-7 N-butyl-4-amino-1,8-naphthalimide 
• 6492-86-0 4-amino-1,8-naphthalic anhydride 
• 92874-17-4 4-bromo-N-butylnaphthalimide 
• 6642-29-1 4-nitronaphthalic-1,8-anhydride 
• 81-84-5 1,8-Naphthalic anhydride 
• 761-65-9 N,N-dibutylformamide 

Relevant academic research and scientific papers

Efficient Intersystem Crossing in the Tr?ger's Base Derived From 4-Amino-1,8-naphthalimide and Application as a Potent Photodynamic Therapy Reagent

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).

A 4-aminonaphthalimide based environmentally sensitive fluorescence probe

A simply synthesized 4-aminonaphthalimide derivative 1 expresses both polarity and viscosity sensitive fluorescence spectra, indicating its potential usage as an environmentally sensitive fluorescence probe. By comparing the fluorescence behavior of 1 with that of a known 4-aminonaphthalimide derivative 2, it was found that the substitution of the 4-amino group has profound influence on the environmentally sensitive fluorescence properties of 4-aminonaphthalimide.

Photocalibrated NO Release from N-Nitrosated Napthalimides upon One-Photon or Two-Photon Irradiation

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.

Synthesis of thionaphthalimides and their dual Hg2+-selective signaling by desulfurization of thioimides

A series of new thionaphthalimide derivatives were prepared, and their Hg2+-selective signaling behavior was investigated in aqueous acetonitrile solution. A monothionaphthalimide (anti) exhibited pronounced Hg2+-selective chromogenic signaling behavior through a solution color change from red to yellow, which was easily detectable by eye. It (anti) also showed prominent off-on type Hg2+-selective fluorescent signaling behavior. The signaling is due to the Hg2+-assisted desulfurization of the thioimide to its imide structure. The presence of other common metal ions did not interfere with the Hg2+-signaling of the monothionaphthalimide (anti). The detection limit of monothionaphthalimide (anti) for the determination of Hg2+ ions in 30% aqueous acetonitrile was estimated to be 2.7 μM.

Efficient sonochemical synthesis of 3- and 4-electron withdrawing ring substituted N-alkyl-1,8-naphthalimides from the related anhydrides

1,8-N-alkyl-naphthalimides substituted with electron withdrawing groups were readily prepared in high yields using ultrasound in aqueous media.

Dual responsive chemosensors for anions: The combination of fluorescent PET (Photoinduced Electron Transfer) and colorimetric chemosensors in a single molecule

The design and synthesis of two novel fluorescent PET anion sensors is described, based on the principle of 'fluorophore-spacer-(anion)receptor'. The sensors 1 and 2 employ simple diaromatic thioureas as anion receptors, and the fluorophore is a naphthalimide moiety that absorbs in the visible part of the spectrum and emits in the green. Upon recognition of anions such as F- and AcO- in DMSO, the fluorescence emission of 1 and 2 was 'switched off', with no significant changes in the UV-vis spectra. This recognition shows a 1:1 binding between the receptor and the anions. In the case of F-, further additions of the anion, gave rise to large changes in the UV-vis spectra, where the λmax at 455 nm was shifted to 550 nm. These changes are thought to be due to the deprotonation of the 4-amino moiety of the naphthalimide fluorophore. This was in fact found to be the case, using simple naphthalimide derivatives such as 6. Sensors 1 and 2 can thus display dual sensing action; where at low concentrations, the fluorescence emission is quenched, and at higher concentrations the absorption spectra are modulated.

Peroxynitrite (ONOO-) generation from the HA-TPP@NORM nanoparticles based on synergistic interactions between nitric oxide and photodynamic therapies for elevating anticancer efficiency

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.

NUCLEOPHILIC DISPLACEMENT OF THE NITRO GROUP IN 2- AND 4-NITRONAPHTHALIC-1,8-ANHYDRIDES AND THEIR DERIVATIVES

The nitro group in 2- and 4-nitronaphthalic-1,8-anhydrides can be substituted by amines in certain cases with retention of the anhydride grouping.

A ratiometric fluorescent probe for the detection of hydroxyl radicals in living cells

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.

Expanding the Breadth of 4-Amino-1,8-naphthalimide Photophysical Properties through Substitution of the Naphthalimide Core

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.