52559-37-2

Upstream product

• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 141-43-5 ethanolamine 
• 83-32-9 acenaphthene 
• 2051-98-1 5-bromoacenaphthene 
• 81-84-5 1,8-Naphthalic anhydride 
• 52559-36-1 4-bromonaphthalene-1,8-dicarboximide 
• 540-51-2 2-bromoethanol 

Downstream Products

• 1212005-14-5 4-[(4-tert-butylphenoxy)]-N-(2-hydroxyethyl)-1,8-naphthalimide 
• 1212005-16-7 4-(2-tert-butylphenoxy)-N-(2-hydroxyethyl)-1,8-naphthalimide 
• 1212005-17-8 4-[2,4-di(tert-butyl)phenoxy]-N-(2-hydroxyethyl)-1,8-naphthalimide 
• 2494-96-4 4-phenoxy-N-(2-hydroxyethyl)-1,8-naphthalimide 
• 1279101-89-1 C₂₄H₂₂N₄O₄S 
• 1279101-90-4 C₂₈H₂₆N₄O₅S 
• 164584-67-2 2-(2-hydroxyethyl)-6-morpholino-1H-benzo[de]isoquinoline-1,3(2H)-dione 
• 1384524-86-0 2-(2-hydroxyethyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl 2,4-dinitrobenzenesulfonate 
• 1360603-54-8 4-vanilin-N-hydroxyethyl-1,8-naphthalimide 

Relevant academic research and scientific papers

Targeted tumor detection: guidelines for developing biotinylated diagnostics

The challenge in achieving precision medicine relies on how to advance and/or enhance new as well as old therapeutic strategies. Here, we highlight the significant role hydrophilicity of biotinylated fluorescent probe's plays on their cellular uptake behaviour.

Naphthalimide-based macrophage nucleus imaging probes

The photophysical properties of naphthalimide-based fluorophores can be easily tuned by chemical manipulation of the substituents on that privileged scaffold. Replacement of a OMe group at position 6 in 2-(hydroxyl)ethyl-naphthalimide derivatives by diverse amines, including 2-(hydroxyl)ethylamine, trans-(4-acetamido)cyclohexylamine and azetidine increases the solvatochromic (ICT) character, while this replacement in 2-(dimethylamino)ethyl-naphthalimide analogues (PET fluorophores) decrease their solvent polarity sensitivity or even reversed them to solvatochromic fluorophores. These fluorophores resulted macrophage nucleus imaging probes, which bind DNA as intercalants and showed low cytotoxicity in human cancer cells.

Solid fluorescence sensors obtained by functionalization of photocrosslinked water-swollen acrylic membranes with 4-piperazine naphthalimide derivatives

A photocrosslinked membrane (M-Cl) based on vinyl-pyrrolidone/butyl acrylate containing ethylene glycol dimethacrylate as a crosslinking agent and methacryloyl chloride as reactive monomer has been prepared for further functionalization. A series of hydroxy substituted piperazine naphthalimide compounds have been synthetized as pH sensitive Off-On fluorescence probes using two methods: microwave and reflux. Three of the derivatives were selected to be anchored to the M-Cl membrane through the acid chloride groups by the Schotten-Baumann reaction. All the obtained water-swollen membranes were characterized using different techniques. Photo-induced electron transfer (PET) and its pH-dependent optical changes were investigated and various photochemical parameters were determined by using pH-dependent absorption and fluorescence spectroscopies. In the pH range of 9.0–4.0, these solid sensors undergo PET process from the piperazine to the naphthalimide moiety leading to a fluorescence quenching. However, in the pH range of 4.0–1.0, the PET is inhibited to give a fluorescence enhancement. The sensitivity of the functionalized membranes to pH changes depended on the size and position of the naphthalimide substituents.

pH-responsive intramolecular FRET-based self-tracking polymer prodrug nanoparticles for real-time tumor intracellular drug release monitoring and imaging

An intramolecular fluorescence resonance energy transfer (FRET)-based macromolecular theranostic prodrug was designed by directly conjugating Doxorubicin (DOX) as the FRET acceptor onto the naphthalimide side groups in the fluorescent copolymer PPEGMA20-PNAP8 as the FRET energy donor via an acid-labile imine bond, without a fluorogenic linker. The proposed PPEGMA20-PNAP8-DOX theranostic prodrug showed a high DOX content of 24.3% owing to a conjugation efficiency of > 93% under mild conjugation conditions. It could easily self-assemble into unique theranostic nanoparticles with a Dh of 71 nm. The theranostic nanoparticles showed excellent pH-triggered DOX release performance with very low premature drug leakage of 6.3% in normal physiological medium over 129 h, while>91% of the conjugated DOX was released in the acidic tumor intracellular microenvironment. MTT assays indicated the enhanced antitumor efficacy of the proposed theranostic nanoparticles compared with free DOX. Furthermore, because drug release was triggered by pH, orange fluorescence was restored to the blue fluorescence of the backbone copolymer. Such self-tracking pH-responsive colorful fluorescence variations during intracellular drug delivery and release are expected to allow real-time tumor intracellular drug release monitoring and imaging diagnosis.

A ratiometric lysosomal pH chemosensor based on fluorescence resonance energy transfer

In this work, we presented a naphthalimide-rhodamine based fluorescence resonance energy transfer system (FRET) NR1 as a ratiometric and intracellular pH probe, in which 1,2,3-triazole was identified as an ideal bridge and biocompatibility. It could selectively monitor pH variations in methanol/HEPES solution at room temperature. When the pH changed from 6.20 to 2.00, both the fluorescence intensities at 580 nm and the intensity ratios, R (I 580 nm/I538 nm) increased, which allowed the detection of pH changes by both normal fluorescence and ratiometric fluorescence methods. The observation is consistent with the increased FRET from the 1,8-naphthalimide (donor) to the ring-opened, colored form of rhodamine (acceptor). Moreover, as NR1 is lysosomal with low cytotoxicity, it will be helpful for investigating the pivotal role of H+ in a biological context, especially in lysosomes through direct intracellular imaging.

Conjugates of 3,4-dimethoxy-4-styrylnaphthalimide and bacteriochlorin for theranostics in photodynamic therapy

New conjugates of fluorophore based on 3,4-dimethoxy-4-styryl-1,8-naphthalimide and photosensitizer bacteriochlorin e differing in the nature of spacer fragments were synthesized and their spectral-luminescent properties were studied. The conjugates effic

A dual pH and temperature responsive polymeric fluorescent sensor and its imaging application in living cells

A polymeric fluorescent sensor PNME, consisting of A4 and N-isopropylacrylamide (NIPAM) units, was synthesized. PNME exhibited dual responses to pH and temperature, and could be used as an intracellular pH sensor for lysosomes imaging. Moreover, it also could sense different temperature change in living cells at 25 and 37°C, respectively.

Colorimetric and fluorescent detection of hydrazine with high sensitivity and excellent selectivity

It is critical to develop probes for rapid, selective, and sensitive detection of the highly toxic hydrazine in both environmental and biological science. In this work, under mild condition, a novel colorimetric and off-on fluorescent probe was synthesized for rapid recognition of hydrazine with excellent selectivity over other various species including some biological species, metal ions and anions. The limit of quantification (LOQ) value was 1.5?×?10??4?M–3.2?×?10??3?M (colorimetric method) and 1.5?×?10??4?M???3.2?×?10??3?M (fluorescent method) with as low as detection limit of 46.2?μM.

Ratiometric fluorescent detection of acidic pH in lysosome with carbon nanodots

It is significant for cell physiology to keep the homeostasis of pH, and it is highly demanded to develop ratiometric fluorescent sensors toward pH. In this work, under mild condition, through the electrostatic interaction between carbon nanodots (CDs) and organic molecules, two novel ratiometric fluorescence hybrid nanosensors were fabricated for sensing acidic pH. These nanohybrid systems possess dual emission peaks at 455 and 527 nm under a single excitation wavelength of 380 nm in acidic pH condition. With the increasing of pH, the fluorescence of the 1,8-naphthalimide derivative completely quenches, while the blue fluorescence of CDs keeps constant. Furthermore, the CDs?organic molecular nanohybrids exhibit excellent anti-disturbance ability, reversible pH sensing ability, and a linear response range in wide pH range respectively. Besides the ability to target lysosome, with one of the nanosensor, stimulated pH change has been successfully tracked in a ratiometric manner via fluorescence imaging.

A guanidine derivative of naphthalimide with excited-state deprotonation coupled intramolecular charge transfer properties and its application

A new fluorophore based on guanidine substituted 1,8-naphthalimide was synthesized and characterized. In aqueous solution, the guanidine group undergoes deprotonation/protonation with a pKa of ～8.5 in the ground-state and ～0.9 in the excited-state. The emission of its protonated and deprotonated forms exhibits a large Stokes shift (Ex/Em: 350/460 nm and 400/580 nm) due to the excited-state intramolecular charge transfer (ICT) process. The protonated form of this fluorophore exhibits dual fluorescence emission (Em: 460 and 580 nm; Ex: 350 nm) that is contributed to by an excited-state deprotonation coupled ICT process. The emission properties of this fluorophore are strongly dependent on the solvent environment, which make it possible to tune the luminescence of the materials made using this fluorophore. The absorption and emission spectra of this fluorophore respond to fluoride ions ratiometrically, showing the potential application as a fluoride ion sensor.