Naphthalimides for labeling and sensing applications

Abstract

Naphthalimide has now become a class of most popular fluorophores for probe design, along with coumarin, fluorescein, rhodamine, BODIPY and cyanine. This account aims at the first-year graduate students as the primary audience and showcases the versatile design principles applicable to the naphthalimide fluorophore when designing a probe or label, with focused examples from the Qian research laboratory. We also provide a general synthetic scheme to naphthalimides of various substitution patterns.

Fluorescent glycoconjugates and their applications

“…Relevant reports about fluorescence applications of glycoconjugates based on 1,8-naphthalimide (NI) can also be summarized such as DNA targeting, potent anticancer activity and cellular imaging agents. [73][74][75][76][77] The NI is particularly attractive due to its convenient derivatization strategy and versatile fluorescence modulating mechanisms. NIs are easily synthesised from the corresponding 1,8-naphthalic anhydrides by reaction with an amine.…”

Design of Nitroso-Modified Naphthylene-Based Fluorophores as Photoactivatable Bioorthogonal Turn-On Probes

“…The generated four-member 1,2-oxazetidine ring is unstable and spontaneously rearranged to tetrahydro-2 H -cyclopenta­[ d ]­isoxazole or terminal alkene moiety based on the different reactivity of nitrogen atom at 3- or 4-position of 1,8-naphthalimide (Figure S19). 15 showcased similar solvatochromic effect and environment-sensitivity as 13 , suggesting the possibility of sensing hydrophobic ligand-binding sites inside proteins (Figure c) . Besides, the second-order rate constant of the reaction between 2 and Mcp was determined to be 0.32 M –1 s –1 , which is 2–5-fold lower than the reaction with Cyh or Spd (Figure S7c).…”

Probing the Local Polarity in Biocompatible Nanocarriers with Solvatofluorochromism of a 4-Carbazole-1,8-naphthalimide Dye

“…1,8-Naphthalimide (NI) dyes are an interesting class of photoluminescent compounds that usually display high photoluminescent quantum yield and fluorescence spectral position sensitive to their environment. This makes them particularly interesting for application as optical sensors, biological fluorescent probes, and even as emissive dopants in metalfree organic light-emitting diodes (OLEDs) [16,17]. The photophysical properties of NIs are often associated with intramolecular charge transfer (CT) transitions that arise when electron-donating moieties are appended to the electron-withdrawing naphthalimide core.…”