A naphthalimide-based fluorescent probe for highly selective detection of histidine in aqueous solution and its application in in vivo imaging

Abstract

A naphthalimide-based fluorescent ensemble probe NPC for selectively detecting His in aqueous solution (10 mM HEPES, pH 7.4) has been reported. Moreover, the application of NPC in in vivo (both in Hela cells and in C. elegans) fluorescence imaging was carried out as well.

An N-nitrosation reactivity-based two-photon fluorescent probe for the specific in situ detection of nitric oxide

“…The benzo[ g ]coumarin moiety and p -phenylenediamine moiety were covalently linked by an amide bond, which could improve the photoinduced electron transfer (PeT)-induced quenching efficiency due to the short distance between the fluorophore and p -phenylenediamine. 12 The N -nitrosation reaction under mild conditions (room temperature, neutral pH) is a specific reaction for monoalkyl aniline and NO, which endows the N -nitrosation-reaction-based fluorescent probe with high selectivity for NO. The lowered reactivity of this structure to other ROS and RNS can be ascribed to the controlled electron density by the introduction of a carbonyl group.…”

The Role of Amino Acids in Neurotransmission and Fluorescent Tools for Their Detection

“…Outside of these cysteine- and thiol-sensitive dyes, three synthetic sensors, one based on coumarin and the other two based on naphthalimide were published for the detection of histidine in cells (Table 2) [ 289 , 290 , 291 ]. The first, CAQA, was reported to be specific but retained a significant response to cysteine and other thiols present in cells; cells were treated with a thiol scavenger to eliminate any interfering thiols [ 289 ].…”

“…Next, NCH-Cu 2+ , is reversible and shows good specific response between zero and 5 µM as well as possible sublocalization to lysosomes [ 291 ]. Lastly, NPC shows a linear response up to 16 µM and has been demonstrated to be applicable in HeLa cells and Caenorhabditis elegans [ 290 ]. However, NPC does show modest responses (<1-fold) to other amino acids.…”

Copper-based reactions in analyte-responsive fluorescent probes for biological applications

“…Amino acid probes based on other metal ions and chemistry for their recognition and detection have been discussed in greater detail in other reviews [50,55]. ( a ) [57] ( b ) [58] ( c ) [59] = Cu 2+ His + Cu -His com pl ex Figure 7. Examples of fluorescent His probes featuring a Cu(II) decomplexation mechansim.…”

“…The Cu(II) complex ensemble has been used to detect His in live MCF-7 (human breast adenocarcinoma) cells and bovine serum albumin. A similar naphthaleneimide-based Cu(II) complex with a tetradentate aminopyridine ligand from Xu and co-workers also shows good selectivity to His over other amino acids, and has been applied in imaging His in both live HeLa cells and C. elegans(Figure 7b)[58]. On the other hand, Liang and co-workers have reported a peptide-based Cu(II) complex-fluorophore ensemble that shows a selective fluorescence turn-on by His over other amino acids(Figure 7c)[59].…”