A versatile AIE fluorogen with selective reactivity to primary amines for monitoring amination, protein labeling, and mitochondrial staining

Abstract

Specific bioconjugation for native primary amines is highly valuable for both chemistry and biomedical research. Despite all the efforts, scientists lack a proper strategy to achieve high selectivity for primary amines, not to mention the requirement of fast response in real applications. Herein, we report a chromone-based aggregation-induced emission (AIE) fluorogen called CMVMN as a self-reporting bioconjugation reagent for selective primary amine identification, and its applications for monitoring bioprocesses of amination and protein labeling. CMVMN is AIE-active and capable of solid-state sensing. Thus, its electrospun films are manufactured for visualization of amine diffusion and leakage process. CMVMN also shows good biocompatibility and potential mitochondria-staining ability, which provides new insight for organelle-staining probe design. Combined with its facile synthesis and good reversibility, CMVMN would not only show wide potential applications in biology, but also offer new possibilities for molecular engineering.

A multiresponsive functional AIEgen for spatiotemporal pattern control and all-round information encryption

“…As expected, dramatic fluorescence enhancement was only observed for aliphatic primary amines. Based on the experimental data and our previous report 37 , a schematic illustration of the selectivity of CPVCM to amines was proposed in Fig. 3d.…”

“…Compared with CMVMN in our previous work, 37 CPVCM was introduced with an additional phenyl group. Therefore, the amination of CPVCM was expected to be more sensitive to the steric hindrance of amines.…”

“…10, a characteristic broad peak emerged at δ 10.5, which was attributed to the resonance of an NH group forming a strong intermolecular hydrogen bond. 37,48 Also, numerous new peaks appeared at a lower field due to the deshielding effect in the ring-opening products.…”

“…Previously, we reported an AIEgen called CMVMN which could undergo specific bioconjugation with primary amines and a rapid and spontaneous reversible amination process in its electrospun films. 37 In view of the great potential of this amination process for developing functional systems, a further study on its mechanism is definitely of academic importance. Coincidently, a concise and efficient photoarrangement was observed for the arylvinyl-substituted chromones.…”

Enrichment of Aggregation-Induced Emission Aggregates Using Acoustic Streaming Tweezers in Microfluidics for Trace Human Serum Albumin Detection

“…In addition, due to their intrinsic design, AIE probes can not only overcome the problems encountered by aggregation-caused quenching ones but also achieve faster and more sensitive target detection . It has become one of the hot spots to detect the biomedical targets including protein, metal cations, and DNA using AIE probes in recent years. The working mechanism of most AIE probes is to obtain insoluble aggregates with the size ranging from tens to about one hundred nanometers by chemical or electrostatic interactions with the target.…”