Multifunctional Near-Infrared Fluorescent Probes with Different Ring-Structure Trigger Groups for Cell Health Monitoring and In Vivo Esterase Activity Detection

Abstract

A series of multifunctional ratiometric near-infrared fluorescent probes (CYOH-3, CYOH-4, CYOH-5, and CYOH-6) for esterase detection are designed by gradually changing the deflection of the plane twist in the molecule. These probes are composed of different ring-structure trigger groups (from threemembered ring to six-membered ring) and the same luminescent group CYOH. These probes show maximum absorption at ∼585 nm and a fluorescence emission peak at ∼655 ± 5 nm. In the presence of esterase, the probes were hydrolyzed to expose the fluorophore CYOH (λ abs = 690 nm, λ em = 710 ± 5 nm), thus exhibiting ratiometric near-infrared fluorescence. The probe CYOH-6 has lower plane deflection angle and better ratiometric (R = I 710±5nm /I 657±4nm ) fluorescence properties than probes CYOH-3, CYOH-4, and CYOH-5. CYOH-6 (six-membered ring) has been successfully used to target esterase in mitochondria and distinguish between dead cells (esterase inactivation) and live cells. In addition, CYOH-6 has been well used for monitoring of esterase activity in zebrafish and mice, which proves that these probes have good prospects for clinical biomedical applications.

Multienzyme-Targeted Fluorescent Probe as a Biosensing Platform for Broad Detection of Pesticide Residues

“…Zebrafish themselves showed no obvious fluorescence. After treating the zebrafish only with 3CP , strong green fluorescence could be observed throughout the zebrafish bodies, particularly the eyes and abdomen (Figure ), and the distribution of the fluorescence signal corresponds to distribution of these enzymes. , To our delight, zebrafish pretreated with all those abovementioned pesticides, including deltamethrin, showed a much lower green fluorescence signal when compared with the zebrafish treated with 3CP alone. Among them, almost no fluorescence can be observed in zebrafish pretreated with carbaryl and deltamethrin.…”

Esterase-Activated Theranostic Prodrug for Dual Organelles-Targeted Imaging and Synergetic Chemo-Photodynamic Cancer Therapy

“…than most of esterase-specific probes. [58][59][60] This high sensitivity towards esterase ensured the further theranostic applications of TPE-QC both in vitro and in vivo.…”

Rational construction of a novel probe for the rapid detection of butyrylcholinesterase stress changes in apoptotic cells

“…The synthetic route of the probe CnN is shown in Scheme 2. Its molecular structure was characterized using 1 HNMR, 13 CNMR and HRMS in the ESI † (Fig. S1-S6).…”

“…[9][10][11][12] However, fluorescent probes enable the in situ imaging of BChE in vivo for detailed insights into changes in enzymatic activity and function. [13][14][15][16][17] As small molecules, fluorescent probes can generate clear fluorescent signals by reacting with BChE. It has a fast reaction speed, high sensitivity and strong selectivity, and has a high temporal and spatial resolution in the detection of actual biological samples.…”