Near-infrared absorption and emission probes with optimal connection bridges for live monitoring of NAD(P)H dynamics in living systems

Syntheses and Applications of Coumarin-Derived Fluorescent Probes for Real-Time Monitoring of NAD(P)H Dynamics in Living Cells across Diverse Chemical Environments

“…Instrumentation. The NMR spectra ( 1 H at 500 MHz and 13 C at 125 MHz) were acquired employing a Bruker NMR spectrometer (Ascend 500) in both DMSO-d 6 and CDCl 3 solvents at a concentration of 2.0 × 10 −2 M. Absorption and emission spectra of the probes were examined using a PerkinElmer Lambda 35 UV/vis spectrometer and a Jobin Yvon Fluoromax-4 spectrofluorometer, respectively. For the mass spectrometry analysis of the probes and their reduced products, a Thermo Scientific LCQ Fleet mass spectrometer was utilized.…”

“…9−24 As a result, fluorescence imaging with fluorescent probes is a powerful tool for studying the molecular mechanisms underlying various physiological and pathological processes, as well as for developing new therapeutic strategies. [9][10][11][12][13][14][15][16][17][18][19][20][21]23,24 Developing fluorescent probes with longer emission wavelengths is critical for reducing the interference from the intrinsic fluorescence properties of NAD(P)H, minimizing signal attenuation, enhancing imaging resolution through deeper tissue penetration of light, and improving the accuracy and sensitivity of fluorescence imaging in live cells. [9][10][11][12][13][14][15][16][17][18][19][20][21]23,24 Our probe formulations are based upon coumarins which are a large family of 2H-chromen-2-one-containing compounds that are widely used as fluorescent fluorophores due to their unique optical and chemical properties, including broad excitation and emission wavelengths, high quantum yield, chemical stability, low toxicity, and ease of modification.…”

“…[9][10][11][12][13][14][15][16][17][18][19][20][21]23,24 Developing fluorescent probes with longer emission wavelengths is critical for reducing the interference from the intrinsic fluorescence properties of NAD(P)H, minimizing signal attenuation, enhancing imaging resolution through deeper tissue penetration of light, and improving the accuracy and sensitivity of fluorescence imaging in live cells. [9][10][11][12][13][14][15][16][17][18][19][20][21]23,24 Our probe formulations are based upon coumarins which are a large family of 2H-chromen-2-one-containing compounds that are widely used as fluorescent fluorophores due to their unique optical and chemical properties, including broad excitation and emission wavelengths, high quantum yield, chemical stability, low toxicity, and ease of modification. 25−29 As a result, coumarins are utilized as a desirable and ideal fluorophore platform for a wide range of applications, such as biological imaging, sensing, and diagnostics for cations, 30 anions, 27,29,31 pH, 32−34 NADH, 17 H 2 S, 27,29,31 cysteine, homocysteine, and glutathione (GSH), 27,29,…”

An activated near-infrared mitochondrion-targetable fluorescent probe for rapid detection of NADH

“…Many NADH fluorescent probes have been designed primarily based on four recognition groups: quinolinium, pyridine, resazurin, and quinone. 8–22 Given that NADH predominantly resides in mitochondria, the development of mitochondrial-targeted fluorescent probes holds greater promise for biological imaging. Most reported probes for mitochondrial NADH detection primarily use 1-methylquinoline salts and another electron acceptor to construct an acceptor–π–acceptor (A–π–A) structure.…”

“…19,20 Recently, our team reported a series of near-infrared fluorescent probes for NADH sensing. 21,22 Nevertheless, these extended conjugated structures often result in delayed response times exceeding 30 min or more. Thus, the development of a rapid-response (within 10 min) mitochondrial-targeted NIR probe for NADH remains a formidable challenge.…”