This paper presents the development of near-infrared (NIR) fluorescent probes, and , engineered from hemicyanine dyes with 1,8-naphthalic and rhodamine derivatives for optimized photophysical properties and precise mitochondrial targeting. Probes and exhibit absorption peaks at 737 nm and low fluorescence in phosphate-buffered saline (PBS) buffer. Notably, their fluorescence intensities, peaking at 684 () and 702 nm (), increase significantly with viscosity, as demonstrated through glycerol-to-PBS ratio experiments.
View Article and Find Full Text PDFA near-infrared fluorescent probe, , was designed by substituting the carbonyl group of the coumarin dye's lactone with a 4-cyano-1-methylpyridinium methylene group and then attaching an electron-withdrawing NADH-sensing methylquinolinium acceptor via a vinyl bond linkage to the coumarin dye at the 4-position. The probe exhibits primary absorption maxima at 603, 428, and 361 nm, and fluoresces weakly at 703 nm. The addition of NAD(P)H results in a significant blue shift in the fluorescence peak from 703 to 670 nm, accompanied by a substantial increase in fluorescence intensity.
View Article and Find Full Text PDFMitochondria, central organelles pivotal for eukaryotic cell function, extend their influence beyond ATP production, encompassing roles in apoptosis, calcium signaling, and biosynthesis. Recent studies spotlight two emerging determinants of mitochondrial functionality: intramitochondrial viscosity and sulfur dioxide (SO) levels. While optimal mitochondrial viscosity governs molecular diffusion and vital processes like oxidative phosphorylation, aberrations are linked with neurodegenerative conditions, diabetes, and cancer.
View Article and Find Full Text PDFACS Appl Bio Mater
August 2024
Fluorescent probes play a crucial role in elucidating cellular processes, with NAD(P)H sensing being pivotal in understanding cellular metabolism and redox biology. Here, the development and characterization of three fluorescent probes, , , and , based on the coumarin platform for monitoring of NAD(P)H levels in living cells are described. Probes and incorporate a coumarin-cyanine hybrid structure with vinyl and thiophene connection bridges to 3-quinolinium acceptors, respectively, while probe introduces a dicyano moiety for replacement of the lactone carbonyl group of probe which increases the reaction rate of the probe with NAD(P)H.
View Article and Find Full Text PDFTwo NAD(P)H-biosensing probes consisting of 1,3,3-trimethyl-3H-indolium and 3-quinolinium acceptors, linked by thiophene, , and 3,4-ethylenedioxythiophene, , bridges are detailed. We synthesized probes and , replacing the thiophene connection in probe with phenyl and 2,1,3-benzothiadiazole units, respectively. Probe was prepared by substituting probe 's 3-quinolinium unit with a 1-methylquinoxalin-1-ium unit.
View Article and Find Full Text PDFWe report a novel method for synthesizing red and deep red cyanine dyes with large Stokes shifts, probes A and B, for live cell NAD(P)H detection. The probes were prepared using thiophene-based organic dyes featuring a π-conjugated bridge of thiophene and 3,4-ethylenedioxythiophene units linking the 1-methylquinolinium acceptor and formyl acceptor, respectively. These probes display weak absorption peaks at 315 nm (A) and 334 nm (B) and negligible fluorescence in the absence of NADH.
View Article and Find Full Text PDFWe describe a simple but efficient approach to make fluorescent probes A and B based on rhodol dyes incorporated with salicyaldehyde moiety for monitoring pH changes in mitochondria under oxidative stresses and hypoxia conditions, and for tracking mitophagy processes. Probes A and B possess p values (p ≈ 6.41 and 6.
View Article and Find Full Text PDFA near-infrared fluorescent probe was prepared for selective detection of reduced nicotinamide adenine dinucleotide (NADH) in live cells. The probe turns off the fluorescence with a closed spironolactone switch. However, reduction of the probe by NADH turns on fluorescence at 740 nm.
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