ArticleJournal of materials chemistry. B2023
Thiophene-based organic dye with large Stokes shift and deep red emission for live cell NAD(P)H detection under varying chemical stimuli.
Article in Journal of materials chemistry. B, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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14 citing papers in PubMed, 27 citations in OpenAlex.
- Mitochondria-targeted dual-responsive fluorescent probe and its application in cellular imaging of NADH and viscosity.Analytical and bioanalytical chemistry · 2026Article
- A Quinolinium-Functionalized Hemicyanine Dye for Ratiometric NAD(P)H Sensing in Live Cells, Kidney Tissues, and Drosophila melanogaster.Sensors and actuators. B, Chemical · 2025Article
- Cyanine-Based Dual-Emission Sensor for Ratiometric NAD(P)H Imaging in Cells, Renal Tissues, and Entire Organisms.ACS applied bio materials · 2025Article
- Real-Time Monitoring of Mitochondrial pH in HeLa Cells,ACS applied bio materials · 2025Article
- Deep-Red Cyanine-Based Fluorescent Probes with 6-Quinolinium Acceptors for Mitochondrial NAD(P)H Imaging in Live Cells and Human Diseased Kidney Tissues.ACS applied bio materials · 2025Article
- A Rhodamine-Based Ratiometric Fluorescent Sensor for Dual-Channel Visible and Near-Infrared Emission Detection of NAD(P)H in Living Cells and Fruit Fly Larvae.ACS applied bio materials · 2025Article
- Near-Infrared Probes Designed with Hemicyanine Fluorophores Featuring Rhodamine and 1,8-Naphthalic Derivatives for Viscosity and HSA Detection in Live Cells.ACS applied bio materials · 2025Article
- Near-Infrared Visualization of NAD(P)H Dynamics in Live Cells andACS applied bio materials · 2024Article
- Deep-Red and Near-Infrared Compact Cyanine Dyes for Sensitive NAD(P)H Sensing in Live Cells and Kidney Disease Tissues.ACS applied bio materials · 2024Article
- Dynamic insights into mitochondrial function: Monitoring viscosity and SOJournal of photochemistry and photobiology. B, Biology · 2024Article
- Syntheses and Applications of Coumarin-Derived Fluorescent Probes for Real-Time Monitoring of NAD(P)H Dynamics in Living Cells across Diverse Chemical Environments.ACS applied bio materials · 2024Article
- Near-infrared Absorption and Emission Probes with Optimal Connection Bridges for Live Monitoring of NAD(P)H Dynamics in Living Systems.Sensors and actuators. B, Chemical · 2024Article
- Sensitive monitoring of NAD(P)H levels within cancer cells using mitochondria-targeted near-infrared cyanine dyes with optimized electron-withdrawing acceptors.Journal of materials chemistry. B · 2024Article
- Highly Sensitive Cyanine Dyes for Rapid Sensing of NAD(P)H in Mitochondria and First-Instar Larvae ofACS applied bio materials · 2023Article
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Authors and funding
10 authors at 1 institution in 1 country.
Funding
Abstract
We 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. However, upon the presence of NADH, new absorption and fluorescence peaks appear at 477 nm and 619 nm for probe A and at 486 nm and 576 nm for probe B, respectively. This is due to the NADH-facilitated reduction of the 1-methylquinolinium unit into 1-methyl-1,4-dihydroquinoline, which then acts as the electron donor for the probes, leading to the formation of well-defined electron donor-acceptor dye systems. Probe A has a large Stokes shift of 144 nm, which allows for better separation between the excitation and emission spectra, reducing spectral overlap and improving the accuracy of fluorescence measurements. The probes are highly selective for NAD(P)H, water-soluble, biocompatible, and easily permeable to cells. They are also photostable and were successfully used to monitor changes in NADH concentration in live cells during glycolysis in the presence of glucose, lactate, and pyruvate, treatment of FCCP and cancer drug cisplatin, and under hypoxia triggered by CoCl
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