ArticleMolecular pharmaceutics2013
pH-sensitive fluorescent dyes: are they really pH-sensitive in cells?
Article in Molecular pharmaceutics, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 74 citations in OpenAlex.
- A Method for in Situ Interfacial pH Detection.The journal of physical chemistry letters · 2025Article
- Nanosensor-based monitoring of autophagy-associated lysosomal acidification in vivo.Nature chemical biology · 2023Article
- High-Throughput Exonuclease Assay Based on the Fluorescent Base Analogue 2-Aminopurine.ACS omega · 2023Article
- Spectral Characterization of Purpurin Dye and Its Application in pH Sensing, Cell Imaging and Apoptosis Detection.Journal of fluorescence · 2022Article
- Article
- Fluorescent nanosensors reveal dynamic pH gradients during biofilm formation.NPJ biofilms and microbiomes · 2021Article
- Visual pH Sensors: From a Chemical Perspective to New Bioengineered Materials.Molecules (Basel, Switzerland) · 2021Review
- Synthesis of a New Amino-Furopyridine-Based Compound as a Novel Fluorescent pH Sensor in Aqueous Solution.ACS omega · 2021Article
- Comparison of 4-Mercaptobenzoic Acid Surface-Enhanced Raman Spectroscopy-Based Methods for pH Determination in Cells.Applied spectroscopy · 2020Article
- Barrier lipid composition and response to plasma lipids: A direct comparison of mouse dorsal back and ear skin.Experimental dermatology · 2020Article
- Fluorescent probes with high pKa values based on traditional, near-infrared rhodamine, and hemicyanine fluorophores for sensitive detection of lysosomal pH variations.Methods (San Diego, Calif.) · 2019Article
- A "weak acid and weak base" type fluorescent probe for sensing pH: mechanism and application in living cells.RSC advances · 2019Article
- Population analysis to increase the robustness of molecular computational identification and its extension into the near-infrared for substantial numbers of small objects.Chemical science · 2019Article
- Cyclodextrin-Promoted Fluorescence Detection of Aromatic Toxicants and Toxicant Metabolites in Commercial Milk Products.Food analytical methods · 2018Article
- Fluorescent Probes for Sensitive and Selective Detection of pH Changes in Live Cells in Visible and Near-infrared Channels.Journal of materials chemistry. B · 2017Article
- Synthesis of Naked-eye Detectable Fluorescent 2H-chromen-2-One 2, 6-Dicyanoanilines: Effect of Substituents and pH on Its Luminous Behavior.Journal of fluorescence · 2017Article
- Interaction of BODIPY dyes with bovine serum albumin: a case study on the aggregation of a click-BODIPY dye.Physical chemistry chemical physics : PCCP · 2016Article
- Using membrane composition to fine-tune the pJournal of materials chemistry. C · 2016Article
- Lysosome triggered near-infrared fluorescence imaging of cellular trafficking processes in real time.Nature communications · 2016Article
- H-Rubies, a new family of red emitting fluorescent pH sensors for living cells.Chemical science · 2015Article
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 2 countries.
Funding
Abstract
Chemically synthesized near-infrared aza-BODIPY dyes displayed off-on fluorescence at acidic pH (pKa = 6.2-6.6) through the suppression of the photoinduced electron transfer and/or internal charge transfer process. The apparent pKas of the dyes were shifted well above physiological pH in a hydrophobic microenvironment, which led to "turned-on" fluorescence in micelles and liposomes at neutral and basic pH. Bovine serum albumin also activated the fluorescence, though to a much lesser extent. When these small molecular dyes entered cells, instead of being fluorescent only in acidic organelles, the whole cytoplasm exhibited fluorescence, with a signal/background ratio as high as ∼10 in no-wash live-cell imaging. The dye 1-labeled cells remained highly fluorescent even after 3 days. Moreover, slight variations of the dye structure resulted in significantly different intracellular fluorescence behaviors, possibly because of their different cellular uptake and intracellular activation capabilities. After the separation of cellular components, the fraction of plasma membrane and endoplasmic reticulum showed the highest fluorescence, further confirming the fluorescence activation by membrane structures. The fluorescence intensity of these dyes at different intracellular pHs (6.80 and 8.00) did not differ significantly, indicating that intracellular pH did not play a critical role. Altogether, we showed here for the first time that the fluorescence of pH-sensitive aza-BODIPY dyes was switched intracellularly not by acidic pH, but by intracellular membranes (and proteins as well). The excellent membrane permeability, ultrahigh fluorescence contrast ratio, persistent fluorescent signal, and minimal biological interference of dye 1 make it an ideal choice for live-cell imaging and in vivo cell tracking. These findings also imply that the intracellular fluorescence properties of pH-sensitive dyes should be carefully examined before they are used as pH indicators.
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Registered trials
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