Development of pH‐Responsive BODIPY Probes for Staining Late Endosome in Live Cells

Miao, Fang; Uchinomiya, Shohei; Ni, Yong; Chang, Young‐Tae; Wu, Jishan

doi:10.1002/cplu.201600249

Cited by 20 publications

(14 citation statements)

References 39 publications

(34 reference statements)

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“…In the presence of an inside acidic pH gradient from pH 7 to pH 5, ammonium cations can still cross the membrane toward the acidic side by transient deprotonation [5–7,46,50] . However, they cannot return because deprotonation of an ammonium cation of p K a ∼10 at pH∼5 is beyond the dynamic range of acidity (Figure 3B) [51–58] . Thus, the passage of ammonium cation across the membrane with an inside acidic pH gradient is irreversible.…”

Section: Introductionmentioning

confidence: 99%

“…Within cells, lysosomes excel with the steepest inside acidic pH gradient [51–71] . Unidirectional penetration along this strong pH gradient makes fluorescently labeled ammonium cations accumulate in the acidic interior of lysosomes (pH∼4.7).…”

Section: Introductionmentioning

confidence: 99%

“…Unidirectional penetration along this strong pH gradient makes fluorescently labeled ammonium cations accumulate in the acidic interior of lysosomes (pH∼4.7). This is the molecular basis of most LysoTrackers [51–58] . Morpholinium cations as in 1 with p K a =7.4 are most commonly used in LysoTrackers (Figure 4).…”

Section: Introductionmentioning

confidence: 99%

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The Dynamic Range of Acidity: Tracking Rules for the Unidirectional Penetration of Cellular Compartments

et al. 2022

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Labeled ammonium cations with pK a ~7.4 accumulate in acidic organelles because they can be neutralized transiently to cross the membrane at cytosolic pH 7.2 but not at their internal pH < 5.5. Retention in early endosomes with less acidic internal pH was achieved recently using weaker acids of up to pK a 9.8. We report here that primary ammonium cations with higher pK a 10.6, label early endosomes more efficiently. This maximized early endosome tracking coincides with increasing labeling of Golgi networks with similarly weak internal acidity. Guanidinium cations with pK a 13.5 cannot cross the plasma membrane in monomeric form and label the plasma membrane with selectivity for vesicles embarking into endocytosis. Selfassembled into micelles, guanidinium cations enter cells like arginine-rich cell-penetrating peptides and, driven by their membrane potential, penetrate mitochondria unidirectionally despite their high inner pH. The resulting tracking rules with an approximated dynamic range of pK a change ~3.5 are expected to be generally valid, thus enabling the design of chemistry tools for biology research in the broadest sense. From a practical point of view, most relevant are two complementary fluorescent flipper probes that can be used to image the mechanics at the very beginning of endocytosis.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Dynamic Range of Acidity: Tracking Rules for the Unidirectional Penetration of Cellular Compartments

et al. 2022

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“… 20 Due to these desirable traits, preparation of BODIPY dyes is currently an active area of research in bioanalysis and bioimaging. 9 , 21 − 24 …”

Section: Introductionmentioning

confidence: 99%

“…As with other organic dyes, BODIPYs can be synthetically modified to suit the target applications and several derivatives have been prepared that resist aggregation and have outstanding aqueous solubility. , Improved aqueous solubility has facilitated their use in aqueous media and minimized cytotoxicity issues commonly seen when organic solvents such as ethanol, dimethylformamide, or dimethyl sulfoxide are required to predissolve and/or load dyes . Due to these desirable traits, preparation of BODIPY dyes is currently an active area of research in bioanalysis and bioimaging. ,− …”

Section: Introductionmentioning

confidence: 99%

Synthesis of Water-Soluble Far-Red-Emitting Amphiphilic BODIPY Dyes

et al. 2018

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We report the synthesis of two water-soluble BODIPY dyes with far-red absorption and near-infrared fluorescence following cell membrane insertion. Introduction of dicationic or dianionic groups imparts water solubility and prevents translocation of the dye through the plasma membrane for highly effective labeling. The dicationic form is particularly well localized to the plasma membrane and resists quenching even after >8 min of continuous light exposure. The dyes are almost completely nonemissive in water and other highly polar solvents, but display high-fluorescence yields in chloroform and upon insertion into the extracellular leaflet.

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