A near-infrared fluorescent probe based on a hemicyanine dye with an oxazolidine switch for mitochondrial pH detection

Mazi, Wafa; Yan, Yunnan; Zhang, Yibin; Xia, Shuai; Wan, Shulin; Tajiri, Momoko; Luck, Rudy L.; Liu, Haiying

doi:10.1039/d0tb02181d

Cited by 34 publications

(10 citation statements)

References 38 publications

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“…On the other hand, increasing of pH to alkaline conditions (in the range of 8–14) was led to increase of fluorescence emission intensity especially for pH in the range of 10–14, and maximum emission was calculated for the pH of 12, 13, and 14. This phenomenon can be attributed to the deprotonation of phenolate hydroxyl groups in alkaline solutions, which induced higher density of negative charges to OX 1 -OH structure and correspondingly increase of electron resonance in its conjugated structure 31 , 32 , 38 , 43 .The photography of colorimetric and fluorometric properties of OX 1 -OH at pH of 1–14 are presented in Fig. 8 C. The observations indicated different colors, fluorescence emissions, and also intensities for the OX 1 -OH solutions, which have potential applications for colorimetric and fluorometric photosensing of pH in aqueous solutions.…”

Section: Resultsmentioning

confidence: 99%

Rewritable acidochromic papers based on oxazolidine for anticounterfeiting and photosensing of polarity and pH of aqueous media

Razavi

Roghani‐Mamaqani

Salami‐Kalajahi

2022

Sci Rep

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Oxazolidine is a new category of stimuli-chromic organic compounds with unique characteristics in response to polarity, pH changes, water, light, and metal ions that were well-known as solvatochromism, acidochromism, hydrochromism, photochromism, and ionochromism, respectively. Therefore, oxazolidine derivatives have been developed for their potential applications in chemosensors, anticounterfeiting, and rewritable hydrochromic papers. In this study, various oxazolidine derivatives containing hydroxyl and naphthalene substituted groups were synthesized by using two different indolenine compounds. The synthesized oxazolidine derivatives were used for investigation of solvatochromism in different solvents, and also acidochromism in various pHs by using UV–Vis and fluorescence spectroscopies. In addition, the oxazolidine derivatives were coated on cellulosic papers using a layer-by-layer strategy to develop rewritable acidochromic papers for printing of security tags on cellulosic papers by using acidic and alkaline solutions as water-based inks. Therefore, the developed rewritable acidochromic papers could be used as security papers.

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Section: Resultsmentioning

confidence: 99%

Rewritable acidochromic papers based on oxazolidine for anticounterfeiting and photosensing of polarity and pH of aqueous media

Razavi

Roghani‐Mamaqani

Salami‐Kalajahi

2022

Sci Rep

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“…HeLa cells were first incubated with AH + and BH + and then treated with FCCP (carbonyl cyanide p-(tri-fluoromethoxy)phenyl-hydrazone) [37][38][39]. After the subsequent treatments, we used fluorescence microscopy to assess the results (Figures 14 and 15).…”

Section: Analysis Of Mitochondrial Localization For Ah + and Bh + Probes In Live Cellsmentioning

confidence: 99%

“…The intensity of this new signal increased as fluorescence in channel II decreased. The appearance of a new fluorescence signal appears to be informative of probe protonation and stabilization of more blue-shifted AH + or BH + and indicative HeLa cells were first incubated with AH + and BH + and then treated with FCCP (carbonyl cyanide p-(tri-fluoromethoxy)phenyl-hydrazone) [37][38][39]. After the subsequent treatments, we used fluorescence microscopy to assess the results (Figures 14 and 15).…”

Section: Analysis Of Mitochondrial Localization For Ah + and Bh + Probes In Live Cellsmentioning

confidence: 99%

Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria

et al. 2021

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Ratiometric near-infrared fluorescent probes (AH+ and BH+) have been prepared for pH determination in mitochondria by attaching dithioacetal and formal residues onto a hemicyanine dye. The reactive formyl group on probe BH+ allows for retention inside mitochondria as it can react with a protein primary amine residue to form an imine under slightly basic pH 8.0. Probes AH+ and BH+ display ratiometric fluorescent responses to pH changes through the protonation and deprotonaton of a hydroxy group in hemicyanine dyes with experimentally determined pKa values of 6.85 and 6.49, respectively. Calculated pKa values from a variety of theoretical methods indicated that the SMDBONDI method of accounting for solvent and van der Waals radii plus including a water molecule located near the site of protonation produced the closest overall agreement with the experimental values at 7.33 and 6.14 for AH+ and BH+ respectively.

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“…pKa = x 0 ; Figure S8 Frontier molecular orbital energy diagram of BP and its opening structure BP + in a vacuum. Transition energies were calculated using the TD-B3LYP method with 6–31G basis sets; Figure S9 Viabilities of HeLa and U87 cells after incubation with different concentrations of BP for 24 h. Reference [ 55 ] are cited in the supplementary materials.…”

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confidence: 99%

Rational Design of Oxazolidine-Based Red Fluorescent pH Probe for Simultaneous Imaging Two Subcellular Organelles

Wang¹,

Fu²,

Tan³

et al. 2022

Biosensors

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A reversible pH-responsive fluorescent probe, BP, was rationally designed and synthesized, based on protonation and deprotonation gave rise to oxazolidine ring open and close. The fluorescence response of BP against pH ranges from 3.78 to 7.54, which is suitable for labeling intracellular pH-dependent organelles. BP displayed strong red emission at a relatively high pH in living HeLa cells and U87 cells. More importantly, this probe exhibited good colocalization with both mitochondria and lysosomes in these two cell lines, attributing to pH-induced structure tautomerism resulting in an oxazolidine ring open and close that triggered effective targeting of these two organelles. As organelle interactions are critical for cellular processes, this strategy of targeting dual organelles through the structure tautomerism is conducive to further developing more effective and advanced probes for real-time imaging of the interaction between mitochondria and lysosomes.

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A near-infrared fluorescent probe based on a hemicyanine dye with an oxazolidine switch for mitochondrial pH detection

Abstract: A near-infrared fluorescent probe (AH+) has been prepared by incorporating an oxazolidine switch into a near-infrared hemicyanine dye for pH detection in the mitochondria of HeLa cells.

Cited by 34 publications

References 38 publications

Rewritable acidochromic papers based on oxazolidine for anticounterfeiting and photosensing of polarity and pH of aqueous media

Rewritable acidochromic papers based on oxazolidine for anticounterfeiting and photosensing of polarity and pH of aqueous media

Ratiometric Near-Infrared Fluorescent Probes Based on Hemicyanine Dyes Bearing Dithioacetal and Formal Residues for pH Detection in Mitochondria

Rational Design of Oxazolidine-Based Red Fluorescent pH Probe for Simultaneous Imaging Two Subcellular Organelles

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