A ratiometric lysosomal pH probe based on the imidazo[1,5-a]pyridine–rhodamine FRET and ICT system

Song, Guoyong; Bai, Su-Yun; Dai, Xi; Cao, Xiaoqun; Zhao, Bao‐Xiang

doi:10.1039/c5ra25947a

Cited by 42 publications

(25 citation statements)

References 42 publications

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“…Imidazopyridine, an important fluorophore contains imidazole moiety fused with pyridine ring . Among the various imidazopyridines the imidazo[1, 5‐a]pyridine (Figure ) is an attractive class of compound due to their potential application in electronic, optoelectronic and photo‐functional materials such as BODYPY organic light‐emitting diodes (OLEDs),, organic thin‐layer field effect transistors (OFETs), fluorescence resonance energy transfer (FRET) materials, fluorescent sensors and as precursors of N‐heterocyclic carbenes ,. Despite the various synthetic strategies of imidazo[1, 5‐a]pyridine derivatives, there are very few studies discussing their photophysical properties ,,.…”

Section: Introductionmentioning

confidence: 99%

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

Mohbiya

Sekar

2018

ChemistrySelect

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Imidazo [1, 5a]pyridine based novel donor-acceptor dyes (2a-e) with the large Stokes shift (ca. 140-200 nm) were synthesized and characterized. We report on the steady-state and nanosecond time-resolved emission studies of 2a-e in different microenvironments which reveal that the dyes 2a-c (average lifetime of 0.65, 1.36 and 1.63 ns respectively) perform reversible proton motion in chloroform due to variable donor group present at the para position of substituted phenyl group attached to imidazopyridine core as an acceptor group whereas 2d and 2e (average lifetime of 3.50 and 4.06 ns respectively) compete with 2a-c in agreement with considerable intramolecular charge transfer (ICT) characteristics. Solvent polarity plots viz. Lippert-Mataga, McRae, and Bakhshiev equation furnish the confirmation of ICT character. Density functional theory (DFT) calculations [(B3LYP/6-311 + +G(d, p)] provide the information of structural as well as the electronic properties of dyes 2a-e. Natural bond orbital (NBO) analyses enlighten the nature of the charge or proton transfer within the selected donor-acceptor orbital interaction with the large energy of stabilization (the donor-acceptor orbital interactions increases in the order 2a > 2b > 2c > 2d > 2e). The large difference in dipole moment (ca. 1.57-21.55 D) results in a strong non-linear optical (NLO) properties. The NLO properties were evaluated theoretically as well as spectroscopically in solvents of different polarities and the resulting hyperpolarizabilities fall within the expected limiting values. These results bring new findings in coupled ICT and proton transfer reactions which will be useful for further research and promising applications in sensing polarity or H-bonding of microenvironments similar to that of the biological ones.

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Section: Introductionmentioning

confidence: 99%

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

Mohbiya

Sekar

2018

ChemistrySelect

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“…Fluorescence pH probes have found wide use in analytical chemistry, bio-analytical chemistry, and cellular biology. Over the past few years, the intelligent design of synthetic methods has led to the development of pH fluorescent probes based on quinoline [9][10][11][12], coumarin [12][13][14], indoles [15][16][17], dansyl [18], rhodamine [19][20][21][22][23], quaternary ammonium salt [24], naphthalimide [25,26], benzothiazole [27], cyanine dyes [28,29]. In particular, pH-sensitive fluorescent probes which operate near neutral pH for intracellular fluorescence imaging have been widely studied [30][31][32][33][34][35][36].…”

Section: Introductionmentioning

confidence: 99%

A quinoline-based fluorometric and colorimetric dual-modal pH probe and its application in bioimaging

Zhu

Zhao

et al. 2018

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The compound (E)-8-hydroxyl-2-[(E)-2-(2, 4-dihydroxyphenyl)vinyl]-quinoline (1) has been developed as a fluorometric and colorimetric dual-modal probe for pH detection in solution and in vivo. Remarkable changes in the fluorescence intensity with large Stokes shifts and colorimetric responses were observed as a function of pH. The sensing mechanisms involving protonation and deprotonation processes over the acidic and alkaline pH ranges were confirmed by H NMR and IR spectroscopic analysis. Furthermore, the application of probe 1 for the imaging of live PC3 cells was successfully achieved. Test strips based on probe 1 were fabricated, and were found to act as a convenient and efficient pH test kits.

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“…10, 19 and 23-26) and the other type for acidic organelles such as lysosomes and endosomes 21,[27][28][29][30][31][32][33][34][35] which function at pH 4.5-6.0. However, the uorescent probes for extreme acidity (pH < 4)…”

Section: -18mentioning

confidence: 99%

A colorimetric and fluorescent pH probe for imaging in E. coli cells

et al. 2017

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A colorimetric and fluorescent pH probe 1-(4-methylphenyl)-3-(4-dimethylaminophenyl) acrylketone (MDAK) was facilely prepared. The probe exhibited strong pH-dependent behavior and responded linearly and rapidly to minor pH fluctuations within the range of 1.53-3.96. In addition, MDAK displayed a notably large Stokes shift of 121 nm. MDAK possessed a highly selective response to H + over other metal ions, amion acids and displayed good photostability and excellent reversibility. Furthermore, it can be applied to visualize extreme acidity in E. coli cells.

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A ratiometric lysosomal pH probe based on the imidazo[1,5-a]pyridine–rhodamine FRET and ICT system

Abstract: A new pH-activatable ratiometric fluorescent probe (RhMP) has been developed based on FRET. This probe displayed good selectivity, and excellent reversibility. In addition, RhMP has low cytotoxicity and has been successfully applied in HeLa cells.

Cited by 42 publications

References 42 publications

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

Tuning ‘Stokes Shift’ and ICT Character by Varying the Donor Group in Imidazo[1,5 a]pyridines: A Combined Optical, DFT, TD‐DFT and NLO Approach

A quinoline-based fluorometric and colorimetric dual-modal pH probe and its application in bioimaging

A colorimetric and fluorescent pH probe for imaging in E. coli cells

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