A deep-red fluorescent molecular rotor based on donor-two-acceptor modular system for imaging mitochondrial viscosity

Yin, Xiaoxing; Yiping, Cai; Cai, Songtao; Jiao, Xiaojie; Liu, Chang; He, Song; Zeng, Xianshun

doi:10.1039/d0ra04935b

Cited by 15 publications

(8 citation statements)

References 41 publications

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“…Probe 17 with large Stokes shift could solely accumulate into mitochondria and indicate the rise of viscosity after stimulation with monensin. In addition, the same group constructed a new viscosity‐sensitive fluorescent probe 18 with a phenolate donor unit and two benzothiazolium acceptor units [45] . Probe 18 showed high sensitivity and selectivity to viscosity.…”

Section: Small Molecular Fluorescent Probes For Viscositymentioning

confidence: 99%

Small Molecular Fluorescent Probes for Imaging of Viscosity in Living Biosystems

Xiao

Tang

2021

Chemistry A European J

118

115

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Viscosity, as a vital microenvironment parameter, is tightly associated with multitudinous cellular processes and diseases. Recently, precise visualization of viscosity has started to arouse more and more interest. However, owing to the complicated character, it is still a huge challenge to directly observe viscosity in living systems. In this regard, mounting fluorescence probes are being increasingly fabricated to map viscosity inside live cells and small animals. In this minireview, the viscosity‐sensitive small molecular fluorescent probes used in bioimaging are comprehensively summarized, mainly focusing on the last three years. Moreover, the current challenges and opportunities for the development of viscosity‐specific fluorescent probes will be discussed.

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Section: Small Molecular Fluorescent Probes For Viscositymentioning

confidence: 99%

Small Molecular Fluorescent Probes for Imaging of Viscosity in Living Biosystems

Xiao

Tang

2021

Chemistry A European J

118

115

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“…An inherent property of cyanine dyes is the resonance delocalization of a positive charge between the two nitrogen atoms connected by the polymethine chain, giving rise to a donor–acceptor π electron (D-π-A) system. In addition, the incorporation of an aromatic ring into the meso position of the polymethine chain can yield turn-on NIR probes based on a donor–two-acceptor π electron (D-2A-π) system. − , The longer the chain, the more extensive the resonance and the smaller the energy gap between the HOMO and LUMO.…”

Section: Results and Discussionmentioning

confidence: 99%

“…In addition, the incorporation of an aromatic ring into the meso position of the polymethine chain can yield turn-on NIR probes based on a donor−two-acceptor π electron (D-2A-π) system. [21][22][23]73 The longer the chain, the more extensive the resonance and the smaller the energy gap between the HOMO and LUMO.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

DNA Minor Groove-Induced cis–trans Isomerization of a Near-Infrared Fluorescent Probe

et al. 2021

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The discovery of small molecules that exhibit turn-on farred or near-infrared (NIR) fluorescence upon DNA binding and understanding how they bind DNA are important for imaging and bioanalytical applications. Here we report the DNA-bound structure and the DNA binding mechanism of quinone cyanine dithiazole (QCy-DT), a recently reported AT-specific turn-on NIR fluorescent probe for doublestranded DNA. The nuclear magnetic resonance (NMR)-derived structure showed minor groove binding but no specific ligand−DNA interactions, consistent with an endothermic and entropy-driven binding mechanism deduced from isothermal titration calorimetry. Minor groove binding is typically fast because it minimally perturbs the DNA structure. However, QCy-DT exhibited unusually slow DNA binding. The cyanine-based probe is capable of cis−trans isomerization due to overlapping methine bridges, with 16 possible slowly interconverting cis/trans isomers. Using NMR, density functional theory, and free energy calculations, we show that the DNA-free and DNA-bound environments of QCy-DT prefer distinctly different isomers, indicating that the origin of the slow kinetics is a cis−trans isomerization and that the minor groove preferentially selects an otherwise unstable cis/trans isomer of QCy-DT. Flux analysis showed the conformational selection pathway to be the dominating DNA binding mechanism at low DNA concentrations, which switches to the induced fit pathway at high DNA concentrations. This report of cis/trans isomerization of a ligand, upon binding the DNA minor groove, expands the prevailing understanding of unique discriminatory powers of the minor groove and has an important bearing on using polymethine cyanine dyes to probe the kinetics of molecular interactions.

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“…Mitochondria are one of the main targets of fluorescent bioimaging because their dynamic is related to numerous cellular processes and dysfunctions [1][2][3]; allowing evaluation of cells behavior. Cationic hydrophobic molecules are reported to accumulate preferentially in mitochondria, [4,5], therefore, cationic dyes are common in cell microscopy for their selective fluorescent imaging [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24]. Indeed, their selectivity arise from the high membrane potential of this organelle, particularly in cancer cells [25,26], which retains lipophilic cations.…”

Section: Introductionmentioning

confidence: 99%

Indazole versus indole-based cationic merocyanines with red shifted in-cellulo emission for selective mitochondria imaging

et al. 2022

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A deep-red fluorescent molecular rotor based on donor-two-acceptor modular system for imaging mitochondrial viscosity

Abstract: A deep-red fluorescence molecular rotor DpCy7 based on donor-two-acceptor modular system has been designed logically and synthesized for sensitive and selective response to viscosity changes and imaging of mitochondrial viscosity in living cells.

Cited by 15 publications

References 41 publications

Small Molecular Fluorescent Probes for Imaging of Viscosity in Living Biosystems

Small Molecular Fluorescent Probes for Imaging of Viscosity in Living Biosystems

DNA Minor Groove-Induced cis–trans Isomerization of a Near-Infrared Fluorescent Probe

Indazole versus indole-based cationic merocyanines with red shifted in-cellulo emission for selective mitochondria imaging

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