Bent-to-planar Si-rhodamines: a distinct rehybridization lights up NIR-II fluorescence for tracking nitric oxide in the Alzheimer's disease brain

Xu, Qingshuang; Zhang, Yutao; Zhu, Mingming; Yan, Chenxu; Mao, Wenle; Zhu, Wei; Guo, Zhiqian

doi:10.1039/d3sc00193h

Cited by 24 publications

(7 citation statements)

References 68 publications

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“…[16] Recently, Guo and colleagues incorporated N atom into asymmetrical DQ-containing Si-pyronin, and developed a novel Si-pyronin dyes (49) with large Stokes shift (260 nm) and NIR II emission maximum (1040 nm). [17] Similar with pyronin dyes, Peňa-Cabrera and colleagues constructed 8-propargylamino BODIPY (51), which also showed the enhanced Stokes shift than its parent dyes (45 nm (51) VS 10 nm (50)). [18] However, the method usually produces a hypochromatic shift of absorption and emission spectrum while enlarges Stokes shift of fluorophores, which is disadvantageous for some applications, such as deep tissue imaging.…”

Section: The Insertion Of the Intermediate N Atommentioning

confidence: 99%

Organic Fluorophores with Large Stokes Shift for Bioimaging and Biosensing

Liu,

Jiang,

et al. 2024

ChemPhotoChem

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Fluorophores and fluorophores‐based probes or labels can visualize the structures and content fluctuations of biomolecules, and have made great progress in the broad range of biomedicine fields. However, many commercially available fluorophores suffer from small Stokes shift, which results in insufficient signal‐to‐noise ratio and self‐quenching in advanced imaging techniques. Moreover, the small Stokes shift also hinders the application of fluorophores in some complex imaging, such as single‐excitation multicolor imaging. In the past two decades, many effects have been made to enlarge Stokes shift of fluorophores. In this review, we clarified the reasons for the small Stokes shift building on the structural analysis of fluorophores, systematically summarize the methods of structural modification to increase Stokes shift, and present some representative applications of fluorophores with large Stokes shift in imaging and sensing.

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Section: The Insertion Of the Intermediate N Atommentioning

confidence: 99%

Organic Fluorophores with Large Stokes Shift for Bioimaging and Biosensing

Liu,

Jiang,

et al. 2024

ChemPhotoChem

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“…[12g,86] Recently, Guo and colleagues combined the power of central N atom and vibrational structures, and excitingly promoted the emission maximum of Si-rhodamine to NIR II region, while increasing the Stokes shift. [87] This strategy has been extended to other fluorophore skeletons such as BODIPY dyes. [88] However, the method usually also results in a hypochromatic shift while increasing Stokes shift.…”

Section: Increasing Stokes Shift Of Organic Fluorophoresmentioning

confidence: 99%

“…Similarly, Guo et al developed two probes for detecting Hg 2 + and NO based on the heteroanthracene dye with large Stokes shift, and in situ tracking NO fluctuations in brains of Alzheimer's mice. [87]…”

Section: The Detection Of Gaseous Signaling Moleculesmentioning

confidence: 99%

Chemical Approaches to Optimize the Properties of Organic Fluorophores for Imaging and Sensing

Jiang,

Liu,

Liu

et al. 2023

Angewandte Chemie

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Organic fluorophores are indispensable tools in cells, tissue and in vivo imaging, and have enabled much progress in the wide range of biological and biomedical fields. However, many available dyes suffer from insufficient performances, such as short absorption and emission wavelength, low brightness, poor stability, small Stokes shift, and unsuitable permeability, restricting their application in advanced imaging technology and complex imaging. Over the past two decades, many efforts have been made to improve these performances of fluorophores. Starting with the luminescence principle of fluorophores, this review clarifies the mechanisms of the insufficient performance for traditional fluorophores to a certain extent, systematically summarizes the modified approaches of optimizing properties, highlights the typical applications of the improved fluorophores in imaging and sensing, and indicates existing problems and challenges in this area. This progress not only proves the significance of improving fluorophores properties, but also provide a theoretical guidance for the development of high‐performance fluorophores.

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“…Regrettably, the three kinds of fluorescent dyes (indocyanine green, fluorescein, and methylene blue) that are widely used in the clinical range all suffer from obvious small Stokes shift and nonideal photostability. − Furthermore, for the range of biomedical research studies, the widely used rhodamine derivative emits photons in the visible spectrum region, which suffers from surface penetration depth and severe autofluorescence from biological tissues. Even though some of the rhodamine derivates were extended to the NIR-II region, the apparent bulky molecular structure caused nonideal solubility. − To solve the defect, it needs to encapsulate to form nanomaterials that broadly limit the sufficient biodistribution and pharmacokinetics study. Hence, it is obvious that only a few small-molecule fluorophores own the above optimal properties in all of these categories.…”

mentioning

confidence: 99%

Molecular Engineering of Sulfone-Xanthone Chromophore for Enhanced Fluorescence Navigation

Zhang,

Xiang,

Liu

et al. 2023

JACS Au

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Enriching the palette of high-performance fluorescent dyes is vital to support the frontier of biomedical imaging. Although various rhodamine skeletons remain the premier type of small-molecule fluorophores due to the apparent high brightness and flexible modifiability, they still suffer from the inherent defect of small Stokes shift due to the nonideal fluorescence imaging signal-to-background ratio. Especially, the rising class of fluorescent dyes, sulfone-substituted xanthone, exhibits great potential, but low chemical stability is also pointed out as the problem. Molecular engineering of sulfone-xanthone to obtain a large Stokes shift and high stability is highly desired, but it is still scarce. Herein, we present the combination modification method for optimizing the performance of sulfone-xanthone. These redesigned fluorescent skeletons owned greatly improved stability and Stokes shift compared with the parent sulfone-rhodamine. To the proof of bioimaging capacity, annexin protein-targeted peptide LS301 was introduced to the most promising dyes, J-S-ARh, to form the tumor-targeted fluorescent probe, J-S-LS301. The resulting probe, J-S-LS301, can be an outstanding fluorescence tool for the orthotopic transplantation tumor model of hepatocellular carcinoma imaging and on-site pathological analysis. In summary, the combination method could serve as a basis for rational optimization of sulfone-xanthone. Overall, the chemistry reported here broadens the scope of accessible sulfone-xanthone functionality and, in turn, enables to facilitate the translation of biomedical research toward the clinical domain.

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Bent-to-planar Si-rhodamines: a distinct rehybridization lights up NIR-II fluorescence for tracking nitric oxide in the Alzheimer's disease brain

Abstract: An ongoing revolution in fluorescence-based technologies has transformed the way that we visualize and manipulate biological events. An enduring goal in this field is to explore high-performance fluorogenic scaffolds that...

Cited by 24 publications

References 68 publications

Organic Fluorophores with Large Stokes Shift for Bioimaging and Biosensing

Organic Fluorophores with Large Stokes Shift for Bioimaging and Biosensing

Chemical Approaches to Optimize the Properties of Organic Fluorophores for Imaging and Sensing

Molecular Engineering of Sulfone-Xanthone Chromophore for Enhanced Fluorescence Navigation

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