Tricarbocyanine<i>N</i>-triazoles: the scaffold-of-choice for long-term near-infrared imaging of immune cells<i>in vivo</i>

Mellanby, Richard J.; Scott, Jamie I.; Mair, Iris; Fernández, Antonio; Saul, Louise; Arlt, Jochen; Moral, Mónica; Vendrell, Marc

doi:10.1039/c8sc00900g

Cited by 53 publications

(46 citation statements)

References 63 publications

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“…The introduction of an azide group could diminish the fluorescence background due to the ICT quenching effect . On the other hand, transformation of the azide into a triazole group will not only suppress ICT, but also enlarges the conjugated system of the fluorophore to yield tunable emission . We envision that azido‐substituted 8‐aminoquine derivatives would serve as excellent building blocks to construct a new class of highly fluorogenic biorthogonal probes.…”

Section: Resultsmentioning

confidence: 99%

Color‐Tunable Light‐up Bioorthogonal Probes for In Vivo Two‐Photon Fluorescence Imaging

Dou

Wang

Duan

et al. 2020

Chemistry A European J

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Light‐up bioorthogonal probes have attracted increasing attention recently due to their capability to directly image diverse biomolecules in living cells without washing steps. The development of bioorthogonal probes with excellent fluorescent properties suitable for in vivo imaging, such as long excitation/emission wavelength, high fluorescence turn‐on ratio, and deep penetration, has been rarely reported. Herein, a series of azide‐based light‐up bioorthogonal probes with tunable colors based on a weak fluorescent 8‐aminoquinoline (AQ) scaffold were designed and synthesized. The azido quinoline derivatives are able to induce large fluorescence enhancement (up to 1352‐fold) after click reaction with alkynes. In addition, the probes could be engineered to exhibit excellent two‐photon properties (δ=542 GM at 780 nm) after further introducing different styryl groups into the AQ scaffold. Subsequent detailed bioimaging experiments demonstrated that these versatile probes can be successfully used for live cell/zebrafish imaging without washing steps. Further in vivo two‐photon imaging experiments demonstrated that these light‐up biorthogonal probe outperformed conventional fluorophores, for example, high signal‐to‐noise ratio and deep tissue penetration. The design strategy reported in this study is a useful approach to realize diverse high‐performance biorthogonal light‐up probes for in vivo studying.

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Section: Resultsmentioning

confidence: 99%

Color‐Tunable Light‐up Bioorthogonal Probes for In Vivo Two‐Photon Fluorescence Imaging

Dou

Wang

Duan

et al. 2020

Chemistry A European J

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show abstract

“…In the last 15 years, there has been a lot of interest to modulate the optical properties of fluorescent scaffolds [ 110–113 ] (e.g., excitation/emission, water solubility, fluorescence lifetime) to generate probes with improved characteristics for in vivo imaging. In addition to widely used commercial fluorophores, such as cyanines or rhodamines, fluorophores with additional features have been developed.…”

Section: Biological Applications Of Fluorescent Cyclic Peptide Probesmentioning

confidence: 99%

Fluorescent cyclic peptides for cell imaging

2020

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Fluorescent cyclic peptides are excellent chemical scaffolds to build optical agents for molecular imaging. In addition to their favorable physicochemical properties, they can be modified with multiple organic fluorophores and generate useful probes for biological assays targeting specific proteins, namely receptors or enzymes. In this article, we review recent advances in the synthetic approaches for the preparation of fluorescent cyclic peptides as well as some of their applications in biological imaging, from in vitro live‐cell imaging studies to in vivo characterization of preclinical models.

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“…Although the direct visualisation of cells and tissues using light has been one of the most informative approaches in diagnostic medical imaging, its limited depth of penetration (less than 1 cm) has hampered its widespread application for in vivo clinical imaging studies. This can partially overcome with the use of near-infrared dyes (i.e., emitting in the spectral range from 650 nm to 900 nm) [97,98], which provide deeper tissue penetration and can be used for whole-body fluorescence tomography in preclinical models.…”

Section: Alternative Modalities For Non-optical In Vivo Imagingmentioning

confidence: 99%

Fluorescent peptides for imaging of fungal cells

Zhao

Mendive‐Tapia

Vendrell

2019

Archives of Biochemistry and Biophysics

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Fungal infections, especially with the advent of antimicrobial resistance, represent a major burden to our society. As a result, there has been an increasing interest in the development of new probes that accelerate the study of fungi-related biological processes and facilitate novel clinical diagnostic and treatment strategies. Fluorescence-based reporters can provide dynamic information at the molecular level with high spatial resolution. However, conventional fluorescent probes for microbes often suffer from low specificity. In the last decade, numerous studies have been reported on the chemical design and application of fluorescent peptides for both in vitro and in vivo imaging of fungal cells. In this article, we review different strategies used in the preparation of fluorescent peptides for pathogenic fungi as well as some of their applications in medical imaging and in mode-of-action mechanistic studies.

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TricarbocyanineN-triazoles: the scaffold-of-choice for long-term near-infrared imaging of immune cellsin vivo

Abstract: Tricarbocyanine N-triazoles are first described as rationally-designed structures to overcome the limitations of NIR dyes for long-term in vivo imaging.

Cited by 53 publications

References 63 publications

Color‐Tunable Light‐up Bioorthogonal Probes for In Vivo Two‐Photon Fluorescence Imaging

Color‐Tunable Light‐up Bioorthogonal Probes for In Vivo Two‐Photon Fluorescence Imaging

Fluorescent cyclic peptides for cell imaging

Fluorescent peptides for imaging of fungal cells

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