A Dual-Modal Molecular Probe for Near-Infrared Fluorescence and Photoacoustic Imaging of Peroxynitrite

Zhang, Jianjian; Zhen, Xu; Zeng, Jianfeng; Pu, Kanyi

doi:10.1021/acs.analchem.8b01879

Cited by 164 publications

(97 citation statements)

References 49 publications

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“…ONOO − leads to the damage of various biomolecules, including proteins, lipids, DNA, carbohydrates, and thiols, by facilitating oxidation reactions; as a result, it leads to various pathological diseases, such as inflammation and cancer, as well as cardiovascular and neurodegenerative diseases . The real‐time sensing of ONOO − in tumors is important for the study of the tumor etiology and select treatment methods . Pu and co‐workers designed a smart PA contrast agent with strong selective sensing of ONOO − and enhanced pH inertness, which was applied to visualize and monitor ONOO − levels in tumors of living mice via ratiometric PA imaging .…”

Section: Biomedical Applicationsmentioning

confidence: 99%

Photoacoustic Imaging: Contrast Agents and Their Biomedical Applications

et al. 2018

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Photoacoustic (PA) imaging as a fast‐developing imaging technique has great potential in biomedical and clinical applications. It is a noninvasive imaging modality that depends on the light‐absorption coefficient of the imaged tissue and the injected PA‐imaging contrast agents. Furthermore, PA imaging provides superb contrast, super spatial resolution, and high penetrability and sensitivity to tissue functional characteristics by detecting the acoustic wave to construct PA images. In recent years, a series of PA‐imaging contrast agents are developed to improve the PA‐imaging performance in biomedical applications. Here, recent progress of PA contrast agents and their biomedical applications are outlined. PA contrast agents are classified according to their components and function, and gold nanocrystals, gold‐nanocrystal assembly, transition‐metal chalcogenides/MXene‐based nanomaterials, carbon‐based nanomaterials, other inorganic imaging agents, small organic molecules, semiconducting polymer nanoparticles, and nonlinear PA‐imaging contrast agents are discussed. The applications of PA contrast agents as biosensors (in the sensing of metal ions, pH, enzymes, temperature, hypoxia, reactive oxygen species, and reactive nitrogen species) and in bioimaging (lymph nodes, vasculature, tumors, and brain tissue) are discussed in detail. Finally, an outlook on the future research and investigation of PA‐imaging contrast agents and their significance in biomedical research is presented.

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Section: Biomedical Applicationsmentioning

confidence: 99%

Photoacoustic Imaging: Contrast Agents and Their Biomedical Applications

et al. 2018

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“…The nitrosative stress marker, peroxynitrite (ONOO - ), has been implicated in the initiation of autophagy in endothelial cells and may work as the first target for imaging autophagy 15,18. Among the various probes reported to image ROS 19-21, those that are designed based on the dearylation of electron-rich diphenylamines into mono-aryl-anilines attracted our interest due to their specifcity towards ONOO - 22-25. Another merit of employing a diphenylamino group as the sensing trigger lies in its function as a good fluorescence quencher.…”

Section: Resultsmentioning

confidence: 99%

Visualizing Autophagic Flux during Endothelial Injury with a Pathway-Inspired Tandem-Reaction Based Fluorogenic Probe

Lei¹,

Ren²,

Wang³

et al. 2019

Theranostics

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Autophagy is a dynamic and complicated catabolic process. Imaging autophagic flux can clearly advance knowledge of its pathophysiology significance. While the most common way autophagy is imaged relies on fluorescent protein-based probes, this method requires substantial genetic manipulation that severely restricts the application. Small fluorescent probes capable of tracking autophagic flux with good spatiotemporal resolution are highly demanable.Methods: In this study, we developed a small-molecule fluorogenic probe (AFG-1) that facilitates real-time imaging of autophagic flux in both intact cells and live mice. AFG-1 is inspired by the cascading nitrosative and acidic microenvironments evolving during autophagy. It operates over two sequential steps. In the first step, AFG-1 responds to the up-regulated peroxynitrite at the initiation of autophagy by its diphenylamino group being oxidatively dearylated to yield a daughter probe. In the second step, the daughter probe responds to the acidic autolysosomes at the late stage of autophagy by being protonated.Results: This pathway-dependent mechanism has been confirmed first by sequentially sensing ONOO- and acid in aqueous solution, and then by imaging autophagic flux in live cells. Furthermore, AFG-1 has been successfully applied to visualize autophagic flux in real-time in live mice following brain ischemic injury, justifying its robustness.Conclusion: Due to the specificity, easy operation, and the dynamic information yielded, AFG-1 should serve as a potential tool to explore the roles of autophagy under various pathological settings.

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“…The probe was equipped with Z-axis gradients coils. Af ull assignment was achieved through 2D experiments:C OSY ( 1 H-1 Hc orrelation), HMQC, HMBC ( 1 H- 13 Cs hort and long correlations, respectively), and J-resolved. The 2D homonuclear NOESY experiments employed 128 t 1 increments with ad well time of 113.6 msa nd am ixing time of 1.5 sw ith ar ecycle delay of 2.5 s. LC/MS analyses were performed by using an Agilent Te chnologies 1260 Infinity (LC) 6120 quadruple (MS) instrument, an Agilent SB-C18 column, 1.8 mm, 2.1 50 mm, column temperature 50 8C, eluent water-acetonitrile + 0.1 %f ormic acid.…”

Section: Methodsmentioning

confidence: 99%

“…On the other hand, turn‐on NIR fluorescent xanthene–cyanine dyes were recently designed for spectrofluorometric and imaging‐based detection of peroxynitrite, fibroblasts, aminopeptidase, nitroxyl, hydrogen polysulfide, carboxylesterase, hypochlorous acid, and glutathionine . These dyes were also proposed for keloid diagnosis and chemo‐photodynamic therapy .…”

Section: Introductionmentioning

confidence: 99%

Peptide‐Driven Targeted Drug‐Delivery System Comprising Turn‐On Near‐Infrared Fluorescent Xanthene–Cyanine Reporter for Real‐Time Monitoring of Drug Release

et al. 2019

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Targeted drug delivery (TDD) is an efficient strategy for cancer treatment. However, the real‐time monitoring of drug delivery is still challenging because of a pronounced lack of TDD systems capable of providing a near‐infrared (NIR) fluorescence signal for the detection of drug‐release events. Herein, a new TDD system, comprising a turn‐on NIR fluorescent reporter attached to an anticancer drug and targeting peptide, is reported. This system provides both TDD and NIR fluorescence monitoring of drug‐release events in target tissue. In this TDD system, a new carboxy‐derivatized xanthene–cyanine (XCy) dye is attached to an anticancer drug, chlorambucil (CLB), through a hydrolytically cleavable ester linker and coupled to a targeting peptide, octreotide amide (OCTA), which is specific to somatostatin receptors SSTR‐2 and STTR‐5 overexpressed on many tumor cells. This OCTA‐G‐XCy‐CLB (G: γ‐aminobutyric acid) conjugate exhibits no detectable fluorescence, whereas, upon the hydrolytic cleavage of the ester linker, a bright NIR fluorescence appears at λ≈710 nm; this signals release of the drug. Real‐time TDD monitoring is demonstrated for the example of the human pancreatic cancer cell line overexpressing SSTR‐2 and STTR‐5, in comparison with the noncancerous Chinese hamster ovary cell line, which contains a reduced number of these receptors.

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A Dual-Modal Molecular Probe for Near-Infrared Fluorescence and Photoacoustic Imaging of Peroxynitrite

Cited by 164 publications

References 49 publications

Photoacoustic Imaging: Contrast Agents and Their Biomedical Applications

Photoacoustic Imaging: Contrast Agents and Their Biomedical Applications

Visualizing Autophagic Flux during Endothelial Injury with a Pathway-Inspired Tandem-Reaction Based Fluorogenic Probe

Peptide‐Driven Targeted Drug‐Delivery System Comprising Turn‐On Near‐Infrared Fluorescent Xanthene–Cyanine Reporter for Real‐Time Monitoring of Drug Release

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