Rhodamine cyclic hydrazide as a fluorescent probe for the detection of hydroxyl radicals

Kim, Minjeong; Ko, Sung-Kyun; Kim, Hyemi; Shin, Injae; Tae, Jinsung

doi:10.1039/c3cc44627a

Cited by 74 publications

(40 citation statements)

References 27 publications

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“…[18][19][20][21][22] Indeed, several elegant fluorescence probes for ·OH have previously been reported using either smallmolecule or nanomaterial fluorophores. [23][24][25][26][27] Nonetheless, the use of these probes is somewhat limited due to the short excitation wavelengths in the UV-vis range, which suffers from shallow tissue penetration depths. Besides, the rather serious background interference in biological samples restricts the sensitivity of detection.…”

Section: Introductionmentioning

confidence: 99%

A Rationally Designed Upconversion Nanoprobe for in Vivo Detection of Hydroxyl Radical

et al. 2015

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The detection of •OH in live organisms is crucial to the understanding of its physiological and pathological roles; while this is too challenging because of the extremely low concentration and high reactivity of the species in the body. Herein, we report the rational design and fabrication of an NIR-light excited luminescence resonance energy transfer-based nanoprobe, which for the first time realizes the in vivo detection of •OH. The nanoprobe is composed of two moieties: upconversion nanoparticles with sandwich structure and bared surface as the energy donor; and mOG, a modified azo dye with tunable light absorption, as both the energy acceptor and the •OH recognizing ligand. The as-constructed nanoprobe exhibited ultrahigh sensitivity (with the quantification limit down to 1.2 femtomolar, several orders of magnitude lower than that of most previous •OH probes), good biocompatibility, and specificity. It was successfully used for monitoring [•OH] levels in live cells and tissues.

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Section: Introductionmentioning

confidence: 99%

A Rationally Designed Upconversion Nanoprobe for in Vivo Detection of Hydroxyl Radical

et al. 2015

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“…[6] Excess COH leads to irreparable damage to neural cells and potentially even to neurological disease. [11][12][13][14][15][16][17][18][19] Given the very high reactivity and low concentration of COH and the particularly complicated construction of the brain, two-photon (TP) fluorescence imaging is the most appropriate for brain imaging because it provides ah igher signal-tobackground ratio,d eeper tissue imaging, higher spatialtemporal resolution, and less specimen photodamage than one-photon (OP) fluorescence imaging. [8][9][10] Fluorescent probes have been developed to reveal the biological functions of COH in living cells,i nz ebrafish, and in the abdomens of mice.…”

mentioning

confidence: 99%

Illuminating the Function of the Hydroxyl Radical in the Brains of Mice with Depression Phenotypes by Two‐Photon Fluorescence Imaging

Wang

Ding

et al. 2019

Angew Chem Int Ed

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Depression is intimately linked with oxidative stress. As one of the most reactive and oxidative reactive oxygen species that is overproduced during oxidative stress,t he hydroxyl radical (COH) can cause macromolecular damage and subsequent neurological diseases.However,due to the high reactivity and lowconcentration of COH, precise exploration of COH in brains remains ac hallenge.T he two-photon fluorescence probe MD-B was developed for in situ COH imaging in living systems.T his probe achieves exceptional selectivity towards COH through the one-electron oxidation of 3-methylpyrazolone as an ew specific recognition site.M D-B can be used to map COH in mouse brain, therebyr evealing that increased COH is positively correlated with the severity of depression phenotypes.F urthermore, COH has been shown to inactivate deacetylase SIRT1,therebyleading to the occurrence and development of depression phenotypes.T his work provides anew strategy for the future treatment of depression.Depression as one of the most common and disabling mental disorders,w ith aw orldwide prevalence of approximately 17 %. [1] However,u nderstanding of the pathophysiology of depression is still rudimentary due to its complex aetiology. [2] Previous findings suggest that oxidative stress contributes to the pathogenesis of depression. [3][4][5] Theh ydroxyl radical (COH) is one of the most reactive and oxidative reactive oxygen species (ROS) that is overproduced during oxidative stress. [6] Excess COH leads to irreparable damage to neural cells and potentially even to neurological disease. [7] Therefore,t here is an urgent need to develop an effective means for tracing COH in living brain to define the relationship between depression and COH levels.Recently,f luorescence imaging has become ar obust approach for real-time monitoring of molecular events in living cells and in vivo because of its non-destructive nature and spatiotemporal resolution. [8][9][10] Fluorescent probes have been developed to reveal the biological functions of COH in living cells,i nz ebrafish, and in the abdomens of mice. [11][12][13][14][15][16][17][18][19] Given the very high reactivity and low concentration of COH and the particularly complicated construction of the brain, two-photon (TP) fluorescence imaging is the most appropriate for brain imaging because it provides ah igher signal-tobackground ratio,d eeper tissue imaging, higher spatialtemporal resolution, and less specimen photodamage than one-photon (OP) fluorescence imaging. [20][21][22][23] Molecular fluorescent probes have some appealing performance characteristics in terms of stability,ease of crossing of the blood-brain barrier (BBB), and easy excretion, which is preferable for the TP in situ imaging of COH in the brains of living mice with depression-like behaviours.However,suitable TP fluorescent probes for brain imaging of COH with specificity,h igh sensitivity,and instantaneous response are still scarce.Inspired by the specific one-electron oxidation reaction between COH and 3-methyl-pyrazolone in the...

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“…Rhodamine‐based probes were developed as OH • imaging agents utilizing their hydrogen extracting ability . The probes were used to image the rise of OH • levels in both A549 and RAW264.7 cells caused by the presence of Fenton reagent (FeSO 4 /H 2 O 2 ), as well as in plant cells (nicotiana tabacum BY‐2 cells and onion epidermal cells) with a high concentration of intracellular OH • .…”

Section: Fluorescent Imaging Agents For Diagnosis Of Ros‐relevant Dismentioning

confidence: 99%

Sensors, Imaging Agents, and Theranostics to Help Understand and Treat Reactive Oxygen Species Related Diseases

et al. 2019

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Reactive oxygen species (ROS) consist of a diverse range of oxidative small molecular ions and free radicals that are produced throughout the body during certain biological processes. Due to their high reactivity, these molecules result in the damage of tissues and cells. Therefore, ROS have been implicated in an array of diseases including cancer, inflammation, and neurodegenerative diseases such as Parkinson's disease and Alzheimer's disease. Owing to the simplicity, sensitivity, and selectivity of fluorescence‐based strategies, many small‐molecular sensors or imaging agents have been developed to sense and visualize ROS both in vitro and in vivo. Likewise, activatable drug delivery and prodrug systems that can be triggered by ROS for disease theranostics (diagnostic and therapeutic combined) have been developed. Herein, recently developed fluorescence‐based sensing and imaging agents for the detection of ROS both intracellularly and in vivo are summarized. In addition, drug delivery, which require activation by ROS to achieve disease theranostics is also discussed.

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Rhodamine cyclic hydrazide as a fluorescent probe for the detection of hydroxyl radicals

Cited by 74 publications

References 27 publications

A Rationally Designed Upconversion Nanoprobe for in Vivo Detection of Hydroxyl Radical

A Rationally Designed Upconversion Nanoprobe for in Vivo Detection of Hydroxyl Radical

Illuminating the Function of the Hydroxyl Radical in the Brains of Mice with Depression Phenotypes by Two‐Photon Fluorescence Imaging

Sensors, Imaging Agents, and Theranostics to Help Understand and Treat Reactive Oxygen Species Related Diseases

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