Target-activated streptavidin–biotin controlled binding probe

Wu, Yung-Peng; Chew, Chee Ying; Li, Tian-Neng; Chung, Tzu-Hsuan; Chang, En-Hao; Lam, Chak Hin; Tan, Kui‐Thong

doi:10.1039/c7sc04014h

Cited by 22 publications

(22 citation statements)

References 50 publications

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“…The typical procedure to introduce such a residue exploits the 4-hydroxymethylphenylboronic acid pinacol ester in which the hydroxyl group is converted, often in situ , into an acid chloride in a reaction with triphosgene (Srikun et al, 2008 ; Chung et al, 2011 ; Zhu D. et al, 2013 ) in the presence of a base in various solvents, which reacts further with the target amino group. There are some examples in which this approach is also used to mask the nitrogen atom on biotin (Chung et al, 2018 ; Wu Y. P. et al, 2018 ) or methylene blue (Hu et al, 2019 ) or in aliphatic systems (Lippert et al, 2010 ; Zhu D. et al, 2013 ; Yik-Sham Chung et al, 2018 ).…”

Section: Synthetic Approaches To Boronate-based Molecular Probesmentioning

confidence: 99%

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

et al. 2020

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Boronate-based molecular probes are emerging as one of the most effective tools for detection and quantitation of peroxynitrite and hydroperoxides. This review discusses the chemical reactivity of boronate compounds in the context of their use for detection of biological oxidants, and presents examples of the practical use of those probes in selected chemical, enzymatic, and biological systems. The particular reactivity of boronates toward nucleophilic oxidants makes them a distinct class of probes for redox biology studies. We focus on the recent progress in the design and application of boronate-based probes in redox studies and perspectives for further developments.

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Section: Synthetic Approaches To Boronate-based Molecular Probesmentioning

confidence: 99%

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

et al. 2020

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“…We believe that the cell‐impermeable ONOO‐CBP probe can overcome this problem to study the time course of ONOO − secretion upon IFN‐γ stimulation. In a separate study, our CBP approach was successfully employed to determine the time course of ONOO − burst in RAW264.7 cells under PMA‐stimulated conditions …”

Section: Resultsmentioning

confidence: 99%

“…Previously, we demonstrated that a novel chemical probe design based on the controlled binding of streptavidin and biotin could be used to detect secreted ONOO − at the cell surface . However, the application of this approach to study fundamental biological questions remained elusive.…”

Section: Introductionmentioning

confidence: 96%

Imaging and Quantification of Secreted Peroxynitrite at the Cell Surface by a Streptavidin–Biotin‐Controlled Binding Probe

Chung

Chew

et al. 2018

ChemBioChem

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The ability to detect and image secreted peroxynitrite (ONOO−) along the extracellular surface of a single cell is biologically significant, as ONOO− generally exerts its function for host defense and signal transductions at the plasma membrane. However, as a result of the short lifetime and fast diffusion rate of small ONOO−, precise determination of the ONOO− level at the cell surface remains a challenging task. In this paper, the use of a membrane‐anchored streptavidin–biotin‐controlled binding probe (CBP), ONOO‐CBP, to determine quantitatively the ONOO− level at the cell surface and to investigate the effect of different stimulants on the production of ONOO− along the plasma membrane of macrophages is reported. Our results revealed that the combination of NO synthase (iNOS) and NADPH oxidase (NOX) activators was highly effective in inducing ONOO− secretion, achieving more than a 25‐fold increase in ONOO− relative to untreated cells. After 1 h of phorbol‐12‐myristate‐13‐acetate (PMA) stimulation, the amount of ONOO− secreted by RAW264.7 macrophages was similar to the condition treated with 25 μm 3‐morpholinosydnonimine hydrochloride (SIN‐1), which was estimated to release about 20 μm of ONOO− into Dulbecco's modified Eagle's medium (DMEM) in 1 h. This novel approach should open up new opportunities to image various reactive oxygen and nitrogen species secreted at the plasma membrane that cannot be simply achieved by conventional analytical methods.

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“…The magnetism is another well-confirmed targeting strategy, and ultrasmall superparamagnetic iron oxide nanoparticles (USIONPs) are often chosen for this aim, although their drug loadings are not high 21 . Due to the very strong binding of avidin–biotin 22 , 23 , it is used for pretargeting 24 , cell probe 25 , biosensor detection 26 and promotion of nanocarrier penetration to tumor tissue 27 .…”

Section: Introductionmentioning

confidence: 99%

A magnetism/laser-auxiliary cascaded drug delivery to pulmonary carcinoma

Lin

Yin

Chen

et al. 2020

Acta Pharmaceutica Sinica B

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Although high-efficiency targeted delivery is investigated for years, the efficiency of tumor targeting seems still a hard core to smash. To overcome this problem, we design a three-step delivery strategy based on streptavidin–biotin interaction with the help of c(RGDfK), magnetic fields and lasers. The ultrasmall superparamagnetic iron oxide nanoparticles (USIONPs) modified with c(RGDfK) and biotin are delivered at step 1, followed by streptavidin and the doxorubicin (Dox) loaded nanosystems conjugated with biotin at steps 2 and 3, respectively. The delivery systems were proved to be efficient on A549 cells. The co-localization of signal for each step revealed the targeting mechanism. The external magnetic field could further amplify the endocytosis of USPIONs based on c(RGDfK), and magnify the uptake distinctions among different test groups. Based on photoacoustic imaging, laser-heating treatment could enhance the permeability of tumor venous blood vessels and change the insufficient blood flow in cancer. Then, it was noticed in vivo that only three-step delivery with laser-heating and magnetic fields realized the highest tumor distribution of nanosystem. Finally, the magnetism/laser-auxiliary cascaded delivery exhibited the best antitumor efficacy. Generally, this study demonstrated the necessity of combining physical, biological and chemical means of targeting.

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Target-activated streptavidin–biotin controlled binding probe

Abstract: The streptavidin–biotin controlled binding probe has several advantages for the detection of enzymes and reactive small molecules, such as minimal background, multiple signal amplification steps, and wide selection of the optimal dyes for detection.

Cited by 22 publications

References 50 publications

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

Boronate-Based Probes for Biological Oxidants: A Novel Class of Molecular Tools for Redox Biology

Imaging and Quantification of Secreted Peroxynitrite at the Cell Surface by a Streptavidin–Biotin‐Controlled Binding Probe

A magnetism/laser-auxiliary cascaded drug delivery to pulmonary carcinoma

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