Phosphorylated lipid-conjugated oligonucleotide selectively anchors on cell membranes with high alkaline phosphatase expression

Cheng, Jinghui; He, Jiabei; Zou, Jianmei; Xuan, Wenjing; Fu, Ting; Wang, Ruowen; Tan, Weihong

doi:10.1038/s41467-019-10639-6

Cited by 83 publications

(52 citation statements)

References 28 publications

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“…cell membrane-targeted bioimaging | precipitating fluorochrome | antidiffusion probe | long-term in situ imaging | in vivo bioimaging T he cell membrane is a glycerophospholipid bilayer that contains a variety of biomolecules, notably, lipids, carbohydrates, and proteins, which play indispensable roles in both pathological and physiological processes ranging from cell signaling to apoptosis and extracellular matrix processing (1)(2)(3)(4)(5). Therefore, bioimaging of membrane-associated biomolecules is significant for basic biological research and disease diagnosis (6,7).…”

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confidence: 99%

A de novo strategy to develop NIR precipitating fluorochrome for long-term in situ cell membrane bioimaging

Lyu

Huang

et al. 2021

Proc. Natl. Acad. Sci. U.S.A.

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Cell membrane–targeted bioimaging is a prerequisite for studying the roles of membrane-associated biomolecules in various physiological and pathological processes. However, long-term in situ bioimaging on the cell membrane with conventional fluorescent probes leads to diffusion into cells from the membrane surface. Therefore, we herein proposed a de novo strategy to construct an antidiffusion probe by integrating a fluorochrome characterized by strong hydrophobicity and low lipophilicity, with an enzyme substrate to meet this challenge. This precipitating fluorochrome HYPQ was designed by conjugating the traditionally strong hydrophobic solid-state fluorochrome 6-chloro–2-(2-hydroxyphenyl) quinazolin-4(3H)-one (HPQ) with a 2-(2-methyl–4H-chromen–4-ylidene) malononitrile group to obtain closer stacking to lower lipophilicity and elongate emission to the far-red to near-infrared wavelength. As proof-of-concept, the membrane-associated enzyme γ-glutamyltranspeptidase (GGT) was selected as a model enzyme to design the antidiffusion probe HYPQG. Then, benefiting from the precipitating and stable signal properties of HYPQ, in situ imaging of GGT on the membrane was successfully realized. Moreover, after HYPQG was activated by GGT, the fluorescence signal on the cell membrane remained unchanged, with incubation time even extending to 6 h, which is significant for in situ monitoring of enzymatic activity. In vivo testing subsequently showed that the tumor region could be accurately defined by this probe after long-term in situ imaging of tumor-bearing mice. The excellent performance of HYPQ indicates that it may be an ideal alternative for constructing universal antidiffusion fluorescent probes, potentially providing an efficient tool for accurate imaging-guided surgery in the future.

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confidence: 99%

A de novo strategy to develop NIR precipitating fluorochrome for long-term in situ cell membrane bioimaging

Lyu

Huang

et al. 2021

Proc. Natl. Acad. Sci. U.S.A.

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“…modified with phosphate group were further designed to improve their water solubilities and endow them with enzymatic responsiveness, as the phosphate group is the substrate of alkaline phosphatase (ALP) that plays a significant role in cell signaling pathway and has become an important biomarker in cancer diagnosis. [50][51][52][53] The obtained E/Z-TPAN-OM isomers retained the same stereo-structure as their individual precursor and displayed different fluorescence quantum yields. As the E/Z-TPAN-POH and their hydrolysis product, E/Z-TPAN-OH (Figure 7a), eluted out with different time scales, the ALP-catalyzed hydrolysis of E/Z-TPAN-POH could therefore be quantitatively monitored by HPLC.…”

Section: As the Cellular Uptake Of E/z-tpan-om And E/z-tpan-oh Was Limited E/z-tpan-pohmentioning

confidence: 91%

AIE Stereoisomers with Huge Differences in Luminescence Behavior and Biomedical Activity

He¹,

Kwok²,

Lam³

et al. 2020

Preprint

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Stereoisomers that differ only in spatial orientation of their atoms could exhibit distinctive properties and have attracted immense interest in drug development and material science. Herein, a series of AIE-featured stereoisomers with pronounced difference in luminescent and biomedical activities were efficiently synthesized and easily purified. One of the isomers in the E/Z pair is emissive with high fluorescence quantum yield at room temperature, while the other one is nearly non-emissive. As the isomers could transform between each other under UV irradiation, the light-up cell imaging was successfully demonstrated using the non-emissive isomer as a turn-on probe via isomerization process. Analysis of crystal packing patterns illustrated that the contrasts in void space possibly caused the difference in molecular motion and thus led to their distinct luminescence properties. Further, the E/Z isomers displayed remarkable difference in enzymatic conversion rates and cellular toxicities for several cancer cell lines. The distinctive luminescence properties of the isomeric pair provided a powerful tool to image those divergencies in biomedical activity, holding great potential for visualizable drug screening and development.

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“…[ 124,125 ] Among these strategies, DNA nanostructure‐based method have the unique advantage to mediate protein interaction on the membrane. [ 108,111,126–128 ] For example, LaBean and co‐workers found that the transforming growth factor β (TGF β ) signaling pathway can be sensitized by adding functionalized DNA nanostructures in mouse mammary epithelial cell line (NMuMG cells). [ 129 ] In 2014, Teixeira and co‐workers developed a “nanocalipers,” a DNA origami nanostructure, modified with ligands at well‐defined positions to spatially control the membrane receptor function.…”

Section: Application Of Dna Nanostructures In Cell Membrane Engineeringmentioning

confidence: 99%

Recent Advances of DNA Nanostructure‐Based Cell Membrane Engineering

Feng

Sun

et al. 2021

Adv Healthcare Materials

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Materials that can regulate the composition and structure of the cell membrane to fabricate engineered cells with defined functions are in high demand. Compared with other biomolecules, DNA has unique advantages in cell membrane engineering due to its excellent programmability and biocompatibility. Especially, the near‐atomic scale precision of DNA nanostructures facilitates the investigation of structure–property relations on the cell membrane. In this review, first the state of the art of functional DNA nanostructures is summarized, and then the overview of the use of DNA nanostructures to engineer the cell membrane is presented. Subsequently, applications of DNA nanostructures in modifying cell membrane morphology, controlling ions transport, and synthesizing high precise liposomes are highlighted. Finally, the challenges and outlook on using DNA nanostructures for cell membrane engineering are discussed.

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Phosphorylated lipid-conjugated oligonucleotide selectively anchors on cell membranes with high alkaline phosphatase expression

Cited by 83 publications

References 28 publications

A de novo strategy to develop NIR precipitating fluorochrome for long-term in situ cell membrane bioimaging

A de novo strategy to develop NIR precipitating fluorochrome for long-term in situ cell membrane bioimaging

AIE Stereoisomers with Huge Differences in Luminescence Behavior and Biomedical Activity

Recent Advances of DNA Nanostructure‐Based Cell Membrane Engineering

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