Intracellular fluorogenic supramolecular assemblies for self-reporting bioorthogonal prodrug activation

Zhao, Yan; Yao, Qingxin; Chen, Jiali; Zhang, Ruijia; Song, Jialei; Gao, Yuan

doi:10.1039/d2bm00972b

Cited by 6 publications

(2 citation statements)

References 47 publications

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“…In 2022, Gao et al 79 constructed a self-reporting bioorthogonal prodrug activation system using fluorescence emission to interpret prodrug activation events. In designed reactive oxygen species (ROS)-instructed supramolecular assemblies, the bioorthogonal reaction handle of tetrazine had a dual role as a fluorescence quencher and prodrug activator.…”

Section: Supramolecular-interaction-induced Fluorogenic Reactions And...mentioning

confidence: 99%

Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells

Chen

Jiang

Hao

et al. 2023

Chemical & Biomedical Imaging

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Section: Supramolecular-interaction-induced Fluorogenic Reactions And...mentioning

confidence: 99%

Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells

Chen

Jiang

Hao

et al. 2023

Chemical & Biomedical Imaging

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“…For this purpose, N -azidoacetylmannosamine (Ac 4 ManNAz) can utilize the cell’s synthetic machinery to introduce azide groups on the cell membrane surface through the sialic acid biosynthetic pathway. , Regardless of tumor type or subtype, such azide reporter groups generate many target molecules that can serve as new active target sites to react with external chemical groups [such as dibenzoazacyclooctyne (DBCO), acetylene, and phosphine] . Benefiting from the typically excessive expression of sialic acid on the surface of tumor cells, this strategy can be used to label tumor cells in the areas of cell imaging, , drug delivery, , etc. Hence, using the bioorthogonal chemistry, a novel heterogeneous CTCs capture method independent of immunoaffinity recognition can be constructed, which can ignore the phenotypic changes of heterogeneous CTCs and create a highly biocompatible and effective pathway for the capture of heterogeneous CTCs.…”

Section: Introductionmentioning

confidence: 99%

Engineered Leukocyte Biomimetic Colorimetric Sensor Enables High-Efficient Detection of Tumor Cells Based on Bioorthogonal Chemistry

Li,

Jia,

Zhu

et al. 2024

ACS Appl. Mater. Interfaces

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Accurate detection of heterogeneous circulating tumor cells (CTCs) is critical as they can make tumor cells more aggressive, drug-resistant, and metastasizing. Although the leukocyte membrane coating strategy is promising in meeting the challenge of detecting heterogeneous CTCs due to its inherent antiadhesive properties, it is still limited by the reduction or loss of expression of known markers. Bioorthogonal glycol-metabolic engineering is expected to break down this barrier by feeding the cells with sugar derivatives with a unique functional group to establish artificial targets on the surface of tumor cells. Herein, an engineered leukocyte biomimetic colorimetric sensor was accordingly fabricated for high-efficient detection of heterogeneous CTCs. Compared with conventional leukocyte membrane coating, the sensor could covalently bound to the heterogeneous CTCs models fed with Ac 4 ManNAz in vitro through the synergy of bioorthogonal chemistry and metabolic glycoengineering, ignoring the phenotypic changes of heterogeneous CTCs. Meanwhile, a sandwich structure composed of leukocyte biomimetic layer/CTCs/MoS 2 nanosheet was formed for visual detection of HeLa cells as low as 10 cells mL −1 . Overall, this approach can overcome the dependence of conventional cell membrane biomimetic technology on specific cell phenotypes and provide a new viewpoint to highly efficiently detect heterogeneous CTCs.

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A Concerted Enzymatic and Bioorthogonal Approach for Extra‐ and Intracellular Activation of Environment‐Sensitive Ruthenium(II)‐Based Imaging Probes and Photosensitizers

et al. 2023

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In this article, we report a novel targeting strategy involving the combination of an enzymeinstructed self-assembly (EISA) moiety and a strained cycloalkyne to generate large accumulation of bioorthogonal sites in cancer cells. These bioorthogonal sites can serve as activation triggers in different regions for transition metal-based probes, which are new ruthenium(II) complexes carrying a tetrazine unit for controllable phosphorescence and singlet oxygen generation. Importantly, the environment-sensitive emission of the complexes can be further enhanced in the hydrophobic regions offered by the large supramolecular assemblies, which is highly advantageous to biological imaging.Additionally, the (photo)cytotoxicity of the large supramolecular assemblies containing the complexes was investigated, and the results illustrate that cellular localization (extracellular and intracellular) imposes a profound impact on the efficiencies of photosensitizers.

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Intracellular fluorogenic supramolecular assemblies for self-reporting bioorthogonal prodrug activation

Abstract: Visual drug delivery system (DDS) is in urgent need for precision medicine. DDS mediated bioorthogonal prodrug activation strategies have showed remarkable advantages in enlarging therapeutic index via alleviation of adverse...

Cited by 6 publications

References 47 publications

Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells

Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells

Engineered Leukocyte Biomimetic Colorimetric Sensor Enables High-Efficient Detection of Tumor Cells Based on Bioorthogonal Chemistry

A Concerted Enzymatic and Bioorthogonal Approach for Extra‐ and Intracellular Activation of Environment‐Sensitive Ruthenium(II)‐Based Imaging Probes and Photosensitizers

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