Redox-Mediated Disassembly to Build Activatable Trimodal Probe for Molecular Imaging of Biothiols

Zheng, Mengmeng; Wang, Yuqi; Shi, Hua; Hu, Yuxuan; Feng, Liandong; Luo, Zhiliang; Zhou, Mi; He, Jian; Zhou, Zhengyang; Zhang, Yan; Ye, Deju

doi:10.1021/acsnano.6b05030

Cited by 83 publications

(76 citation statements)

References 76 publications

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“…Different to the aforementioned examples of using biothiols to control probe self-assembly,w eh ave recently reported a redox-mediated disassembly strategy based on the CBT-Cys reaction. [101] In our study,w ee mployed the CBT-Cys reaction to build as mall molecule probe 7 that showed ah igh propensity to form self-assembling nanoparticles under physiological conditions ( Figure 11). After reactionw ith reductive biothiols, the disulfide in probe 7 was cleaved and the nanoparticles were disassembled, affording amino firefly luciferin analogue 8 with increased fluorescence emission while reduced 1 H-MRI contrast.…”

Section: Imaging Of the Redox Environmentmentioning

confidence: 73%

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Firefly Luciferin‐Inspired Biocompatible Chemistry for Protein Labeling and In Vivo Imaging

Wang

Luo

et al. 2017

Chemistry A European J

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Biocompatible reactions have emerged as versatile tools to build various molecular imaging probes that hold great promise for the detection of biological processes in vitro and/or in vivo. In this Minireview, we describe the recent advances in the development of a firefly luciferin-inspired biocompatible reaction between cyanobenzothiazole (CBT) and cysteine (Cys), and highlight its versatility to label proteins and build multimodality molecular imaging probes. The review starts from the general introduction of biocompatible reactions, which is followed by briefly describing the development of the firefly luciferin-inspired biocompatible chemistry. We then discuss its applications for the specific protein labeling and for the development of multimodality imaging probes (fluorescence, bioluminescence, MRI, PET, photoacoustic, etc.) that enable high sensitivity and spatial resolution imaging of redox environment, furin and caspase-3/7 activity in living cells and mice. Finally, we offer the conclusions and our perspective on the various and potential applications of this reaction. We hope that this review will contribute to the research of biocompatible reactions for their versatile applications in protein labeling and molecular imaging.

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Section: Imaging Of the Redox Environmentmentioning

confidence: 73%

“…The chemical structure of redox-activatable trimodal imaging probe 7 and the proposed chemical conversion in reducinge nvironment. Reprinted with persmission from reference[101].Chem. Eur.J.2018, 24,5707 -5722 www.chemeurj.org 3.3.…”

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confidence: 99%

Firefly Luciferin‐Inspired Biocompatible Chemistry for Protein Labeling and In Vivo Imaging

Wang

Luo

et al. 2017

Chemistry A European J

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“…To date, with the development of hybrid instrument technology for multimodal imaging, great effort has been put in the development of probes containing multimodal imaging signals . Although a variety of multifunctional NPs have been developed to allow multimodality imaging based on their easy surface functionalization,[5,18a,19] intracellular self‐assembly strategies in use to fabricate nanoprobes in situ for multimodality imaging are not many . This motivates us to design new, “smart,” sophisticated precursors to meet this need.…”

Section: Discussionmentioning

confidence: 99%

Intracellular Self‐Assembly of Nanoprobes for Molecular Imaging

Hai

Liang

2018

Adv. Biosys.

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being conjugated with targeting warheads and loaded with a large number of diverse imaging agents, the multifunctional NPs are fabricated for multimodal imaging with enhanced imaging sensitivity and selectivity. Second, the uptake of NPs with appropriate size by the kidney (renal clearance) and reticular endothelial system of the liver is lower. Therefore, increased circulation time and more chances to reach the target site are achieved by NPs than small molecules. [6] Third, due to the enhanced permeability and retention effect induced by the fenestrated vasculature structures, NPs are more efficiently accumulated at the vascular angiogenic sites like tumors. [7] Fourth, once uptaken by the cells (or tissues), NPs always have longer retention time (i.e., aggregation/assembly-induced retention effect) in the cells (or the bodies) than small molecular probes, which is good for molecular imaging. [8] Nevertheless, NPs always face the problems of reproducibility and quantification, difficulty in their fabrication, as well as cell membrane translocation when applied for molecular imaging. [9] Luckily, a "smart" intracellular self-assembly strategy emerged at the right moment to overcome the above limitations of NPs, which starts with a small molecular probe to quickly translocate cell membrane but ends up with nanostructures (nanoparticles or nanofibers) with amplified imaging signals and longer retention time at the targeted sites. Intracellular Self-Assembly of NanoprobesSelf-assembly is a prevalent and important process in nature, for example, the 25 nm wide microtubules to govern cellular mitosis, 5-6 nm thick cell membranes to maintain cell integrity, and 2 nm wide DNA double strand to store genetic information are the typical presentations of molecular self-assembly in biological systems. [10] Molecular self-assembly is a "bottomup" fabrication process in which small building blocks selfassemble through various noncovalent interactions (e.g., π-π stacking, hydrogen bonding, metal coordination, host-guest interaction, electrostatic, hydrophobic, and van der Waals interactions) to build up highly ordered nanostructures. [11] Up to date, lots of self-assembly systems have been developed to ex situ or in situ fabricate biocompatible nanomaterials for biomedical applications. [8] Compared with ex situ self-assembly, in situ self-assembly (e.g., intracellular self-assembly) in which small molecules transform into nanoprobes under intelligent Molecular imaging can be roughly defined as the characterization and measurement of biological processes at the molecular and cellular level. Nanoprobes (NPs) are advantageous over small molecular probes for molecular imaging in the amount of signaling molecule as well as signal intensity. Compared with ex situ self-assembling strategies for NP fabrication, those intracellular intelligent self-assembling strategies that use small molecules to prepare NPs in situ with amplified signals and longer retention time are more efficient and attractive. This review summarizes recent adva...

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“…In particular, fluorescent probes have attracted much attention due to their advantages of real‐time imaging and high spatial resolution. It also has extensive applications in molecular imaging (Qiu et al., ; Shi et al., ; Zheng et al., ), disease diagnosis (Chen et al., ; Luo et al., ), and drug development (Liu, Bajjuri, Liu, & Sinha, ; Qi et al., ). Among them, enzyme‐activated fluorescent probes have become the focus of recent research studies, because they can provide accurate information about the enzyme activity and show potential in disease diagnosis (Chen et al., ; Hai et al., ; Luo et al., ; Shaulov‐Rotem et al., ).…”

Section: Introductionmentioning

confidence: 99%

A protease‐responsive fluorescent probe for sensitive imaging of legumain activity in living tumor cells

Liu

et al. 2019

Chem Biol Drug Des

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Legumain, a lysosomal cysteine protease, is critical for pathological progression and has been found to play an important role in the occurrence and development of several cancers. However, its biological functions remain few recognized. To further understand the role of legumain activity in tumor progression, a legumain proteaseresponsive fluorescent probe was developed in the present study. The probe 1 was synthesized by conjugating an aminoluciferin fluorophore with an alanine-alanineasparagine (AAN) peptide sequence. The successful synthesis of probe 1 was validated by NMR and MS spectra as well as HPLC analysis. The probe 1 was non-toxic and exhibited great stability in the physiological solutions. More importantly, compared with the aminoluciferin fluorophore, the peptide conjugation may dramatically increase the targeting specificity. Probe 1 was able to effectively detect the legumain activity in living HCT116 cells through fluorescence imaging. All these results implied that probe 1 could act as a promising fluorescent probe specialized for the monitoring of legumain activity in living cells. K E Y W O R D Scancers, fluorescence imaging, HCT116 cells, legumain, targeting specificity | 1495 LI et aL.

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Redox-Mediated Disassembly to Build Activatable Trimodal Probe for Molecular Imaging of Biothiols

Cited by 83 publications

References 76 publications

Firefly Luciferin‐Inspired Biocompatible Chemistry for Protein Labeling and In Vivo Imaging

Firefly Luciferin‐Inspired Biocompatible Chemistry for Protein Labeling and In Vivo Imaging

Intracellular Self‐Assembly of Nanoprobes for Molecular Imaging

A protease‐responsive fluorescent probe for sensitive imaging of legumain activity in living tumor cells

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