A molecular-logic gate for COX-2 and NAT based on conformational and structural changes: visualizing the progression of liver disease

Chen, Yuehua; Wang, Yuzhu; Yang, Yonggang; Li, Yuhuan; Yafu, Wang; Wang, Ge; James, Tony D.; Xuan, Xiaopeng; Zhang, Hua; Liu, Yufang

doi:10.1039/d0sc00574f

Cited by 18 publications

(3 citation statements)

References 34 publications

(36 reference statements)

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“…NaBu is also a wellknown inducer of GGT activity on the cell membrane (52,53). At the same time, it has been confirmed that NaBu might improve chemotherapy effect as a differentiating agent (49)(50)(51)(52). Therefore, considering the imaging advantage of HYPQG for in situ visualization of GGT on the cell membrane, we further applied HYPQG to study the relationship between GGT activity and NaBu stimulation in HepG2 cells.…”

Section: Resultsmentioning

confidence: 98%

“…The docking simulation results showed that the reaction sites of probe HYPQG and AMCG had obvious hydrogen bond interactions with the active catalytic site of GGT (SI Appendix, Fig. S16A) (49,50). However, the HTPQG failed to dock into the ligand-binding pocket of GGT to form hydrogen bond interactions due to the large steric hindrance, which further caused the bad reactivity (SI Appendix, Fig.…”

Section: Resultsmentioning

confidence: 99%

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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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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

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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“…Therefore, monitoring the activity of biomacromolecules is essential for understanding the progression of diseases including diabetes, cardiovascular disease, and cancer. 172–175…”

Section: Pet-based Fluorescent Probes For Biomacromoleculesmentioning

confidence: 99%

Photoinduced electron transfer (PeT) based fluorescent probes for cellular imaging and disease therapy

et al. 2023

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De Novo Design of Near‐Infrared Fluorescent Agents Activated by Peroxynitrite and Glutathione‐Responsive Imaging for Diabetic Liver Disease

Jiang,

Zhang,

Liu

et al. 2023

Adv Healthcare Materials

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Diabetes and its complications, such as diabetes liver disease, have become a major problem puzzling people's health. The detection of redox states in its pathological process can effectively help us gain a deeper understanding of the disease. The pair of oxidation‐reduction substances peroxynitrite (ONOO−) and glutathione (GSH) have been considered to be closely related to their occurrence and development. Thus, direct visualization of ONOO− and GSH in diabetes liver disease is critical to evaluate the disease at the molecular level. Herein, we prepared two activatable agents NTCF‐ONOO− and NTCF‐GSH for selectively detecting ONOO− and GSH through protection and deprotection strategies based on hydroxyl and amino groups of near‐infrared fluorophore. Fluorescence imaging of exogenous and endogenous ONOO− and GSH changes in living cells and in vivo was observed. Importantly, we visualized the ONOO− and GSH level in the diabetes liver disease cellular model and explored the possible redox imbalance mechanism related to NAD+ and NADH in this process. Moreover, these probes can sensitively recognize ONOO− and GSH in the process of oxidative stress resulting from by streptozotocin and streptozotocin/acetaminophen‐induced complex diabetic liver disease in vivo. In addition, they can be applied for monitoring the clinical serum sample related with diabetic patients.This article is protected by copyright. All rights reserved

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A molecular-logic gate for COX-2 and NAT based on conformational and structural changes: visualizing the progression of liver disease

Abstract: Lighting up the relevant lesion boundaries during operations is vital for guiding the effective resection of hepatopathic tissue.

Cited by 18 publications

References 34 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

Photoinduced electron transfer (PeT) based fluorescent probes for cellular imaging and disease therapy

De Novo Design of Near‐Infrared Fluorescent Agents Activated by Peroxynitrite and Glutathione‐Responsive Imaging for Diabetic Liver Disease

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