De novo design of an ultrasensitive fluorogenic probe for aminopeptidase N sensing in living system

Liu, Shi-Yu; Wang, Huiling; Zou, Xiaoting; Nie, Gang

doi:10.1016/j.snb.2022.131828

Cited by 14 publications

(6 citation statements)

References 58 publications

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“…However, on adding different concentrations of chymotrypsin, the fluorescence signal was recovered and reached a platform at a dose range of around 30–50 μg/mL (Figure b), and the required reaction time gradually decreased with increasing enzyme concentration (Figure c); thus, TMBIHF could serve as a turn-on sensor for chymotrypsin, which was also confirmed by the high-performance liquid chromatography (HPLC)-based analyses (Figure S6). Meanwhile, the fluorescence response of TMBIHF toward a low dose range (0.1–1 μg/mL) of chymotrypsin was further tested and showed a good linear relationship (Figure d), from which the limit of detection (LOD = 3σ/ k ) could be determined to be 67 ng/mL using a previously reported method, which was close to those of previously developed probes. , …”

Section: Resultssupporting

confidence: 79%

De Novo Design of a Highly Selective Nonpeptide Fluorogenic Probe for Chymotrypsin Activity Sensing in a Living System

et al. 2022

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Chymotrypsin, an extensively known proteolytic enzyme, plays a substantial role in maintaining physiological functions, including protein digestion, immune response, and tissue repair. To date, intense attention has been focused on the invention of efficient and sensitive chemical tools for chymotrypsin activity measurement. Among them, the “nonpeptide”-based chymotrypsin probe design strategy utilizing the esterase activity of chymotrypsin has been well-developed due to its low cost and high atom-economy feature. However, the ester-bond-based nature of these probes make them possibly vulnerable to esterases and active chemicals. These defects strictly restricted the application of the previously reported probes, especially for imaging in living systems. Therefore, to acquire fluorogenic probes with sufficient stability and specificity for chymotrypsin sensing in a complicated biological environment, a more stable skeleton for nonpeptide-based chymotrypsin probe construction is urgently needed. Herein, a novel nonpeptide-based fluorogenic probe for specific chymotrypsin activity sensing was designed and synthesized by the substitution of an ester-based linker with a heptafluorobutylamide moiety. The acquired probe, named TMBIHF, showed high selectivity toward various enzymes and reactive chemicals, while it retained high sensitivity and catalytic efficiency toward chymotrypsin. Moreover, TMBIHF was successfully applied for monitoring chymotrypsin activity and pancreas development in live zebrafish, specific sensing of exogenous and endogenous chymotrypsin in nude mice, and visualizing chymotrypsin-like activity-dependent cellular apoptosis, thus providing an alternative and reliable way for chymotrypsin-targeted biosensor or prodrug construction.

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Section: Resultssupporting

confidence: 79%

De Novo Design of a Highly Selective Nonpeptide Fluorogenic Probe for Chymotrypsin Activity Sensing in a Living System

et al. 2022

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“…Recently, many APN response fluorescent probes have been developed, their structures are shown in Figure 7. [45][46][47][48][49][50][51][52][53][54][55][56][57][58][59][60][61][62][63] Coumarin and its derivatives are traditional bluefluorescence labels, and many probes are designed with them. The cutting-edge design of these probes primarily focuses on creating an amide substrate through the interaction of L-leucine or L-alanine with a colorimetric or fluorescent reporter, such as β-naphthylamine, p-nitroaniline, or 7-amino-4-methylcoumarin.…”

Section: Fluorescent Probesmentioning

confidence: 99%

“…In 2022, Liu et al Reported a NIR fluorescent Probe 27 activated by APN to meet the goal. [54] In Probe 27, an unnatural amino acid, 2-Aminobutyric acid (Abu), replaced the common natural recognition group, Alanine. Simulated molecular docking verified its efficient binding feature.…”

Section: Fluorescent Probesmentioning

confidence: 99%

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Recent Advances of Aminopeptidases‐Responsive Small‐Molecular Probes for Bioimaging

Xu,

Cui,

et al. 2024

Chemistry An Asian Journal

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Aminopeptidases, enzymes with critical roles in human body, are emerging as vital biomarkers for metabolic processes and diseases. Aberrant aminopeptidase levels are often associated with diseases, particularly cancer. Small‐molecule probes, such as fluorescent, fluorescent/photoacoustics, bioluminescent, and chemiluminescent probes, are essential tools in the study of aminopeptidases‐related diseases. The fluorescent probes provide real‐time insights into protein activities, offering high sensitivity in specific locations, and precise spatiotemporal results. Additionally, photoacoustic probes offer signals that are able to penetrate deeper tissues. Bioluminescent and chemiluminescent probes can enhance in vivo imaging abilities by reducing the background. This comprehensive review is focused on small‐molecule probes that respond to four key aminopeptidases: aminopeptidase N, leucine aminopeptidase, Pyroglutamate aminopeptidase 1, and Prolyl Aminopeptidase, and their utilization in imaging tumors and afflicted regions. In this review, the design strategy of small‐molecule probes, the variety of designs from previous studies, and the opportunities of future bioimaging applications are discussed, serving as a roadmap for future research, sparking innovations in aminopeptidase‐responsive probe development, and enhancing our understanding of these enzymes in disease diagnostics and treatment.

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“…[15][16][17][18][19] Although ratiometric probes activated by specific biological milieus of the tumor region are more sensitive than the "off-on" probes, it is difficult to quantify the intensity with accuracy when applied in clinic. [20][21][22] So far, few color-convertible fluorescent probes achieved by the change of emission wavelength are reported. The color-convertible probes combine the advantages of the ratiometric probes along with dual-color changes, which could enable the differentiation of cancer and normal cells through different colors with human eyes.…”

Section: Introductionmentioning

confidence: 99%

An aminopeptidase N-based color-convertible fluorescent nano-probe for cancer diagnosis

et al. 2023

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De novo design of an ultrasensitive fluorogenic probe for aminopeptidase N sensing in living system

Cited by 14 publications

References 58 publications

De Novo Design of a Highly Selective Nonpeptide Fluorogenic Probe for Chymotrypsin Activity Sensing in a Living System

De Novo Design of a Highly Selective Nonpeptide Fluorogenic Probe for Chymotrypsin Activity Sensing in a Living System

Recent Advances of Aminopeptidases‐Responsive Small‐Molecular Probes for Bioimaging

An aminopeptidase N-based color-convertible fluorescent nano-probe for cancer diagnosis

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