A bestatin-based fluorescent probe for aminopeptidase N cell imaging

Chen, Hui; Wang, Hui; Qin, Xiaojun; Chen, Chen; Feng, Lei; Chen, Laizhong; Du, Lüpei; Li, Minyong

doi:10.1016/j.cclet.2015.01.023

Cited by 13 publications

(7 citation statements)

References 24 publications

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“…The newly prepared probe (probe 75) introduced amide group weakened the ICT effect, causing the fluorescence emission wavelength to blue shift, which was used for cell imaging [198]. Subsequently, in order to improve the targetability of the probes, a inhibitor type-based probe was prepared by integrating Bestatin with naphthimide (probe 76) [199], which has the same inhibitory ability as Bestatin and has a good imaging effect in cells.…”

Section: Progress In Fluorescent Probes Of Ggtmentioning

confidence: 99%

Review on the recent progress in the development of fluorescent probes targeting enzymes

Rajapaksha

Guo

et al. 2021

Methods Appl. Fluoresc.

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Enzymes are very important for biological processes in a living being, performing similar or multiple tasks in and out of cells, tissues and other organisms at a particular location. The abnormal activity of particular enzyme usually caused serious diseases such as Alzheimer’s disease, Parkinson’s disease, cancers, diabetes, cardiovascular diseases, arthritis etc. Hence, nondestructive and real-time visualization for certain enzyme is very important for understanding the biological issues, as well as the drug administration and drug metabolism. Fluorescent cellular probe-based enzyme detection in vitro and in vivo has become broad interest for human disease diagnostics and therapeutics. This review highlights the recent findings and designs of highly sensitive and selective fluorescent cellular probes targeting enzymes for quantitative analysis and bioimaging.

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Section: Progress In Fluorescent Probes Of Ggtmentioning

confidence: 99%

Review on the recent progress in the development of fluorescent probes targeting enzymes

Rajapaksha

Guo

et al. 2021

Methods Appl. Fluoresc.

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“…A probe for APN that was based on a bestatin (267, Figure 22) scaffold and included a fluorophore, biotin, and an alkyne moiety (for click-chemistry applications) has been described, but imaging results were not reported (Harbut et al 2008). A probe based on bestatin (267, Figure 22) linked to 4-amino-1,8-naphthalimide (Bes-Green) was shown to inhibit APN and to image APN in ovarian clear cell carcinoma (ES-2) cells (Chen et al 2015). Cyanine dye Cy 5.5 linked to a hydroxamic acid-based APN inhibitor (Cy 5.5-23) has been reported as an imaging probe (Hahnenkamp et al 2013;Chen et al 2013a); Cy 5.5-23 binds to APN-positive BT-549 breast cancer cells but not to APN-negative BT-20 cells, as shown by fluorescence microscopy.…”

Section: Substrates Apn Catalyzes the Hydrolysis Of N-ter-mentioning

confidence: 99%

The mercapturic acid pathway

Hanna

Anders

2019

Critical Reviews in Toxicology

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The mercapturic acid pathway is a major route for the biotransformation of xenobiotic and endobiotic electrophilic compounds and their metabolites. Mercapturic acids (N-acetyl-L-cysteine S-conjugates) are formed by the sequential action of the glutathione transferases, c-glutamyltransferases, dipeptidases, and cysteine S-conjugate N-acetyltransferase to yield glutathione S-conjugates, L-cysteinylglycine S-conjugates, L-cysteine S-conjugates, and mercapturic acids; these metabolites constitute a "mercapturomic" profile. Aminoacylases catalyze the hydrolysis of mercapturic acids to form cysteine S-conjugates. Several renal transport systems facilitate the urinary elimination of mercapturic acids; urinary mercapturic acids may serve as biomarkers for exposure to chemicals. Although mercapturic acid formation and elimination is a detoxication reaction, L-cysteine S-conjugates may undergo bioactivation by cysteine Sconjugate b-lyase. Moreover, some L-cysteine S-conjugates, particularly L-cysteinyl-leukotrienes, exert significant pathophysiological effects. Finally, some enzymes of the mercapturic acid pathway are described as the so-called "moonlighting proteins," catalytic proteins that exert multiple biochemical or biophysical functions apart from catalysis.

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“…It is also approved in Japan as an adjuvant drug for treating patients with acute nonlymphocytic leukemia [ 77 , 78 ]. Recently, a green fluorescent bestatin conjugate was prepared and used for fluorescence imaging of ovarian cancer [ 79 ]. A potential concern with this approach is low specificity for APN since bestatin is known to target twelve different aminopeptidases [ 80 ].…”

Section: Nonreactive Apn-targeting Agentsmentioning

confidence: 99%

Molecular Imaging of Aminopeptidase N in Cancer and Angiogenesis

Schreiber

Smith

2018

Contrast Media & Molecular Imaging

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This review focuses on recent advances in the molecular imaging of aminopeptidase N (APN, also known as CD13), a zinc metalloenzyme that cleaves N-terminal neutral amino acids. It is overexpressed in multiple cancer types and also on the surface of vasculature undergoing angiogenesis, making it a promising target for molecular imaging and targeted therapy. Molecular imaging probes for APN are divided into two large subgroups: reactive and nonreactive. The structures of the reactive probes (substrates) contain a reporter group that is cleaved and released by the APN enzyme. The nonreactive probes are not cleaved by the enzyme and contain an antibody, peptide, or nonpeptide for targeting the enzyme exterior or active site. Multivalent homotopic probes utilize multiple copies of the same targeting unit, whereas multivalent heterotopic molecular probes are equipped with different targeting units for different receptors. Several recent preclinical cancer imaging studies have shown that multivalent APN probes exhibit enhanced tumor specificity and accumulation compared to monovalent analogues. The few studies that have evaluated APN-specific probes for imaging angiogenesis have focused on cardiac regeneration. These promising results suggest that APN imaging can be expanded to detect and monitor other diseases that are associated with angiogenesis.

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A bestatin-based fluorescent probe for aminopeptidase N cell imaging

Cited by 13 publications

References 24 publications

Review on the recent progress in the development of fluorescent probes targeting enzymes

Review on the recent progress in the development of fluorescent probes targeting enzymes

The mercapturic acid pathway

Molecular Imaging of Aminopeptidase N in Cancer and Angiogenesis

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