Development of Small-Molecule Fluorescent Probes Targeting Enzymes

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2022 Jul 27

PMID 35889374

Authors

Yuan-Xiang Li

Dong-Tai Xie

Ya-Xi Yang

Zhao Chen

Wu-Yingzheng Guo

Wen-Chao Yang

Affiliations

Soon will be listed here.

Abstract

As biological catalysts, enzymes are vital in controlling numerous metabolic reactions. The regulation of enzymes in living cells and the amount present are indicators of the metabolic status of cell, whether in normal condition or disease. The small-molecule fluorescent probes are of interest because of their high sensitivity and selectivity, as well as their potential for automated detection. Fluorescent probes have been useful in targeting particular enzymes of interest such as proteases and caspases. However, it is difficult to develop an ideal fluorescent probe for versatile purposes. In the future, the design and synthesis of enzyme-targeting fluorescent probes will focus more on improving the selectivity, sensitivity, penetration ability and to couple the fluorescent probes with other available imaging molecules/technologies.

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References

Lee W, Ham W, Kim J . Roles of NAD(P)H:quinone Oxidoreductase 1 in Diverse Diseases. Life (Basel). 2021; 11(12). PMC: 8703842. DOI: 10.3390/life11121301. View

Liu H, Chen L, Xu C, Li Z, Zhang H, Zhang X . Recent progresses in small-molecule enzymatic fluorescent probes for cancer imaging. Chem Soc Rev. 2018; 47(18):7140-7180. DOI: 10.1039/c7cs00862g. View

Dai N, Kool E . Fluorescent DNA-based enzyme sensors. Chem Soc Rev. 2011; 40(12):5756-70. PMC: 5575859. DOI: 10.1039/c0cs00162g. View

Sakamoto S, Komatsu T, Watanabe R, Zhang Y, Inoue T, Kawaguchi M . Multiplexed single-molecule enzyme activity analysis for counting disease-related proteins in biological samples. Sci Adv. 2020; 6(11):eaay0888. PMC: 7065886. DOI: 10.1126/sciadv.aay0888. View

Tang C, Du Y, Liang Q, Cheng Z, Tian J . Development of a Novel Histone Deacetylase-Targeted Near-Infrared Probe for Hepatocellular Carcinoma Imaging and Fluorescence Image-Guided Surgery. Mol Imaging Biol. 2019; 22(3):476-485. DOI: 10.1007/s11307-019-01389-4. View

Lampe J, Fernandez C, Nath A, Atkins W . Nile Red is a fluorescent allosteric substrate of cytochrome P450 3A4. Biochemistry. 2007; 47(2):509-16. DOI: 10.1021/bi7013807. View

Widen J, Tholen M, Yim J, Antaris A, Casey K, Rogalla S . AND-gate contrast agents for enhanced fluorescence-guided surgery. Nat Biomed Eng. 2020; 5(3):264-277. PMC: 7969380. DOI: 10.1038/s41551-020-00616-6. View

Arrowsmith C, Audia J, Austin C, Baell J, Bennett J, Blagg J . The promise and peril of chemical probes. Nat Chem Biol. 2015; 11(8):536-41. PMC: 4706458. DOI: 10.1038/nchembio.1867. View

Yagishita A, Ueno T, Tsuchihara K, Urano Y . Amino BODIPY-Based Blue Fluorescent Probes for Aldehyde Dehydrogenase 1-Expressing Cells. Bioconjug Chem. 2021; 32(2):234-238. DOI: 10.1021/acs.bioconjchem.0c00565. View

10.

Isaacson K, Jensen M, Subrahmanyam N, Ghandehari H . Matrix-metalloproteinases as targets for controlled delivery in cancer: An analysis of upregulation and expression. J Control Release. 2017; 259:62-75. PMC: 5537048. DOI: 10.1016/j.jconrel.2017.01.034. View

11.

Coon M . Omega oxygenases: nonheme-iron enzymes and P450 cytochromes. Biochem Biophys Res Commun. 2005; 338(1):378-85. DOI: 10.1016/j.bbrc.2005.08.169. View

12.

Sabanayagam C, Eid J, Meller A . Long time scale blinking kinetics of cyanine fluorophores conjugated to DNA and its effect on Förster resonance energy transfer. J Chem Phys. 2005; 123(22):224708. DOI: 10.1063/1.2136157. View

13.

Liu S, Xiong H, Yang J, Yang S, Li Y, Yang W . Discovery of Butyrylcholinesterase-Activated Near-Infrared Fluorogenic Probe for Live-Cell and In Vivo Imaging. ACS Sens. 2018; 3(10):2118-2128. DOI: 10.1021/acssensors.8b00697. View

14.

Santucci A, Bernardini G, Braconi D, Petricci E, Manetti F . 4-Hydroxyphenylpyruvate Dioxygenase and Its Inhibition in Plants and Animals: Small Molecules as Herbicides and Agents for the Treatment of Human Inherited Diseases. J Med Chem. 2017; 60(10):4101-4125. DOI: 10.1021/acs.jmedchem.6b01395. View

15.

Myochin T, Hanaoka K, Iwaki S, Ueno T, Komatsu T, Terai T . Development of a series of near-infrared dark quenchers based on Si-rhodamines and their application to fluorescent probes. J Am Chem Soc. 2015; 137(14):4759-65. DOI: 10.1021/jacs.5b00246. View

16.

Yang Y, Qi F, Qian Y, Bao X, Zhang H, Ma B . Developing Push-Pull Hydroxylphenylpolyenylpyridinium Chromophores as Ratiometric Two-Photon Fluorescent Probes for Cellular and Intravital Imaging of Mitochondrial NQO1. Anal Chem. 2021; 93(4):2385-2393. DOI: 10.1021/acs.analchem.0c04279. View

17.

Rajapaksha A, Fu Y, Guo W, Liu S, Li Z, Xiong C . Review on the recent progress in the development of fluorescent probes targeting enzymes. Methods Appl Fluoresc. 2021; 9(3). DOI: 10.1088/2050-6120/abf988. View

18.

Liu S, Qu R, Li R, Yan Y, Sun Y, Yang W . An Activity-Based Fluorogenic Probe Enables Cellular and in Vivo Profiling of Carboxylesterase Isozymes. Anal Chem. 2020; 92(13):9205-9213. DOI: 10.1021/acs.analchem.0c01554. View

19.

Gao J, Yin X, Li M, Chen J, Tan J, Zhao Z . Rational design of fluorescent probes for targeted in vivo nitroreductase visualization. Org Biomol Chem. 2020; 18(25):4744-4747. DOI: 10.1039/d0ob00082e. View

20.

Li H, Yao Q, Sun W, Shao K, Lu Y, Chung J . Aminopeptidase N Activatable Fluorescent Probe for Tracking Metastatic Cancer and Image-Guided Surgery via Spraying. J Am Chem Soc. 2020; 142(13):6381-6389. DOI: 10.1021/jacs.0c01365. View