Design and Synthesis of a Novel Photoaffinity Probe for Labelling EGF Receptor Tyrosine Kinases

Overview

Journal J Enzyme Inhib Med Chem

Specialty Biochemistry

Date 2017 Jul 19

PMID 28718674

Citations 1

Authors

You-Guang Zheng

Xiao-Qing Wu

Jun Su

Ping Jiang

Liang Xu

Jian Gao

Bin Cai

Min Ji

Affiliations

Soon will be listed here.

Abstract

The epidermal growth factor receptor (EGFR) and HER2 are two important tyrosine kinases that play crucial roles in signal transduction pathways that regulate numerous cellular functions including proliferation, differentiation, migration, and angiogenesis. In the past 20 years, many proteomic methods have emerged as powerful methods to evaluate proteins in biological processes and human disease states. Among them, activity-based protein profiling (ABPP) is one useful approach for the functional analysis of proteins. In this study, a novel photoaffinity probe 11 was designed and synthesised to assess the target profiling of the reactive group in the photoaffinity probe 11. Biological evaluation was performed, and the results showed that the novel photoaffinity probe binds to EGFR and HER2 proteins and it hits targets by the reactive group.

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References

Evans M, Cravatt B . Mechanism-based profiling of enzyme families. Chem Rev. 2006; 106(8):3279-301. DOI: 10.1021/cr050288g. View

Wu X, Li M, Qu Y, Tang W, Zheng Y, Lian J . Design and synthesis of novel Gefitinib analogues with improved anti-tumor activity. Bioorg Med Chem. 2010; 18(11):3812-22. PMC: 2890262. DOI: 10.1016/j.bmc.2010.04.046. View

Tan L, Akahane K, McNally R, Reyskens K, Ficarro S, Liu S . Development of Selective Covalent Janus Kinase 3 Inhibitors. J Med Chem. 2015; 58(16):6589-606. PMC: 4777322. DOI: 10.1021/acs.jmedchem.5b00710. View

Kaschani F, Nickel S, Pandey B, Cravatt B, Kaiser M, van der Hoorn R . Selective inhibition of plant serine hydrolases by agrochemicals revealed by competitive ABPP. Bioorg Med Chem. 2011; 20(2):597-600. PMC: 3634566. DOI: 10.1016/j.bmc.2011.06.040. View

Sadaghiani A, Verhelst S, Bogyo M . Tagging and detection strategies for activity-based proteomics. Curr Opin Chem Biol. 2006; 11(1):20-8. DOI: 10.1016/j.cbpa.2006.11.030. View

Friedman Ohana R, Kirkland T, Woodroofe C, Levin S, Uyeda H, Otto P . Deciphering the Cellular Targets of Bioactive Compounds Using a Chloroalkane Capture Tag. ACS Chem Biol. 2015; 10(10):2316-24. DOI: 10.1021/acschembio.5b00351. View

Li J, Fang B, Kinose F, Bai Y, Kim J, Chen Y . Target Identification in Small Cell Lung Cancer via Integrated Phenotypic Screening and Activity-Based Protein Profiling. Mol Cancer Ther. 2016; 15(2):334-42. PMC: 4747823. DOI: 10.1158/1535-7163.MCT-15-0444. View

Romeo E, Ponzano S, Armirotti A, Summa M, Bertozzi F, Garau G . Activity-Based Probe for N-Acylethanolamine Acid Amidase. ACS Chem Biol. 2015; 10(9):2057-2064. PMC: 4575644. DOI: 10.1021/acschembio.5b00197. View

Jessani N, Cravatt B . The development and application of methods for activity-based protein profiling. Curr Opin Chem Biol. 2004; 8(1):54-9. DOI: 10.1016/j.cbpa.2003.11.004. View

10.

Salisbury C, Cravatt B . Optimization of activity-based probes for proteomic profiling of histone deacetylase complexes. J Am Chem Soc. 2008; 130(7):2184-94. DOI: 10.1021/ja074138u. View

11.

Cosmai L, Gallieni M, Porta C . Renal toxicity of anticancer agents targeting HER2 and EGFR. J Nephrol. 2015; 28(6):647-57. DOI: 10.1007/s40620-015-0226-9. View

12.

Tebbutt N, Pedersen M, Johns T . Targeting the ERBB family in cancer: couples therapy. Nat Rev Cancer. 2013; 13(9):663-73. DOI: 10.1038/nrc3559. View

13.

Lo Conte M, Lin J, Wilson M, Carroll K . A Chemical Approach for the Detection of Protein Sulfinylation. ACS Chem Biol. 2015; 10(8):1825-30. PMC: 4605140. DOI: 10.1021/acschembio.5b00124. View

14.

Yang P, Liu K . Activity-based protein profiling: recent advances in probe development and applications. Chembiochem. 2015; 16(5):712-24. DOI: 10.1002/cbic.201402582. View

15.

Schulke J, McAllister L, Geoghegan K, Parikh V, Chappie T, Verhoest P . Chemoproteomics demonstrates target engagement and exquisite selectivity of the clinical phosphodiesterase 10A inhibitor MP-10 in its native environment. ACS Chem Biol. 2014; 9(12):2823-32. DOI: 10.1021/cb500671j. View

16.

Krishnamurthy D, Barrios A . Profiling protein tyrosine phosphatase activity with mechanistic probes. Curr Opin Chem Biol. 2009; 13(4):375-81. DOI: 10.1016/j.cbpa.2009.07.017. View

17.

Ravez S, Castillo-Aguilera O, Depreux P, Goossens L . Quinazoline derivatives as anticancer drugs: a patent review (2011 - present). Expert Opin Ther Pat. 2015; 25(7):789-804. DOI: 10.1517/13543776.2015.1039512. View