Developments of bioorthogonal handle-containing photo-crosslinkers for photoaffinity labeling.

Photoaffinity labeling (PAL) has been widely applied in various research areas such as medicinal chemistry, chemical biology and structural biology, owing to its capability of investigating non-covalent ligand-protein interactions under native environments and elucidating protein structures, functions etc. One important application of this technique is to use affinity-based proteome profiling (AfBP) coupled with bioimaging for profiling drug-target interactions in situ. In order to accurately report drug-target interactions via these approaches, several considerations as follows need to be made: (1) maximally retaining bioactivities of photoprobes upon functionalization with a photoreactive group and a reporter tag from a parental compound; (2) performing proteome profiling and imaging in situ simultaneously, to monitor drug-target interactions in different manners; and (3) developing excellent photo-crosslinkers capable of photo-crosslinking and fluorescence turn-on at the same time. With these considerations in mind, we have developed three versions of "minimalist" bioorthogonal handle-containing photo-crosslinkers (L3-L6) during the years and successfully applied them in all kinds of small bioactive molecules for protein labeling and cellular imaging studies. In this mini-review, the features and functions of these linkers are specifically highlighted and summarized.

[1]  C. Che,et al.  Cyclometalated Gold(III) Complexes Containing N-Heterocyclic Carbene Ligands Engage Multiple Anti-Cancer Molecular Targets. , 2017, Angewandte Chemie.

[2]  S. Sieber,et al.  Target identification of natural products by activity based protein profiling and a whole proteome inventory of background photocrosslinker binding , 2016 .

[3]  S. Yao,et al.  Fluorescent Probes for Single-Step Detection and Proteomic Profiling of Histone Deacetylases. , 2016, Journal of the American Chemical Society.

[4]  Jasmina Marjanovic,et al.  2-Aryl-5-carboxytetrazole as a New Photoaffinity Label for Drug Target Identification , 2016, Journal of the American Chemical Society.

[5]  I. Choi,et al.  A bioorthogonal approach for imaging the binding between Dasatinib and its target proteins inside living cells. , 2016, Chemical communications.

[6]  M. Won,et al.  Identification of Targets of the HIF-1 Inhibitor IDF-11774 Using Alkyne-Conjugated Photoaffinity Probes. , 2016, Bioconjugate chemistry.

[7]  Jongmin Park,et al.  Nonspecific protein labeling of photoaffinity linkers correlates with their molecular shapes in living cells. , 2016, Chemical communications.

[8]  K. Lim,et al.  Puromycin Analogues Capable of Multiplexed Imaging and Profiling of Protein Synthesis and Dynamics in Live Cells and Neurons. , 2016, Angewandte Chemie.

[9]  Chu Wang,et al.  Photo-induced coupling reactions of tetrazoles with carboxylic acids in aqueous solution: application in protein labelling. , 2016, Chemical communications.

[10]  S. Yao,et al.  Tetrazole Photoclick Chemistry: Reinvestigating Its Suitability as a Bioorthogonal Reaction and Potential Applications. , 2016, Angewandte Chemie.

[11]  Jongmin Park,et al.  Investigation of Specific Binding Proteins to Photoaffinity Linkers for Efficient Deconvolution of Target Protein. , 2016, ACS chemical biology.

[12]  Neal K. Devaraj,et al.  Inverse Electron-Demand Diels–Alder Bioorthogonal Reactions , 2016, Topics in Current Chemistry.

[13]  David J. Lapinsky,et al.  Recent developments and applications of clickable photoprobes in medicinal chemistry and chemical biology. , 2015, Future medicinal chemistry.

[14]  Tianlu Wang,et al.  Fluorescein Derivatives as Bifunctional Molecules for the Simultaneous Inhibiting and Labeling of FTO Protein. , 2015, Journal of the American Chemical Society.

[15]  Ian Collins,et al.  Photoaffinity labeling in target- and binding-site identification. , 2015, Future medicinal chemistry.

[16]  N. Brandon,et al.  Chemoproteomics demonstrates target engagement and exquisite selectivity of the clinical phosphodiesterase 10A inhibitor MP-10 in its native environment. , 2014, ACS chemical biology.

[17]  S. Yao,et al.  "Minimalist" cyclopropene-containing photo-cross-linkers suitable for live-cell imaging and affinity-based protein labeling. , 2014, Journal of the American Chemical Society.

[18]  E. Weerapana,et al.  Applications of Copper-Catalyzed Click Chemistry in Activity-Based Protein Profiling , 2014, Molecules.

[19]  Yuguo Zheng,et al.  Target identification of biologically active small molecules via in situ methods. , 2013, Current opinion in chemical biology.

[20]  R. Weissleder,et al.  Bioorthogonal approach to identify unsuspected drug targets in live cells. , 2013, Angewandte Chemie.

[21]  S. Son,et al.  Identification of malate dehydrogenase 2 as a target protein of the HIF-1 inhibitor LW6 using chemical probes. , 2013, Angewandte Chemie.

[22]  Sang J. Chung,et al.  Recent Advances in Target Characterization and Identification by Photoaffinity Probes , 2013, Molecules.

[23]  S. Sze,et al.  Design and synthesis of minimalist terminal alkyne-containing diazirine photo-crosslinkers and their incorporation into kinase inhibitors for cell- and tissue-based proteome profiling. , 2013, Angewandte Chemie.

[24]  Karl G. Kempf,et al.  Synthesis of penicillenol C1 and of a bis-azide analogue for photoaffinity labeling. , 2013, The Journal of organic chemistry.

[25]  B. Cravatt,et al.  Proteome-wide Mapping of Cholesterol-Interacting Proteins in Mammalian Cells , 2013, Nature Methods.

[26]  Dustin J Maly,et al.  Affinity-based probes based on type II kinase inhibitors. , 2012, Journal of the American Chemical Society.

[27]  David J. Lapinsky,et al.  Tandem photoaffinity labeling-bioorthogonal conjugation in medicinal chemistry. , 2012, Bioorganic & medicinal chemistry.

[28]  Shao Q Yao,et al.  Cell-based proteome profiling of potential dasatinib targets by use of affinity-based probes. , 2012, Journal of the American Chemical Society.

[29]  M. Meijler,et al.  Diazirine based photoaffinity labeling. , 2012, Bioorganic & medicinal chemistry.

[30]  H. Overkleeft,et al.  Photoaffinity labeling in activity-based protein profiling. , 2012, Topics in current chemistry.

[31]  Anna K. Schrey,et al.  Dasatinib, imatinib and staurosporine capture compounds - Complementary tools for the profiling of kinases by Capture Compound Mass Spectrometry (CCMS). , 2011, Journal of proteomics.

[32]  Shao Q Yao,et al.  Proteome profiling reveals potential cellular targets of staurosporine using a clickable cell-permeable probe. , 2011, Chemical communications.

[33]  S. Sieber,et al.  Evaluation of α-pyrones and pyrimidones as photoaffinity probes for affinity-based protein profiling. , 2011, The Journal of organic chemistry.

[34]  Anna K. Schrey,et al.  Comprehensive identification of staurosporine-binding kinases in the hepatocyte cell line HepG2 using Capture Compound Mass Spectrometry (CCMS). , 2010, Journal of proteome research.

[35]  M. Hashimoto,et al.  Recent Progress in Diazirine‐Based Photoaffinity Labeling , 2008 .

[36]  Michael M. Madden,et al.  A photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins. , 2008, Angewandte Chemie.

[37]  G. Superti-Furga,et al.  The Btk tyrosine kinase is a major target of the Bcr-Abl inhibitor dasatinib , 2007, Proceedings of the National Academy of Sciences.

[38]  M. Bogyo,et al.  Tagging and detection strategies for activity-based proteomics. , 2007, Current opinion in chemical biology.

[39]  E. Vodovozova.  Photoaffinity labeling and its application in structural biology , 2007, Biochemistry (Moscow).

[40]  M. Hashimoto,et al.  Cross-linking chemistry and biology: development of multifunctional photoaffinity probes. , 2005, Chemical record.

[41]  F. Westheimer,et al.  The photolysis of diazoacetylchymotrypsin. , 1962, The Journal of biological chemistry.