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Journal articles on the topic 'Bioorthogonal'

Author: Grafiati

Published: 4 June 2021

Last updated: 31 January 2023

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1

Kormos, Attila, Alexandra Egyed, Jasmine M. Olvany, et al. "A Bioorthogonal Double Fluorogenic Probe to Visualize Protein–DNA Interaction." Chemosensors 10, no. 1 (2022): 37. http://dx.doi.org/10.3390/chemosensors10010037.

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Two sets of bioorthogonally applicable, double fluorogenic probes, capable of sensing DNA–protein interactions, were prepared by installing an azide or tetrazine motif onto structurally fluorogenic, DNA sensitive frames. Installation of these bioorthogonal functions onto DNA intercalating dyes furnished these scaffolds with reactivity based fluorogenicity, rendering these probes double-fluorogenic, AND-type logic switches that require the simultaneous occurrence of a bioorthogonal reaction and interaction with DNA to trigger high intensity fluorescence. The probes were evaluated for double flu

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2

Xiao, Yu, Wenxuan Wang, Xiaohua Tian, et al. "A Versatile Surface Bioengineering Strategy Based on Mussel-Inspired and Bioclickable Peptide Mimic." Research 2020 (June 25, 2020): 1–12. http://dx.doi.org/10.34133/2020/7236946.

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In this work, we present a versatile surface engineering strategy by the combination of mussel adhesive peptide mimicking and bioorthogonal click chemistry. The main idea reflected in this work derived from a novel mussel-inspired peptide mimic with a bioclickable azide group (i.e., DOPA4-azide). Similar to the adhesion mechanism of the mussel foot protein (i.e., covalent/noncovalent comediated surface adhesion), the bioinspired and bioclickable peptide mimic DOPA4-azide enables stable binding on a broad range of materials, such as metallic, inorganic, and organic polymer substrates. In additi

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3

Hennessy, James. "Bioorthogonal catalysts." Nature Materials 14, no. 8 (2015): 750. http://dx.doi.org/10.1038/nmat4380.

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4

Chen, Xueqian, Yong Zhang, Qing Yuan, et al. "Bioorthogonal chemistry in metal clusters: a general strategy for the construction of multifunctional probes for bioimaging in living cells and in vivo." Journal of Materials Chemistry B 9, no. 33 (2021): 6614–22. http://dx.doi.org/10.1039/d1tb00836f.

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5

Franzini, Raphael M., and Titas Deb. "The Unique Bioorthogonal Chemistry of Isonitriles." Synlett 31, no. 10 (2020): 938–44. http://dx.doi.org/10.1055/s-0039-1690849.

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The isocyano group is the structurally most compact bioorthogonal group known. It reacts with tetrazines under physiological conditions and has great potential for widespread use in the biosciences. In this account, we highlight the unique properties of the isocyano group as a bioorthogonal functionality. Protecting group chemistry based on the reaction of isonitriles and tetrazines that allows releasing payloads is a particular focus of the article. We further discuss the atypical steric attractions that take place in the transition state of the reaction between isonitriles and tetrazines, wh

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6

Lin, Mingwei, Shanshan Zou, Xinxing Liao, et al. "Ruthenium(ii) complexes as bioorthogonal two-photon photosensitizers for tumour-specific photodynamic therapy against triple-negative breast cancer cells." Chemical Communications 57, no. 36 (2021): 4408–11. http://dx.doi.org/10.1039/d1cc00661d.

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We developed the first Ru(ii) complex-based bioorthogonal two-photon photosensitizers. Through bioorthogonal labelling, they realize effective tumour-specific photodynamic therapy against triple-negative breast cancer cells.

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7

Tu, Julian, Dennis Svatunek, Saba Parvez, et al. "Isonitrile-responsive and bioorthogonally removable tetrazine protecting groups." Chemical Science 11, no. 1 (2020): 169–79. http://dx.doi.org/10.1039/c9sc04649f.

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Tetrazylmethyl groups are reported here as bioorthogonal protecting groups that are readily removed by isonitriles, establishing a valuable addition to the dissociative bioorthogonal chemistry and synthetic methodology toolboxes.

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8

Chen, Zhaowei, Hongjun Li, Yijie Bian, et al. "Bioorthogonal catalytic patch." Nature Nanotechnology 16, no. 8 (2021): 933–41. http://dx.doi.org/10.1038/s41565-021-00910-7.

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9

Patterson, David M., and Jennifer A. Prescher. "Orthogonal bioorthogonal chemistries." Current Opinion in Chemical Biology 28 (October 2015): 141–49. http://dx.doi.org/10.1016/j.cbpa.2015.07.006.

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10

Tu, Julian, Minghao Xu, and Raphael M. Franzini. "Dissociative Bioorthogonal Reactions." ChemBioChem 20, no. 13 (2019): 1615–27. http://dx.doi.org/10.1002/cbic.201800810.

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11

Handula, Maryana, Kuo-Ting Chen, and Yann Seimbille. "IEDDA: An Attractive Bioorthogonal Reaction for Biomedical Applications." Molecules 26, no. 15 (2021): 4640. http://dx.doi.org/10.3390/molecules26154640.

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The pretargeting strategy has recently emerged in order to overcome the limitations of direct targeting, mainly in the field of radioimmunotherapy (RIT). This strategy is directly dependent on chemical reactions, namely bioorthogonal reactions, which have been developed for their ability to occur under physiological conditions. The Staudinger ligation, the copper catalyzed azide-alkyne cycloaddition (CuAAC) and the strain-promoted [3 + 2] azide–alkyne cycloaddition (SPAAC) were the first bioorthogonal reactions introduced in the literature. However, due to their incomplete biocompatibility and

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12

Wang, Yayue, Chang Zhang, Haoxing Wu, and Ping Feng. "Activation and Delivery of Tetrazine-Responsive Bioorthogonal Prodrugs." Molecules 25, no. 23 (2020): 5640. http://dx.doi.org/10.3390/molecules25235640.

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Prodrugs, which remain inert until they are activated under appropriate conditions at the target site, have emerged as an attractive alternative to drugs that lack selectivity and show off-target effects. Prodrugs have traditionally been activated by enzymes, pH or other trigger factors associated with the disease. In recent years, bioorthogonal chemistry has allowed the creation of prodrugs that can be chemically activated with spatio-temporal precision. In particular, tetrazine-responsive bioorthogonal reactions can rapidly activate prodrugs with excellent biocompatibility. This review summa

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13

Sun, Jiayu, Jie Li, Hongbao Sun, Chunling Li, and Haoxing Wu. "Concise Synthesis of Functionalized Cyclobutene Analogues for Bioorthogonal Tetrazine Ligation." Molecules 26, no. 2 (2021): 276. http://dx.doi.org/10.3390/molecules26020276.

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Novel bioorthogonal tools enable the development of new biomedical applications. Here we report the concise synthesis of a series of aryl-functionalized cyclobutene analogues using commercially available starting materials. Our study demonstrates that cyclobutene acts as a small, strained dienophile to generate stable substrates suitable for bioorthogonal tetrazine ligation.

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14

Sun, Jiayu, Jie Li, Hongbao Sun, Chunling Li, and Haoxing Wu. "Concise Synthesis of Functionalized Cyclobutene Analogues for Bioorthogonal Tetrazine Ligation." Molecules 26, no. 2 (2021): 276. http://dx.doi.org/10.3390/molecules26020276.

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Novel bioorthogonal tools enable the development of new biomedical applications. Here we report the concise synthesis of a series of aryl-functionalized cyclobutene analogues using commercially available starting materials. Our study demonstrates that cyclobutene acts as a small, strained dienophile to generate stable substrates suitable for bioorthogonal tetrazine ligation.

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15

Ravasco, João M. J. M., Jaime A. S. Coelho, Alexandre F. Trindade, and Carlos A. M. Afonso. "Synthesis and reactivity/stability study of double-functionalizable strained trans-cyclooctenes for tetrazine bioorthogonal reactions." Pure and Applied Chemistry 92, no. 1 (2020): 15–23. http://dx.doi.org/10.1515/pac-2019-0201.

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AbstractThe unique ability of the bioorthogonal pairs to withstand and unaffect biological processes while maintaining high selectivity towards each other sparked the interest in better probing and controlling biological functions. In early years, trans-cyclooctene (TCO)/tetrazine ligation readily standed out by encompassing most of the bioorthogonal criteria such as its excellent biocompatibility, selectivity and efficiency, and as a result of high HOMO-LUMO gap. Modifications on the TCO scaffold such as cyclopropanation render bicyclononene-based TCOs with high enhancement of its reactivity,

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16

Szatmári, Ágnes, Gergely B. Cserép, Tibor Á. Molnár, et al. "A Genetically Encoded Isonitrile Lysine for Orthogonal Bioorthogonal Labeling Schemes." Molecules 26, no. 16 (2021): 4988. http://dx.doi.org/10.3390/molecules26164988.

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Bioorthogonal click-reactions represent ideal means for labeling biomolecules selectively and specifically with suitable small synthetic dyes. Genetic code expansion (GCE) technology enables efficient site-selective installation of bioorthogonal handles onto proteins of interest (POIs). Incorporation of bioorthogonalized non-canonical amino acids is a minimally perturbing means of enabling the study of proteins in their native environment. The growing demand for the multiple modification of POIs has triggered the quest for developing orthogonal bioorthogonal reactions that allow simultaneous m

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17

Santamaría, Jesús, and Asier Unciti-Broceta. "Bioorthogonal Catalysis Goes Chiral." Chem 6, no. 8 (2020): 1853–55. http://dx.doi.org/10.1016/j.chempr.2020.07.004.

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18

Shih, Hui-Wen, David N. Kamber, and Jennifer A. Prescher. "Building better bioorthogonal reactions." Current Opinion in Chemical Biology 21 (August 2014): 103–11. http://dx.doi.org/10.1016/j.cbpa.2014.07.002.

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19

Sletten, Ellen M., and Carolyn R. Bertozzi. "A Bioorthogonal Quadricyclane Ligation." Journal of the American Chemical Society 133, no. 44 (2011): 17570–73. http://dx.doi.org/10.1021/ja2072934.

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20

Zhang, Han, Kevin T. Dicker, Xian Xu, Xinqiao Jia, and Joseph M. Fox. "Interfacial Bioorthogonal Cross-Linking." ACS Macro Letters 3, no. 8 (2014): 727–31. http://dx.doi.org/10.1021/mz5002993.

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21

Verhelst, Steven H. L., Kimberly M. Bonger, and Lianne I. Willems. "Bioorthogonal Reactions in Activity-Based Protein Profiling." Molecules 25, no. 24 (2020): 5994. http://dx.doi.org/10.3390/molecules25245994.

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Activity-based protein profiling (ABPP) is a powerful technique to label and detect active enzyme species within cell lysates, cells, or whole animals. In the last two decades, a wide variety of applications and experimental read-out techniques have been pursued in order to increase our understanding of physiological and pathological processes, to identify novel drug targets, to evaluate selectivity of drugs, and to image probe targets in cells. Bioorthogonal chemistry has substantially contributed to the field of ABPP, as it allows the introduction of tags, which may be bulky or have unfavora

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22

Wang, Zhipeng A., Yan-Yu Liang, and Ji-Shen Zheng. "Reductive Amination/Alkylation Reactions: The Recent Developments, Progresses, and Applications in Protein Chemical Biology Studies." Current Organic Synthesis 15, no. 6 (2018): 755–61. http://dx.doi.org/10.2174/1570179415666180522093905.

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The chemical modifications of proteins or protein complexes have been a challenging but fruitful task in the post-genomic era. Bioorthogonal reactions play an important role for the purpose of selective functionalization, localization, and labeling of proteins with natural or non-natural structures. Among these reactions, reductive amination stands out as one of the typical bioorthogonal reactions with high efficiency, good biocompatibility, and versatile applications. However, not many specific reviews exist to discuss the mechanism, kinetics, and their applications in a detailed manner. In t

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23

Hirschbiegel, Cristina-Maria, Stefano Fedeli, Xianzhi Zhang, et al. "Enhanced Design of Gold Catalysts for Bioorthogonal Polyzymes." Materials 15, no. 18 (2022): 6487. http://dx.doi.org/10.3390/ma15186487.

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Bioorthogonal chemistry introduces nonbiogenic reactions that can be performed in biological systems, allowing for the localized release of therapeutic agents. Bioorthogonal catalysts can amplify uncaging reactions for the in situ generation of therapeutics. Embedding these catalysts into a polymeric nanoscaffold can protect and modulate the catalytic activity, improving the performance of the resulting bioorthogonal “polyzymes”. Catalysts based on nontoxic metals such as gold(I) are particularly attractive for therapeutic applications. Herein, we optimized the structural components of a metal

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24

Row, R. David, Sean S. Nguyen, Andrew J. Ferreira, and Jennifer A. Prescher. "Chemically triggered crosslinking with bioorthogonal cyclopropenones." Chemical Communications 56, no. 74 (2020): 10883–86. http://dx.doi.org/10.1039/d0cc04600k.

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25

Dong, Ping, Xueyi Wang, Junwei Zheng, et al. "Recent Advances in Targeting Nuclear Molecular Imaging Driven by Tetrazine Bioorthogonal Chemistry." Current Medicinal Chemistry 27, no. 23 (2020): 3924–43. http://dx.doi.org/10.2174/1386207322666190702105829.

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Molecular imaging techniques apply sophisticated technologies to monitor, directly or indirectly, the spatiotemporal distribution of molecular or cellular processes for biomedical, diagnostic, or therapeutic purposes. For example, Single-Photon Emission Computed Tomography (SPECT) and Positron Emission Tomography (PET) imaging, the most representative modalities of molecular imaging, enable earlier and more accurate diagnosis of cancer and cardiovascular diseases. New possibilities for noninvasive molecular imaging in vivo have emerged with advances in bioorthogonal chemistry. For example, tet

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26

Neumann, Kevin, Alessia Gambardella, Annamaria Lilienkampf, and Mark Bradley. "Tetrazine-mediated bioorthogonal prodrug–prodrug activation." Chemical Science 9, no. 36 (2018): 7198–203. http://dx.doi.org/10.1039/c8sc02610f.

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27

Chen, Nan, Zeyu Qiao, and Chu Wang. "A chemoselective reaction between protein N-homocysteinylation and azides catalyzed by heme(ii)." Chemical Communications 55, no. 25 (2019): 3654–57. http://dx.doi.org/10.1039/c9cc00055k.

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28

Bird, Robert E., Steven A. Lemmel, Xiang Yu, and Qiongqiong Angela Zhou. "Bioorthogonal Chemistry and Its Applications." Bioconjugate Chemistry 32, no. 12 (2021): 2457–79. http://dx.doi.org/10.1021/acs.bioconjchem.1c00461.

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29

Liang, Tingxizi, Zhaowei Chen, Hongjun Li, and Zhen Gu. "Bioorthogonal catalysis for biomedical applications." Trends in Chemistry 4, no. 2 (2022): 157–68. http://dx.doi.org/10.1016/j.trechm.2021.11.008.

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30

Sabatino, Valerio, V. B. Unnikrishnan, and Gonçalo J. L. Bernardes. "Transition metal mediated bioorthogonal release." Chem Catalysis 2, no. 1 (2022): 39–51. http://dx.doi.org/10.1016/j.checat.2021.12.007.

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31

Schäfer, Rebecca J. B., Matthew R. Aronoff, and Helma Wennemers. "Recent Advances in Bioorthogonal Reactions." CHIMIA International Journal for Chemistry 73, no. 4 (2019): 308–12. http://dx.doi.org/10.2533/chimia.2019.308.

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32

Schäfer, Rebecca J. B., Mattia R. Monaco, Mao Li, Alina Tirla, Pablo Rivera-Fuentes, and Helma Wennemers. "The Bioorthogonal Isonitrile–Chlorooxime Ligation." Journal of the American Chemical Society 141, no. 47 (2019): 18644–48. http://dx.doi.org/10.1021/jacs.9b07632.

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33

Devaraj, Neal K. "The Future of Bioorthogonal Chemistry." ACS Central Science 4, no. 8 (2018): 952–59. http://dx.doi.org/10.1021/acscentsci.8b00251.

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34

Bertozzi, Carolyn R. "A Decade of Bioorthogonal Chemistry." Accounts of Chemical Research 44, no. 9 (2011): 651–53. http://dx.doi.org/10.1021/ar200193f.

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35

Soares, Jitesh. "A Win for Bioorthogonal Chemistry." ACS Chemical Biology 7, no. 5 (2012): 781–82. http://dx.doi.org/10.1021/cb300211a.

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36

Patterson, David M., Lidia A. Nazarova, and Jennifer A. Prescher. "Finding the Right (Bioorthogonal) Chemistry." ACS Chemical Biology 9, no. 3 (2014): 592–605. http://dx.doi.org/10.1021/cb400828a.

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37

Lang, Kathrin, and Jason W. Chin. "Bioorthogonal Reactions for Labeling Proteins." ACS Chemical Biology 9, no. 1 (2014): 16–20. http://dx.doi.org/10.1021/cb4009292.

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38

Hong, Senlian, Liang Lin, Min Xiao, and Xing Chen. "Live-cell bioorthogonal Raman imaging." Current Opinion in Chemical Biology 24 (February 2015): 91–96. http://dx.doi.org/10.1016/j.cbpa.2014.10.018.

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39

Borrmann, Annika, and Jan C. M. van Hest. "Bioorthogonal chemistry in living organisms." Chemical Science 5, no. 6 (2014): 2123. http://dx.doi.org/10.1039/c3sc52768a.

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40

Fan, Xinyuan, Jie Li, and Peng R. Chen. "Bioorthogonal chemistry in living animals." National Science Review 4, no. 3 (2017): 300–302. http://dx.doi.org/10.1093/nsr/nwx010.

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41

Godinat, Aurélien, Arkadiy A. Bazhin, and Elena A. Goun. "Bioorthogonal chemistry in bioluminescence imaging." Drug Discovery Today 23, no. 9 (2018): 1584–90. http://dx.doi.org/10.1016/j.drudis.2018.05.022.

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42

Wu, Haoxing, and Neal K. Devaraj. "Mining Proteomes Using Bioorthogonal Probes." Cell Chemical Biology 23, no. 7 (2016): 751–53. http://dx.doi.org/10.1016/j.chembiol.2016.07.005.

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43

Kurpiers, Thomas, and Henning D Mootz. "Bioorthogonal Ligation in the Spotlight." Angewandte Chemie International Edition 48, no. 10 (2009): 1729–31. http://dx.doi.org/10.1002/anie.200805454.

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44

An, Peng, Hsuan-Yi Wu, Tracey M. Lewandowski, and Qing Lin. "Hydrophilic azaspiroalkenes as robust bioorthogonal reporters." Chemical Communications 54, no. 99 (2018): 14005–8. http://dx.doi.org/10.1039/c8cc07432a.

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45

Allott, Louis, Cen Chen, Marta Braga, et al. "Detecting hypoxia in vitro using 18F-pretargeted IEDDA “click” chemistry in live cells." RSC Advances 11, no. 33 (2021): 20335–41. http://dx.doi.org/10.1039/d1ra02482e.

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46

Pujari, Suresh S., Yi Zhang, Shaofei Ji, Mark D. Distefano, and Natalia Y. Tretyakova. "Site-specific cross-linking of proteins to DNA via a new bioorthogonal approach employing oxime ligation." Chemical Communications 54, no. 49 (2018): 6296–99. http://dx.doi.org/10.1039/c8cc01300d.

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47

Tang, Li, Qian Yin, Yunxiang Xu, et al. "Bioorthogonal oxime ligation mediated in vivo cancer targeting." Chemical Science 6, no. 4 (2015): 2182–86. http://dx.doi.org/10.1039/c5sc00063g.

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48

Sinha, Santu, Nilanjana Das Saha, Ranjan Sasmal, et al. "Reversible encapsulations and stimuli-responsive biological delivery from a dynamically assembled cucurbit[7]uril host and nanoparticle guest scaffold." Journal of Materials Chemistry B 6, no. 44 (2018): 7329–34. http://dx.doi.org/10.1039/c8tb01596a.

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49

Doerflinger, Anaëlle, Nam Nguyen Quang, Edmond Gravel, et al. "Biotin-functionalized targeted polydiacetylene micelles." Chemical Communications 54, no. 29 (2018): 3613–16. http://dx.doi.org/10.1039/c8cc00553b.

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50

Mao, Xianxian, Wei Li, Shiyu Zhu, et al. "Bifunctional pyridoxal derivatives as efficient bioorthogonal reagents for biomacromolecule modifications." Chemical Communications 56, no. 55 (2020): 7601–4. http://dx.doi.org/10.1039/d0cc02722g.

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