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Journal articles on the topic 'Photocaging'

Author: Grafiati

Published: 4 June 2021

Last updated: 27 July 2025

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1

Li, Ao, Claudia Turro, and Jeremy J. Kodanko. "Ru(ii) polypyridyl complexes as photocages for bioactive compounds containing nitriles and aromatic heterocycles." Chemical Communications 54, no. 11 (2018): 1280–90. http://dx.doi.org/10.1039/c7cc09000e.

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2

Sõrmus, Tanel, Darja Lavogina, Erki Enkvist, Asko Uri, and Kaido Viht. "Efficient photocaging of a tight-binding bisubstrate inhibitor of cAMP-dependent protein kinase." Chemical Communications 55, no. 74 (2019): 11147–50. http://dx.doi.org/10.1039/c9cc04978a.

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3

Behara, Krishna Kalyani, Y. Rajesh, Yarra Venkatesh, Bhaskar Rao Pinninti, Mahitosh Mandal, and N. D. Pradeep Singh. "Cascade photocaging of diazeniumdiolate: a novel strategy for one and two photon triggered uncaging with real time reporting." Chemical Communications 53, no. 68 (2017): 9470–73. http://dx.doi.org/10.1039/c7cc04635a.

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4

Mangubat-Medina, Alicia E., Hallie O. Trial, Reyner D. Vargas, et al. "Red-shifted backbone N–H photocaging agents." Organic & Biomolecular Chemistry 18, no. 27 (2020): 5110–14. http://dx.doi.org/10.1039/d0ob00923g.

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5

Szymański, Wiktor, Willem A. Velema, and Ben L. Feringa. "Photocaging of Carboxylic Acids: A Modular Approach." Angewandte Chemie International Edition 53, no. 33 (2014): 8682–86. http://dx.doi.org/10.1002/anie.201402665.

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6

Szymański, Wiktor, Willem A. Velema, and Ben L. Feringa. "Photocaging of Carboxylic Acids: A Modular Approach." Angewandte Chemie 126, no. 33 (2014): 8826–30. http://dx.doi.org/10.1002/ange.201402665.

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7

Ren, Mingguang, Zihong Li, Jing Nie, Li Wang, and Weiying Lin. "A photocaged fluorescent probe for imaging hypochlorous acid in lysosomes." Chemical Communications 54, no. 66 (2018): 9238–41. http://dx.doi.org/10.1039/c8cc04926b.

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By combining the advantages of the photocaging technology and traditional analyte-responsive fluorescent probes, we designed and synthesized the first photocaged lysosomal-targeted fluorescent HOCl probe (PL-HA), which is capable of remote light-controlled intracellular target recognition of HOCl in lysosomes.

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8

Schnermann, Martin J., and Youngjae You. "Editorial: Special Issue on Emerging Developments in Photocaging." Photochemistry and Photobiology 98, no. 2 (2022): 287. http://dx.doi.org/10.1111/php.13600.

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9

Deiters, Alexander, and Hrvoje Lusic. "A New Photocaging Group for Aromatic N-Heterocycles." Synthesis 2006, no. 13 (2006): 2147–50. http://dx.doi.org/10.1055/s-2006-942424.

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10

Barone, Mariarita, Maria T. Sciortino, Daniela Zaccaria, Antonino Mazzaglia, and Salvatore Sortino. "Nitric oxide photocaging platinum nanoparticles with anticancer potential." Journal of Materials Chemistry 18, no. 45 (2008): 5531. http://dx.doi.org/10.1039/b809121h.

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11

Mangubat-Medina, Alicia E., Samuel C. Martin, Kengo Hanaya, and Zachary T. Ball. "A Vinylogous Photocleavage Strategy Allows Direct Photocaging of Backbone Amide Structure." Journal of the American Chemical Society 140, no. 27 (2018): 8401–4. http://dx.doi.org/10.1021/jacs.8b04893.

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12

So, Wing Ho, Clarence T. T. Wong, and Jiang Xia. "Peptide photocaging: A brief account of the chemistry and biological applications." Chinese Chemical Letters 29, no. 7 (2018): 1058–62. http://dx.doi.org/10.1016/j.cclet.2018.05.015.

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13

Anhäuser, Lea, Nils Klöcker, Fabian Muttach, et al. "A Benzophenone‐Based Photocaging Strategy for the N7 Position of Guanosine." Angewandte Chemie International Edition 59, no. 8 (2020): 3161–65. http://dx.doi.org/10.1002/anie.201914573.

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14

Pinheiro, A. V., P. Baptista, and J. C. Lima. "Light activation of transcription: photocaging of nucleotides for control over RNA polymerization." Nucleic Acids Research 36, no. 14 (2008): e90-e90. http://dx.doi.org/10.1093/nar/gkn415.

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15

Sharma, Rajgopal, Jessica D. Knoll, Philip D. Martin, Izabela Podgorski, Claudia Turro, and Jeremy J. Kodanko. "Ruthenium Tris(2-pyridylmethyl)amine as an Effective Photocaging Group for Nitriles." Inorganic Chemistry 53, no. 7 (2014): 3272–74. http://dx.doi.org/10.1021/ic500299s.

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16

Li, Ao, Claudia Turro, and Jeremy J. Kodanko. "Ru(II) Polypyridyl Complexes Derived from Tetradentate Ancillary Ligands for Effective Photocaging." Accounts of Chemical Research 51, no. 6 (2018): 1415–21. http://dx.doi.org/10.1021/acs.accounts.8b00066.

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17

Berrade, Luis, Youngeun Kwon, and Julio A. Camarero. "Photomodulation of Protein Trans-Splicing Through Backbone Photocaging of the DnaE Split Intein." ChemBioChem 11, no. 10 (2010): 1368–72. http://dx.doi.org/10.1002/cbic.201000157.

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18

Arora, Karan, Jessica K. White, Rajgopal Sharma, et al. "Effects of Methyl Substitution in Ruthenium Tris(2-pyridylmethyl)amine Photocaging Groups for Nitriles." Inorganic Chemistry 55, no. 14 (2016): 6968–79. http://dx.doi.org/10.1021/acs.inorgchem.6b00650.

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19

Su, Meng, Jie Wang, and XinJing Tang. "Photocaging Strategy for Functionalisation of Oligonucleotides and Its Applications for Oligonucleotide Labelling and Cyclisation." Chemistry - A European Journal 18, no. 31 (2012): 9628–37. http://dx.doi.org/10.1002/chem.201103833.

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20

Zheng, Yang, Meichun Gao, Maikel Wijtmans, Henry F. Vischer, and Rob Leurs. "Synthesis and Pharmacological Characterization of New Photocaged Agonists for Histamine H3 and H4 Receptors." Pharmaceuticals 17, no. 4 (2024): 536. http://dx.doi.org/10.3390/ph17040536.

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The modulation of biological processes with light-sensitive chemical probes promises precise temporal and spatial control. Yet, the design and synthesis of suitable probes is a challenge for medicinal chemists. This article introduces a photocaging strategy designed to modulate the pharmacology of histamine H3 receptors (H3R) and H4 receptors (H4R). Employing the photoremovable group BODIPY as the caging entity for two agonist scaffolds—immepip and 4-methylhistamine—for H3R and H4R, respectively, we synthesized two BODIPY-caged compounds, 5 (VUF25657) and 6 (VUF25678), demonstrating 10–100-fol

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21

Boháčová, Soňa, Zuzana Vaníková, Lenka Poštová Slavětínská, and Michal Hocek. "Protected 2′-deoxyribonucleoside triphosphate building blocks for the photocaging of epigenetic 5-(hydroxymethyl)cytosine in DNA." Organic & Biomolecular Chemistry 16, no. 30 (2018): 5427–32. http://dx.doi.org/10.1039/c8ob01106k.

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2′-Deoxyribonucleoside triphosphates containing 5-(hydroxymethyl)cytosine protected with photocleavable groups were prepared and studied as substrates for the enzymatic synthesis of DNA containing a photocaged epigenetic 5hmC base.

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22

Hoffelner, Beate Sandra, Stanislav Andreev, Nicole Plank, and Pierre Koch. "Photocaging of Pyridinylimidazole-Based Covalent JNK3 Inhibitors Affords Spatiotemporal Control of the Binding Affinity in Live Cells." Pharmaceuticals 16, no. 2 (2023): 264. http://dx.doi.org/10.3390/ph16020264.

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The concept of photocaging represents a promising approach to acquire spatiotemporal control over molecular bioactivity. To apply this strategy to pyridinylimidazole-based covalent JNK3 inhibitors, we used acrylamido-N-(4-((4-(4-(4-fluorophenyl)-1-methyl-2-(methylthio)-1H-imidazol-5-yl)pyridin-2-yl)amino)phenyl)benzamide (1) as a lead compound to design novel covalent inhibitors of JNK3 by modifying the amide bond moiety in the linker. The newly synthesized inhibitors demonstrated IC50 values in the low double-digit nanomolar range in a radiometric kinase assay. They were further characterized

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23

Vaníková, Zuzana, Martina Janoušková, Milada Kambová, Libor Krásný, and Michal Hocek. "Switching transcription with bacterial RNA polymerase through photocaging, photorelease and phosphorylation reactions in the major groove of DNA." Chemical Science 10, no. 14 (2019): 3937–42. http://dx.doi.org/10.1039/c9sc00205g.

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24

Michailidou, Freideriki, Nils Klöcker, Nicolas V. Cornelissen, et al. "Engineered SAM Synthetases for Enzymatic Generation of AdoMet Analogs with Photocaging Groups and Reversible DNA Modification in Cascade Reactions." Angewandte Chemie International Edition 60, no. 1 (2020): 480–85. http://dx.doi.org/10.1002/anie.202012623.

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25

Lin, Qiuning, Lipeng Yang, Zhiqiang Wang, et al. "Coumarin Photocaging Groups Modified with an Electron-Rich Styryl Moiety at the 3-Position: Long-Wavelength Excitation, Rapid Photolysis, and Photobleaching." Angewandte Chemie 130, no. 14 (2018): 3784–88. http://dx.doi.org/10.1002/ange.201800713.

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26

Lin, Qiuning, Lipeng Yang, Zhiqiang Wang, et al. "Coumarin Photocaging Groups Modified with an Electron-Rich Styryl Moiety at the 3-Position: Long-Wavelength Excitation, Rapid Photolysis, and Photobleaching." Angewandte Chemie International Edition 57, no. 14 (2018): 3722–26. http://dx.doi.org/10.1002/anie.201800713.

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27

Negi, Arvind, Kavindra Kumar Kesari, and Anne Sophie Voisin-Chiret. "Light-Activating PROTACs in Cancer: Chemical Design, Challenges, and Applications." Applied Sciences 12, no. 19 (2022): 9674. http://dx.doi.org/10.3390/app12199674.

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Nonselective cell damage remains a significant limitation of radiation therapies in cancer. Decades of successful integration of radiation therapies with other medicinal chemistry strategies significantly improved therapeutic benefits in cancer. Advancing in such technologies also led to the development of specific photopharmcology-based approaches that improved the cancer cell selectivity and provided researchers with spatiotemporal control over the degradation of highly expressed proteins in cancer (proteolysis targeting chimeras, PROTACs) using a monochrome wavelength light source. Two spec

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28

Venkatesh, Yarra, Y. Rajesh, S. Karthik, et al. "Photocaging of Single and Dual (Similar or Different) Carboxylic and Amino Acids by Acetyl Carbazole and its Application as Dual Drug Delivery in Cancer Therapy." Journal of Organic Chemistry 81, no. 22 (2016): 11168–75. http://dx.doi.org/10.1021/acs.joc.6b02152.

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29

Fleming, Cassandra, Morten Grøtli, and Joakim Andréasson. "On-Command Regulation of Kinase Activity using PhotonicStimuli." ChemPhotoChem 3 (January 25, 2019): 318–26. https://doi.org/10.1002/cptc.201800253.

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To better understand the relationship between kinase activity and cellular behaviour, the use of light as an external stimulus to modulate kinase activity with high spatiotemporal resolution has gained increasing interest of late. Herein we highlight the progress made towards the development of light‐responsive kinase enzymes and small molecule inhibitors.

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30

Michailidou, Freideriki, Nils Klöcker, Nicolas V. Cornelissen, et al. "Cover Picture: Engineered SAM Synthetases for Enzymatic Generation of AdoMet Analogs with Photocaging Groups and Reversible DNA Modification in Cascade Reactions (Angew. Chem. Int. Ed. 1/2021)." Angewandte Chemie International Edition 60, no. 1 (2020): 1. http://dx.doi.org/10.1002/anie.202015604.

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31

Monteiro, Diana C. F., Emmanuel Amoah, Cromarte Rogers, and Arwen R. Pearson. "Using photocaging for fast time-resolved structural biology studies." Acta Crystallographica Section D Structural Biology 77, no. 10 (2021). http://dx.doi.org/10.1107/s2059798321008809.

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Careful selection of photocaging approaches is critical to achieve fast and well synchronized reaction initiation and perform successful time-resolved structural biology experiments. This review summarizes the best characterized and most relevant photocaging groups previously described in the literature. It also provides a walkthrough of the essential factors to consider in designing a suitable photocaged molecule to address specific biological questions, focusing on photocaging groups with well characterized spectroscopic properties. The relationships between decay rates (k in s−1), quantum y

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32

Hartmann, Denis, and Michael John Booth. "Handcuffed antisense oligonucleotides for light-controlled cell-free expression." Chemical Communications, 2023. http://dx.doi.org/10.1039/d3cc01374j.

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Developing simple methods to silence antisense oligonucleotides (ASOs) using photocages opens up the possibility of precise regulation of biological systems. Here, we have developed a photocaging strategy based on ‘handcuffing’...

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33

Mangubat-Medina, Alicia E., and Zachary T. Ball. "Triggering biological processes: methods and applications of photocaged peptides and proteins." Chemical Society Reviews, 2021. http://dx.doi.org/10.1039/d0cs01434f.

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Photocaging groups provide spatiotemporal control of function. This review surveys approaches to the design and synthesis of photocaged peptides and proteins, and provides an overview of the ways in which these tools have been applied to answer biological questions.

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34

Lusic, Hrvoje, and Alexander Deiters. "A New Photocaging Group for Aromatic N-Heterocycles." ChemInform 37, no. 45 (2006). http://dx.doi.org/10.1002/chin.200645122.

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35

Layden, Aryanna E., Xiang Ma, Caroline A. Johnson, Xinyi J. He, Stanley A. Buczynski, and Matthew R. Banghart. "A Biomimetic C-Terminal Extension Strategy for Photocaging Amidated Neuropeptides." Journal of the American Chemical Society, August 31, 2023. http://dx.doi.org/10.1021/jacs.3c03913.

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36

Moser, Sandra, Gloria Hans, Jiahui Ma, et al. "Synthesis of monodisperse inorganic polyphosphate polyP10 via a photocaging strategy." Chemical Science, 2025. https://doi.org/10.1039/d5sc04037j.

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Inorganic polyphosphate (polyP), a linear biopolymer composed only of orthophosphate units, has emerged as a molecule of critical biological importance across species. While commercially available polyPs are polydisperse mixtures –...

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37

Kaufmann, Janik, Patricia Müller, Eleni Andreadou, and Alexander Heckel. "Green‐Light Activatable BODIPY and Coumarin 5’‐Caps for Oligonucleotide Photocaging." Chemistry – A European Journal, April 14, 2022. http://dx.doi.org/10.1002/chem.202200477.

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38

Ovcharenko, Anna, Florian P. Weissenboeck, and Andrea Rentmeister. "Tag‐Free Internal RNA Labeling and Photocaging Based on mRNA Methyltransferases." Angewandte Chemie International Edition, December 22, 2020. http://dx.doi.org/10.1002/anie.202013936.

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39

Ovcharenko, Anna, Florian P. Weissenboeck, and Andrea Rentmeister. "Tag‐Free Internal RNA Labeling and Photocaging Based on mRNA Methyltransferases." Angewandte Chemie, December 22, 2020. http://dx.doi.org/10.1002/ange.202013936.

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40

Gagarin, Aleksey A., Artem S. Minin, Vadim A. Shevyrin, Irena P. Kostova, Enrico Benassi, and Nataliya P. Belskaya. "Photocaging of Carboxylic Function Bearing Biomolecules by New Thiazole Derived Fluorophore." Chemistry – A European Journal, August 2, 2023. http://dx.doi.org/10.1002/chem.202302079.

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The design and synthesis of a new fluorophore containing an arylidene thiazole scaffold resulted in a compound with good photophysical characteristics. Furthermore, the thiazole C5‐methyl group was easily modified into specific functional groups (CH2Br and CH2OH) for the formation of a series of photocourier molecules containing model compounds (benzoic acids), as well as prodrugs, including salicylic acid, caffeic acid, and chlorambucil via a “benzyl” linker. Spectral characteristics (1Н, 13С NMR, and high‐resolution mass spectra) corresponded to the proposed structures. The photocourier mole

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41

Wang, Yu, Jingnan Chen, Xiao Hua, et al. "Photocaging of Activity‐based Ubiquitin Probes via a C‐Terminal Backbone Modification Strategy." Angewandte Chemie, April 23, 2022. http://dx.doi.org/10.1002/ange.202203792.

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42

Lu, Mingzhu, Haifeng Liu, Ruiqing Xiang, et al. "Photocaging of N-pyridinyl amide scaffold-based PIM inhibitors for spatiotemporal controlled anticancer bioactivity." Bioorganic & Medicinal Chemistry, March 2025, 118159. https://doi.org/10.1016/j.bmc.2025.118159.

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43

Gagarin, Aleksey, Artem Minin, Vadim A. Shevyrin, Enrico Benassi, and Nataliya Pavlovna Belskaya. "Photocaging of Amino Acids and Short Peptides by Arylidenethiazoles: Mechanism, Photochemical Characteristics and Biological Behaviour." Journal of Materials Chemistry B, 2024. http://dx.doi.org/10.1039/d4tb01441c.

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A series of fluorophores based on (5-methyl-4-phenylthiazol-2-yl)-3-phenylacrylonitrile (MPTA) core was designed and synthesised for photo caging of amino acids and peptides. The photophysical characteristics of these compounds and their hybrids...

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44

Klöcker, Nils, Florian P. Weissenboeck, Melissa van Dülmen, Petr Špaček, Sabine Hüwel, and Andrea Rentmeister. "Photocaged 5′ cap analogues for optical control of mRNA translation in cells." Nature Chemistry, June 20, 2022. http://dx.doi.org/10.1038/s41557-022-00972-7.

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AbstractThe translation of messenger RNA (mRNA) is a fundamental process in gene expression, and control of translation is important to regulate protein synthesis in cells. The primary hallmark of eukaryotic mRNAs is their 5′ cap, whose molecular contacts to the eukaryotic translation initiation factor eIF4E govern the initiation of translation. Here we report 5′ cap analogues with photo-cleavable groups (FlashCaps) that prohibit binding to eIF4E and resist cleavage by decapping enzymes. These compounds are compatible with the general and efficient production of mRNAs by in vitro transcription

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45

Löffler, Max, Stefan Frühschulz, Zoe Rockel, Matija Pečak, Robert Tampé, and Ralph Wieneke. "Antigen Delivery Controlled by an On‐Demand Photorelease." Angewandte Chemie International Edition, May 31, 2024. http://dx.doi.org/10.1002/anie.202405035.

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To eliminate infected and cancerous cells, antigen processing and presentation play a pivotal role through the recognition of antigenic peptides displayed on Major Histocompatibility Complex class I (MHC I) molecules. Here, we developed a photostimulated antigen release system that enables the temporal inception of antigen flux. Simple and effective photocaging of the human immunodeficiency virus (HIV)‐Nef73‐derived epitope, a representative high‐affinity MHC I ligand, was provided by steric hindrance to block the recognition by the transporter associated with antigen processing (TAP) in the p

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46

Löffler, Max, Stefan Frühschulz, Zoe Rockel, Matija Pečak, Robert Tampé, and Ralph Wieneke. "Antigen Delivery Controlled by an On‐Demand Photorelease." Angewandte Chemie, May 31, 2024. http://dx.doi.org/10.1002/ange.202405035.

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To eliminate infected and cancerous cells, antigen processing and presentation play a pivotal role through the recognition of antigenic peptides displayed on Major Histocompatibility Complex class I (MHC I) molecules. Here, we developed a photostimulated antigen release system that enables the temporal inception of antigen flux. Simple and effective photocaging of the human immunodeficiency virus (HIV)‐Nef73‐derived epitope, a representative high‐affinity MHC I ligand, was provided by steric hindrance to block the recognition by the transporter associated with antigen processing (TAP) in the p

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47

Zhang, ZongWei, MaoMao He, Ran Wang, JiangLi Fan, XiaoJun Peng, and Wen Sun. "Development of Ruthenium Nanophotocages with Red or Near‐Infrared Light‐Responsiveness." ChemBioChem, October 14, 2023. http://dx.doi.org/10.1002/cbic.202300606.

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The development of light‐triggered ruthenium (Ru) nanophotocages has revolutionized conventional methods of drug administration, thereby facilitating cancer therapy in a noninvasive and temperate manner. Ru nanophotocages employ a distinct approach known as photoactivated chemotherapy (PACT), wherein light‐induced ligand dissociation yields a toxic metal complex or a ligand capable of performing other functions such as optically controlled protein degradation and drug delivery. Simultaneously, this process is accompanied by the generation of reactive oxygen species (ROS), which serve as an eff

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48

Kuznetsov, Kirill M., Kallol Purkait, Pierre Mesdom, et al. "Synthesis, Characterization, and Biological Evaluation of Red Light‐Activatable BODIPY‐Caged Ceritinib Compounds." Helvetica Chimica Acta, April 10, 2025. https://doi.org/10.1002/hlca.202500023.

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In this work, we aimed at photocaging the well‐known anticancer agents dasatinib, ceritinib, gemcitabine, and combretastatin A4 with red‐light activatable 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY)‐based cages using a carbonate/carbamate linking strategy. Due to the synthetic challenges discussed in this article, we only obtained two target compounds, namely two caged ceritinib compounds. The latter were characterized in‐depth by nuclear magnetic resonance spectroscopy (NMR, 1H, COSY, 13C), high‐resolution mass spectrometry (HRMS), infrared (IR) spectroscopy, and their purity was eval

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49

Peters, Aileen, Eric Herrmann, Nicolas V. Cornelissen, Nils Klöcker, Daniel Kümmel, and Andrea Rentmeister. "Visible‐Light Removable Photocaging Groups Accepted by MjMAT Variant: Structural Basis and Compatibility with DNA and RNA Methyltransferases." ChemBioChem 23, no. 1 (2021). http://dx.doi.org/10.1002/cbic.202100437.

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50

Hartmann, Denis, and Michael J. Booth. "Accessible light-controlled knockdown of cell-free protein synthesis using phosphorothioate-caged antisense oligonucleotides." Communications Chemistry 6, no. 1 (2023). http://dx.doi.org/10.1038/s42004-023-00860-2.

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AbstractControlling cell-free expression of a gene to protein with non-invasive stimuli is vital to the future application of DNA nanodevices and synthetic cells. However, little emphasis has been placed on developing light-controlled ‘off’ switches for cell-free expression. Light-activated antisense oligonucleotides have been developed to induce gene knockdown in living cells; however, they are complicated to synthesise and have not been tested in cell-free systems. Developing simple, accessible methods to produce light-activated antisense oligonucleotides will be crucial for allowing their a

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