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A Sunscreen-Based Photocage for Carbonyl Groups

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A Sunscreen-Based Photocage for Carbonyl Groups

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dc.contributor.author Lineros-Rosa, Mauricio es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.contributor.author Lhiaubet, Virginie Lyria es_ES
dc.date.accessioned 2021-04-21T03:31:12Z
dc.date.available 2021-04-21T03:31:12Z
dc.date.issued 2020-06-05 es_ES
dc.identifier.issn 0947-6539 es_ES
dc.identifier.uri http://hdl.handle.net/10251/165396
dc.description This is the peer reviewed version of the following article: M. Lineros-Rosa, M. A. Miranda, V. Lhiaubet-Vallet, Chem. Eur. J. 2020, 26, 7205, which has been published in final form at https://doi.org/10.1002/chem.202000123. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. es_ES
dc.description.abstract [EN] Photolabile protecting groups (PPGs) have been exploited in a wide range of chemical and biological applications, due to their ability to provide spatial and temporal control over light-triggered activation. In this work, we explore the concept of a new photocage compound based on the commercial UVA/UVB filter oxybenzone (OB; 2-hydroxy-4-methoxybenzophenone) for photoprotection and controlled release of carbonyl groups. The point here is that oxybenzone not only acts as a mere PPG, but also provides, once released, UV photoprotection to the carbonyl derivative. This design points to a possible therapeutic approach to reduce the severe photoadverse effects of drugs containing a carbonyl chromophore. es_ES
dc.description.sponsorship This work was supported by the Spanish Government (project PGC2018-096684-B-I00) and the Universitat Politecnica de Valencia (FPI grant to M.L.-R.). Carmen Clemente Martínez is acknowledged for her technical help during the UPLC-HRMS experiments. es_ES
dc.language Inglés es_ES
dc.publisher John Wiley & Sons es_ES
dc.relation.ispartof Chemistry - A European Journal es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Laser spectroscopy es_ES
dc.subject Photocages es_ES
dc.subject Photochemistry es_ES
dc.subject Photoprotection es_ES
dc.subject Solar filters es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title A Sunscreen-Based Photocage for Carbonyl Groups es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1002/chem.202000123 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-096684-B-I00/ES/REPARACION DEL ADN POR PROCESOS MULTIFOTONICOS/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Lineros-Rosa, M.; Miranda Alonso, MÁ.; Lhiaubet, VL. (2020). A Sunscreen-Based Photocage for Carbonyl Groups. Chemistry - A European Journal. 26(32):7205-7211. https://doi.org/10.1002/chem.202000123 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1002/chem.202000123 es_ES
dc.description.upvformatpinicio 7205 es_ES
dc.description.upvformatpfin 7211 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 26 es_ES
dc.description.issue 32 es_ES
dc.identifier.pmid 32189405 es_ES
dc.relation.pasarela S\425468 es_ES
dc.contributor.funder Universitat Politècnica de València es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES
dc.description.references Silva, J. M., Silva, E., & Reis, R. L. (2019). Light-triggered release of photocaged therapeutics - Where are we now? Journal of Controlled Release, 298, 154-176. doi:10.1016/j.jconrel.2019.02.006 es_ES
dc.description.references Klausen, M., Dubois, V., Verlhac, J., & Blanchard‐Desce, M. (2019). Tandem Systems for Two‐Photon Uncaging of Bioactive Molecules. ChemPlusChem, 84(6), 589-598. doi:10.1002/cplu.201900139 es_ES
dc.description.references Brieke, C., Rohrbach, F., Gottschalk, A., Mayer, G., & Heckel, A. (2012). Light‐Controlled Tools. Angewandte Chemie International Edition, 51(34), 8446-8476. doi:10.1002/anie.201202134 es_ES
dc.description.references Brieke, C., Rohrbach, F., Gottschalk, A., Mayer, G., & Heckel, A. (2012). Lichtgesteuerte Werkzeuge. Angewandte Chemie, 124(34), 8572-8604. doi:10.1002/ange.201202134 es_ES
dc.description.references Šolomek, T., Wirz, J., & Klán, P. (2015). Searching for Improved Photoreleasing Abilities of Organic Molecules. Accounts of Chemical Research, 48(12), 3064-3072. doi:10.1021/acs.accounts.5b00400 es_ES
dc.description.references Klán, P., Šolomek, T., Bochet, C. G., Blanc, A., Givens, R., Rubina, M., … Wirz, J. (2012). Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy. Chemical Reviews, 113(1), 119-191. doi:10.1021/cr300177k es_ES
dc.description.references Herrmann, A. (2007). Kontrollierte Freisetzung flüchtiger Verbindungen unter milden Reaktionsbedingungen: von der Natur zu Alltagsprodukten. Angewandte Chemie, 119(31), 5938-5967. doi:10.1002/ange.200700264 es_ES
dc.description.references Wang, P. (2017). Developing photolabile protecting groups based on the excited state meta effect. Journal of Photochemistry and Photobiology A: Chemistry, 335, 300-310. doi:10.1016/j.jphotochem.2016.11.031 es_ES
dc.description.references Griesbeck, A., Kropf, C., Porschen, B., Landes, A., Hinze, O., Huchel, U., & Gerke, T. (2016). Photocaged Hydrocarbons, Aldehydes, Ketones, Enones, and Carboxylic Acids and Esters that Release by the Norrish II Cleavage Protocol and Beyond: Controlled Photoinduced Fragrance Release. Synthesis, 49(03), 539-553. doi:10.1055/s-0036-1588645 es_ES
dc.description.references Herrmann, A. (2012). Using photolabile protecting groups for the controlled release of bioactive volatiles. Photochem. Photobiol. Sci., 11(3), 446-459. doi:10.1039/c1pp05231d es_ES
dc.description.references Falvey, D. E., & Sundararajan, C. (2004). Photoremovable protecting groups based on electron transfer chemistry. Photochemical & Photobiological Sciences, 3(9), 831. doi:10.1039/b406866a es_ES
dc.description.references Hébert, J., & Gravel, D. (1974). o-Nitrophenylethylene Glycol: a Photosensitive Protecting Group for Aldehydes and Ketones. Canadian Journal of Chemistry, 52(1), 187-189. doi:10.1139/v74-030 es_ES
dc.description.references Gravel, D., Hebert, J., & Thoraval, D. (1983). o-Nitrophenylethylene glycol as photoremovable protective group for aldehydes and ketones: syntheses, scope, and limitations. Canadian Journal of Chemistry, 61(2), 400-410. doi:10.1139/v83-072 es_ES
dc.description.references Wang, P., Hu, H., & Wang, Y. (2007). Application of the Excited State Meta Effect in Photolabile Protecting Group Design. Organic Letters, 9(15), 2831-2833. doi:10.1021/ol071085c es_ES
dc.description.references Wang, P., Hu, H., & Wang, Y. (2007). Novel Photolabile Protecting Group for Carbonyl Compounds. Organic Letters, 9(8), 1533-1535. doi:10.1021/ol070346f es_ES
dc.description.references Yang, H., Zhang, X., Zhou, L., & Wang, P. (2011). Development of a Photolabile Carbonyl-Protecting Group Toolbox. The Journal of Organic Chemistry, 76(7), 2040-2048. doi:10.1021/jo102429g es_ES
dc.description.references Kostikov, A. P., Malashikhina, N., & Popik, V. V. (2009). Caging of Carbonyl Compounds as Photolabile (2,5-Dihydroxyphenyl)ethylene Glycol Acetals. The Journal of Organic Chemistry, 74(4), 1802-1804. doi:10.1021/jo802612f es_ES
dc.description.references Blanc, A., & Bochet, C. G. (2002). Bis(o-nitrophenyl)ethanediol:  A Practical Photolabile Protecting Group for Ketones and Aldehydes. The Journal of Organic Chemistry, 68(3), 1138-1141. doi:10.1021/jo026347x es_ES
dc.description.references Yu, J., Tang, W.-J., Wang, H.-B., & Song, Q.-H. (2007). Anthraquinon-2-ylethyl-1′,2′-diol (Aqe-diol) as a new photolabile protecting group for aldehydes and ketones. Journal of Photochemistry and Photobiology A: Chemistry, 185(1), 101-105. doi:10.1016/j.jphotochem.2006.05.010 es_ES
dc.description.references Lu, M., Fedoryak, O. D., Moister, B. R., & Dore, T. M. (2003). Bhc-diol as a Photolabile Protecting Group for Aldehydes and Ketones. Organic Letters, 5(12), 2119-2122. doi:10.1021/ol034536b es_ES
dc.description.references Levrand, B., & Herrmann, A. (2006). Light-induced controlled release of fragrance aldehydes from 1-alkoxy-9,10-anthraquinones for applications in functional perfumery. Flavour and Fragrance Journal, 21(3), 400-409. doi:10.1002/ffj.1728 es_ES
dc.description.references Levrand, B., & Herrmann, A. (2007). Controlled Light-Induced Release of Volatile Aldehydes and Ketones by Photofragmentation of 2-Oxo-(2-phenyl)acetates. CHIMIA International Journal for Chemistry, 61(10), 661-664. doi:10.2533/chimia.2007.661 es_ES
dc.description.references Griesbeck, A. G., Hinze, O., Görner, H., Huchel, U., Kropf, C., Sundermeier, U., & Gerke, T. (2012). Aromatic aldols and 1,5-diketones as optimized fragrance photocages. Photochemical & Photobiological Sciences, 11(3), 587. doi:10.1039/c2pp05286e es_ES
dc.description.references Brinson, R. G., & Jones, P. B. (2004). Caged trans-4-Hydroxy-2-nonenal. Organic Letters, 6(21), 3767-3770. doi:10.1021/ol048478l es_ES
dc.description.references Brinson, R. G., Hubbard, S. C., Zuidema, D. R., & Jones, P. B. (2005). Two new anthraquinone photoreactions. Journal of Photochemistry and Photobiology A: Chemistry, 175(2-3), 118-128. doi:10.1016/j.jphotochem.2005.03.027 es_ES
dc.description.references Blankespoor, R. L., DeVries, T., Hansen, E., Kallemeyn, J. M., Klooster, A. M., Mulder, J. A., … Vander Griend, D. A. (2002). Photochemical Synthesis of Aldehydes in the Solid Phase. The Journal of Organic Chemistry, 67(8), 2677-2681. doi:10.1021/jo025508u es_ES
dc.description.references McHale, W. A., & Kutateladze, A. G. (1998). An Efficient Photo-SET-Induced Cleavage of Dithiane−Carbonyl Adducts and Its Relevance to the Development of Photoremovable Protecting Groups for Ketones and Aldehydes. The Journal of Organic Chemistry, 63(26), 9924-9931. doi:10.1021/jo981697y es_ES
dc.description.references Li, Z., Wan, Y., & Kutateladze, A. G. (2003). Dithiane-Based Photolabile Amphiphiles:  Toward Photolabile Liposomes1,2. Langmuir, 19(16), 6381-6391. doi:10.1021/la034188m es_ES
dc.description.references Majjigapu, J. R. R., Kurchan, A. N., Kottani, R., Gustafson, T. P., & Kutateladze, A. G. (2005). Release and Report:  A New Photolabile Caging System with a Two-Photon Fluorescence Reporting Function. Journal of the American Chemical Society, 127(36), 12458-12459. doi:10.1021/ja053654m es_ES
dc.description.references Kottani, R., Valiulin, R. A., & Kutateladze, A. G. (2006). Direct screening of solution phase combinatorial libraries encoded with externally sensitized photolabile tags. Proceedings of the National Academy of Sciences, 103(38), 13917-13921. doi:10.1073/pnas.0606380103 es_ES
dc.description.references Majjigapu, K., Majjigapu, J. R. R., & Kutateladze, A. G. (2007). Photoamplification and Multiple Tag Release in a Linear Peptide-Based Array of Dithiane Adducts. Angewandte Chemie International Edition, 46(32), 6137-6140. doi:10.1002/anie.200701512 es_ES
dc.description.references Majjigapu, K., Majjigapu, J. R. R., & Kutateladze, A. G. (2007). Photoamplification and Multiple Tag Release in a Linear Peptide-Based Array of Dithiane Adducts. Angewandte Chemie, 119(32), 6249-6252. doi:10.1002/ange.200701512 es_ES
dc.description.references Vath, P., Falvey, D. E., Barnhurst, L. A., & Kutateladze, A. G. (2001). Photoinduced C−C Bond Cleavage in Dithiane−Carbonyl Adducts:  A Laser Flash Photolysis Study. The Journal of Organic Chemistry, 66(8), 2887-2890. doi:10.1021/jo010102n es_ES
dc.description.references Štacko, P., Šebej, P., Veetil, A. T., & Klán, P. (2012). Carbon–Carbon Bond Cleavage in Fluorescent Pyronin Analogues Induced by Yellow Light. Organic Letters, 14(18), 4918-4921. doi:10.1021/ol302244f es_ES
dc.description.references Aparici-Espert, I., Cuquerella, M. C., Paris, C., Lhiaubet-Vallet, V., & Miranda, M. A. (2016). Photocages for protection and controlled release of bioactive compounds. Chemical Communications, 52(99), 14215-14218. doi:10.1039/c6cc08175d es_ES
dc.description.references Aparici-Espert, I., Miranda, M., & Lhiaubet-Vallet, V. (2018). Sunscreen-Based Photocages for Topical Drugs: A Photophysical and Photochemical Study of A Diclofenac-Avobenzone Dyad. Molecules, 23(3), 673. doi:10.3390/molecules23030673 es_ES
dc.description.references Marin, M., Lhiaubet-Vallet, V., & Miranda, M. A. (2012). Enhanced Photochemical [6π] Electrocyclization within the Lipophilic Protein Binding Site. Organic Letters, 14(7), 1788-1791. doi:10.1021/ol3003805 es_ES
dc.description.references Görner, H. (2008). Photoinduced Oxygen Uptake of Diphenylamines in Solution and Their Ring Closure Revisited. The Journal of Physical Chemistry A, 112(6), 1245-1250. doi:10.1021/jp076788q es_ES


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